Citation: 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[J]. Chinese Journal of Structural Chemistry, ;2016, 35(11): 1686-1693. doi: 10.14102/j.cnki.0254-5861.2011-1213 shu

A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP

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a Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan 030006, China;
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b Fenyang College Shanxi Medical University, Fenyang, Shanxi 032200, China;
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c Beijing Synchrotron Radiation Facility, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: LU Li-Ping, ZHU Miao-Li,
Received Date: 23 March 2016
Available Online: 17 May 2016
Fund Project: Supported by NNSFC (Nos. 21271121, 21471092, 21571118) (Nos. 21271121, 21471092, 21571118)

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, M_r=501.97, D_c=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>2σ(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.
- copper(II) complex,
- N-(4-hydroxybenzyl)-L-serine,
- crystal structure,
- inhibitor,
- PTP1B,
- TCPTP
1. [1]
  PAN Rong-Kai , LI Guo-Bi , LIU Sheng-Gui , YANG Gui-Zhen , ZHOU Xiao-Ping , CHEN Xiao-Ying . Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane. Chinese Journal of Structural Chemistry, 2016, 35(3): 348-354. doi: 10.14102/j.cnki.0254-5861.2011-0893
2. [2]
  Yuan Feng Tong , Pei Zhang , Feng Chen , Ling Hua Hao , Fei Ye , Jin Ying Tian , Song Wu . Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors. Chinese Chemical Letters, 2010, 21(12): 1415-1418. doi: 10.1016/j.cclet.2010.07.005
3. [3]
  LI Wei , LI Chang-Hong , LI Heng-Feng , TAN Xiong-Wen . Synthesis, Crystal Structure, Spectroscopic Characterization, Thermal Stability and Magnetic Properties of a Dinuclear Copper(II) Complex. Chinese Journal of Structural Chemistry, 2015, 34(5): 794-798. doi: 10.14102/j.cnki.0254-5861.2011-0780
4. [4]
  LI Chang-Hong , LI Wei , HU Han-Xiang , HU Bo-Nian . Hydrothermal Synthesis, Crystal Structure, Thermal Stability and Magnetic Properties of a Dinuclear Copper(II) Complex. Chinese Journal of Structural Chemistry, 2016, 34(10): 1553-1557. doi: 10.14102/j.cnki.0254-5861.2011-0911
5. [5]
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6. [6]
  TAI Xi-Shi , WANG Xin , YOU Hai-Ying . Synthesis, Crystal Structure and Antitumor Activity of a New Zn(II) Complex Based on N-Acetyl-L-phenylalanine and 1,10-Phenanthroline. Chinese Journal of Structural Chemistry, 2016, 35(4): 586-590. doi: 10.14102/j.cnki.0254-5861.2011-0910
7. [7]
  WANG Xiu-Yan , ZHAO Zhong-Yu , LIU Rui , XU Ye , LI Xin-Hang , XU Zhan-Lin . Synthesis, Crystal Structure and Luminescence of a New Zn(II) Complex [Zn(1,2,3-HBTC)(L)]₂ Constructed by Mixed Ligands. Chinese Journal of Structural Chemistry, 2015, 34(5): 725-728. doi: 10.14102/j.cnki.0254-5861.2011-0545
8. [8]
  PAN Ya-Ru , SUN Ming , LI Xiu-Mei . Synthesis, Crystal Structure and Theoretical Calculations of a Nickel(II) Coordination Polymer Assembled by 4,4'-Oxydibenzoic Acid and 1,3-Bis(imidazol-1-ylmethyl)-benzene Ligands. Chinese Journal of Structural Chemistry, 2015, 34(5): 710-718. doi: 10.14102/j.cnki.0254-5861.2011-0557
9. [9]
  Ayse ERCAG , Sema Oztürk YILDIRIM , Mehmet AKKURT , Mahmure Ustün OZGUR , Frank W. HEINEMANN . Novel Isatin-Schiff Base Cu (H) and Ni(H) Complexes. X-ray Crystal Structure of Bis[3-(4-hexylphenylimino)-1H-indol-2(3H)-one]-dichlorocopper(H) Complex. Chinese Chemical Letters, 2006, 17(2): 243-246.
10. [10]
  ZHAO Teng , WANG Yu-Hong , SONG Rui-Feng . Two Novel Mercury(II) and Copper(II) Complexes Based on (5-Chloro-quinolin-8-yloxy)acetic Acid^①. Chinese Journal of Structural Chemistry, 2016, 35(7): 1137-1144. doi: 10.14102/j.cnki.0254-5861.2011-1034
11. [11]
  Feng Changjun , He Hongmei , Li Jing . CoMFA Model Study on the Inhibitory Activity of Novel Triazol-ethiadiazole Derivatives on PTP1B. Chemistry, 2019, 82(10): 946-949.
12. [12]
  Qiu Yun CHEN , Qing Shan LIU , Christopher J. SCHOFIELD . Synthesis and Bioassay of 4-Substituted 2-Oxoglutaric Acids. Chinese Chemical Letters, 2006, 17(2): 156-158.
13. [13]
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14. [14]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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