Synthesis,Crystal Structure and Protein Tyrosine Phosphatase Inhibition of a Copper(Ⅱ) Complex with N-(2-Pyridylmethyl)-L-serine†

doi:10.7503/cjcu20160563

Abstract

Abstract:

The reaction of the reduced Schiff base HL [N-(2-pyridylmethyl)-L-serine] with CuCl₂·2H₂O in molar ratio of 1∶1 in methanol solution afforded a new neutral mononuclear complex [CuLCl(H₂O)](Ⅰ). The structure was determined by single-crystal X-ray diffraction and further characterized by elemental analysis, FTIR, electrospray ionization mass spectrometry and powder X-ray diffraction. In complex Ⅰ, the Cu(Ⅱ) ion adopts five-coordinated mode in a square pyramidal configuration which is completed by one oxygen and two nitrogen atoms from the L^- anion, one chloride anion and one water molecule. The discrete copper coordination units were extended into a 2D supramolecular network through the intermolecular interactions. The bioactivity of the compound as a potential PTPs(Protein Tyrosine Phosphatases) inhibitory agent in vitro was investigated, displaying potent inhibition against PTP1B(IC₅₀=0.32 μmol/L) and TCPTP(IC₅₀=0.45 μmol/L).

Key words: Copper(Ⅱ) complex, N-(2-Pyridylmethyl)-L-serine, Inhibitor, PTP1B, TCPTP

CLC Number:

O614.121

TrendMD:

LI Yanhong, YUAN Caixia, LU Liping, ZHU Miaoli, FU Xueqi, XING Shu, GAO Zengqiang. Synthesis,Crystal Structure and Protein Tyrosine Phosphatase Inhibition of a Copper(Ⅱ) Complex with N-(2-Pyridylmethyl)-L-serine^†[J]. Chem. J. Chinese Universities, 2016, 37(12): 2138.

Figures/Tables 8

References 35

[1]	Kobzar O. L., Trush V. V., Tanchuk V. Y., Zhilenkov A. V., Troshin P. A., Vovk A. I., Bioorg. Med. Chem. Lett., 2014, 24(14), 3175—3179
[2]	Liu S. J., Zeng L. F., Wu L., Yu X., Xue T., Gunawan A. M., Long Y. Q., Zhang Z. Y., J. Am. Chem. Soc., 2008, 130(50), 17075—17084
[3]	Lu L. P., Zhu M. L., Antioxid. Redox. Signal., 2014, 20(14), 2210—2224
[4]	Elchebly M., Payette P., Michaliszyn E., Cromlish W., Collins S., Loy A. L., Normandin D., Cheng A., Himms-Hagen J., Chan C. C., Ramachandran C., Gresser M. J., Tremblay M. L., Kennedy B. P., Science, 1999, 283(5407), 1544—1548
[5]	Zhang S., Zhang Z. Y., Drug Discov. Today, 2007, 12(9/10), 373—381
[6]	Zhang H. Q., Zhang Q. Y., Li J., Liu D., Wu X. F., Shan Y. K., Chem. J. Chinese Universities, 2012, 33(2), 243—250
	(张恒强, 张其颖, 李佳, 刘东, 吴小芳, 单永奎. 高等学校化学学报,2012, 33(2), 243—250)
[7]	Ong J. X., Yap C. W., Ang W. H., Inorg. Chem., 2012, 51(22), 12483—12492
[8]	Lin J. J., Meng F. Y., Li X. H., Chinese J. Struct. Chem., 2015, 34(1), 41—48
	(林娟娟, 蒙法艳, 李雪华. 结构化学,2015, 34(1), 41—48 )
[9]	Li M., Huang S. J., Ye C., Xie Y. R., Spectrochim. Acta A, 2015, 150, 290—300
[10]	Li Y., Lu L. P., Zhu M. L., Wang Q. M., Yuan C. X., Xing S., Fu X. Q., Mei Y. H., Biometals, 2011, 24(6), 993—1004
[11]	Wang Q. M., Lu L. P., Yuan C. X., Pei K., Liu Z. W., Guo M. L., Zhu M. L., Chem. Commun., 2010, 46(20), 3547—3549
[12]	Wang Q. M., Zhu M. L., Lu L. P., Yuan C. X., Xing S., Fu X. Q., Dalton Trans., 2011, 40(48), 12926—12934
[13]	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., Chem. Commun., 2012, 48(8), 1153—1155
[14]	Ma L., Lu L. P., Zhu M. L., Wang Q. M., Li Y., Xing S., Fu X. Q., Gao Z. Q., Dong Y. H., Dalton Trans., 2011, 40(24), 6532—6540
[15]	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., J. Inorg. Biochem., 2011, 105(9), 1138—1147
[16]	Yuan C. X., Lan S. F., Lu L. P., Chinese J. Inorg. Chem., 2015, 31(5), 915—922
	(袁彩霞, 兰淑芬, 卢丽萍. 无机化学学报,2015, 31(5), 915—922)
[17]	Han H., Lu L. P., Wang Q. M., Zhu M. L., Yuan C. X., Xing S., Fu X. Q., Dalton Trans., 2012, 41(36), 11116—11124
[18]	Lu L. P., Wang S. L., Zhu M. L., Liu Z. W., Guo M. L., Xing S., Fu X. Q., Biometals, 2010, 23(6), 1139—1147
[19]	Lu L. P., Gao X. L., Zhu M. L., Wang S. L., Wu Q., Xing S., Fu X. Q., Liu Z. W., Guo M. L., Biometals, 2012, 25(3), 599—610
[20]	Yuan C. X., Lu L. P., Gao X. L., Wu Y. B., Guo M. L., Li Y., Fu X. Q., Zhu M. L., J. Biol. Inorg. Chem., 2009, 14(6), 841—851
[21]	Yuan C. X., Lu L. P., Wu Y. B., Liu Z. W., Guo M. L., Xing S., Fu X. Q., Zhu M. L., J. Inorg. Biochem., 2010, 104(9), 978—986
[22]	Otwinowski Z., Minor W., Methods Enzymol., 1997, 276, 307—326
[23]	Sheldrick G. M., Acta Cryst., 2015, C71, 3—8
[24]	Yang C.T., Vetrichelvan M., Yang X. D., Moubaraki B., Murray K. S., Vittal J. J.,Dalton Trans., 2004, (1), 113—121
[25]	Yang X. L., Xie M. H., Zou C., Wu C. D., CrystEngComm., 2011, 13(21), 6422—6430
[26]	Jia L., Jiang P., Xu J., Hao Z. Y., Xu X. M., Chen L. H., Wu J. C., Tang N., Wang Q., Vittal J. J., Inorg. Chim. Acta, 2010, 363(5), 855—865
[27]	Wang N., Yu X. Y., Zhang X., Gao W. P., Xin R., Zhang H., Yang Y. Y., Qu X. S., J. Coord. Chem., 2014, 67(5), 837—846
[28]	Wang X. B., Ranford J. D., Vittal J. J., J. Mol. Struct., 2006, 796(1—3), 28—35
[29]	Li X. F., Liu T. F., Hu B., Li G. L., Zhang H., Cao R., Cryst. Growth Des., 2010, 10(7), 3051—3059
[30]	Zheng C. Y., Qiu Q. M., Hao L., Li H., Chem. Res. Chinese Universities, 2016, 32(1), 1—7
[31]	Yang S. P., Han L. J., Pan Y., Wang D. Q., Zhao C., Wang B., Chem. J. Chinese Universities, 2012, 33(1), 14—21
	(杨树平, 韩立军, 潘燕, 王大奇, 赵翠, 王波. 高等学校化学学报,2012, 33(1), 14—21)
[32]	Zhang Q. F., Zhou Z. Y., Wang X., Lu J., Chem. Res. Chinese Universities, 2016, 32(2), 165—171
[33]	Zheng D. G., Hu J. R., Chinese J. Struct. Chem., 2012, 31(6), 867—871
	(郑大贵, 胡久荣. 结构化学,2012, 31(6), 867—871)
[34]	He Y. F., Chen M. Q., Dai L. Y., Zhang G. R., Li Q., Wang L. S., Chem. J. Chinese Universities, 2006, 27(5), 812—816
	(贺云飞, 陈民勤, 戴立益, 张贵荣, 李强, 王麟生. 高等学校化学学报,2006, 27(5), 812—816)
[35]	Brown I. D., Chem. Rev., 2009, 109(12), 6858—6919

CCDC number	1494101	Z	2
Empirical formula	C₉H₁₃ClCuN₂O₄	D_c/(g·cm^-3)	1.811
Formula weight	312.20	μ/mm^-1	2.218
Radiation type	Synchrotron(beamline 3W1A at BSRF), λ=0.07200 nm	F(000) θ range for data collection/(°)	318 3.309—25.999
T/K	100	Limiting indices	-7≤h≤0; -7≤k≤7;
Crystal system	Monoclinic		-17≤l≤17
Space group	P2₁	Reflections collected, unique	1974, 1886(R_int=0.0318)
a/nm	0.6377(1)	Completeness to θ(%)	98.6(θ=25.595°)
b/nm	0.6375(1)	Data/restraints/parameters	1886/1/155
c/nm	1.4400(3)	GOF on F²	1.137
α/(°)	90	Final R indices[I>2σ(I)]	R₁=0.0414, wR₂=0.1163
β/(°)	102.07(3)	R indices(all data)	R₁=0.0411, wR₂=0.1161
γ/(°)	90	(Δρ)_max,(Δρ)_min /(e·nm^-3)	729 and -860
V/nm³	0.5725(2)

CCDC number	1494101	Z	2
Empirical formula	C₉H₁₃ClCuN₂O₄	D_c/(g·cm^-3)	1.811
Formula weight	312.20	μ/mm^-1	2.218
Radiation type	Synchrotron(beamline 3W1A at BSRF), λ=0.07200 nm	F(000) θ range for data collection/(°)	318 3.309—25.999
T/K	100	Limiting indices	-7≤h≤0; -7≤k≤7;
Crystal system	Monoclinic		-17≤l≤17
Space group	P2₁	Reflections collected, unique	1974, 1886(R_int=0.0318)
a/nm	0.6377(1)	Completeness to θ(%)	98.6(θ=25.595°)
b/nm	0.6375(1)	Data/restraints/parameters	1886/1/155
c/nm	1.4400(3)	GOF on F²	1.137
α/(°)	90	Final R indices[I>2σ(I)]	R₁=0.0414, wR₂=0.1163
β/(°)	102.07(3)	R indices(all data)	R₁=0.0411, wR₂=0.1161
γ/(°)	90	(Δρ)_max,(Δρ)_min /(e·nm^-3)	729 and -860
V/nm³	0.5725(2)

Cu1—O1	0.1970(5)	Cu1—N2	0.1997(5)	Cu1—O4	0.2362(5)
Cu1—Cl1	0.22417(17)	Cu1—N1	0.2009(5)
O1—Cu1—N1	82.7(3)	N2—Cu1—Cl1	98.43(18)	N1—Cu1—O4	90.6(2)
O1—Cu1—Cl1	95.04(15)	O1—Cu1—N2	166.3(2)	N1—Cu1—N2	83.7(3)
O1—Cu1—O4	90.6(2)	N1—Cu1—Cl1	165.1(2)	N2—Cu1—O4	88.4(2)
Cl1—Cu1—O4	104.21(13)

Cu1—O1	0.1970(5)	Cu1—N2	0.1997(5)	Cu1—O4	0.2362(5)
Cu1—Cl1	0.22417(17)	Cu1—N1	0.2009(5)
O1—Cu1—N1	82.7(3)	N2—Cu1—Cl1	98.43(18)	N1—Cu1—O4	90.6(2)
O1—Cu1—Cl1	95.04(15)	O1—Cu1—N2	166.3(2)	N1—Cu1—N2	83.7(3)
O1—Cu1—O4	90.6(2)	N1—Cu1—Cl1	165.1(2)	N2—Cu1—O4	88.4(2)
Cl1—Cu1—O4	104.21(13)

D—H…A	d(D—H)/nm	d(H…A)/nm	d(D…A)/nm	ÐDHA/(°)
O3—H3…O1^a	0.0840	0.1975	0.2810	172.79
O4—H4C…O2^b	0.0820	0.2323	0.2919	130.03
O4—H4D…O2^c	0.0820	0.1963	0.2774	169.98
N1—H1…Cl1^a	0.1000	0.2582	0.3401	139.04
C4—H4B…O4^a	0.0990	0.2469	0.3392	154.84
C9—H9…Cl1	0.0950	0.2792	0.3355	118.91