Synthesis and mechanistic studies of novel spin-labeled combretastatin derivatives as potential antineoplastic agents

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 5, 2013, Pages 1248-1256

  Liu, Ying Qian ^a   Li, Xiao Jing ^a   Zhao, Chun Yan ^a   Nan, Xiang ^a   Tian, Jing ^a   Morris Natschke, Susan L ^b   Zhang, Zhi Jun ^a   Yang, Xiao Ming ^b   Yang, Liu ^d   Li, Lin Hai ^a   Zhou, Xing Wen ^a   Lee, Kuo Hsiung ^b,c  

^a LANZHOU UNIVERSITY   (China)

^b University of North Carolina   (United States)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

^d LANZHOU JIAOTONG UNIVERSITY   (China)

Author keywords

Combretastatin; Cytotoxicity; Mechanistic analysis; Nitroxide; Spin labeled

Indexed keywords

3' N (1'' OXYL 2'',2'',5'',5'' TETRAMETHYL 3'' PYRROLIDINYLCARBONYL) AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' TETRAHYDROPYRIDINYLCARBONYL) AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N (1''' OXYL 2'',2'',5'',5'' TETRAMETHYL 3'' PYRROLINYLCARBONYL) AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO ALANINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO ISOLEUCINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO METHIONINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO PHENYLALANINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO PROLINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO TYROSINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; 3' N [N (1'' OXYL 2'',2'',6'',6'' TETRAMETHYL 4'' PIPERIDINYLCARBONYL) LEVO VALINYL] AMIDO 3 AMINO DEOXYCOMBRETASTATIN A4; ANTINEOPLASTIC AGENT; COMBRETASTATIN; ETOPOSIDE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE ARREST; CELL STRAIN HEPG2; CELL STRAIN K 562; CELL STRAIN SGC 7901; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MICROTUBULE ASSEMBLY; MITOSIS; POLYMERIZATION; SPIN LABELING;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BIBENZYLS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HEP G2 CELLS; HUMANS; K562 CELLS; MITOSIS; SPIN LABELS; TUBULIN; TUBULIN MODULATORS;

EID: 84873733214     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.12.046     Document Type: Article

References (27)

1. A. Cirla, and J. Mann Nat. Prod. Rep. 20 2003 558
2. N.H. Nam Curr. Med. Chem. 10 2003 1697
3. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033
4. D.W. Siemann, D.J. Chaplin, and P.A. Walicke Expert Opin. Invest. Drugs 18 2009 189
5. G.M. Tozer, C. Kanthou, C.S. Parkins, and S.A. Hill Int. J. Exp. Pathol. 83 2002 21
6. A. Chaudhary, S.N. Pandeya, P. Kumar, P.P. Sharma, S. Gupta, N. Soni, K.K. Verma, and G. Bhardwaj Mini-Rev. Med. Chem. 7 2007 1186
7. N. Naik, and R. Braslau Synthesis and applications of optically active nitroxides Tetrahedron 54 1998 99
8. -B.P. Soule, F. Hyodo, K. Matsumoto, N.L. Simone, J.A. Cook, M.C. Krishna, and J.B. Mitchell Free Radical Biol. Med. 42 2007 1632
9. Z.D. Raikov, A.T. Atanasov, and E.T. Raikova Med. Hypotheses 60 2003 387
10. V.G. Gadjeva Int. J. Pharm. 247 2002 39
11. A. Zheleva, S. Stanilova, Z. Dobreva, and Z. Zhelev Int. J. Pharm. 222 2001 237
12. Y.Q. Liu, X. Tian, L. Yang, and Z.C. Zhan Europ J. Med. Chem. 43 2008 2610
13. X. Tian, Y.G. Wang, M.G. Yang, and Y.Z. Chen Life Sci. 60 1997 511
14. Y. Jin, S.W. Chen, and X. Tian Bioorg. Med. Chem. 14 2006 3062
15. X. Tian, F.M. Zhang, and W.G. Li Life Sci. 70 2002 2433
16. Z.W. Zhang, J.Q. Zhang, L. Hui, S.W. Chen, and X. Tian Europ J. Med. Chem. 45 2010 1673
17. Y.Q. Liu, E. Ohkoshi, L.H. Li, L. Yang, and K.H. Lee Bioorg. Med. Chem. Lett. 22 2012 920
18. Y.Q. Liu, L. Yang, and X. Tian Curr. Bioact. Compd. 3 2007 73
19. X.J. Li, L. Yang, Y.Q. Liu, and C. Li Nat. Prod. Res. 26 2012 1271
20. K. Gaukroger, J.A. Hadfield, L.A. Hepworth, N.J. Lawrence, and A.T. McGown J. Org. Chem. 66 2001 8135
21. G.R. Pettit, C.R. Anderson, D.L. Herald, M.K. Jung, D.J. Lee, E. Hamel, and R.K. Pettit J. Med. Chem. 46 2003 525
22. Y.Q. Liu, and X. Tian Synth. Commun. 35 2005 2749
23. L.V. Rubinstein, R.H. Shoemaker, and K.D. Paull J. Natl. Cancer Inst. 82 1990 1113
24. G.R. Pettit, S.B. Singh, E. Hamel, C.M. Lin, D.S. Alberts, and D. Garcia-Kendall Experentia 45 1989 209
25. C.M. Lin, H.H. Ho, G.R. Pettit, and E. Hamel Biochemistry 28 1989 6984
26. R. Gambari, M. Terada, A. Bank, R.A. Rifkind, and P.A. Marks Proc. Natl. Acad. Sci. U.S.A. 75 1978 3801
27. E. Hamel, and C.M. Lin Biochemistry 23 1984 4173