Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities(397 views) Carella A, Roviello V, Iannitti R, Palumbo R, La Manna S, Marasco D, Trifuoggi M, Diana R, Roviello GN
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
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
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
Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
No results.
Evaluating the biological properties of synthetic 4-nitrophenyl functionalized benzofuran derivatives with telomeric DNA binding and antiproliferative activities
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 ViewExport to BibTeXExport to EndNote