Citation: YUAN Cai-Xia, LAN Shu-Fen, LU Li-Ping. Evaluation of Cu(Ⅱ) Complexes with Schiff Base of Salicylanilide as the Inhibitors of Protein Tyrosine Phosphatases[J]. Chinese Journal of Inorganic Chemistry, ;2015, (5): 915-922. doi: 10.11862/CJIC.2015.127 shu

Evaluation of Cu(Ⅱ) Complexes with Schiff Base of Salicylanilide as the Inhibitors of Protein Tyrosine Phosphatases

1.
Institute of Molecular Science, the Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China

Corresponding author: LU Li-Ping,
Received Date: 17 November 2014
Available Online: 27 January 2015
Fund Project: 国家自然科学基金(No.21001070,21171109,21471092) (No.21001070,21171109,21471092)高等学校博士学科点专项科研基金(No.20121401110005) (No.20121401110005)山西省自然科学基金(No.2011021006-2) (No.2011021006-2)山西省回国留学人员科研项目(No.2012-004)资助项目。 (No.2012-004)

To improve the inhibitory selectivity and explore the substitution effect of the Schiff base ligands on the inhibitory effect of the complex against the PTPs, three Cu(Ⅱ) complexes, [Cu(X-pimp)₂] (X-pimp=2-((4-X-phenylimino)methyl) phenol), X=Cl, Br, and Acetyl), were prepared and characterized by X-ray, EA, IR, UV-Vis and ESI-MS. Taking [Cu(Cl-pimp)₂] complex as an example, the solution species distribution with different pH values and the main existing form under the pH neutral condition were investigated using both the pHpotentiometric and UV titrations, indicating that the ration of Cl-pimp ligand and Cu(Ⅱ) ion in the complex was 2:1 in an aqueous solution and [Cu(Cl-pimp)₂H_-1]^- is the main existing form in the pHneutral condition. Then the inhibitory activities of these complexes against above-mentioned protein tyrosine phosphatase 1B(PTP1B), T-cell protein tyrosine phosphatase(TCPTP), Src homology phosphatase 1 (SHP-1), and Src homology phosphates 2 (SHP-2) was evaluated using IC₅₀ values. The results revealed that these three complexes showed similar inhibitory behaviours, i.e. potent effect against PTP1B and TCPTP (0.20 μmol·L^-1 50 <0.31 μmol·L^-1), the relatively lower effect against SHP-1 (2.7 μmol·L^-1 < IC₅₀ <4.7 μmol·L^-1), while negligible effect against SHP-2 (IC₅₀ >100 μmol·L^-1), which indicated that the type of substituents on the papa position of phenylimino of the Schiff base ligand did not influence the inhibitory effect of the complexes against PTPs obviously. However, comparing the current results to that of the above-mentioned previous work, we can find that the change in the position of the substituents may change the selectivity of inhibitory effect of the complexes against PTPs. The interactions between the complexes and PTPs were studied using [Cu(Cl-pimp)₂] and PTP1B as the representatives. The kinetics assays showed that the complex inhibited PTP1B in a non-competitive mode and the inhibition constant was calculated to be 0.35 μmol·L^-1. The fluorescence titration revealed that the complex bound to PTp1B with the molar ration of 1:1 and the binding constant of 9.3×10⁶ L·mol^-1. We infer that the [Cu(Cl-pimp)₂] complex may bind firmly to inactive area of PTP1B and indirectly lead to the structural changes to the active center, which inhibits the activity of PTP1B.
- Schiff base;Cu(Ⅱ) complex;protein tyrosine phosphatases;inhibitor;substituent effect
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