Citation: Lei Zhao, Jiu-Jiu Zhou, Xin-Ying Huang, Li-Ping Cheng, Wan Pang, Zhen-Peng Kai, Fan-Hong Wu. Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs[J]. Chinese Chemical Letters, ;2015, 26(8): 993-999. doi: 10.1016/j.cclet.2015.05.003 shu

Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs

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School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China

Corresponding author: Wan Pang, Zhen-Peng Kai, Fan-Hong Wu,
Received Date: 25 February 2015
Available Online: 27 April 2015
Fund Project: This work was supported by the National Natural Science Foundation of China (Nos. 21472126, 21402122) (Nos. 21472126, 21402122)Shanghai Municipal Natural Science Foundation (No. 12ZR450200). (No. 12ZR450200)

A total of 11 novel combretastatin A-4 (CA-4) analogs were designed, synthesized, and evaluated for the anti-proliferative effects in tumor cells. The compounds represent four structural classes: (i) hydrogenated derivatives, (ii) ethoxyl derivatives, (iii) amino derivatives and (iv) pro-drugs. Biological evaluations demonstrate that multiple structural features control the biological potency. Three of the compounds, sit-1, sit-2 and sit-3, have potent anti-proliferative activity against multiple cancer cell lines. Their pro-drugs were synthesized to increase water solubility. Structure-activity relationship study and Surflex-Docking were studied in this paper. These results will be useful for the design of new CA-4 analogs that are structurally related to the SAR study.
- Combretastatin A-4,
- Anti-proliferative,
- Synthesized
1. [1]
  [1] G.R. Pettit, G.M. Cragg, D.L. Herald, J.M. Schmidt, P. Lohavanijaya, Isolation and structure of combretastatin, Can. J. Chem. 60 (1982) 1374-1376.
2. [2]
  [2] G.R. Pettit, S.B. Singh, E. Hamel, et al., Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4, Experientia 45 (1989) 209-211.
3. [3]
  [3] A.A.E. El-Zayat, D. Degen, S. Drabek, et al., In vitro evaluation of the antineoplastic activity of combretastatin A-4, a natural product from Combretum caffrum (arid shrub), Anticancer Drugs 4 (1993) 19-25.
4. [4]
  [4] G.R. Pettit, B.E. Toki, D.L. Herald, et al., Antineoplastic agents. 410. Asymmetric hydroxylation of trans-combretastatin A-4, J. Med. Chem. 42 (1999) 1459-1465.
5. [5]
  [5] G.R. Pettit, M.R. Rhodes, D.L. Herald, et al., Antineoplastic agents 393. Synthesis of the trans-isomer of combretastatin A-4 prodrug, Anti-Cancer Drug Des. 13 (1999) 981-993.
6. [6]
  [6] K. Ohsumi, R. Nakagawa, Y. Fukuda, et al., Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships, J. Med. Chem. 41 (1998) 3022-3032.
7. [7]
  [7] E.D. Durrant, J. Richards, A. Tripathi, et al., Development of water soluble derivatives of cis-3 4',5-trimethoxy-3'-aminostilbene for optimization and use in cancer therapy, Invest. New Drugs 27 (2009) 41-52.
8. [8]
  [8] P. Tresca, D. Tosi, L. Doorn, et al., Phase I and pharmacologic study of the vascular disrupting agent ombrabulin (Ob) combined with docetaxel (D) in patients (pts) with advanced solid tumors, J. Clin. Oncol. 28 (2010) 3023.
9. [9]
  [9] J.H. Jiang, C.H. Zheng, C.Q. Wang, et al., Synthesis and biological evaluation of 5,6,7-trimethoxy-1-benzylidene-3,4-dihydro-naphthalen-2-one as tubulin-polymerization inhibitors, Chin. Chem. Lett. (2015), http://dx.doi.org/10.1016/ j.cclet.2015.03.022.
10. [10]
  [10] W.P. Shen, Y.J. Diao, H.M. Jin, J.P. Wang, J.G. Wang［32_TD$DIF］, Polymer-supported preparation of Combretastatin A4 using poly(4-(chlorodiphenylmethyl)styrene) as solid carrier, CN1704393A, 2005.
11. [11]
  [11] G.R. Pettit, M.R. Rhodes, D.L. Herald, et al., Antineoplastic agents. 445. Synthesis and evaluation of structural modifications of (Z)-and (E)-combretastatin A-4, J. Med. Chem. 48 (2005) 4087-4099.
12. [12]
  [12] Z.P. Kai, Y. Ling, W.J. Liu, F. Zhao, X.L. Yang, The study of solution conformation of allatostatins by 2-D NMR and molecular modeling, Biochim. Biophys. Acta 1764 (2006) 70-75.
13. [13]
  [13] R. Spitzer, A.N. Jain, Surflex-Dock: docking benchmarks and real-world application, J. Comput. Aided Mol. Des. 26 (2012) 687-699.
14. [14]
  [14] F.H. Wu, W.G. Zhou, F.M. Xu, F.H. Xiao, Ethoxy diphenyl ethane derivates, preparation processes and medical application as tubulin polymerization inhibitor, CN101723813A［34_TD$DIF］, 2010.
15. [15]
  [15] O. Taratula, P.A. Hill, Y.B. Bai, N.S. Khan, I. Dmochowski, Shorter synthesis of trifunctionalized cryptophane-A derivatives, Org. Lett. 13 (2011) 1414-1417.
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沈阳化工大学材料科学与工程学院沈阳 110142