Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)- hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 10, 2005, Pages 3565-3575

  Lin, Chi Fong ^b   Lo, Yu Hsiang ^a   Hsieh, Ming Chu ^a   Chen, Yi Hua ^a   Wang, Jeh Jeng ^a   Wu, Ming Jung ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b CHUNG HWA UNIVERSITY OF MEDICAL TECHNOLOGY   (Taiwan)

Author keywords

Antitumor agents; Caspase; Enediyne; G2 M blocker

Indexed keywords

1,2 BIS(2 ANILINYL)ETHYNYLBENZENE; 1,2 BIS(2 ANISOLYL)ETHYNYLBENZENE; 1,2 BIS(2 PYRAZINYL)ETHYNYLBENZENE; 1,2 BIS(2 PYRIDINYL)ETHYNYLBENZENE; 1,2 BIS(2 THIEANISOLYL)ETHYNYLBENZENE; 1,2 BIS(2 THIENYL)ETHYNYLBENZENE; 1,2 BIS(2 TRIFLUOROMETHYLPHENYL)ETHYNYLBENZENE; 1,4 BIS[6 (2 ANILINYL) 3 HEXEN 1,5 DIYNYL]BENZENE; 1,6 BIS(2 ANILINYL) 3 HEXEN 1,5 DIYNE; 1,6 BIS(2 ANISOLYL) 3 HEXEN 1,5 DIYNE; 1,6 DIPYRIDINYL 3 HEXEN 1,5 DIYNE; 2 [6 (2 ANISOLYL) 3 HEXEN 1,5 DIYNYL]ANILINE; 2 [6 (2 PYRAZINYL) 3 HEXEN 1,5 DIYNYL]ANILINE; 2 [6 (2 PYRIDINYL) 3 HEXEN 1,5 DIYNYL]ANILINE; 2 [6 (2 THIEANISOLYL) 3 HEXEN 1,5 DIYNYL]ANILINE; 2 [6 (2 THIENYL) 3 HEXEN 1,5 DIYNYL]ANILINE; ALKYNE DERIVATIVE; ANILINE DERIVATIVE; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; CASPASE 3; UNCLASSIFIED DRUG; [1 (2 ANILINYLETHYNYL) 2 (2 ANISOLYLETHYNYL)]BENZENE; [1 (2 ANILINYLETHYNYL) 2 (2 PYRAZINYLETHYNYL)]BENZENE; [1 (2 ANILINYLETHYNYL) 2 (2 PYRIDINYLETHYNYL)]BENZENE; [1 (2 ANILINYLETHYNYL) 2 (2 THIEANISOLYLETHYNYL)]BENZENE; [1 (2 ANILINYLETHYNYL) 2 (2 THIENYLETHYNYL)]BENZENE;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE; CELL CYCLE G2 PHASE; COLORIMETRY; CONTROLLED STUDY; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; STATISTICAL SIGNIFICANCE;

EID: 17444431167     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.02.062     Document Type: Article

References (37)

1. G.B. Jones, G. Hynd, J.M. Wright, A. Purohit, G.W. Plourde, R.S. Huber, J.E. Mathews, A. Li, M.W. Kilgore, G.J. Bubley, M. Yancisin, and M.A. Brown J. Org. Chem. 66 2001 3688
2. I.V. Alabugin, M. Manoharan, and S.V. Kovalenko Org. Lett. 4 2002 1119
3. S. Walkers, K.G. Valentine, and D. Kahne J. Am. Chem. Soc. 112 1990 6428
4. L. Dark, N. Iwasawa, S. Danishefsky, and D.M. Crother Proc. Natl. Acad. Sci. U.S.A. 88 1991 7464
5. L.F. Povirk, and I.H. Goldberg Biochemistry 19 1980 4773
6. A.G. Myers, E.Y. Kuo, and N.S. Finny J. Am. Chem. Soc. 111 1989 8057
7. L.S. Kappen, and I.H. Goldberg Nucleic Acid Res. 5 1978 2959
8. G.B. Jones, J.M. Wright, G. Hynd, J.K. Wyatt, M. Yancisin, and M.A. Brown Org. Lett. 2 2000 1863
9. M.J. Wu, C.F. Lin, S.H. Chen, and F.C. Lee J. Chem. Soc., Perkin Trans. 1 1999 2875
10. D.M. Wendi, and S.M. Kerwin J. Am. Chem. Soc. 119 1997 1464
11. A. Tarli, and K.K. Wang J. Org. Chem. 62 1997 8841
12. C.F. Lin, and M.J. Wu J. Org. Chem. 62 1997 4546
13. M.J. Wu, C.F. Lin, and C.W. Ong Bioorg. Med. Chem. Lett. 6 1996 675
14. M.J. Wu, C.F. Lin, J.S. Wu, and H.T. Chen Tetrahedron Lett. 35 1994 1879
15. S.L. Xu, and H.W. Moore J. Org. Chem. 57 1992 326
16. A.G. Myers Tetrahedron Lett. 28 1987 4493
17. T.P. Lockhart, P.B. Comita, and R.G. Bergman J. Am. Chem. Soc. 103 1981 4082
18. R.R. Jones, and R.G. Bergman J. Am. Chem. Soc. 94 1972 660
19. R.G. Bergman Acc. Chem. Res. 6 1973 25
20. C.F. Lin, W.D. Lu, P.C. Hsieh, Y.H. Kuo, C.J. Wang, and M.J. Wu Helv. Chim. Acta 8 2002 2564
21. C.F. Lin, P.C. Hsieh, W.D. Lu, H.F. Chiu, and M.J. Wu Bioorg. Med. Chem. 9 2001 1707
22. Y.H. Lo, C.F. Lin, M.C. Hsieh, and M.J. Wu Bioorg. Med. Chem. 12 2004 1047
23. The cytotoxic evaluations of compounds 3-23 were supported by National Cancer Institute
24. A. Herunsalee, M. Isobe, and T. Goto Tetrahedron 23 1991 3727
25. R.J. McMahon, R.J. Halter, R.L. Fimmen, R.J. Wilson, S.A. Peebles, R.L. Kuczkowski, and J.F. Stanton J. Am. Chem. Soc. 5 2000 939
26. J.A. Walker, S.P. Bitler, and F. Wudl J. Org. Chem. 24 1984 4733
27. T. Tsukiyama, and M. Isobe Tetrahedron Lett. 51 1992 7911
28. M.M. McPhee, and S.M. Kerwin J. Org. Chem. 26 1996 9385
29. E. Bosch, and L. Jeffries Tetrahedron Lett. 46 2001 8141
30. A. Arcadi, S. Cacchi, and F. Marinelli Tetrahedron Lett. 19 1989 2581
31. K.L. Simth, and P.S. Ray Heterocycles 1 1997 11
32. K. Sonogashira, T. Yatake, Y. Tohda, S. Takahashi, and N. Hagihara Chem. Commun. 1977 291
33. M.R. Boyd Status of implementation of the NCI human tumor cell in vitro primary drug screen Am. Assoc. Cancer Res. 30 1989 652
34. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Poull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Cambell, J. Mayo, and M. Boyd J. Natl. Cancer Inst. 83 1991 757
35. The primary anticancer assays of compounds 3-23 were tested for three tumor cell lines consisting of the MCF7 (breast cancer), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer). Compounds 3, 6-7, 9-10, 15-17, and 20-21, which reduced the growth of any one of the cell lines to approximately 32% or less were passed on for evaluation in the full panel of 60 cell lines
36. H. Wajant, K. Pfizenmaier, and P. Scheurich Cell Death Differen. 10 2003 45
37. B. Martin, M. Kirsty, S.W. Chan, J.P. Luzio, S. Robert, and P. Weissberg Science 282 1998 290