Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities (397 views)
Int J Biol Macromol (ISSN: 0141-8130linking, 1879-0003electronic), 2019 Jan; 121: 77-88.
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Paper type: Research Journal Article,
Impact factor: 4.784, 5-year impact factor: 4.731
Url: https://doi.org/10.1016/j.ijbiomac.2018.09.153
Keywords: Antiproliferative, Benzofuran, Nucleic Acid-Interaction, Prostate Cancer, Telomeric Dna, 7 (2 Methoxyethyl) 3 (methoxyethyl) 2, 6 Diamino 4 (4 Nitrophenyl)benzo[1, 2 B:4, 5 B, ]difuran 3, 7 Dicarboxylate, Benzofuran Derivative, Butyl 2 Amino 5 Hydroxy 4 (4 Nitrophenyl)benzofuran 3 Carboxylate, Dibutyl 2, Methoxyethyl 2 Amino 5 Hydroxy 4 (4 Nitrophenyl)benzofuran 3 Carboxylate, Unclassified Drug, Antineoplastic Activity, Antiproliferative Activity, Article, Cell Cycle Progression, Circular Dichroism, Controlled Study, Drug Dna Binding, Drug Structure, Drug Synthesis, Fluorescence Analysis, Human, Human Cell, Lipophilicity, Physical Chemistry, Prostate Cancer Cell Line, Thermostability, Benzofurannucleic Acid-Interactionprostate Cancerantiproliferativetelomeric Dna, Antineoplastic Agents Chemistry Metabolism Pharmacology, Benzofurans Chemistry Metabolism Pharmacology, Cell Proliferation Drug Effects, Cell Survival Drug Effects, Dna Metabolism, Drug Screening Assays, Antitumor, Nitrophenols Chemistry, Pc-3 Cells, S Phase Cell Cycle Checkpoints Drug Effects, Structure-Activity Relationship, Telomere Genetics,
Affiliations:
*** IBB - CNR ***
University of Naples Federico II, Department of Chemical Sciences, Via Cintia 21, I-80126 Naples, Italy.
Analytical Chemistry for the Environment and CeSMA (Advanced Metrologic Service Center), University of Naples Federico II, Corso N. Protopisani, 80146 Naples, Italy.
CNR, Institute of Biostructure and Bioimaging - (Via Mezzocannone Site and Headquarters), 80134 Naples, Italy.
n class="bibliodetails">University of Naples Federico II, Department of Chemical Sciences, Via Cintia 21, I-80126 Naples, Italy.
References:
McGrath, N.A., Brichacek, M., Njardarson, J.T., A graphical journey of innovative organic architectures that have improved our lives (2010) J. Chem. Educ., 87, pp. 1348-134
Barra, M., Biasiucci, M., Cassinese, A., D'Angelo, P., Barone, A.C., Carella, A., Roviello, A., Direct current and alternating current electrical transport properties of regioregular poly[3-(4-alkoxyphenyl)-thiophenes] (2007) J. Appl. Phys., 102, pp. 1-7
Carella, A., Centore, R., Mager, L., Barsella, A., Fort, A., Crosslinkable organic glasses with quadratic nonlinear optical activity (2007) Org. Electron. Physics, Mater. Appl., 8, pp. 57-62
Parker, T.C., Marder, S.R., Synthetic Methods in Organic Electronic and Photonic Materials: A Practical Guide (2015), http://pubs.rsc.org/en/content/ebook/978-1-84973-986-3#!divbookcontent, (Accessed 1 June 2017)
Wang, C., Dong, H., Hu, W., Liu, Y., Zhu, D., Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics (2012) Chem. Rev., 112, pp. 2208-2267
Khanam, H., Shamsuzzaman, Bioactive benzofuran derivatives: a review (2015) Eur. J. Med. Chem., 97, pp. 483-504
Desimone, R., Currie, K., Mitchell, S., Darrow, J., Pippin, D., Privileged structures: applications in drug discovery (2004) Comb. Chem. High Throughput Screen., 7, pp. 473-493
Alper-Hayta, S., Arisoy, M., Temiz-Arpaci, Ö., Yildiz, I., Aki, E., Özkan, S., Kaynak, F., Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles (2008) Eur. J. Med. Chem., 43, pp. 2568-2578
Soni, J.N., Soman, S.S., Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid (2014) Eur. J. Med. Chem., 75, pp. 77-81
Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S., Sugano, Y., 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents (2004) Bioorg. Med. Chem. Lett., 14, pp. 455-458
Xie, F., Zhu, H., Zhang, H., Lang, Q., Tang, L., Huang, Q., Yu, L., In vitro and in vivo characterization of a benzofuran derivative, a potential anticancer agent, as a novel Aurora B kinase inhibitor (2015) Eur. J. Med. Chem., 89, pp. 310-319
Thévenin, M., Thoret, S., Grellier, P., Dubois, J., Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth (2013) Bioorg. Med. Chem., 21, pp. 4885-4892
Wang, Y.-N., Liu, M.-F., Hou, W.-Z., Xu, R.-M., Gao, J., Lu, A.-Q., Xie, M.-P., Wang, S.-J., Bioactive benzofuran derivatives from Cortex Mori Radicis, and their neuroprotective and analgesic activities mediated by mGluR1 (2017) Molecules, 22, p. 236
Ashok, D., Sudershan, K., Khalilullah, M., Solvent-free microwave-assisted synthesis of E-(1)-(6-benzoyl-3,5-dimethylfuro[3′,2′:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones and their antibacterial activity (2012) Green Chem. Lett. Rev., 5, pp. 121-125
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., Novel benzodifuran analogs as potent 5-HT2Areceptor agonists with ocular hypotensive activity (2007) Bioorg. Med. Chem. Lett., 17, pp. 2998-3002
Roviello, G.N., Roviello, V., Musumeci, D., Pedone, C., Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA (2013) Biol. Chem., 394, pp. 1235-1239
Musumeci, D., Roviello, G.N., Rigione, G., Capasso, D., Di Gaetano, S., Riccardi, C., Roviello, V., Montesarchio, D., Benzodifuran derivatives as potential antiproliferative agents: possible correlation between their bioactivity and aggregation properties (2017) Chempluschem, 82, pp. 251-260
Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M., Pizzoferrato, R., Second harmonic generation in polymers containing a new azo chromophore based on phenylnitrobenzoxazole (2002) J. Polym. Sci. A Polym. Chem., 40, pp. 1468-1475
Justin Thomas, K.R., Baheti, A., Fluorene based organic dyes for dye sensitised solar cells: structure–property relationships (2013) Mater. Technol., 28, pp. 71-87
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Ninno, D., Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: synthesis, electronic properties and crystal structure (2012) Dyes Pigments, 95, pp. 116-125
Huang, P., Du, J., Biewer, M.C., Stefan, M.C., Sherburn, M.S., Isoda, S., Komatsu, K., Stefan, M.C., Developments of furan and benzodifuran semiconductors for organic photovoltaics (2015) J. Mater. Chem. A, 3, pp. 6244-6257
Borbone, F., Tarallo, O., Roviello, V., Caruso, U., Pirozzi, B., Roviello, A., Novel rigid rod polymers from a thermal cyclization reaction (2015) Eur. Polym. J., 63, pp. 80-89
Anderson, K.W., Ikawa, T., Tundel, R.E., Buchwald, S.L., The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans (2006)
Guo, X., Yu, R., Li, H., Li, Z., Iron-catalyzed tandem oxidative coupling and annulation: an efficient approach to construct polysubstituted benzofurans (2009) J. Am. Chem. Soc., 131, pp. 17387-17393
Li, C., Zhang, Y., Li, P., Wang, L., Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols (2011) J. Organomet. Chem., 76, pp. 4692-4696
Yue, D., Yao, T., Larock, R.C., Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization (2005) J. Organomet. Chem., 70, pp. 10292-10296
Singh, F., Wirth, T., Hypervalent iodine mediated oxidative cyclization of o-hydroxystilbenes into benzo- and naphthofurans (2012) Synthesis-Stuttgart, 44, pp. 1171-1177
Alves, C.M.A., Naik, S., Coutinho, P.J.G., Gonalves, M.S.T., Novel DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)-9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides: synthesis and photophysical studies (2011) Tetrahedron Lett., 52, pp. 112-116
Huo, L., Huang, Y., Fan, B., Guo, X., Jing, Y., Zhang, M., Li, Y., Hou, J., Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer (2012) Chem. Commun., 48, p. 3318
King, T.J., Newall, C.E., 175. The chemistry of colour reactions. The craven reaction (1965) J. Chem. Soc., p. 974
Kon, G.A.R., Brady, O.L., Porter, M.D., Craven, R., Notes (1931) J. Chem. Soc., p. 1604
Obushak, M., Synthesis of heterocycles on the basic of arylation products of unsaturated compounds. Part 9. Dialkyl 2,6-diamino-4-arylfuro[2′,3′:4,5]benzo[b]furan-3,7-dicarboxylates from 2-aryl-1,4-benzoquinones and cyanoacetic esters (2002) Pol. J. Chem., pp. 1419-1424. , https://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-article-BUJ1-0021-0006, (Accessed 1 June 2017)
Carlson, B.W., Miller, L.L., Mechanism of the oxidation of NADH by quinones. energetics of one-electron and hydride routes (1985) J. Am. Chem. Soc., 107, pp. 479-485
Li, X.Y., He, B.F., Luo, H.J., Huang, N.Y., Deng, W.Q., 3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: a combined experimental and theoretical investigation (2013) Bioorg. Med. Chem. Lett., 23, pp. 4617-4621
Weinlich, R., Oberst, A., Beere, H.M., Green, D.R., Necroptosis in development, inflammation and disease (2017) Nat. Rev. Mol. Cell Biol., 18, pp. 127-136
McIlwain, D.R., Berger, T., Mak, T.W., Caspase functions in cell death and disease (2013) Cold Spring Harb. Perspect. Biol., 5, pp. 1-28
Incles, C.M., Schultes, C.M., Kempski, H., Koehler, H., Kelland, L.R., Neidle, S., A G-quadruplex telomere targeting agent produces p16-associated senescence and chromosomal fusions in human prostate cancer cells (2004) Mol. Cancer Ther., 3, pp. 1201-1206. , http://www.ncbi.nlm.nih.gov/pubmed/15486186, (Accessed 28 August 2018)
Khaw, A.K., Silasudjana, M., Banerjee, B., Suzuki, M., Baskar, R., Hande, M.P., Inhibition of telomerase activity and human telomerase reverse transcriptase gene expression by histone deacetylase inhibitor in human brain cancer cells (2007) Mutat. Res. Fundam. Mol. Mech. Mutagen., 625, pp. 134-144
Sherr, C.J., The pezcoller lecture: cancer cell cycles revisited (2000) Cancer Res., pp. 3689-3695. , http://www.ncbi.nlm.nih.gov/pubmed/10919634, (Accessed 24 May 2018)
De Boer, L., Oakes, V., Beamish, H., Giles, N., Stevens, F., Somodevilla-Torres, M., Desouza, C., Gabrielli, B., Cyclin A/cdk2 coordinates centrosomal and nuclear mitotic events (2008) Oncogene, 27, pp. 4261-4268
Tsai, Y.C., Qi, H., Lin, C.P., Lin, R.K., Kerrigan, J.E., Rzuczek, S.G., Lavoie, E.J., Liu, L.F., A G-quadruplex stabilizer induces M-phase cell cycle arrest (2009) J. Biol. Chem., 284, pp. 22535-22543
Zhou, G., Liu, X., Li, Y., Xu, S., Ma, C., Wu, X., Cheng, Y., Chen, Y., Telomere targeting with a novel G-quadruplex-interactive ligand BRACO-19 induces T-loop disassembly and telomerase displacement in human glioblastoma cells (2016) Oncotarget, 7, pp. 14925-14939
Hudson, J.S., Ding, L., Le, V., Lewis, E., Graves, D., Recognition and binding of human telomeric G-quadruplex DNA by unfolding protein 1 (2014) Biochemistry, 53, pp. 3347-3356
Ambrus, A., Chen, D., Dai, J., Bialis, T., Jones, R.A., Yang, D., Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution (2006) Nucleic Acids Res., 34, pp. 2723-2735
Fuggetta, M.P., De Mico, A., Cottarelli, A., Morelli, F., Zonfrillo, M., Ulgheri, F., Peluso, P., Spanu, P., Synthesis and enantiomeric separation of a novel spiroketal derivative: a potent human telomerase inhibitor with high in vitro anticancer activity (2016) J. Med. Chem., 59, pp. 9140-9149
Jain, A.K., Reddy, V.V., Paul, A., Muniyappa, K., Bhattacharya, S., Synthesis and evaluation of a novel class of G-quadruplex-stabilizing small molecules based on the 1,3-phenylene-bis(piperazinyl benzimidazole) system (2009) Biochemistry, 48, pp. 10693-10704
Mendez, M.A., Szalai, V.A., Fluorescence of unmodified oligonucleotides: a tool to probe G-quadruplex DNA structure (2009) Biopolymers, 91, pp. 841-850
Russo, A., Scognamiglio, P.L., Hong Enriquez, R.P., Santambrogio, C., Grandori, R., Marasco, D., Giordano, A., Fortuna, S., In silico generation of peptides by replica exchange Monte Carlo: docking-based optimization of maltose-binding-protein ligands (2015) PLoS One, 10
Gao, S., Cao, Y., Yan, Y., Xiang, X., Guo, X., Correlations between fluorescence emission and base stacks of nucleic acid G-quadruplexes (2016) RSC Adv., 6, pp. 94531-94538
n style="font-size: 16px;">McGrath, N.A., Brichacek, M., Njardarson, J.T., A graphical journey of innovative organic architectures that have improved our lives (2010) J. Chem. Educ., 87, pp. 1348-134
Barra, M., Biasiucci, M., Cassinese, A., D'Angelo, P., Barone, A.C., Carella, A., Roviello, A., Direct current and alternating current electrical transport properties of regioregular poly[3-(4-alkoxyphenyl)-thiophenes] (2007) J. Appl. Phys., 102, pp. 1-7
Carella, A., Centore, R., Mager, L., Barsella, A., Fort, A., Crosslinkable organic glasses with quadratic nonlinear optical activity (2007) Org. Electron. Physics, Mater. Appl., 8, pp. 57-62
Parker, T.C., Marder, S.R., Synthetic Methods in Organic Electronic and Photonic Materials: A Practical Guide (2015), http://pubs.rsc.org/en/content/ebook/978-1-84973-986-3#!divbookcontent, (Accessed 1 June 2017)
Wang, C., Dong, H., Hu, W., Liu, Y., Zhu, D., Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics (2012) Chem. Rev., 112, pp. 2208-2267
Khanam, H., Shamsuzzaman, Bioactive benzofuran derivatives: a review (2015) Eur. J. Med. Chem., 97, pp. 483-504
Desimone, R., Currie, K., Mitchell, S., Darrow, J., Pippin, D., Privileged structures: applications in drug discovery (2004) Comb. Chem. High Throughput Screen., 7, pp. 473-493
Alper-Hayta, S., Arisoy, M., Temiz-Arpaci, Ö., Yildiz, I., Aki, E., Özkan, S., Kaynak, F., Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles (2008) Eur. J. Med. Chem., 43, pp. 2568-2578
Soni, J.N., Soman, S.S., Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid (2014) Eur. J. Med. Chem., 75, pp. 77-81
Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S., Sugano, Y., 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents (2004) Bioorg. Med. Chem. Lett., 14, pp. 455-458
Xie, F., Zhu, H., Zhang, H., Lang, Q., Tang, L., Huang, Q., Yu, L., In vitro and in vivo characterization of a benzofuran derivative, a potential anticancer agent, as a novel Aurora B kinase inhibitor (2015) Eur. J. Med. Chem., 89, pp. 310-319
Thévenin, M., Thoret, S., Grellier, P., Dubois, J., Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth (2013) Bioorg. Med. Chem., 21, pp. 4885-4892
Wang, Y.-N., Liu, M.-F., Hou, W.-Z., Xu, R.-M., Gao, J., Lu, A.-Q., Xie, M.-P., Wang, S.-J., Bioactive benzofuran derivatives from Cortex Mori Radicis, and their neuroprotective and analgesic activities mediated by mGluR1 (2017) Molecules, 22, p. 236
Ashok, D., Sudershan, K., Khalilullah, M., Solvent-free microwave-assisted synthesis of E-(1)-(6-benzoyl-3,5-dimethylfuro[3′,2′:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones and their antibacterial activity (2012) Green Chem. Lett. Rev., 5, pp. 121-125
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., Novel benzodifuran analogs as potent 5-HT2Areceptor agonists with ocular hypotensive activity (2007) Bioorg. Med. Chem. Lett., 17, pp. 2998-3002
Roviello, G.N., Roviello, V., Musumeci, D., Pedone, C., Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA (2013) Biol. Chem., 394, pp. 1235-1239
Musumeci, D., Roviello, G.N., Rigione, G., Capasso, D., Di Gaetano, S., Riccardi, C., Roviello, V., Montesarchio, D., Benzodifuran derivatives as potential antiproliferative agents: possible correlation between their bioactivity and aggregation properties (2017) Chempluschem, 82, pp. 251-260
Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M., Pizzoferrato, R., Second harmonic generation in polymers containing a new azo chromophore based on phenylnitrobenzoxazole (2002) J. Polym. Sci. A Polym. Chem., 40, pp. 1468-1475
Justin Thomas, K.R., Baheti, A., Fluorene based organic dyes for dye sensitised solar cells: structure–property relationships (2013) Mater. Technol., 28, pp. 71-87
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Ninno, D., Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: synthesis, electronic properties and crystal structure (2012) Dyes Pigments, 95, pp. 116-125
Huang, P., Du, J., Biewer, M.C., Stefan, M.C., Sherburn, M.S., Isoda, S., Komatsu, K., Stefan, M.C., Developments of furan and benzodifuran semiconductors for organic photovoltaics (2015) J. Mater. Chem. A, 3, pp. 6244-6257
Borbone, F., Tarallo, O., Roviello, V., Caruso, U., Pirozzi, B., Roviello, A., Novel rigid rod polymers from a thermal cyclization reaction (2015) Eur. Polym. J., 63, pp. 80-89
Anderson, K.W., Ikawa, T., Tundel, R.E., Buchwald, S.L., The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans (2006)
Guo, X., Yu, R., Li, H., Li, Z., Iron-catalyzed tandem oxidative coupling and annulation: an efficient approach to construct polysubstituted benzofurans (2009) J. Am. Chem. Soc., 131, pp. 17387-17393
Li, C., Zhang, Y., Li, P., Wang, L., Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols (2011) J. Organomet. Chem., 76, pp. 4692-4696
Yue, D., Yao, T., Larock, R.C., Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization (2005) J. Organomet. Chem., 70, pp. 10292-10296
Singh, F., Wirth, T., Hypervalent iodine mediated oxidative cyclization of o-hydroxystilbenes into benzo- and naphthofurans (2012) Synthesis-Stuttgart, 44, pp. 1171-1177
Alves, C.M.A., Naik, S., Coutinho, P.J.G., Gonalves, M.S.T., Novel DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)-9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides: synthesis and photophysical studies (2011) Tetrahedron Lett., 52, pp. 112-116
Huo, L., Huang, Y., Fan, B., Guo, X., Jing, Y., Zhang, M., Li, Y., Hou, J., Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer (2012) Chem. Commun., 48, p. 3318
King, T.J., Newall, C.E., 175. The chemistry of colour reactions. The craven reaction (1965) J. Chem. Soc., p. 974
Kon, G.A.R., Brady, O.L., Porter, M.D., Craven, R., Notes (1931) J. Chem. Soc., p. 1604
Obushak, M., Synthesis of heterocycles on the basic of arylation products of unsaturated compounds. Part 9. Dialkyl 2,6-diamino-4-arylfuro[2′,3′:4,5]benzo[b]furan-3,7-dicarboxylates from 2-aryl-1,4-benzoquinones and cyanoacetic esters (2002) Pol. J. Chem., pp. 1419-1424. , https://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-article-BUJ1-0021-0006, (Accessed 1 June 2017)
Carlson, B.W., Miller, L.L., Mechanism of the oxidation of NADH by quinones. energetics of one-electron and hydride routes (1985) J. Am. Chem. Soc., 107, pp. 479-485
Li, X.Y., He, B.F., Luo, H.J., Huang, N.Y., Deng, W.Q., 3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: a combined experimental and theoretical investigation (2013) Bioorg. Med. Chem. Lett., 23, pp. 4617-4621
Weinlich, R., Oberst, A., Beere, H.M., Green, D.R., Necroptosis in development, inflammation and disease (2017) Nat. Rev. Mol. Cell Biol., 18, pp. 127-136
McIlwain, D.R., Berger, T., Mak, T.W., Caspase functions in cell death and disease (2013) Cold Spring Harb. Perspect. Biol., 5, pp. 1-28
Incles, C.M., Schultes, C.M., Kempski, H., Koehler, H., Kelland, L.R., Neidle, S., A G-quadruplex telomere targeting agent produces p16-associated senescence and chromosomal fusions in human prostate cancer cells (2004) Mol. Cancer Ther., 3, pp. 1201-1206. , http://www.ncbi.nlm.nih.gov/pubmed/15486186, (Accessed 28 August 2018)
Khaw, A.K., Silasudjana, M., Banerjee, B., Suzuki, M., Baskar, R., Hande, M.P., Inhibition of telomerase activity and human telomerase reverse transcriptase gene expression by histone deacetylase inhibitor in human brain cancer cells (2007) Mutat. Res. Fundam. Mol. Mech. Mutagen., 625, pp. 134-144
Sherr, C.J., The pezcoller lecture: cancer cell cycles revisited (2000) Cancer Res., pp. 3689-3695. , http://www.ncbi.nlm.nih.gov/pubmed/10919634, (Accessed 24 May 2018)
De Boer, L., Oakes, V., Beamish, H., Giles, N., Stevens, F., Somodevilla-Torres, M., Desouza, C., Gabrielli, B., Cyclin A/cdk2 coordinates centrosomal and nuclear mitotic events (2008) Oncogene, 27, pp. 4261-4268
Tsai, Y.C., Qi, H., Lin, C.P., Lin, R.K., Kerrigan, J.E., Rzuczek, S.G., Lavoie, E.J., Liu, L.F., A G-quadruplex stabilizer induces M-phase cell cycle arrest (2009) J. Biol. Chem., 284, pp. 22535-22543
Zhou, G., Liu, X., Li, Y., Xu, S., Ma, C., Wu, X., Cheng, Y., Chen, Y., Telomere targeting with a novel G-quadruplex-interactive ligand BRACO-19 induces T-loop disassembly and telomerase displacement in human glioblastoma cells (2016) Oncotarget, 7, pp. 14925-14939
Hudson, J.S., Ding, L., Le, V., Lewis, E., Graves, D., Recognition and binding of human telomeric G-quadruplex DNA by unfolding protein 1 (2014) Biochemistry, 53, pp. 3347-3356
Ambrus, A., Chen, D., Dai, J., Bialis, T., Jones, R.A., Yang, D., Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution (2006) Nucleic Acids Res., 34, pp. 2723-2735
Fuggetta, M.P., De Mico, A., Cottarelli, A., Morelli, F., Zonfrillo, M., Ulgheri, F., Peluso, P., Spanu, P., Synthesis and enantiomeric separation of a novel spiroketal derivative: a potent human telomerase inhibitor with high in vitro anticancer activity (2016) J. Med. Chem., 59, pp. 9140-9149
Jain, A.K., Reddy, V.V., Paul, A., Muniyappa, K., Bhattacharya, S., Synthesis and evaluation of a novel class of G-quadruplex-stabilizing small molecules based on the 1,3-phenylene-bis(piperazinyl benzimidazole) system (2009) Biochemistry, 48, pp. 10693-10704
Mendez, M.A., Szalai, V.A., Fluorescence of unmodified oligonucleotides: a tool to probe G-quadruplex DNA structure (2009) Biopolymers, 91, pp. 841-850
Russo, A., Scognamiglio, P.L., Hong Enriquez, R.P., Santambrogio, C., Grandori, R., Marasco, D., Giordano, A., Fortuna, S., In silico generation of peptides by replica exchange Monte Carlo: docking-based optimization of maltose-binding-protein ligands (2015) PLoS One, 10
Gao, S., Cao, Y., Yan, Y., Xiang, X., Guo, X., Correlations between fluorescence emission and base stacks of nucleic acid G-quadruplexes (2016) RSC Adv., 6, pp. 94531-94538
Int J Biol Macromol (ISSN: 0141-8130linking, 1879-0003electronic), 2019 Jan; 121: 77-88.
Export to BibTeX Export to EndNote
Paper type: Research Journal Article,
Impact factor: 4.784, 5-year impact factor: 4.731
Url: https://doi.org/10.1016/j.ijbiomac.2018.09.153
Keywords: Antiproliferative, Benzofuran, Nucleic Acid-Interaction, Prostate Cancer, Telomeric Dna, 7 (2 Methoxyethyl) 3 (methoxyethyl) 2, 6 Diamino 4 (4 Nitrophenyl)benzo[1, 2 B:4, 5 B, ]difuran 3, 7 Dicarboxylate, Benzofuran Derivative, Butyl 2 Amino 5 Hydroxy 4 (4 Nitrophenyl)benzofuran 3 Carboxylate, Dibutyl 2, Methoxyethyl 2 Amino 5 Hydroxy 4 (4 Nitrophenyl)benzofuran 3 Carboxylate, Unclassified Drug, Antineoplastic Activity, Antiproliferative Activity, Article, Cell Cycle Progression, Circular Dichroism, Controlled Study, Drug Dna Binding, Drug Structure, Drug Synthesis, Fluorescence Analysis, Human, Human Cell, Lipophilicity, Physical Chemistry, Prostate Cancer Cell Line, Thermostability, Benzofurannucleic Acid-Interactionprostate Cancerantiproliferativetelomeric Dna, Antineoplastic Agents Chemistry Metabolism Pharmacology, Benzofurans Chemistry Metabolism Pharmacology, Cell Proliferation Drug Effects, Cell Survival Drug Effects, Dna Metabolism, Drug Screening Assays, Antitumor, Nitrophenols Chemistry, Pc-3 Cells, S Phase Cell Cycle Checkpoints Drug Effects, Structure-Activity Relationship, Telomere Genetics,
Affiliations:
*** IBB - CNR ***
University of Naples Federico II, Department of Chemical Sciences, Via Cintia 21, I-80126 Naples, Italy.
Analytical Chemistry for the Environment and CeSMA (Advanced Metrologic Service Center), University of Naples Federico II, Corso N. Protopisani, 80146 Naples, Italy.
CNR, Institute of Biostructure and Bioimaging - (Via Mezzocannone Site and Headquarters), 80134 Naples, Italy.
n class="bibliodetails">University of Naples Federico II, Department of Chemical Sciences, Via Cintia 21, I-80126 Naples, Italy.
References:
McGrath, N.A., Brichacek, M., Njardarson, J.T., A graphical journey of innovative organic architectures that have improved our lives (2010) J. Chem. Educ., 87, pp. 1348-134
Barra, M., Biasiucci, M., Cassinese, A., D'Angelo, P., Barone, A.C., Carella, A., Roviello, A., Direct current and alternating current electrical transport properties of regioregular poly[3-(4-alkoxyphenyl)-thiophenes] (2007) J. Appl. Phys., 102, pp. 1-7
Carella, A., Centore, R., Mager, L., Barsella, A., Fort, A., Crosslinkable organic glasses with quadratic nonlinear optical activity (2007) Org. Electron. Physics, Mater. Appl., 8, pp. 57-62
Parker, T.C., Marder, S.R., Synthetic Methods in Organic Electronic and Photonic Materials: A Practical Guide (2015), http://pubs.rsc.org/en/content/ebook/978-1-84973-986-3#!divbookcontent, (Accessed 1 June 2017)
Wang, C., Dong, H., Hu, W., Liu, Y., Zhu, D., Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics (2012) Chem. Rev., 112, pp. 2208-2267
Khanam, H., Shamsuzzaman, Bioactive benzofuran derivatives: a review (2015) Eur. J. Med. Chem., 97, pp. 483-504
Desimone, R., Currie, K., Mitchell, S., Darrow, J., Pippin, D., Privileged structures: applications in drug discovery (2004) Comb. Chem. High Throughput Screen., 7, pp. 473-493
Alper-Hayta, S., Arisoy, M., Temiz-Arpaci, Ö., Yildiz, I., Aki, E., Özkan, S., Kaynak, F., Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles (2008) Eur. J. Med. Chem., 43, pp. 2568-2578
Soni, J.N., Soman, S.S., Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid (2014) Eur. J. Med. Chem., 75, pp. 77-81
Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S., Sugano, Y., 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents (2004) Bioorg. Med. Chem. Lett., 14, pp. 455-458
Xie, F., Zhu, H., Zhang, H., Lang, Q., Tang, L., Huang, Q., Yu, L., In vitro and in vivo characterization of a benzofuran derivative, a potential anticancer agent, as a novel Aurora B kinase inhibitor (2015) Eur. J. Med. Chem., 89, pp. 310-319
Thévenin, M., Thoret, S., Grellier, P., Dubois, J., Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth (2013) Bioorg. Med. Chem., 21, pp. 4885-4892
Wang, Y.-N., Liu, M.-F., Hou, W.-Z., Xu, R.-M., Gao, J., Lu, A.-Q., Xie, M.-P., Wang, S.-J., Bioactive benzofuran derivatives from Cortex Mori Radicis, and their neuroprotective and analgesic activities mediated by mGluR1 (2017) Molecules, 22, p. 236
Ashok, D., Sudershan, K., Khalilullah, M., Solvent-free microwave-assisted synthesis of E-(1)-(6-benzoyl-3,5-dimethylfuro[3′,2′:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones and their antibacterial activity (2012) Green Chem. Lett. Rev., 5, pp. 121-125
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., Novel benzodifuran analogs as potent 5-HT2Areceptor agonists with ocular hypotensive activity (2007) Bioorg. Med. Chem. Lett., 17, pp. 2998-3002
Roviello, G.N., Roviello, V., Musumeci, D., Pedone, C., Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA (2013) Biol. Chem., 394, pp. 1235-1239
Musumeci, D., Roviello, G.N., Rigione, G., Capasso, D., Di Gaetano, S., Riccardi, C., Roviello, V., Montesarchio, D., Benzodifuran derivatives as potential antiproliferative agents: possible correlation between their bioactivity and aggregation properties (2017) Chempluschem, 82, pp. 251-260
Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M., Pizzoferrato, R., Second harmonic generation in polymers containing a new azo chromophore based on phenylnitrobenzoxazole (2002) J. Polym. Sci. A Polym. Chem., 40, pp. 1468-1475
Justin Thomas, K.R., Baheti, A., Fluorene based organic dyes for dye sensitised solar cells: structure–property relationships (2013) Mater. Technol., 28, pp. 71-87
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Ninno, D., Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: synthesis, electronic properties and crystal structure (2012) Dyes Pigments, 95, pp. 116-125
Huang, P., Du, J., Biewer, M.C., Stefan, M.C., Sherburn, M.S., Isoda, S., Komatsu, K., Stefan, M.C., Developments of furan and benzodifuran semiconductors for organic photovoltaics (2015) J. Mater. Chem. A, 3, pp. 6244-6257
Borbone, F., Tarallo, O., Roviello, V., Caruso, U., Pirozzi, B., Roviello, A., Novel rigid rod polymers from a thermal cyclization reaction (2015) Eur. Polym. J., 63, pp. 80-89
Anderson, K.W., Ikawa, T., Tundel, R.E., Buchwald, S.L., The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans (2006)
Guo, X., Yu, R., Li, H., Li, Z., Iron-catalyzed tandem oxidative coupling and annulation: an efficient approach to construct polysubstituted benzofurans (2009) J. Am. Chem. Soc., 131, pp. 17387-17393
Li, C., Zhang, Y., Li, P., Wang, L., Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols (2011) J. Organomet. Chem., 76, pp. 4692-4696
Yue, D., Yao, T., Larock, R.C., Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization (2005) J. Organomet. Chem., 70, pp. 10292-10296
Singh, F., Wirth, T., Hypervalent iodine mediated oxidative cyclization of o-hydroxystilbenes into benzo- and naphthofurans (2012) Synthesis-Stuttgart, 44, pp. 1171-1177
Alves, C.M.A., Naik, S., Coutinho, P.J.G., Gonalves, M.S.T., Novel DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)-9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides: synthesis and photophysical studies (2011) Tetrahedron Lett., 52, pp. 112-116
Huo, L., Huang, Y., Fan, B., Guo, X., Jing, Y., Zhang, M., Li, Y., Hou, J., Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer (2012) Chem. Commun., 48, p. 3318
King, T.J., Newall, C.E., 175. The chemistry of colour reactions. The craven reaction (1965) J. Chem. Soc., p. 974
Kon, G.A.R., Brady, O.L., Porter, M.D., Craven, R., Notes (1931) J. Chem. Soc., p. 1604
Obushak, M., Synthesis of heterocycles on the basic of arylation products of unsaturated compounds. Part 9. Dialkyl 2,6-diamino-4-arylfuro[2′,3′:4,5]benzo[b]furan-3,7-dicarboxylates from 2-aryl-1,4-benzoquinones and cyanoacetic esters (2002) Pol. J. Chem., pp. 1419-1424. , https://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-article-BUJ1-0021-0006, (Accessed 1 June 2017)
Carlson, B.W., Miller, L.L., Mechanism of the oxidation of NADH by quinones. energetics of one-electron and hydride routes (1985) J. Am. Chem. Soc., 107, pp. 479-485
Li, X.Y., He, B.F., Luo, H.J., Huang, N.Y., Deng, W.Q., 3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: a combined experimental and theoretical investigation (2013) Bioorg. Med. Chem. Lett., 23, pp. 4617-4621
Weinlich, R., Oberst, A., Beere, H.M., Green, D.R., Necroptosis in development, inflammation and disease (2017) Nat. Rev. Mol. Cell Biol., 18, pp. 127-136
McIlwain, D.R., Berger, T., Mak, T.W., Caspase functions in cell death and disease (2013) Cold Spring Harb. Perspect. Biol., 5, pp. 1-28
Incles, C.M., Schultes, C.M., Kempski, H., Koehler, H., Kelland, L.R., Neidle, S., A G-quadruplex telomere targeting agent produces p16-associated senescence and chromosomal fusions in human prostate cancer cells (2004) Mol. Cancer Ther., 3, pp. 1201-1206. , http://www.ncbi.nlm.nih.gov/pubmed/15486186, (Accessed 28 August 2018)
Khaw, A.K., Silasudjana, M., Banerjee, B., Suzuki, M., Baskar, R., Hande, M.P., Inhibition of telomerase activity and human telomerase reverse transcriptase gene expression by histone deacetylase inhibitor in human brain cancer cells (2007) Mutat. Res. Fundam. Mol. Mech. Mutagen., 625, pp. 134-144
Sherr, C.J., The pezcoller lecture: cancer cell cycles revisited (2000) Cancer Res., pp. 3689-3695. , http://www.ncbi.nlm.nih.gov/pubmed/10919634, (Accessed 24 May 2018)
De Boer, L., Oakes, V., Beamish, H., Giles, N., Stevens, F., Somodevilla-Torres, M., Desouza, C., Gabrielli, B., Cyclin A/cdk2 coordinates centrosomal and nuclear mitotic events (2008) Oncogene, 27, pp. 4261-4268
Tsai, Y.C., Qi, H., Lin, C.P., Lin, R.K., Kerrigan, J.E., Rzuczek, S.G., Lavoie, E.J., Liu, L.F., A G-quadruplex stabilizer induces M-phase cell cycle arrest (2009) J. Biol. Chem., 284, pp. 22535-22543
Zhou, G., Liu, X., Li, Y., Xu, S., Ma, C., Wu, X., Cheng, Y., Chen, Y., Telomere targeting with a novel G-quadruplex-interactive ligand BRACO-19 induces T-loop disassembly and telomerase displacement in human glioblastoma cells (2016) Oncotarget, 7, pp. 14925-14939
Hudson, J.S., Ding, L., Le, V., Lewis, E., Graves, D., Recognition and binding of human telomeric G-quadruplex DNA by unfolding protein 1 (2014) Biochemistry, 53, pp. 3347-3356
Ambrus, A., Chen, D., Dai, J., Bialis, T., Jones, R.A., Yang, D., Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution (2006) Nucleic Acids Res., 34, pp. 2723-2735
Fuggetta, M.P., De Mico, A., Cottarelli, A., Morelli, F., Zonfrillo, M., Ulgheri, F., Peluso, P., Spanu, P., Synthesis and enantiomeric separation of a novel spiroketal derivative: a potent human telomerase inhibitor with high in vitro anticancer activity (2016) J. Med. Chem., 59, pp. 9140-9149
Jain, A.K., Reddy, V.V., Paul, A., Muniyappa, K., Bhattacharya, S., Synthesis and evaluation of a novel class of G-quadruplex-stabilizing small molecules based on the 1,3-phenylene-bis(piperazinyl benzimidazole) system (2009) Biochemistry, 48, pp. 10693-10704
Mendez, M.A., Szalai, V.A., Fluorescence of unmodified oligonucleotides: a tool to probe G-quadruplex DNA structure (2009) Biopolymers, 91, pp. 841-850
Russo, A., Scognamiglio, P.L., Hong Enriquez, R.P., Santambrogio, C., Grandori, R., Marasco, D., Giordano, A., Fortuna, S., In silico generation of peptides by replica exchange Monte Carlo: docking-based optimization of maltose-binding-protein ligands (2015) PLoS One, 10
Gao, S., Cao, Y., Yan, Y., Xiang, X., Guo, X., Correlations between fluorescence emission and base stacks of nucleic acid G-quadruplexes (2016) RSC Adv., 6, pp. 94531-94538
n style="font-size: 16px;">McGrath, N.A., Brichacek, M., Njardarson, J.T., A graphical journey of innovative organic architectures that have improved our lives (2010) J. Chem. Educ., 87, pp. 1348-134
Barra, M., Biasiucci, M., Cassinese, A., D'Angelo, P., Barone, A.C., Carella, A., Roviello, A., Direct current and alternating current electrical transport properties of regioregular poly[3-(4-alkoxyphenyl)-thiophenes] (2007) J. Appl. Phys., 102, pp. 1-7
Carella, A., Centore, R., Mager, L., Barsella, A., Fort, A., Crosslinkable organic glasses with quadratic nonlinear optical activity (2007) Org. Electron. Physics, Mater. Appl., 8, pp. 57-62
Parker, T.C., Marder, S.R., Synthetic Methods in Organic Electronic and Photonic Materials: A Practical Guide (2015), http://pubs.rsc.org/en/content/ebook/978-1-84973-986-3#!divbookcontent, (Accessed 1 June 2017)
Wang, C., Dong, H., Hu, W., Liu, Y., Zhu, D., Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics (2012) Chem. Rev., 112, pp. 2208-2267
Khanam, H., Shamsuzzaman, Bioactive benzofuran derivatives: a review (2015) Eur. J. Med. Chem., 97, pp. 483-504
Desimone, R., Currie, K., Mitchell, S., Darrow, J., Pippin, D., Privileged structures: applications in drug discovery (2004) Comb. Chem. High Throughput Screen., 7, pp. 473-493
Alper-Hayta, S., Arisoy, M., Temiz-Arpaci, Ö., Yildiz, I., Aki, E., Özkan, S., Kaynak, F., Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles (2008) Eur. J. Med. Chem., 43, pp. 2568-2578
Soni, J.N., Soman, S.S., Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid (2014) Eur. J. Med. Chem., 75, pp. 77-81
Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S., Sugano, Y., 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents (2004) Bioorg. Med. Chem. Lett., 14, pp. 455-458
Xie, F., Zhu, H., Zhang, H., Lang, Q., Tang, L., Huang, Q., Yu, L., In vitro and in vivo characterization of a benzofuran derivative, a potential anticancer agent, as a novel Aurora B kinase inhibitor (2015) Eur. J. Med. Chem., 89, pp. 310-319
Thévenin, M., Thoret, S., Grellier, P., Dubois, J., Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth (2013) Bioorg. Med. Chem., 21, pp. 4885-4892
Wang, Y.-N., Liu, M.-F., Hou, W.-Z., Xu, R.-M., Gao, J., Lu, A.-Q., Xie, M.-P., Wang, S.-J., Bioactive benzofuran derivatives from Cortex Mori Radicis, and their neuroprotective and analgesic activities mediated by mGluR1 (2017) Molecules, 22, p. 236
Ashok, D., Sudershan, K., Khalilullah, M., Solvent-free microwave-assisted synthesis of E-(1)-(6-benzoyl-3,5-dimethylfuro[3′,2′:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones and their antibacterial activity (2012) Green Chem. Lett. Rev., 5, pp. 121-125
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., Novel benzodifuran analogs as potent 5-HT2Areceptor agonists with ocular hypotensive activity (2007) Bioorg. Med. Chem. Lett., 17, pp. 2998-3002
Roviello, G.N., Roviello, V., Musumeci, D., Pedone, C., Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA (2013) Biol. Chem., 394, pp. 1235-1239
Musumeci, D., Roviello, G.N., Rigione, G., Capasso, D., Di Gaetano, S., Riccardi, C., Roviello, V., Montesarchio, D., Benzodifuran derivatives as potential antiproliferative agents: possible correlation between their bioactivity and aggregation properties (2017) Chempluschem, 82, pp. 251-260
Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M., Pizzoferrato, R., Second harmonic generation in polymers containing a new azo chromophore based on phenylnitrobenzoxazole (2002) J. Polym. Sci. A Polym. Chem., 40, pp. 1468-1475
Justin Thomas, K.R., Baheti, A., Fluorene based organic dyes for dye sensitised solar cells: structure–property relationships (2013) Mater. Technol., 28, pp. 71-87
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Ninno, D., Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: synthesis, electronic properties and crystal structure (2012) Dyes Pigments, 95, pp. 116-125
Huang, P., Du, J., Biewer, M.C., Stefan, M.C., Sherburn, M.S., Isoda, S., Komatsu, K., Stefan, M.C., Developments of furan and benzodifuran semiconductors for organic photovoltaics (2015) J. Mater. Chem. A, 3, pp. 6244-6257
Borbone, F., Tarallo, O., Roviello, V., Caruso, U., Pirozzi, B., Roviello, A., Novel rigid rod polymers from a thermal cyclization reaction (2015) Eur. Polym. J., 63, pp. 80-89
Anderson, K.W., Ikawa, T., Tundel, R.E., Buchwald, S.L., The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans (2006)
Guo, X., Yu, R., Li, H., Li, Z., Iron-catalyzed tandem oxidative coupling and annulation: an efficient approach to construct polysubstituted benzofurans (2009) J. Am. Chem. Soc., 131, pp. 17387-17393
Li, C., Zhang, Y., Li, P., Wang, L., Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols (2011) J. Organomet. Chem., 76, pp. 4692-4696
Yue, D., Yao, T., Larock, R.C., Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization (2005) J. Organomet. Chem., 70, pp. 10292-10296
Singh, F., Wirth, T., Hypervalent iodine mediated oxidative cyclization of o-hydroxystilbenes into benzo- and naphthofurans (2012) Synthesis-Stuttgart, 44, pp. 1171-1177
Alves, C.M.A., Naik, S., Coutinho, P.J.G., Gonalves, M.S.T., Novel DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)-9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides: synthesis and photophysical studies (2011) Tetrahedron Lett., 52, pp. 112-116
Huo, L., Huang, Y., Fan, B., Guo, X., Jing, Y., Zhang, M., Li, Y., Hou, J., Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer (2012) Chem. Commun., 48, p. 3318
King, T.J., Newall, C.E., 175. The chemistry of colour reactions. The craven reaction (1965) J. Chem. Soc., p. 974
Kon, G.A.R., Brady, O.L., Porter, M.D., Craven, R., Notes (1931) J. Chem. Soc., p. 1604
Obushak, M., Synthesis of heterocycles on the basic of arylation products of unsaturated compounds. Part 9. Dialkyl 2,6-diamino-4-arylfuro[2′,3′:4,5]benzo[b]furan-3,7-dicarboxylates from 2-aryl-1,4-benzoquinones and cyanoacetic esters (2002) Pol. J. Chem., pp. 1419-1424. , https://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-article-BUJ1-0021-0006, (Accessed 1 June 2017)
Carlson, B.W., Miller, L.L., Mechanism of the oxidation of NADH by quinones. energetics of one-electron and hydride routes (1985) J. Am. Chem. Soc., 107, pp. 479-485
Li, X.Y., He, B.F., Luo, H.J., Huang, N.Y., Deng, W.Q., 3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: a combined experimental and theoretical investigation (2013) Bioorg. Med. Chem. Lett., 23, pp. 4617-4621
Weinlich, R., Oberst, A., Beere, H.M., Green, D.R., Necroptosis in development, inflammation and disease (2017) Nat. Rev. Mol. Cell Biol., 18, pp. 127-136
McIlwain, D.R., Berger, T., Mak, T.W., Caspase functions in cell death and disease (2013) Cold Spring Harb. Perspect. Biol., 5, pp. 1-28
Incles, C.M., Schultes, C.M., Kempski, H., Koehler, H., Kelland, L.R., Neidle, S., A G-quadruplex telomere targeting agent produces p16-associated senescence and chromosomal fusions in human prostate cancer cells (2004) Mol. Cancer Ther., 3, pp. 1201-1206. , http://www.ncbi.nlm.nih.gov/pubmed/15486186, (Accessed 28 August 2018)
Khaw, A.K., Silasudjana, M., Banerjee, B., Suzuki, M., Baskar, R., Hande, M.P., Inhibition of telomerase activity and human telomerase reverse transcriptase gene expression by histone deacetylase inhibitor in human brain cancer cells (2007) Mutat. Res. Fundam. Mol. Mech. Mutagen., 625, pp. 134-144
Sherr, C.J., The pezcoller lecture: cancer cell cycles revisited (2000) Cancer Res., pp. 3689-3695. , http://www.ncbi.nlm.nih.gov/pubmed/10919634, (Accessed 24 May 2018)
De Boer, L., Oakes, V., Beamish, H., Giles, N., Stevens, F., Somodevilla-Torres, M., Desouza, C., Gabrielli, B., Cyclin A/cdk2 coordinates centrosomal and nuclear mitotic events (2008) Oncogene, 27, pp. 4261-4268
Tsai, Y.C., Qi, H., Lin, C.P., Lin, R.K., Kerrigan, J.E., Rzuczek, S.G., Lavoie, E.J., Liu, L.F., A G-quadruplex stabilizer induces M-phase cell cycle arrest (2009) J. Biol. Chem., 284, pp. 22535-22543
Zhou, G., Liu, X., Li, Y., Xu, S., Ma, C., Wu, X., Cheng, Y., Chen, Y., Telomere targeting with a novel G-quadruplex-interactive ligand BRACO-19 induces T-loop disassembly and telomerase displacement in human glioblastoma cells (2016) Oncotarget, 7, pp. 14925-14939
Hudson, J.S., Ding, L., Le, V., Lewis, E., Graves, D., Recognition and binding of human telomeric G-quadruplex DNA by unfolding protein 1 (2014) Biochemistry, 53, pp. 3347-3356
Ambrus, A., Chen, D., Dai, J., Bialis, T., Jones, R.A., Yang, D., Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution (2006) Nucleic Acids Res., 34, pp. 2723-2735
Fuggetta, M.P., De Mico, A., Cottarelli, A., Morelli, F., Zonfrillo, M., Ulgheri, F., Peluso, P., Spanu, P., Synthesis and enantiomeric separation of a novel spiroketal derivative: a potent human telomerase inhibitor with high in vitro anticancer activity (2016) J. Med. Chem., 59, pp. 9140-9149
Jain, A.K., Reddy, V.V., Paul, A., Muniyappa, K., Bhattacharya, S., Synthesis and evaluation of a novel class of G-quadruplex-stabilizing small molecules based on the 1,3-phenylene-bis(piperazinyl benzimidazole) system (2009) Biochemistry, 48, pp. 10693-10704
Mendez, M.A., Szalai, V.A., Fluorescence of unmodified oligonucleotides: a tool to probe G-quadruplex DNA structure (2009) Biopolymers, 91, pp. 841-850
Russo, A., Scognamiglio, P.L., Hong Enriquez, R.P., Santambrogio, C., Grandori, R., Marasco, D., Giordano, A., Fortuna, S., In silico generation of peptides by replica exchange Monte Carlo: docking-based optimization of maltose-binding-protein ligands (2015) PLoS One, 10
Gao, S., Cao, Y., Yan, Y., Xiang, X., Guo, X., Correlations between fluorescence emission and base stacks of nucleic acid G-quadruplexes (2016) RSC Adv., 6, pp. 94531-94538
Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
Four 4-nitrophenyl-functionalized benzofuran (BF1, BF2) and benzodifuran (BDF1,BDF2) compounds were synthesized by a convenient route based on the Craven reaction. All the compounds underwent a detailed chemical-physical characterization to evaluate their structural, thermal and optical properties. An investigation on the therapeutic potential of the reported compounds was performed by analysing their antiproliferative activity on prostatic tumour cells (PC-3). In both classes of compounds, anticancer potential is in direct correlation with the lipophilicity. From our study it emerged that antiproliferative activity was higher for benzofuran derivatives as compared to benzodifuran systems. Moreover, we report a mechanistic study relative to the most promising molecule, i.e. the apolar benzofuran BF1, that relates the antiproliferative properties found in our investigation to its ability to bind telomeric DNA (proven by CD and fluorescence techniques on tel22 G4 DNA), and highlights its unexpected impact on cell cycle
Four 4-nitrophenyl-functionalized benzofuran (BF1, BF2) and benzodifuran (BDF1,BDF2) compounds were synthesized by a convenient route based on the Craven reaction. All the compounds underwent a detailed chemical-physical characterization to evaluate their structural, thermal and optical properties. An investigation on the therapeutic potential of the reported compounds was performed by analysing their antiproliferative activity on prostatic tumour cells (PC-3). In both classes of compounds, anticancer potential is in direct correlation with the lipophilicity. From our study it emerged that antiproliferative activity was higher for benzofuran derivatives as compared to benzodifuran systems. Moreover, we report a mechanistic study relative to the most promising molecule, i.e. the apolar benzofuran BF1, that relates the antiproliferative properties found in our investigation to its ability to bind telomeric DNA (proven by CD and fluorescence techniques on tel22 G4 DNA), and highlights its unexpected impact on cell cycle
Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
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Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
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* A new biologically active molecular scaffold: crystal structure of 7-(3-hydroxyphenyl)-4-methyl-2H-[1, 2, 4]triazolo[3, 2-c][1, 2, 4]triazole and selective antiproliferative activity of three isomeric triazolo-triazoles (104 views)
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D'Amora A, Cucciolito M, E , Iannitti R, Morelli G, Palumbo R, Ruffo F, Tesauro D
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Faggiano A, Modica R, Severino R, Camera L, Fonti R, Del Prete M, Chiofalo MG, Aria M, Ferolla P, Vitale G, Pezzullo L, Colao A
* The antiproliferative effect of pasireotide LAR alone and in combination with everolimus in patients with medullary thyroid cancer: a single-center, open-label, phase II, proof-of-concept study (208 views)
Endocrine (ISSN: 1355-008xlinking), 2018 Oct; 62(1): 46-56.
Impact Factor: 3.179
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Petraglia F, Singh AA, Carafa V, Nebbioso A, Conte M, Scisciola L, Valente S, Baldi A, Mandoli A, Petrizzi VB, Ingenito C, De Falco S, Cicatiello V, Apicella I, Janssen-megens EM, Kim B, Yi G, Logie C, Heath S, Ruvo M, Wierenga ATJ, Flicek P, Yaspo ML, Della Valle V, Bernard O, Tomassi S, Novellino E, Feoli A, Sbardella G, Gut I, Vellenga E, Stunnenberg HG, Mai A, Martens JHA, Altucci L
* Combined HAT/EZH2 modulation leads to cancer-selective cell death (284 views)
Oncotarget (ISSN: 1949-2553electronic, 1949-2553linking), 2018 May 22; 9(39): 25630-25646.
Impact Factor: 5.008
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Riccardi C, Musumeci D, Capuozzo A, Irace C, King S, Russo Krauss I, Paduano L, Montesarchio D
* "dressing up" an Old Drug: An Aminoacyl Lipid for the Functionalization of Ru(III)-Based Anticancer Agents (197 views)
Acs Biomater Sci Eng (ISSN: 2373-9878), 2018; 4(1): 163-174.
Impact Factor: 0
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Bonaccorso C, Grasso G, Musso N, Barresi V, Condorelli DF, La Mendola D, Rizzarelli E
* Water soluble glucose derivative of thiocarbohydrazone acts as ionophore with cytotoxic effects on tumor cells (317 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 1873-3344electronic), 2018; 182: 92-102.
Impact Factor: 3.317
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Oliveri V, Lanza V, Milardi D, Viale M, Maric I, Sgarlata C, Vecchio G
* Amino- and chloro-8-hydroxyquinolines and their copper complexes as proteasome inhibitors and antiproliferative agents (462 views)
Metallomics (ISSN: 1756-5901, 1756-591x), 2017 Oct 18; 9(10): 1439-1446.
Impact Factor: 4.069
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Roviello GN, Iannitti R, Palumbo R, Simonyan H, Vicidomini C, Roviello V
* Lac-L-TTA, a novel lactose-based amino acid-sugar conjugate for anti-metastatic applications (337 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2017 May 06; 49(8): 1347-1353.
Impact Factor: 2.906
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Roviello GN, Iannitti R, Roviello V, Palumbo R, Simonyan H, Vicidomini C
* Synthesis and biological evaluation of a novel Amadori compound (406 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2017 Feb; 49(2): 327-335.
Impact Factor: 2.906
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Musumeci D, Roviello GN, Rigione G, Capasso D, Di Gaetano S, Riccardi C, Roviello V, Montesarchio D
* Benzodifuran derivatives as potential antiproliferative agents: possible correlation between the bioactivity and their aggregation properties (476 views)
Chempluschem, 2017; 82: 251-260.
Impact Factor: 2.8
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Accardo A, Del Zoppo L, Morelli G, Condorelli D, Barresi V, Musso N, Spampinato G, Bellia F, Tabbì G, Rizzarelli E
* Liposome antibody-ionophore conjugate antiproliferative activity increases by cellular metallostasis alteration (216 views)
Med Chem Comm, 2016 Sep; 7: 2364-2367.
Impact Factor: 2.319
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Soprano M, Sorriento D, Rusciano MR, Maione AS, Limite G, Forestieri P, D'Angelo D, D'Alessio M, Campiglia P, Formisano P, Iaccarino G, Bianco R, Illario M
* Oxidative Stress Mediates the Antiproliferative Effects of Nelfinavir in Breast Cancer Cells (249 views)
Plosone (ISSN: 1932-6203, 1932-6203electronic, 1932-6203linking), 2016 Jun 9; 11(6): e0155970-e0155970.
Impact Factor: 2.806
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Conson M, Cella L, Pacelli R
* Risk stratification in prostate cancer treated with radiation therapy: a window of opportunity for new clinical trials (226 views)
Translational Cancer Research, 2016; N/D: N/D-N/D.
Impact Factor: 1.2
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D'Avino V, Palma G, Liuzzi R, Conson M, Doria F, Salvatore M, Pacelli R, Cella L
* Prediction of gastrointestinal toxicity after external beam radiotherapy for localized prostate cancer (424 views)
Radiat Oncol (ISSN: 1748-717x), 2015 Apr 8; 10(1): 80-80.
Impact Factor: 2.466
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Carotenuto M, de Antonellis P, Chiarolla CM, Attanasio C, Damiani V, Boffa I, Aiese N, Pedone E, Accordi B, Basso G, Navas L, Imbimbo C, Zollo M
* A therapeutic approach to treat prostate cancer by targeting Nm23-H1/h-Prune interaction (326 views)
N-S Arch Pharmacol (ISSN: 0028-1298), 2015 Feb; 388(2): 257-269.
Impact Factor: 2.376
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Mügge C, Marzo T, Massai L, Hildebrandt J, Ferraro G, Rivera-Fuentes P, Metzler-Nolte N, Merlino A, Messori L, Weigand W
* Platinum(II) Complexes with O, S Bidentate Ligands: Biophysical Characterization, Antiproliferative Activity, and Crystallographic Evidence of Protein Binding (331 views)
Inorg Chem (ISSN: 0020-1669, 1520-510x, 0020-1669linking), 2015; 54(17): 8560-8570.
Impact Factor: 4.82
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Ringhieri P, Iannitti R, Nardon C, Palumbo R, Fregona D, Morelli G, Accardo A
* Target selective micelles for bombesin receptors incorporating Au(III)-dithiocarbamato complexes (443 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2014 Oct 1; 473(1-2): 194-202.
Impact Factor: 3.65
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Capasso D, De Paola I, Liguoro A, Del Gatto A, Di Gaetano S, Guarnieri D, Saviano M, Zaccaro L
* Rgdechi-Hcit: Alpha V Beta 3 Selective Pro-Apoptotic Peptide As Potential Carrier For Drug Delivery Into Melanoma Metastatic Cells (454 views)
Plosone (ISSN: 1932-6203, 1932-6203electronic, 1932-6203linking), 2014 Sep 23; 9(9): e106441-e106441.
Impact Factor: 3.234
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Rai M, Kon K, Ingle A, Duran N, Galdiero S, Galdiero M
* Broad-spectrum bioactivities of silver nanoparticles: the emerging trends and future prospects (727 views)
Appl Microbiol Biot (ISSN: 0175-7598), 2014 Mar; 98(5): 1951-1961.
Impact Factor: 3.337
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Cella L, D'Avino V, Liuzzi R, Conson M, Doria F, Faiella A, Loffredo F, Salvatore M, Pacelli R
* Multivariate normal tissue complication probability modeling of gastrointestinal toxicity after external beam radiotherapy for localized prostate cancer (389 views)
Radiation Oncology (ISSN: 1748-717x), 2013 Sep 23; 8(1): 221-221.
Impact Factor: 2.36
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Roviello GN, Roviello V, Musumeci D, Pedone C
* Synthesis of a novel benzodifuran derivative and its molecular recognition of poly rA RNA (362 views)
Biol Chem Biological Chemistry (ISSN: 1437-4315, 1431-6730), 2013 Sep; 394(9): 1235-1239.
Impact Factor: 2.689
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Nande R, Greco A, Gossman MS, Lopez JP, Claudio L, Salvatore M, Brunetti A, Denvir J, Howard CM, Claudio PP
* Microbubble-assisted p53, RB, and p130 gene transfer in combination with radiation therapy in prostate cancer (457 views)
Current Gene Therapy (ISSN: 1875-5631, 1566-5232), 2013 Jun 1; 13(3): 163-174.
Impact Factor: 4.906
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Storto G, Gallicchio R, Pellegrino T, Nardelli A, Capacchione D, Sirignano C, Pace L
* Impact of F-18-fluoride PET-CT on implementing early treatment of painful bone metastases with Sm-153 EDTMP (346 views) (PDF 10 views)
Nucl Med Biol (ISSN: 0969-8051, 0883-2897, 0969-8051linking), 2013 May; 40(4): 518-523.
Impact Factor: 2.408
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Bera S, De Rosa V, Rachidi W, Diamond AM
* Does a role for selenium in DNA damage repair explain apparent controversies in its use in chemoprevention? (594 views)
Mutagenesismutagenesis (ISSN: 0267-8357, 1464-3804electronic, 0267-8357linking), 2013 Mar; 28(2): 127-134.
Impact Factor: 3.497
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Tedesco I, Russo M, Bilotto S, Spagnuolo C, Scognamiglio A, Palumbo R, Nappo A, Iacomino G, Moio L, Russo GL
* Dealcoholated red wine induces autophagic and apoptotic cell death in an osteosarcoma cell line (493 views)
Food Chem Toxicol (ISSN: 0278-6915), 2013; 60: 377-384.
Impact Factor: 2.61
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Carotenuto A, Cipolletta E, Gomez-Monterrey I, Sala M, Vernieri E, Limatola A, Bertamino A, Musella S, Sorriento D, Grieco P, Trimarco B, Novellino E, Iaccarino G, Campiglia P
* Design, synthesis and efficacy of novel G protein-coupled receptor kinase 2 inhibitors (526 views)
Eur J Med Chem (ISSN: 0223-5234, 1768-3254, 1768-3254electronic), 2013; 69: 384-392.
Impact Factor: 3.432
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Accardo A, Mansi R, Salzano G, Morisco A, Aurilio M, Parisi A, Maione F, Cicala C, Ziaco B, Tesauro D, Aloj L, De Rosa G, Morelli G
* Bombesin peptide antagonist for target-selective delivery of liposomal doxorubicin on cancer cells (410 views)
Journal Of Drug Targeting (ISSN: 1061-186x), 2012 Nov 21; 21(3): 240-249.
Impact Factor: 2.768
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De Rosa V, Erkekoǧlu P, Forestier A, Favier A, Hincal F, Diamond AM, Douki T, Rachidi W
* Low doses of selenium specifically stimulate the repair of oxidative DNA damage in LNCaP prostate cancer cells (490 views)
Free Radic Res Free Radical Research (ISSN: 1071-5762), 2012; 46(2): 105-115.
Impact Factor: 3.279
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Accardo A, Salsano G, Morisco A, Aurilio M, Parisi A, Maione F, Cicala C, Tesauro D, Aloj L, De Rosa G, Morelli G
* Peptide-modified liposomes for selective targeting of bombesin receptors overexpressed by cancer cells: A potential theranostic agent (381 views)
Int J Nanomed (ISSN: 1176-9114, 1178-2013, 1178-2013electronic), 2012; 7: 2007-2017.
Impact Factor: 3.463
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Cuocolo A
Current research in nuclear medicine and molecular imaging in Italy: Highlights of the 10th National Congress of the Italian Association of Nuclear Medicine and Molecular Imaging (462 views)
Q J Nucl Med Mol Im (ISSN: 1824-4785, 1824-4478, 1824-4785linking), 2011 Jun; 55(3): 280-300.
Impact Factor: 1.724
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Vergara A, Merlino A, Pizzo E, D'Alessio G, Mazzarella L
* A novel method for detection of selenomethionine incorporation in protein crystals via Raman microscopy (389 views)
Acta Crystallogr D Biol Crystallogr (ISSN: 0907-4449, 0907-4449linking), 2008 Feb; 64: 167-171.
Impact Factor: 2.943
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Messere A, Fabbri E, Borgatti M, Gambari R, Di Blasio B, Pedone C, Romanelli A
* Antiproliferative activity of Pt(II) and Pd(II) phosphine complexes with thymine and thymidine (308 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2007 Feb; 101(2): 254-260.
Impact Factor: 3.663
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D'Andrea LD, Del Gatto A, Pedone C, Benedetti E
* Peptide-based molecules in angiogenesis (827 views)
Chem Biol Drug Des (ISSN: 1747-0277, 1747-0285, 1747-0277linking), 2006 Feb; 67(2): 115-126.
Impact Factor: 2.507
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Russo M, Tedesco I, Iacomino G, Palumbo R, Galano G, Russo GL
* Dietary phytochemicals in chemoprevention of cancer (348 views)
Curr Med Chem (ISSN: 1568-0134), 2005; 5(1): 61-72.
Impact Factor: 3.715
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Cella L, Lomax A, Miralbell R
* New techniques in hadrontherapy: Intensity modulated proton beams (274 views)
Phys Med (ISSN: 1120-1797, 1120-1797linking), 2001; 17(SUPPL.1): 100-102.
Impact Factor: 0.556
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Cella L, Lomax A, Miralbell R
* Potential role of intensity modulated proton beams in prostate cancer radiotherapy (323 views)
Int J Radiat Oncol (ISSN: 0360-3016, 1879-355x, 1879-355xelectronic), 2001; 49(1): 217-223.
Impact Factor: 3.327
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47 Records (45 excluding Abstracts).
Total impact factor: 140.304 (134.662 excluding Abstracts).
Total 5 year impact factor: 123.364 (117.204 excluding Abstracts).
Total impact factor: 140.304 (134.662 excluding Abstracts).
Total 5 year impact factor: 123.364 (117.204 excluding Abstracts).
397 views. Last view on Tuesday 14 March 2023, 6:27:03
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