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.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.317, 5-year impact factor: 3.386
Url: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85041802059&doi=10.1016%2fj.jinorgbio.2018.01.019&partnerID=40&md5=9da557283d09a48777fe7a8267f3e3d7
Keywords: Cancer, Copper, Glycoconjugates, Ionophores, Thiocarbohidrazones, Zinc, 1 Amino 3 [1 (2 Pyridyl)ethylideneamino]thiourea, 1 [1 (2 Pyridyl)ethylideneamino] 3 [[3, 5 Trihydroxy 6 (hydroxymethyl)tetrahydropyran 2 Yl]amino]thiourea, Copper Complex, Cytotoxic Agent, Fluorouracil, Glucose Derivative, Hydrazone Derivative, Unclassified Drug, Zinc Complex, Antiproliferative Activity, Article, Cancer Cell Line, Carbon Nuclear Magnetic Resonance, Cell Survival, Circular Dichroism, Column Chromatography, Cytotoxicity Assay, Density Functional Theory, Drug Cytotoxicity, Electrospray Mass Spectrometry, Human, Human Cell, Mda-Mb-231 Cell Line, Nctc 2544 Cell Line, Nuclear Overhauser Effect, Prostate Adenocarcinoma Cell Line, Proton Nuclear Magnetic Resonance, Stoichiometry, Ultraviolet Spectroscopy, Ultraviolet Visible Spectroscopy,
Affiliations:
*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale A. Doria 6, Catania, 95125, Italy
Consorzio Interuniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici, via Celso Ulpiani, 27, Bari, 70125, Italy
Consiglio Nazionale delle Ricerche, Istituto di Biostrutture e Bioimmagini (IBB-CNR), Via P. Gaifami 18, Catania, 95126, Italy
Dipartimento Scienze Biomediche e Biotecnologiche, Sez. Biochimica Medica, via S. Sofia 64, Catania, I-95125, Italy
Dipartimento di Farmacia, Università di Pisa, Via Bonanno Pisano 6, Pisa, 56126, Italy
References:
Rosenberg, B., VanCamp, L., (1970) Cancer Res., 30, pp. 1799-180
Dilruba, S., Kalayda, G.V., (2016) Cancer Chemother. Pharmacol., 77, pp. 1103-1124
Palermo, G., Magistrato, A., Riedel, T., von Erlach, T., Davey, C.A., Dyson, P.J., Rothlisberger, U., (2016) ChemMedChem, 11, pp. 1199-1210
Cisnetti, F., Gautier, A., (2013) Angew. Chem. Int. Ed., 52, pp. 11976-11978
Schmitt, S.M., Frezza, M., Dou, Q.P., (2012) Front. Biosci. (Schol. Ed.), 4, pp. 375-391. , http://www.ncbi.nlm.nih.gov/pubmed/22202066, (Accessed 9 November 2016)
Ndagi, U., Mhlongo, N., Soliman, M., (2017) Drug Des. Devel. Ther., 11, pp. 599-616
Khan, R.A., de Almeida, A., Al-Farhan, K., Alsalme, A., Casini, A., Ghazzali, M., Reedijk, J., (2016) J. Inorg. Biochem., 165, pp. 128-135
Wilson, J.T., Jiang, X., McGill, B.C., Lisic, E.C., Deweese, J.E., (2016) Chem. Res. Toxicol., 29, pp. 649-658
Akladios, F.N., Andrew, S.D., Parkinson, C.J., (2016) Biometals, 29, pp. 157-170
Patil, V., Sodji, Q.H., Kornacki, J.R., Mrksich, M., Oyelere, A.K., (2013) J. Med. Chem., 56, pp. 3492-3506
Yu, H., Zhou, Y., Lind, S.E., Ding, W.-Q., (2009) Biochem. J., 417, pp. 133-139
Marzano, C., Pellei, M., Tisato, F., Santini, C., (2009) Anti Cancer Agents Med. Chem., 9, pp. 185-211
Murakami, M., Hirano, T., (2008) Cancer Sci., 99, pp. 1515-1522
Alam, S., Kelleher, S.L., (2012) Nutrients, 4, pp. 875-903
Yaman, M., (2006) Curr. Med. Chem., 13, pp. 2513-2525
Franklin, R.B., Feng, P., Milon, B., Desouki, M.M., Singh, K.K., Kajdacsy-Balla, A., Bagasra, O., Costello, L.C., (2005) Mol. Cancer, 4, p. 32
Prasad, A.S., Kucuk, O., (2002) Cancer Metastasis Rev., 21, pp. 291-295
La Mendola, D., Giacomelli, C., Rizzarelli, E., (2016) Curr. Top. Med. Chem., 16, pp. 3103-3130
Ding, W.-Q., Lind, S.E., (2009) IUBMB Life, 61, pp. 1013-1018
Ishida, S., Andreux, P., Poitry-Yamate, C., Auwerx, J., Hanahan, D., (2013) Proc. Natl. Acad. Sci. U. S. A., 110, pp. 19507-19512
Crowe, A., Jackaman, C., Beddoes, K.M., Ricciardo, B., Nelson, D.J., (2013) PLoS One, 8
Pan, Q., Rosenthal, D.T., Bao, L., Kleer, C.G., Merajver, S.D., (2009) Clin. Cancer Res., 15, pp. 7441-7446
Pan, Q., Kleer, C.G., van Golen, K.L., Irani, J., Bottema, K.M., Bias, C., De Carvalho, M., Merajver, S.D., (2002) Cancer Res., 62, pp. 4854-4859. , http://cancerres.aacrjournals.org/content/62/17/4854.long, (Accessed 30 July 2017)
Donadelli, M., Dalla Pozza, E., Scupoli, M.T., Costanzo, C., Scarpa, A., Palmieri, M., (2009) Biochim. Biophys. Acta, Mol. Cell Res., 1793, pp. 273-280
Cen, D., Brayton, D., Shahandeh, B., Meyskens, F.L., Farmer, P.J., (2004) J. Med. Chem., 47, pp. 6914-6920
Merlot, A.M., Kalinowski, D.S., Richardson, D.R., (2013) Antioxid. Redox Signal., 18, pp. 973-1006
Mckenzie-Nickson, S., Bush, A.I., Barnham, K.J., (2016) Curr. Top. Med. Chem., 16, pp. 3058-3068
Kalinowski, D.S., Quach, P., Richardson, D.R., (2009) Future Med. Chem., 1, pp. 1143-1151
Zhu, L., Zhou, B., Chen, X., Jiang, H., Shao, J., Yen, Y., (2009) Biochem. Pharmacol., 78, pp. 1178-1185
Stacy, A.E., Palanimuthu, D., Bernhardt, P.V., Kalinowski, D.S., Jansson, P.J., Richardson, D.R., (2016) J. Med. Chem., 59, pp. 4965-4984
Guo, Z.-L., Richardson, D.R., Kalinowski, D.S., Kovacevic, Z., Tan-Un, K.C., Chan, G.C.-F., (2016) J. Hematol. Oncol., 9
Enyedy, É.A., Nagy, N.V., Zsigó, É., Kowol, C.R., Arion, V.B., Keppler, B.K., Kiss, T., (2010) Eur. J. Inorg. Chem., 2010, pp. 1717-1728
Park, K.C., Fouani, L., Jansson, P.J., Wooi, D., Sahni, S., Lane, D.J.R., Palanimuthu, D., Richardson, D.R., (2016) Metallomics, 8, pp. 874-886
Denoyer, D., Masaldan, S., La Fontaine, S., Cater, M.A., (2015) Metallomics, 7, pp. 1459-1476
Tan, C.-P., Lu, Y.-Y., Ji, L.-N., Mao, Z.-W., (2014) Metallomics, 6, p. 978
Jungwirth, U., Kowol, C.R., Keppler, B.K., Hartinger, C.G., Berger, W., Heffeter, P., (2011) Antioxid. Redox Signal., 15, pp. 1085-1127
Serda, M., Kalinowski, D.S., Rasko, N., Potůčková, E., Mrozek-Wilczkiewicz, A., Musiol, R., Małecki, J.G., Polanski, J., (2014) PLoS One, 9
Lovejoy, D.B., Sharp, D.M., Seebacher, N., Obeidy, P., Prichard, T., Stefani, C., Basha, M.T., Richardson, D.R., (2012) J. Med. Chem., 55, pp. 7230-7244
Grguric-Sipka, S., Kowol, C.R., Valiahdi, S.-M., Eichinger, R., Jakupec, M.A., Roller, A., Shova, S., Keppler, B.K., (2007) Eur. J. Inorg. Chem., 2007, pp. 2870-2878
Odenike, O.M., Larson, R.A., Gajria, D., Dolan, M.E., Delaney, S.M., Karrison, T.G., Ratain, M.J., Stock, W., (2008) Investig. New Drugs, 26, pp. 233-239
Ibrahim, A.A., Khaledi, H., Ali, H.M., (2014) Polyhedron, 81, pp. 457-464
Tandon, S.S., Dul, M.-C., Lee, J.L., Dawe, L.N., Anwar, M.U., Thompson, L.K., (2011) Dalton Trans., 40, pp. 3466-3475
Dragancea, D., Addison, A.W., Zeller, M., Foster, M.E., Prushan, M.J., Thompson, L.K., Revenco, M.D., Hunter, A.D., (2010) Inorg. Chim. Acta, 363, pp. 2065-2070
Moubaraki, B., Murray, K.S., Ranford, J.D., Vittal, J.J., Wang, X., Xu, Y., (1999) J. Chem. Soc. Dalton Trans., 33, pp. 3573-3578
Soares, M.A., Lessa, J.A., Mendes, I.C., Da Silva, J.G., dos Santos, R.G., Salum, L.B., Daghestani, H., Beraldo, H., (2012) Bioorg. Med. Chem., 20, pp. 3396-3409
Lovejoy, D.B., Jansson, P.J., Brunk, U.T., Wong, J., Ponka, P., Richardson, D.R., (2011) Cancer Res., 71, pp. 5871-5880
Pastuch-Gawołek, G., Malarz, K., Mrozek-Wilczkiewicz, A., Musioł, M., Serda, M., Czaplinska, B., Musiol, R., (2016) Eur. J. Med. Chem., 112, pp. 130-144
Upadhyay, M., Samal, J., Kandpal, M., Singh, O.V., Vivekanandan, P., (2013) Pharmacol. Ther., 137, pp. 318-330
Vander Heiden, M.G., Cantley, L.C., Thompson, C.B., (2009) Science (80-.), 324, pp. 1029-1033
Mineo, P., Vitalini, D., La Mendola, D., Rizzarelli, E., Scamporrino, E., Vecchio, G., (2004) J. Inorg. Biochem., 98, pp. 254-265
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., Gaussian 09, Revis. B.01, Gaussian, Inc., Wallingford CT. (2009)
Becke, A.D., (1993) J. Chem. Phys., 98, pp. 5648-5652
Frisch, M.J., Pople, J.A., Binkley, J.S., (1984) J. Chem. Phys., 80, pp. 3265-3269
Accardo, A., Del Zoppo, L., Morelli, G., Condorelli, D.F., Barresi, V., Musso, N., Spampinato, G., Rizzarelli, E., (2016) Med. Chem. Commun., 7, pp. 2364-2367
Barresi, V., Trovato-Salinaro, A., Spampinato, G., Musso, N., Castorina, S., Rizzarelli, E., Condorelli, D.F., (2016) FEBS Open Bio., 6, pp. 794-806
Scherf, U., Ross, D.T., Waltham, M., Smith, L.H., Lee, J.K., Tanabe, L., Kohn, K.W., Weinstein, J.N., (2000) Nat. Genet., 24, pp. 236-244
Blumenkopf, T.A., Harrington, J.A., Koble, C.S., Bankston, D.D., Morrison, R.W., Bigham, E.C., Styles, V.L., Spector, T., (1992) J. Med. Chem., 35, pp. 2306-2314
Bubb, W.A., (2003) Concepts Magn. Reson., 19A, pp. 1-19
Zhang, Q., Ames, J.M., Smith, R.D., Baynes, J.W., Metz, T.O., (2009) J. Proteome Res., 8, pp. 754-769
Ames, J.M., BROWNING | Nonenzymatic (2003) Encycl. Food Sci. Nutr., pp. 665-672. , Elsevier
Turner, J.J., Wilschut, N., Overkleeft, H.S., Klaffke, W., van der Marel, G.A., van Boom, J.H., (1999) Tetrahedron Lett., 40, pp. 7039-7042
Holland, J.P., Aigbirhio, F.I., Betts, H.M., Bonnitcha, P.D., Burke, P., Christlieb, M., Churchill, G.C., Warren, J.E., (2007) Inorg. Chem., 46, pp. 465-485
Mosmann, T., (1983) J. Immunol. Methods, 65
Lozano-Pérez, A.A., Gil, A.L., Pérez, S.A., Cutillas, N., Meyer, H., Pedreño, M., Aznar-Cervantes, S.D., Ruiz, J., (2015) Dalton Trans., 44, pp. 13513-13521
Mohindru, A., Fisher, J.M., Rabinovitz, M., (1983) Nature, 303, pp. 64-65
Huang, X., Atwood, C.S., Moir, R.D., Hartshorn, M.A., Tanzi, R.E., Bush, A.I., (2004) JBIC, J. Biol. Inorg. Chem., 9, pp. 954-960
J Chem Res (ISSN: 0162-0134, 1873-3344, 1873-3344electronic), 2018; 182: 92-102.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.317, 5-year impact factor: 3.386
Url: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85041802059&doi=10.1016%2fj.jinorgbio.2018.01.019&partnerID=40&md5=9da557283d09a48777fe7a8267f3e3d7
Keywords: Cancer, Copper, Glycoconjugates, Ionophores, Thiocarbohidrazones, Zinc, 1 Amino 3 [1 (2 Pyridyl)ethylideneamino]thiourea, 1 [1 (2 Pyridyl)ethylideneamino] 3 [[3, 5 Trihydroxy 6 (hydroxymethyl)tetrahydropyran 2 Yl]amino]thiourea, Copper Complex, Cytotoxic Agent, Fluorouracil, Glucose Derivative, Hydrazone Derivative, Unclassified Drug, Zinc Complex, Antiproliferative Activity, Article, Cancer Cell Line, Carbon Nuclear Magnetic Resonance, Cell Survival, Circular Dichroism, Column Chromatography, Cytotoxicity Assay, Density Functional Theory, Drug Cytotoxicity, Electrospray Mass Spectrometry, Human, Human Cell, Mda-Mb-231 Cell Line, Nctc 2544 Cell Line, Nuclear Overhauser Effect, Prostate Adenocarcinoma Cell Line, Proton Nuclear Magnetic Resonance, Stoichiometry, Ultraviolet Spectroscopy, Ultraviolet Visible Spectroscopy,
Affiliations:
*** IBB - CNR ***
Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale A. Doria 6, Catania, 95125, Italy
Consorzio Interuniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici, via Celso Ulpiani, 27, Bari, 70125, Italy
Consiglio Nazionale delle Ricerche, Istituto di Biostrutture e Bioimmagini (IBB-CNR), Via P. Gaifami 18, Catania, 95126, Italy
Dipartimento Scienze Biomediche e Biotecnologiche, Sez. Biochimica Medica, via S. Sofia 64, Catania, I-95125, Italy
Dipartimento di Farmacia, Università di Pisa, Via Bonanno Pisano 6, Pisa, 56126, Italy
References:
Rosenberg, B., VanCamp, L., (1970) Cancer Res., 30, pp. 1799-180
Dilruba, S., Kalayda, G.V., (2016) Cancer Chemother. Pharmacol., 77, pp. 1103-1124
Palermo, G., Magistrato, A., Riedel, T., von Erlach, T., Davey, C.A., Dyson, P.J., Rothlisberger, U., (2016) ChemMedChem, 11, pp. 1199-1210
Cisnetti, F., Gautier, A., (2013) Angew. Chem. Int. Ed., 52, pp. 11976-11978
Schmitt, S.M., Frezza, M., Dou, Q.P., (2012) Front. Biosci. (Schol. Ed.), 4, pp. 375-391. , http://www.ncbi.nlm.nih.gov/pubmed/22202066, (Accessed 9 November 2016)
Ndagi, U., Mhlongo, N., Soliman, M., (2017) Drug Des. Devel. Ther., 11, pp. 599-616
Khan, R.A., de Almeida, A., Al-Farhan, K., Alsalme, A., Casini, A., Ghazzali, M., Reedijk, J., (2016) J. Inorg. Biochem., 165, pp. 128-135
Wilson, J.T., Jiang, X., McGill, B.C., Lisic, E.C., Deweese, J.E., (2016) Chem. Res. Toxicol., 29, pp. 649-658
Akladios, F.N., Andrew, S.D., Parkinson, C.J., (2016) Biometals, 29, pp. 157-170
Patil, V., Sodji, Q.H., Kornacki, J.R., Mrksich, M., Oyelere, A.K., (2013) J. Med. Chem., 56, pp. 3492-3506
Yu, H., Zhou, Y., Lind, S.E., Ding, W.-Q., (2009) Biochem. J., 417, pp. 133-139
Marzano, C., Pellei, M., Tisato, F., Santini, C., (2009) Anti Cancer Agents Med. Chem., 9, pp. 185-211
Murakami, M., Hirano, T., (2008) Cancer Sci., 99, pp. 1515-1522
Alam, S., Kelleher, S.L., (2012) Nutrients, 4, pp. 875-903
Yaman, M., (2006) Curr. Med. Chem., 13, pp. 2513-2525
Franklin, R.B., Feng, P., Milon, B., Desouki, M.M., Singh, K.K., Kajdacsy-Balla, A., Bagasra, O., Costello, L.C., (2005) Mol. Cancer, 4, p. 32
Prasad, A.S., Kucuk, O., (2002) Cancer Metastasis Rev., 21, pp. 291-295
La Mendola, D., Giacomelli, C., Rizzarelli, E., (2016) Curr. Top. Med. Chem., 16, pp. 3103-3130
Ding, W.-Q., Lind, S.E., (2009) IUBMB Life, 61, pp. 1013-1018
Ishida, S., Andreux, P., Poitry-Yamate, C., Auwerx, J., Hanahan, D., (2013) Proc. Natl. Acad. Sci. U. S. A., 110, pp. 19507-19512
Crowe, A., Jackaman, C., Beddoes, K.M., Ricciardo, B., Nelson, D.J., (2013) PLoS One, 8
Pan, Q., Rosenthal, D.T., Bao, L., Kleer, C.G., Merajver, S.D., (2009) Clin. Cancer Res., 15, pp. 7441-7446
Pan, Q., Kleer, C.G., van Golen, K.L., Irani, J., Bottema, K.M., Bias, C., De Carvalho, M., Merajver, S.D., (2002) Cancer Res., 62, pp. 4854-4859. , http://cancerres.aacrjournals.org/content/62/17/4854.long, (Accessed 30 July 2017)
Donadelli, M., Dalla Pozza, E., Scupoli, M.T., Costanzo, C., Scarpa, A., Palmieri, M., (2009) Biochim. Biophys. Acta, Mol. Cell Res., 1793, pp. 273-280
Cen, D., Brayton, D., Shahandeh, B., Meyskens, F.L., Farmer, P.J., (2004) J. Med. Chem., 47, pp. 6914-6920
Merlot, A.M., Kalinowski, D.S., Richardson, D.R., (2013) Antioxid. Redox Signal., 18, pp. 973-1006
Mckenzie-Nickson, S., Bush, A.I., Barnham, K.J., (2016) Curr. Top. Med. Chem., 16, pp. 3058-3068
Kalinowski, D.S., Quach, P., Richardson, D.R., (2009) Future Med. Chem., 1, pp. 1143-1151
Zhu, L., Zhou, B., Chen, X., Jiang, H., Shao, J., Yen, Y., (2009) Biochem. Pharmacol., 78, pp. 1178-1185
Stacy, A.E., Palanimuthu, D., Bernhardt, P.V., Kalinowski, D.S., Jansson, P.J., Richardson, D.R., (2016) J. Med. Chem., 59, pp. 4965-4984
Guo, Z.-L., Richardson, D.R., Kalinowski, D.S., Kovacevic, Z., Tan-Un, K.C., Chan, G.C.-F., (2016) J. Hematol. Oncol., 9
Enyedy, É.A., Nagy, N.V., Zsigó, É., Kowol, C.R., Arion, V.B., Keppler, B.K., Kiss, T., (2010) Eur. J. Inorg. Chem., 2010, pp. 1717-1728
Park, K.C., Fouani, L., Jansson, P.J., Wooi, D., Sahni, S., Lane, D.J.R., Palanimuthu, D., Richardson, D.R., (2016) Metallomics, 8, pp. 874-886
Denoyer, D., Masaldan, S., La Fontaine, S., Cater, M.A., (2015) Metallomics, 7, pp. 1459-1476
Tan, C.-P., Lu, Y.-Y., Ji, L.-N., Mao, Z.-W., (2014) Metallomics, 6, p. 978
Jungwirth, U., Kowol, C.R., Keppler, B.K., Hartinger, C.G., Berger, W., Heffeter, P., (2011) Antioxid. Redox Signal., 15, pp. 1085-1127
Serda, M., Kalinowski, D.S., Rasko, N., Potůčková, E., Mrozek-Wilczkiewicz, A., Musiol, R., Małecki, J.G., Polanski, J., (2014) PLoS One, 9
Lovejoy, D.B., Sharp, D.M., Seebacher, N., Obeidy, P., Prichard, T., Stefani, C., Basha, M.T., Richardson, D.R., (2012) J. Med. Chem., 55, pp. 7230-7244
Grguric-Sipka, S., Kowol, C.R., Valiahdi, S.-M., Eichinger, R., Jakupec, M.A., Roller, A., Shova, S., Keppler, B.K., (2007) Eur. J. Inorg. Chem., 2007, pp. 2870-2878
Odenike, O.M., Larson, R.A., Gajria, D., Dolan, M.E., Delaney, S.M., Karrison, T.G., Ratain, M.J., Stock, W., (2008) Investig. New Drugs, 26, pp. 233-239
Ibrahim, A.A., Khaledi, H., Ali, H.M., (2014) Polyhedron, 81, pp. 457-464
Tandon, S.S., Dul, M.-C., Lee, J.L., Dawe, L.N., Anwar, M.U., Thompson, L.K., (2011) Dalton Trans., 40, pp. 3466-3475
Dragancea, D., Addison, A.W., Zeller, M., Foster, M.E., Prushan, M.J., Thompson, L.K., Revenco, M.D., Hunter, A.D., (2010) Inorg. Chim. Acta, 363, pp. 2065-2070
Moubaraki, B., Murray, K.S., Ranford, J.D., Vittal, J.J., Wang, X., Xu, Y., (1999) J. Chem. Soc. Dalton Trans., 33, pp. 3573-3578
Soares, M.A., Lessa, J.A., Mendes, I.C., Da Silva, J.G., dos Santos, R.G., Salum, L.B., Daghestani, H., Beraldo, H., (2012) Bioorg. Med. Chem., 20, pp. 3396-3409
Lovejoy, D.B., Jansson, P.J., Brunk, U.T., Wong, J., Ponka, P., Richardson, D.R., (2011) Cancer Res., 71, pp. 5871-5880
Pastuch-Gawołek, G., Malarz, K., Mrozek-Wilczkiewicz, A., Musioł, M., Serda, M., Czaplinska, B., Musiol, R., (2016) Eur. J. Med. Chem., 112, pp. 130-144
Upadhyay, M., Samal, J., Kandpal, M., Singh, O.V., Vivekanandan, P., (2013) Pharmacol. Ther., 137, pp. 318-330
Vander Heiden, M.G., Cantley, L.C., Thompson, C.B., (2009) Science (80-.), 324, pp. 1029-1033
Mineo, P., Vitalini, D., La Mendola, D., Rizzarelli, E., Scamporrino, E., Vecchio, G., (2004) J. Inorg. Biochem., 98, pp. 254-265
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., Gaussian 09, Revis. B.01, Gaussian, Inc., Wallingford CT. (2009)
Becke, A.D., (1993) J. Chem. Phys., 98, pp. 5648-5652
Frisch, M.J., Pople, J.A., Binkley, J.S., (1984) J. Chem. Phys., 80, pp. 3265-3269
Accardo, A., Del Zoppo, L., Morelli, G., Condorelli, D.F., Barresi, V., Musso, N., Spampinato, G., Rizzarelli, E., (2016) Med. Chem. Commun., 7, pp. 2364-2367
Barresi, V., Trovato-Salinaro, A., Spampinato, G., Musso, N., Castorina, S., Rizzarelli, E., Condorelli, D.F., (2016) FEBS Open Bio., 6, pp. 794-806
Scherf, U., Ross, D.T., Waltham, M., Smith, L.H., Lee, J.K., Tanabe, L., Kohn, K.W., Weinstein, J.N., (2000) Nat. Genet., 24, pp. 236-244
Blumenkopf, T.A., Harrington, J.A., Koble, C.S., Bankston, D.D., Morrison, R.W., Bigham, E.C., Styles, V.L., Spector, T., (1992) J. Med. Chem., 35, pp. 2306-2314
Bubb, W.A., (2003) Concepts Magn. Reson., 19A, pp. 1-19
Zhang, Q., Ames, J.M., Smith, R.D., Baynes, J.W., Metz, T.O., (2009) J. Proteome Res., 8, pp. 754-769
Ames, J.M., BROWNING | Nonenzymatic (2003) Encycl. Food Sci. Nutr., pp. 665-672. , Elsevier
Turner, J.J., Wilschut, N., Overkleeft, H.S., Klaffke, W., van der Marel, G.A., van Boom, J.H., (1999) Tetrahedron Lett., 40, pp. 7039-7042
Holland, J.P., Aigbirhio, F.I., Betts, H.M., Bonnitcha, P.D., Burke, P., Christlieb, M., Churchill, G.C., Warren, J.E., (2007) Inorg. Chem., 46, pp. 465-485
Mosmann, T., (1983) J. Immunol. Methods, 65
Lozano-Pérez, A.A., Gil, A.L., Pérez, S.A., Cutillas, N., Meyer, H., Pedreño, M., Aznar-Cervantes, S.D., Ruiz, J., (2015) Dalton Trans., 44, pp. 13513-13521
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Water soluble glucose derivative of thiocarbohydrazone acts as ionophore with cytotoxic effects on tumor cells
A novel water-soluble ionophore based on the thiocarbohydrazone moiety conjugated with glucose (GluTch) was synthesized through a simple two-step procedure. Structural elucidation was carried out in water solution by means of various spectroscopic techniques (NMR, UV–Vis, and CD), electrospray ionization mass spectrometry and density functional theory calculations. The flexible nature of the thiocarbohydrazone moiety of the new glycoderivative compound induced both different coordination motifs and stoichiometry towards copper and zinc. Cytotoxicity assays of the ligands on the human normal keratinocyte NCTC-2544, MDA-MB-231 breast cancer and PC-3 human prostate adenocarcinoma cell lines demonstrated that i) higher activity on cancer cells growth inhibition compared to a normal cell line; ii) the introduction of the glucose unit does not alter the cytotoxic activity of the underivatized ionophore ligand and iii) the presence of copper ion improves the activity of the thiocarbohydrazones. © 2018 Elsevier Inc.
A novel water-soluble ionophore based on the thiocarbohydrazone moiety conjugated with glucose (GluTch) was synthesized through a simple two-step procedure. Structural elucidation was carried out in water solution by means of various spectroscopic techniques (NMR, UV–Vis, and CD), electrospray ionization mass spectrometry and density functional theory calculations. The flexible nature of the thiocarbohydrazone moiety of the new glycoderivative compound induced both different coordination motifs and stoichiometry towards copper and zinc. Cytotoxicity assays of the ligands on the human normal keratinocyte NCTC-2544, MDA-MB-231 breast cancer and PC-3 human prostate adenocarcinoma cell lines demonstrated that i) higher activity on cancer cells growth inhibition compared to a normal cell line; ii) the introduction of the glucose unit does not alter the cytotoxic activity of the underivatized ionophore ligand and iii) the presence of copper ion improves the activity of the thiocarbohydrazones. © 2018 Elsevier Inc.
Water soluble glucose derivative of thiocarbohydrazone acts as ionophore with cytotoxic effects on tumor cells
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Water soluble glucose derivative of thiocarbohydrazone acts as ionophore with cytotoxic effects on tumor cells
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Barresi V, Spampinato G, Musso N, Trovato Salinaro A, Rizzarelli E, Condorelli DF
* ATOX1 gene silencing increases susceptibility to anticancer therapy based on copper ionophores or chelating drugs (719 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2016; 156: 145-152.
Impact Factor: 3.348
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Lanza V, D'Agata R, Iacono G, Bellia F, Spoto G, Vecchio G
* Cyclam glycoconjugates as lectin ligands and protective agents of metal-induced amyloid aggregation (517 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2015; 153: 377-382.
Impact Factor: 3.205
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Oliveri V, Bellia F, Vecchio G
* Cyclodextrin 3-functionalized with 8-hydroxyquinoline as an antioxidant inhibitor of metal-induced amyloid aggregation (426 views)
Chempluschem (ISSN: 2192-6506), 2015; 80(4): 762-770.
Impact Factor: 2.836
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Oliveri V, Bellia F, Pietropaolo A, Vecchio G
* Unusual Cyclodextrin Derivatives as a New Avenue to Modulate Self- and Metal-Induced Aβ Aggregation (546 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2015; 21(40): 14047-14059.
Impact Factor: 5.771
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Grasso GI, Arena G, Bellia F, Rizzarelli E, Vecchio G
* Copper(II)-chelating homocarnosine glycoconjugate as a new multifunctional compound (575 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2014 Feb; 131: 56-63.
Impact Factor: 3.444
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Arena G, Attanasio F, Zhang D, Yang Y, Bartsch RA, Sgarlata C
* Selective sensing of Hg2+ by a proton-ionizable calix[4]arene fluoroionophore (347 views)
Anal Bioanal Chem (ISSN: 1618-2642), 2013 Jan; 405(2-3): 1133-1137.
Impact Factor: 3.578
View Export to BibTeX Export to EndNote
* ATOX1 gene silencing increases susceptibility to anticancer therapy based on copper ionophores or chelating drugs (719 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2016; 156: 145-152.
Impact Factor: 3.348
View Export to BibTeX Export to EndNote
Lanza V, D'Agata R, Iacono G, Bellia F, Spoto G, Vecchio G
* Cyclam glycoconjugates as lectin ligands and protective agents of metal-induced amyloid aggregation (517 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2015; 153: 377-382.
Impact Factor: 3.205
View Export to BibTeX Export to EndNote
Oliveri V, Bellia F, Vecchio G
* Cyclodextrin 3-functionalized with 8-hydroxyquinoline as an antioxidant inhibitor of metal-induced amyloid aggregation (426 views)
Chempluschem (ISSN: 2192-6506), 2015; 80(4): 762-770.
Impact Factor: 2.836
View Export to BibTeX Export to EndNote
Oliveri V, Bellia F, Pietropaolo A, Vecchio G
* Unusual Cyclodextrin Derivatives as a New Avenue to Modulate Self- and Metal-Induced Aβ Aggregation (546 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2015; 21(40): 14047-14059.
Impact Factor: 5.771
View Export to BibTeX Export to EndNote
Grasso GI, Arena G, Bellia F, Rizzarelli E, Vecchio G
* Copper(II)-chelating homocarnosine glycoconjugate as a new multifunctional compound (575 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2014 Feb; 131: 56-63.
Impact Factor: 3.444
View Export to BibTeX Export to EndNote
Arena G, Attanasio F, Zhang D, Yang Y, Bartsch RA, Sgarlata C
* Selective sensing of Hg2+ by a proton-ionizable calix[4]arene fluoroionophore (347 views)
Anal Bioanal Chem (ISSN: 1618-2642), 2013 Jan; 405(2-3): 1133-1137.
Impact Factor: 3.578
View Export to BibTeX Export to EndNote
6 Records (6 excluding Abstracts).
Total impact factor: 22.182 (22.182 excluding Abstracts).
Total 5 year impact factor: 22.107 (22.107 excluding Abstracts).
Total impact factor: 22.182 (22.182 excluding Abstracts).
Total 5 year impact factor: 22.107 (22.107 excluding Abstracts).
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