Synthesis, crystal structure and biological evaluation of spectroscopic characterization of Ni(II) and Co(II) complexes with N-salicyloil-N′-maleoil-hydrazine as anticholinergic and antidiabetic agents
Gulnar Gondolova
Department of the Azerbaijan National Academy of Sciences, Institute of Ecology and Natural Resources, Ganja, Azerbaijan
Search for more papers by this authorCorresponding Author
Parham Taslimi
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, Turkey
Correspondence
Dr. Parham Taslimi
E-mails: [email protected], [email protected]
Search for more papers by this authorAjdar Medjidov
Department of “Coordination compounds”, Institute of Catalysis and Inorganic Chemistry Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorVagif Farzaliyev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorAfsun Sujayev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorMansura Huseynova
Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorOnur Şahin
Scientific and Technological Research Application and Research Center, Sinop University, Sinop, Turkey
Search for more papers by this authorBahattin Yalçın
Department of Chemistry, Faculty of Arts Sciences, Marmara University, Istanbul, Turkey
Search for more papers by this authorFikret Turkan
Health Services Vocational School, Igdır University, Igdır, Turkey
Search for more papers by this authorİlhami Gulçin
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, Turkey
Search for more papers by this authorGulnar Gondolova
Department of the Azerbaijan National Academy of Sciences, Institute of Ecology and Natural Resources, Ganja, Azerbaijan
Search for more papers by this authorCorresponding Author
Parham Taslimi
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, Turkey
Correspondence
Dr. Parham Taslimi
E-mails: [email protected], [email protected]
Search for more papers by this authorAjdar Medjidov
Department of “Coordination compounds”, Institute of Catalysis and Inorganic Chemistry Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorVagif Farzaliyev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorAfsun Sujayev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorMansura Huseynova
Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Search for more papers by this authorOnur Şahin
Scientific and Technological Research Application and Research Center, Sinop University, Sinop, Turkey
Search for more papers by this authorBahattin Yalçın
Department of Chemistry, Faculty of Arts Sciences, Marmara University, Istanbul, Turkey
Search for more papers by this authorFikret Turkan
Health Services Vocational School, Igdır University, Igdır, Turkey
Search for more papers by this authorİlhami Gulçin
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, Turkey
Search for more papers by this authorAbstract
[Ni(C11H9N2O5)2(H2O)2]•3(C3H7NO) (1) and [Co(C11H9N2O5)2(H2O)2]•3(C3H7NO) (2) are synthesized and characterized by elemental analysis, FT-IR spectra, magnetic susceptibility, and thermal analysis. In addition, the crystal structure of Ni(II) complex is presented. Both complexes show distorted octahedral geometry. In 1 and 2, metal ions are coordinated by two oxygen atoms of salicylic residue and two nitrogen atoms of maleic amide residue from two ligands, and two oxygen atoms from two water molecules. In this paper, both compounds showed excellent inhibitory effects against human carbonic anhydrase (hCA) isoforms I, and II, α-glycosidase, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE). Compounds 1 and 2 had Ki values of 18.36 ± 4.38 and 26.61 ± 7.54 nM against hCA I and 13.81 ± 3.02 and 29.56 ± 6.52 nM against hCA II, respectively. On the other hand, their Ki values were found to be 487.45 ± 54.18 and 453.81 ± 118.61 nM against AChE and 199.21 ± 50.35 and 409.41 ± 6.86 nM against BChE, respectively.
REFERENCES
- 1M. T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Bioorg. Med. Chem. 2006, 14, 366.
- 2N. Terzioğlu, A. Gürsoy, Eur. J. Med. Chem. 2003, 38, 781.
- 3P. Vicini, F. Zani, P. Cozzini, I. Doytchinova, Eur. J. Med. Chem. 2002, 37, 64.
- 4A. Walcourt, M. Loyevsky, D. B. Lovejoy, V. R. Gordeuk, D. R. Richardson, Int. J. Biochem. Cell Biol. 2004, 36, 401.
- 5J. Patole, U. Sandbhor, S. Padhye, D. N. Deobagkar, C. E. Anson, A. Powell, Bioorg. Med. Chem. Let. 2003, 13, 51.
- 6D. Moon, J. Song, B. J. Kim, , B. J. Suh, M. S. Lah, Inorg. Chem. 2004, 11, 1919.
- 7S. Lin, S. X. Liu, Z. Chen, B. Z. Lin, S. Gao, Inorg.Chem. 2004, 11, 2222.
- 8R. P. John, K. Lee, B. J. Suh, H. Rhee, M. S. Lah, Inorg. Chem. 2005, 44, 7109.
- 9R. P. John, J. Park, D. Moon, K. Lee, M. S. Lah, Chem. Commun. 2006, 3699.
- 10M. L. Liu, J. M. Dou, D. C. Li, D. Q. Wang, J. Z. Cui, Transition Met Chem. 2012, 37, 117.
- 11D. Li, S. Wang, H. Xu, Y. Yang, S. Zeng, J. Zhao, D. Wang, Dou, J. Inorg. Chim. Acta. 2010, 365, 85.
- 12H. Yin, J. Cui, Y. Qiao, Inorg. Chem. Commun. 2008, 11, 684.
- 13P. Taslimi, İ. Gulcin, B. Ozgeris, S. Goksu, F. Tumer, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 152.
- 14H. İ. Gül, K. Kucukoglu, C. Yamali, S. Bilginer, H. Yuca, İ. Ozturk, P. Taslimi, İ. Gülçin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 568.
- 15P. Taslimi, İ. Gülçin, N. Öztaşkın, Y. Çetinkaya, S. Göksu, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 603.
- 16D. Ozmen Ozgun, C. Yamali, H. İ. Gül, P. Taslimi, İ. Gülçin, T. Yanik, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1498.
- 17A. Sujayev, E. Garibov, P. Taslimi, İ. Gülçin, S. Gojayeva, V. Farzaliyev, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1531.
- 18B. Turan, K. Sendil, E. Sengul, M. S. Gultekin, P. Taslimi, İ. Gulcin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 79–88.
- 19F. Özbey, P. Taslimi, İ. Gulcin, A. Maraş, S. Goksu, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 79.
- 20E. Garibov, P. Taslimi, A. Sujayev, Z. Bingöl, S. Çetinkaya, İ. Gulcin, S. Beydemir, V. Farzaliyev, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1–9.
- 21K. Aksu, B. Özgeriş, P. Taslimi, A. Naderi, İ. Gülçin, S. Göksu, Arch. Pharm. 2016, 349, 944.
- 22P. Taslimi, A. Sujayev, S. Mamedova, P. Kalın, İ. Gulcin, N. Sadeghian, S. Beydemir, Ö. İ. Küfrevioglu, S. H. Alwasel, V. Farzaliyev, S. Mamedov, J. Enzyme Inhib. Med. Chem. 2017, 32, 137–145.
- 23P. Taslimi, C. Caglayan, İ. Gulçin, J. Biochem. Mol. Toxicol. 2017, 31, e21995.
- 24P. Taslimi, H. Akıncıoğlu, İ. Gulçin, J. Biochem. Mol. Toxicol. 2017, 31, e21973.
- 25P. Taslimi, İ. Gulçin, J. Biochem. Mol. Toxicol. 2017, 31, e21956.
- 26G. M. Sheldrick, ActaCryst. 2008, A64, 112.
- 27G. M. Sheldrick, ActaCryst. 2015, C71, 3.
10.1107/S2053273314026370 Google Scholar
- 28APEX2, Bruker AXS Inc. Madison Wisconsin USA (2013)
- 29Mercury, version 3.3; CCDC, available online via ccdc.cam.ac.uk/products/mercury.
- 30L. J. J. Farrugia, Apply. Cryst. 1999, 32, 837.
- 31H. İ. Gül, M. Tuğrak, H. Sakagami, P. Taslimi, İ. Gülçin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1619.
- 32H. I. Gul, E. Mete, P. Taslimi, I. Gulcin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2017, 32, 189.
- 33H. I. Gül, A. Demirtas, G. Ucar, P. Taslimi, İ. Gülçin, Lett. Drug Des. Discov. 2017, 14, 573.
- 34J. A. Verpoorte, S. Mehta, J. T. Edsall, J .Biol. Chem. 1967, 242, 4221.
- 35M. M. Bradford, Anal. Biochem. 1976, 72, 248.
- 36Ç. Bayrak, P. Taslimi, İ. Gülçin, A. Menzek, Bioorg. Chem. 2017, 72, 359.
- 37G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherston, Biochem. Pharmacol. 1961, 7, 88.
- 38A. Aktaş, P. Taslimi, I. Gülçin, Y. Gök, Arch. Pharm. 2017, 350, e1700045.
- 39P. Taslimi, A. Sujayev, E. Garibov, N. Nazarov, Z. Huyut, S. H. Alwasel, İ. Gülçin, J. Biochem. Mol. Toxicol. 2017, 31, e21897.
- 40N. Öztaşkın, P. Taslimi, A. Maraş, S. Göksu, İ. Gülçin, Bioorg. Chem. 2017, 74, 104.
- 41P. Taslimi, S. Osmanova, İ. Gulçin, S. Sardarova, V. Farzaliyev, A. Sujayev, R. Kaya, F. Koc, S. Beydemir, S. H. Alwasel, O. I. Kufrevioglu, J. Biochem. Mol. Toxicol. 2017, 31, e21931.
- 42U. M. Koçyiğit, P. Taslimi, H. Gezegen, İ. Gulçin, M. Ceylan, J. Biochem. Mol. Toxicol. 2017, 31, e21938.
- 43Y. Tao, Y. Zhang, Y. Cheng, Y. Wang, Biomed. Chrom. 2013, 27, 148.
- 44M. Toeller, Eur. J. Clin. Invest. 1994, 24, 31.
- 45H. Lineweaver, D. Burk, J. Am. Chem. Soc. 1934, 56, 658.
- 46U. Lee, B. K. Koo, Bull. Korean Chem. Soc. 2005, 26, 925.
- 47J. Valdés-Martínez, R. A. Toscano, A. Zentella-Dehesa, M. M. Salberg, G. A. Bain, D. X. West, Polyhedron 1996, 15, 427.
- 48S. Anu, J. V. Singh, E-J. Chem. 2012, 9, 1835.
10.1155/2012/521345 Google Scholar
- 49U. M. Koçyiğit, Y. Budak, F. Eligüzel, P. Taslimi, D. Kılıç, İ. Gulçin, M. Ceylan, Arch. Pharm. 2017, 350, e1700198.
- 50F. Erdemir, D. Barut Celepci, A. Aktaş, P. Taslimi, Y. Gök, H. Karabıyık, İ. Gulçin, J. Mol. Struc. 2018, 1155, 797.
- 51U. M. Koçyiğit, Y. Budak, M. B. Gürdere, F. Ertürk, B. Yencilek, P. Taslimi, İ. Gulçin, M. Ceylan, Arch. Physiol. Biochem 2018, 124, 61.
- 52İ. Gulçin, M. Abbasova, P. Taslimi, Z. Huyut, L. Safarova, A. Sujayev, V. Farzaliyev, S. Beydemir, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2017, 32, 1174.
- 53T. Daştan, U. M. Koçyiğit, S. D. Daştan, C. Kiliçkaya, P. Taslimi, Ç. Özge, M. Koparir, A. Çetin, C. Orek, İ. Gulçin, J. Biochem. Mol. Toxicol. 2017, 31, e21971.
- 54U. M. Koçyiğit, A. Taşkıran, P. Taslimi, A. Yokuş, Y. Temel, İ. Gulçin, J. Biochem. Mol. Toxicol. 2017, 31, e21972.
- 55H. Wang, Y. J. Du, H. C. Song, Food Chem. 2010, 123, 6–13.
- 56L. Zhang, S. Hogan, J. R. Li, S. Sun, C. Canning, S. J. Zheng, K. Zhou, Food Chem. 2011, 126, 466.
- 57H. Teng, L. Chen, T. Fang, B. Yuan, Q. Lin, J. Funct. Foods 2017, 28, 306.
- 58M. Torres-Naranjo, A. Suarez, G. Gilardoni, L. Cartuche, P. Flores, V. Morocho, Molecules 2016, 21, 1461.
- 59N.P. Singh, Anu, J.V. Singh, E-J. Chem. 2012, 9, 1835–1842.
- 60J. Valdés-Martínez, R. A. Toscano, A. Zentella-Dehesa, M. M. Salberg, G. A. Bain, D. X. West, Polyhedron 1996, 15, 427–431.