Syntheses, quantum mechanical modeling, biomolecular interaction and in vitro anticancer – Tubulin activity of thiosemicarbazones

Bioorganic Chemistry - Tập 102 - Trang 104081 - 2020
Janet Sabina Xavier1, Karthikeyan Jayabalan1, V. Ragavendran2, A. NityanandaShetty3
1Department of Chemistry, Sathyabama Institute of Science and Technology, Chennai, 600119, India
2Department of Physics, Sri Chandrasekharendra Saraswathi Viswa Mahavidyalaya, Kanchipuram 631561, India
3Department of Chemistry, National Institute of Technology Karnataka, Mangalore,575025, India

Tài liệu tham khảo

Jakupec, 2008, Dalton Trans., 2, 183, 10.1039/B712656P Campbell, 1975, Coord. Chem. Rev., 15, 279, 10.1016/S0010-8545(00)80276-3 Lobana, 2009, Coord. Chem. Rev., 253, 977, 10.1016/j.ccr.2008.07.004 Dilworth, 2012, Inorg. Chim. Acta, 389, 3, 10.1016/j.ica.2012.02.019 Arion, 2002, J. Inorg. Biochem., 91, 298, 10.1016/S0162-0134(02)00419-1 Kizilcikli, 2007, Folia Microbiol., 52, 15, 10.1007/BF02932132 Kalinowski, 2009, Future Med. Chem., 1, 1143, 10.4155/fmc.09.80 Mahalingam, 2010, Polyhedron, 29, 3363, 10.1016/j.poly.2010.09.019 Glisoni, 2012, Eur. J. Pharm. Sci., 3, 596, 10.1016/j.ejps.2012.07.018 Soares, 2017, Bioorg. Med. Chem. Lett., 27, 3546, 10.1016/j.bmcl.2017.05.057 Murren, 2003, Clinical Cancer Res., 9, 4092 https://www.drugbank.ca/drugs/DB11940. Miklos, 2015, Triapine-mediated ABCB1 induction via PKC induces widespread therapy unresponsiveness but is not underlying acquired triapine resistance, Cancer Lett., 361, 112, 10.1016/j.canlet.2015.02.049 Romagnoli, 2010, Bioorg. Med. Chem., 18, 5114, 10.1016/j.bmc.2010.05.068 Nogales, 2001, Annu. Rev. Biophys. Biomol. Struct., 30, 397, 10.1146/annurev.biophys.30.1.397 Romagnoli, 2009, Bioorg. Med. Chem., 17, 6862, 10.1016/j.bmc.2009.08.027 Qi, 2006, J. Org. Chem., 71, 2881, 10.1021/jo052542a Qin, 2009, Dyes Pigments, 82, 329, 10.1016/j.dyepig.2009.02.002 Arslan, 2018, ZekeriyaBiyiklioglu, Inorg. Chim. Acta, 471, 121, 10.1016/j.ica.2017.10.020 Ferrari, 2002, J. Inorg. Biochem., 90, 113, 10.1016/S0162-0134(02)00428-2 Parrilha, 2011, Eur. J. Med. Chem., 46, 1473, 10.1016/j.ejmech.2011.01.041 Raja, 2011, Synth. React. Inorg. Met. Org. Chem., 41, 716, 10.1080/15533174.2011.568809 Rebolledo, 2005, J. Inorg. Biochem., 99, 698, 10.1016/j.jinorgbio.2004.11.022 Hall, 2000, Pharmazie, 55, 937 Ainscough, 1998, J. Inorg. Biochem., 70, 175, 10.1016/S0162-0134(98)10011-9 Conklin, 2004, J. Nutr., 134, 3201S, 10.1093/jn/134.11.3201S DralleMjos, 2014, Chem. Rev., 114, 4540, 10.1021/cr400460s M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, et al., Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2010. Becke, 1993, J. Phys. Chem. A, 98, 5648, 10.1063/1.464913 Lee, 1988, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Glenening, 2001 Weinhold, 2001, Chemistry: a new twist on molecular shape, Nature, 411, 539, 10.1038/35079225 Reed, 1988, Chem. Rev., 88, 899, 10.1021/cr00088a005 Erbudak, 1978, Solid State Commun., 27, iii, 10.1016/0038-1098(78)90710-X Rao, 1962, Spectrochim. Acta, 18, 54 Bellamy, 1960, J. Chem. Soc., 2218, 10.1039/JR9600002218 E. Huheey, E.A. Keiter, R.L. Keiter, Inorganic Chemistry Principles of Structure and Reactivity, fourth ed., Harper Collins College Publishers, New York, 1993. Joseph.M et al, 2004. Sreekanth, 2003, J. Mol. Struct., 655, 47, 10.1016/S0022-2860(03)00209-6 Seena, 2007, Polyhedron, 26, 829, 10.1016/j.poly.2006.09.040 Sreekanth, 2005, J. Mol. Struct., 737, 61, 10.1016/j.molstruc.2004.10.036 Philip, 2004, Polyhedron, 23, 1225, 10.1016/j.poly.2004.02.004 N. Sampath, Rita Mathews, M.N. Ponnuswamy, Lin-Woo Kang, Mol. Cryst. Liq. Cryst. 518(1) (2010) 151. Hao, 2010, Acta Crystallogr. Sect. E, 66, 2528, 10.1107/S1600536810035701 Ragavendran, 2017, Vibrational Spectrosc., 92, 35, 10.1016/j.vibspec.2017.04.006 Ragavendran, 2019, J. Mol. Struct., 1184, 593, 10.1016/j.molstruc.2019.02.057 Chocholousova, 2004, Phys. Chem. Chem. Phys., 6, 37, 10.1039/B314148A Chung, 1997, J. Phys. Chem. A, 101, 4628, 10.1021/jp963942s Grabowski, 2011, J. Phys. Chem. A, 115, 12789, 10.1021/jp203908n Rodziewicz, 2005, ChemPhysChem, 6, 1282, 10.1002/cphc.200500047 Pandey, 2015, RSC Adv., 5, 79661, 10.1039/C5RA17309D Hobza, 2000, Chem. Rev., 100, 4253, 10.1021/cr990050q Kryachko, 2000, Hydrogen Bonding—New Insights, 293 Joseph, 2007, J. Am. Chem. Soc., 129, 4620, 10.1021/ja067545z Scheiner, 2002, J. Phys. Chem. A, 106, 1784, 10.1021/jp013702z Yang, 2006, Int. J. Quantum Chem., 106, 1199, 10.1002/qua.20873 Bondi, 1966, J. Phys. Chem., 70, 3006, 10.1021/j100881a503 Klein, 2006, Chem. Phys. Lett., 425, 128, 10.1016/j.cplett.2006.04.109 Dolbier, 1980, Tetrahedron Lett., 21, 785, 10.1016/S0040-4039(00)71504-8 Wolfe, 1989, Isr. J. Chem., 29, 221, 10.1002/ijch.198900030 Aires-de-Sousa, 2002, Anal. Chem., 74, 80, 10.1021/ac010737m Binev, 2004, J. Chem. Inf. Comput. Sci., 44, 940, 10.1021/ci034228s Chen, 2012, J. Agric. Food Chem., 60, 1542, 10.1021/jf204420x Chang, 2009, An updated review of tyrosinase inhibitors, Int. J. Mol. Sci., 10, 2440, 10.3390/ijms10062440 Pillaiyar, 2017, J. Enzyme Inhib. Med. Chem., 32, 403, 10.1080/14756366.2016.1256882 Serda, 2012, Molecules, 17, 13483, 10.3390/molecules171113483 Türkpençe, 2013, Comput. Theor. Chem., 1025, 35, 10.1016/j.comptc.2013.10.001 Burcu Arslan, 2014, Chem. Phys., 439, 1, 10.1016/j.chemphys.2014.05.006 Rozas, 1998, J. Phys. Chem. A, 102, 9925, 10.1021/jp9824813 Sardroud, 2020, Polyhedron, 175, 10.1016/j.poly.2019.114218 Yunyun Wang, Wen Gu, Yu Shan, Fei Liu, Xu Xu, Yiqin Yang, Qiangjian Zhang, Yan Zhang, HongboKuang, Zhonglong Wang, Shifa Wang, Bioorg. Med. Chem. Lett. 27 (2017) 2360–2363. Pingaew, 2010, Molecules, 15, 988, 10.3390/molecules15020988 Mulliken, 1934, J. Chem. Phys., 2, 782, 10.1063/1.1749394 Mulliken, 1935, J. Chem. Phys., 3, 573, 10.1063/1.1749731 Malarz, 2018, Oncotarget, 9, 17689, 10.18632/oncotarget.24844 Yu, 2011, Mol. Pharmacol, 79, 921, 10.1124/mol.111.071324 Rejmund, 2018, PLoS One, 13, 10.1371/journal.pone.0188767 Mrozek-Wilczkiewicz, 2019, Eur. J. Med. Chem., 171, 180, 10.1016/j.ejmech.2019.03.027