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
1. [1]
  [1] Daniel K G, Gupta P, Harach R H, et al. Biochem. Pharmacol., 2004,67:1139-2251
2. [2]
  [2] Tonks N K. Nat. Rev. Mol. Cell Biol., 2006,7:833-846
3. [3]
  [3] Hendriks W J, Elson A, Harroch S, et al. FEBS J., 2013, 280:708-730
4. [4]
  [4] Stuible M, Doody K M, Tremblay M L. Cancer Metastasis Rev., 2008,27:215-230
5. [5]
  [5] Jiang Z X, Zhang Z Y. Cancer Metastasis Rev., 2008,27:263-272
6. [6]
  [6] Lu L P, Zhu M L. Antioxid. Redox Signaling, 2014,20:2210-2224
7. [7]
  [7] LI Peng-Yu(李鹏宇), LU Li-Ping(卢丽萍). Chinese J. Inorg. Chem.(无机化学学报), 2013,29(9):1830-1834
8. [8]
  [8] Forte G, Bocca B, Peruzzu A, et al. Biol. Trace Elem. Res., 2013,156:79-90
9. [9]
  [9] Majumder S, Chatterjee S, Pal S, et al. Biometals, 2009,22: 377-384
10. [10]
  [10] Vanco J, Marek J, Travnicek Z, et al. J. Inorg. Biochem., 2008,102:595-605
11. [11]
  [11] Qazzaz M, Abdul-Ghani R, Metani M, et al. Biol. Trace Elem. Res., 2013,154:88-96
12. [12]
  [12] YE Xing-Pei(叶行培), WANG Guan-Jie(王冠杰), PAN Peng (潘鹏), et al. Chinese J. Inorg. Chem.(无机化学学报), 2014, 30(12):2789-2795
13. [13]
  [13] MA Zheng-Ping(马正平), CHEN Qiu-Yun(陈秋云), FENG Ru(封如). Chinese J. Inorg. Chem.(无机化学学报), 2012, 28(11):2395-1400
14. [14]
  [14] Yuan C X, Zhu M L, Wang Q M, et al. Chem. Commun., 2012,48:1153-1155
15. [15]
  [15] Wang Q M, Lu L P, Yuan C X, et al. Chem. Commun., 2010,46:3547-3549
16. [16]
  [16] Wang Q M, Zhu M L, Lu L P, et al. Dalton Trans., 2011,40: 12926-12934
17. [17]
  [17] Ma L, Lu L P, Zhu M L, et al. Dalton Trans., 2011,40:6532-6540
18. [18]
  [18] Ma L, Lu L P, Zhu M L, et al. J. Inorg. Biochem., 2011,105: 1138-1147
19. [19]
  [19] Li Y, Lu L P, Zhu M L, et al. Biometals, 2011,24:993-1004
20. [20]
  [20] Zhu R T, Lu L P, Zhu M L. Inorg. Chim. Acta, 2013,405: 91-97
21. [21]
  [21] Yuan C X, Lu L P, Gao X L, et al. J. Biol. Inorg. Chem., 2009,14:841-851
22. [22]
  [22] GAO Xiao-Li(高晓丽), LU Li-Ping(卢丽萍), ZHU Miao-Li (朱苗力), et al. Acta Chim. Sinica(化学学报), 2009,9:929-936
23. [23]
  [23] Zhu Z, Sun M, Zhang X, et al. Chem. Res. Chin. Univ., 2007, 23:289-296
24. [24]
  [24] Li W N, Zhuang Y, Li H, et al. Chem. Res. Chin. Univ., 2008,24:592-596
25. [25]
  [25] MIAO Qiu-Li(苗秋丽). Thesis for the Master of Jilin University (吉林大学硕士论文). 2010.
26. [26]
  [26] Han H, Lu L P, Wang Q M, et al. Dalton Trans., 2012,41: 11116-11124
27. [27]
  [27] Han Q F, Jian F F, Lu L D, et al. J. Chem. Cystal, 2001,31 (5):247-250
28. [28]
  [28] Yuan C X, Lu L P, Wu Y B, et al. J. Inorg. Biochem., 2010, 104:978-986
29. [29]
  [29] Gans P, Vacca A, Sabatini A. J. Chem. Soc., Dalton Trans., 1985:1195-1200
30. [30]
  [30] Woolley E M, Tomkins J, Hepler L G. J. Solution Chem., 1972,1:341-351
31. [31]
  [31] Takács-Novák K, Box K J, Avdeef A. Int. J. Pharm., 1997, 151:235-248
32. [32]
  [32] Ember B, Kamenecka T, LoGrasso P. Biochemistry, 2008, 47:3076-3084
33. [33]
  [33] Mondal S, Rath S P, Rajak K K, et al. Inorg. Chem., 1998, 37:1713-1719
34. [34]
  [34] CHEN Zhan-Fen(陈战芬), MA Yi-Dan(马艺丹), HUA Luo-Guang(华罗光), et al. Chinese J. Inorg. Chem.(无机化学学报), 2014,30(7):1525-1534
35. [35]
  [35] Ding F, Zhao G Y, Huang J L, et al. Eur. J. Med. Chem., 2009,44:4083-4089
36. [36]
  [36] Wang H Y, Zhang M, Lü Q L, et al. Spectrochim. Acta Part A, 2009,73:682-686
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
4. [4]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
5. [5]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
6. [6]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
7. [7]
  Xiaotian ZHU , Fangding HUANG , Wenchang ZHU , Jianqing ZHAO . Layered oxide cathode for sodium-ion batteries: Surface and interface modification and suppressed gas generation effect. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 254-266. doi: 10.11862/CJIC.20240260
8. [8]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
9. [9]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
10. [10]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
11. [11]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
12. [12]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
13. [13]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
14. [14]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
15. [15]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
16. [16]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
17. [17]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
18. [18]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
19. [19]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
20. [20]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(340)
HTML views(21)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142