Antimitotic activity of diaryl compounds with structural features resembling combretastatin A-4

Anti-Cancer Drugs

Volumn 9, Issue 6, 1998, Pages 545-550

  Aleksandrzak, Krzysztof ^a   McGown, Alan T ^a   Hadfield, John A ^a  

^a CHRISTIE HOSPITAL   (United Kingdom)

Author keywords

Antimitotic; Antitumor; Combretastatin; Molecular modeling

Indexed keywords

ANTIMITOTIC AGENT; COMBRETASTATIN A4; DIARYLAMINE; DIARYLETHER; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CELL CYCLE; CHEMICAL ANALYSIS; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; MOLECULAR MODEL; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TUMOR GROWTH;

EID: 0031869533     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/00001813-199807000-00005     Document Type: Article

References (17)

1. Pettit GR, Singh SB, Hamel E, Lin CM, Alberts DD, GariaKendall D. Antineoplastic agents. 145. Isolation and structure of the strong cell-growth and tubulin inhibitor combretastatin A-4. Experientia 1989; 45: 209-11.
2. Woods JA, Hadfield JA, Pettit GR, Fox BW, McGown AT. The interaction with tubulin of a series of stilbenes based on combretastatin A-4. Br J Cancer 1995; 71: 705-11.
3. Cushman M, Nagarathnam D, Gopal D, Chakraborti AK, Lin CM, Hamel E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J Med Chem 1991; 34: 2579-88.
4. Cushman M, Nagarathnam D, Gopal D, He H-M, Lin CM, Hamel E. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents. J Med Chem 1992; 35: 2293-3306.
5. Getahun Z, Jurd L, Chu PS, Lin CM, Hamel E. Synthesis of alkoxy-substituted diaryl compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions. J Med Chem 1992; 35: 1058-67.
6. McGown AT, Fox BW. Structural and biochemical comparison of the anti-mitotic agents colchicine, combretastatin A-4 and amphethinile. Anti-Cancer Drug Des 1989; 3: 249-54.
7. Mayer W, Fikentscher R, Schmidt J, Schmidt OT. An unusual cleavage of diaryl ethers. Chem Ber 1960; 93: 2761-76.
8. Bolon DA. Free-radical distribution of phenol dimers. J Org Chem 1967; 32: 1584-90.
9. Glombitza W, Woelwer-Rieck U. Antibiotics from algae 38. Base catalysed reactions of multiple hydroxylated diphenyl ethers. Liebigs Ann Chem 1988; 261-6.
10. McGown AT, Fox BW. Differential cytotoxicity of combretastatin A-1 and combretastatin A-4 in two daunorubicin-resistant p388 cell-lines. Cancer Chemother Pharmacol 1990; 26: 79-81.
11. Mosman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity. J Immunol Methods 1983; 65: 55-9.
12. Na GC, Timasheff SN. Interaction of vinblastine with calf brain tubulin: multiple equilibria. Biochemistry 1986; 25: 6214-22.
13. Pettit GR, Singh SB, Niven ML, Hamel E, Schmidt JM. Antineoplastic agents. 124. Isolation, structure, and synthesis of combretastatin A-1 and combretasatin B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum J Nat Prod 1987; 50: 119-31.
14. Woods JA, Hadfield JA, McGown AT, Fox BW. Bioactivity and molecular modelling of diphenylsulfides and diphenylselenides. Bioorg Med Chem 1993; 1: 333-40.
15. McGown AT, Fox BW. Interaction of the novel agent amphethinile with tubulin. Br J Cancer 1989; 59: 865-8.
16. McGown AT, Ewen C, Smith DB, Fox BW. Pre-clinical studies of a novel anti-mitotic agent, amphethinile. Br J Cancer 1988; 57: 157-9.
17. Smith DB, Ewen C, Mackintosh J, et al. A phase I and pharmacokinetic study of amphethinile. Br J Cancer 1988; 57: 623-7.