A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP
李艳红;卢丽萍;朱苗力;袁彩霞;冯思思;高增强
a (Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan 030006, China)
b (Fenyang College Shanxi Medical University, Fenyang, Shanxi 032200, China)
c (Beijing Synchrotron Radiation Facility, Institute of High Energy Physics,Chinese Academy of Sciences, Beijing 100049, China)
A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP
LI Yan-Hong;LU Li-Ping;ZHU Miao-Li;YUAN Cai-Xia;FENG Si-Si;GAO Zeng-Qiang
a (Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan 030006, China)
b (Fenyang College Shanxi Medical University, Fenyang, Shanxi 032200, China)
c (Beijing Synchrotron Radiation Facility, Institute of High Energy Physics,Chinese Academy of Sciences, Beijing 100049, China)
A novel copper(II) complex with the reduced Schiff base, [Cu(L)2]•H2O (I, HL = N-(4-hydroxybenzyl)-L-serine), was prepared in aqueous solution and characterized by elemental analysis, FT-IR, electrospray ionization mass spectrometry and single-crystal X-ray diffraction. Complex I crystallizes in the orthorhombic system, space group P212121, with a = 8.9040(18), b = 9.1530(18), c = 24.891(5) Å, V = 2028.6(7) Å3, Z = 4, C20H26CuN2O9, Mr = 501.97, Dc = 1.644g•cm3, μ = 1.135 mm-1, F(000) = 1044, GOOF = 1.194, the final R = 0.0484 and wR = 0.1420 for 6186 observed reflections (I > 2(I)). In I, two L− anions are coordinated to the copper ion in tridentate and bidentate chelating modes, respectively, resulting in the coordinated geometry of copper ion to be a distorted square pyramid. The intermolecular hydrogen bonds between the complexes, complexes and lattice water molecules lead to a 2D supramolecular network. The bioactivity of the complex as a potential PTPs inhibitory agent in vitro was investigated, displaying potent inhibition against PTP1B (IC50, 0.27 μM) and TCPTP (IC50, 0.57 μM) with a moderate selectivity.
A novel copper(II) complex with the reduced Schiff base, [Cu(L)2]•H2O (I, HL = N-(4-hydroxybenzyl)-L-serine), was prepared in aqueous solution and characterized by elemental analysis, FT-IR, electrospray ionization mass spectrometry and single-crystal X-ray diffraction. Complex I crystallizes in the orthorhombic system, space group P212121, with a = 8.9040(18), b = 9.1530(18), c = 24.891(5) Å, V = 2028.6(7) Å3, Z = 4, C20H26CuN2O9, Mr = 501.97, Dc = 1.644g•cm3, μ = 1.135 mm-1, F(000) = 1044, GOOF = 1.194, the final R = 0.0484 and wR = 0.1420 for 6186 observed reflections (I > 2(I)). In I, two L− anions are coordinated to the copper ion in tridentate and bidentate chelating modes, respectively, resulting in the coordinated geometry of copper ion to be a distorted square pyramid. The intermolecular hydrogen bonds between the complexes, complexes and lattice water molecules lead to a 2D supramolecular network. The bioactivity of the complex as a potential PTPs inhibitory agent in vitro was investigated, displaying potent inhibition against PTP1B (IC50, 0.27 μM) and TCPTP (IC50, 0.57 μM) with a moderate selectivity.
李艳红;卢丽萍;朱苗力;袁彩霞;冯思思;高增强. A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP[J]. 结构化学, 2016, 35(11): 1686-1693.
LI Yan-Hong;LU Li-Ping;ZHU Miao-Li;YUAN Cai-Xia;FENG Si-Si;GAO Zeng-Qiang. A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35(11): 1686-1693.
REFERENCES
(1)Gokce, C.; Gup, R. Synthesis, characterization and DNA interaction of new copper(II) complexes of Schiff base-aroylhydrazones bearing naphthalene ring. J. Photochem. Photobiol. B 2013, 122, 15–23.
(2) Macias, B.; Villa, M. V.; Gomez, B.; Borras, J.; Alzuet, G.; Gonzalez-Alvarez, M.; Castineiras, A. DNA interaction of new copper(II) complexes with sulfonamides as ligands. J. Inorg. Biochem. 2007, 101, 444–451.
(3) Senthil Kumar, R.; Arunachalam, S. DNA binding and antimicrobial studies of some polyethyleneimine-copper(II) complex samples containing 1,10-phenanthroline and L-theronine as co-ligands. Polyhedron 2007, 26, 3255–3262.
(4) Maheswari, P. U.; van der Ster, M.; Smulders, S.; Barends, S.; van Wezel, G. P.; Massera, C.; Roy, S.; den Dulk, H.; Gamez, P.; Reedijk, J. Structure, cytotoxicity, and DNA-cleavage properties of the complex [CuII(pbt)Br2]. Inorg. Chem. 2008, 47, 3719–3727.
(5) Price, K. A.; Caragounis, A.; Paterson, B. M.; Filiz, G.; Volitakis, I.; Masters, C. L.; Barnham, K. J.; Donnelly, P. S.; Crouch, P. J.; White, A. R. Sustained activation of glial cell epidermal growth factor receptor by bis(thiosemicarbazonato) metal complexes is associated with inhibition of protein tyrosine phosphatase activity. J. Med. Chem. 2009, 52, 6606–6620.
(6) Kobzar, O. L.; Trush, V. V.; Tanchuk, V. Y.; Zhilenkov, A. V.; Troshin, P. A.; Vovk, A. I. Fullerene derivatives as a new class of inhibitors of protein tyrosine phosphatases. Bioorg. Med. Chem. Lett. 2014, 24, 3175–3179.
(7) Li, Y.; Lu, L. P.; Zhu, M. L.; Wang, Q. M.; Yuan, C. X.; Xing, S.; Fu, X. Q.; Mei, Y. H. Potent inhibition of protein tyrosine phosphatases by copper complexes with multi-benzimidazole derivatives. Biometals 2011, 24, 993–1004.
(8) Wang, Q. M.; Lu, L. P.; Yuan, C. X.; Pei, K.; Liu, Z. W.; Guo, M. L.; Zhu, M. L. Potent inhibition of protein tyrosine phosphatase 1B by copper complexes: implications for copper toxicity in biological systems. Chem. Commun. 2010, 46, 3547–3549.
(9) Wang, Q. M.; Zhu, M. L.; Lu, L. P.; Yuan, C. X.; Xing, S.; Fu, X. Q. Potent inhibition of protein tyrosine phosphatases by quinquedentate binuclear copper complexes: synthesis, characterization and biological activities. Dalton Trans. 2011, 40, 12926–12934.
(10) Yuan, C. X.; Zhu, M. L.; Wang, Q. M.; Lu, L. P.; Xing, S.; Fu, X. Q.; Jiang, Z.; Zhang, S.; Li, Z. W.; Li, Z. Y.; Zhu, R. T.; Ma, L.; Xu, L. Q. Potent and selective inhibition of T-cell protein tyrosine phosphatase (TCPTP) by a dinuclear copper(II) complex. Chem. commun. 2012, 48, 1153–1155.
(11) Ma, L.; Lu, L. P.; Zhu, M. L.; Wang, Q. M.; Li, Y.; Xing, S.; Fu, X. Q.; Gao, Z. Q.; Dong, Y. H. Mononuclear copper(II) complexes with 3,5-substituted-4-salicylidene-amino-3,5-dimethyl-1,2,4-triazole: synthesis, structure and potent inhibition of protein tyrosine phosphatases. Dalton Trans. 2011, 40, 6532–6540.
(12) Ma, L.; Lu, L. P.; Zhu, M. L.; Wang, Q. M.; Gao, F.; Yuan, C. X.; Wu, Y. B.; Xing, S.; Fu, X. Q.; Mei, Y. H.; Gao, X. L. Dinuclear copper complexes of organic claw: potent inhibition of protein tyrosine phosphatases. J. Inorg. Biochem. 2011, 105, 1138–1147.
(13) Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 1997, 276, 307–326.
(14) Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. 2015, C71, 3–8.
(15) Li, X. Y.; Wang, L. Y.; Song, N.; Ma, B. N.; Zhang, X. J.; Che, G. B. Hydrothermal syntheses and crystal structures of Cd(II) and Cu(II) complexes constructed with 1,3,5-benzenetricarboxylic acid and dipyrido[3,2-a:2΄,3΄-c]phenazine ligands. Chin. J. Struct. Chem. 2015, 34, 1709–1716.
(16) Zheng, D. G.; Hu, J. R. Synthesis and crystal structure of a Cu(II) complex with reduced Schiff-base N-(2-hydroxybenzyl)-D,L-alanine and 4,4΄-bipyridine. Chin. J. Struct. Chem. 2012, 31, 867–871.
(17) Sreenivasulu, B.; Zhao, F.; Gao, S.; Vittal, J. J. Synthesis, structures and catecholase activity of a new series of dicopper(II) complexes of reduced Schiff base ligands. Eur. J. Inorg. Chem. 2006, 2006, 2656–2670.
(18) Cui, H. W.; Xia, Y. F.; Xiang, X. X.; Qin, S. H.; Yang, E. C. Synthesis, structure and magnetism of two Cu(II) 4,5-dichlorophthalate complexes. Chin. J. Struct. Chem. 2015, 34, 1862–1868.
(19) Nagarathinam, M.; Saravanan, K.; Leong, W. L.; Balaya, P.; Vittal, J. J. Hollow nanospheres and flowers of CuS from self-assembled Cu(II) coordination polymer and hydrogen-bonded complexes of N-(2-hydroxybenzyl)-L-serine. Cryst. Growth Des. 2009, 9, 4461–4470.
(20) Lalović, M. M.; Vojinović-Ješić, L. S.; Jovanović, L. S.; Leovac, V. M.; Češljević, V. I.; Divjaković, V. Synthesis, characterization and crystal structure of square-pyramidal copper(II) complexes with pyridoxylidene aminoguanidine. Inorg. Chim. Acta 2012, 388, 157–162.
(21) Yuan, C. X.; Lan, S. F.; Lu, L. P. Evaluation of Cu(II) complexes with Schiff base of salicylanilide as the inhibitors of protein tyrosine phosphatases. Chin. J. Inorg. Chem. 2015, 31, 915–922.
2016, Vol. 35 
