Gallic acid based steroidal phenstatin analogues for selective targeting of breast cancer cells through inhibiting tubulin polymerization

Steroids

Volumn 77, Issue 8-9, 2012, Pages 878-886

  Parihar, Swati ^a   Gupta, Atul ^a   Chaturvedi, Amit K ^a   Agarwal, Jyoti ^a   Luqman, Suaib ^a   Changkija, Bendangla ^b   Manohar, Murli ^b   Chanda, Debabrata ^a   Chanotiya, C S ^a   Shanker, Karuna ^a   Dwivedi, Anila ^b   Konwar, Rituraj ^b   Negi, Arvind S ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Acute oral toxicity; Anticancer; Gallic acid; Phenstatin; Tubulin polymerization inhibition

Indexed keywords

[3 HYDROXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 HYDROXY,3,5 DIMETHOXYPHENYL)METHANE; [3 HYDROXYLESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 HYDROXY,3 METHOXYPHENYL)METHANONE; [3 HYDROXYLESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 HYDROXY,3,5 DIMETHOXYPHENYL)METHANONE; [3 HYDROXYLESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 METHOXYPHENYL)METHANONE; [3 HYDROXYLESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 METHYLPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10) TRIEN 17BETA ACETATE 2YL] (4 METHOXYPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10) TRIEN,17BETA ACETATE 2YL] (3,4,5 TRIMETHOXYPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (3,4 DIMETHOXYPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (3,4 METHYLENEDIOXYPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (3,4,5 TRIMETHOXYPHENYL)METHANE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 BROMOPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 METHOXYPHENYL)METHANE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 METHYLPHENYL)METHANONE; [3 METHOXYESTRA 1,3,5 (10)TRIEN,17BETA ACETATE 2YL] (4 TRIMETHOXYPHENYL)METHANONE; ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; GALLIC ACID; PACLITAXEL; PHENSTATIN; STEROID; TAMOXIFEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BREAST CANCER; CANCER CELL CULTURE; CANCER CELL DESTRUCTION; CELL STRAIN MCF 7; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG STRUCTURE; FEMALE; HUMAN; HUMAN CELL; IN VIVO STUDY; MALE; MELTING POINT; MICROTUBULE ASSEMBLY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; FEMALE; GALLIC ACID; HUMANS; POLYMERIZATION; RATS; RATS, SPRAGUE-DAWLEY; TUBULIN;

MUS; RATTUS;

EID: 84861648492     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.03.012     Document Type: Article

References (30)

1. S. Sommer, and S.A. Fuqua Estrogen receptor and breast cancer Cancer Biology 11 2001 339 352 (Pubitemid 33016029)
2. F. Minutolo, M. Macchia, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Estrogen receptor β ligands: recent advances and biomedical applications Med Res Rev 31 2011 364 442
3. B.B. Sherwin Estrogen and cognitive functioning in women Endocr Rev 24 2003 133 151 (Pubitemid 36515282)
4. W. Godolphin, J.M. Elwood, and J.J. Spinelli Estrogen receptor quantitation and staging as complementary prognostic indicators in breast cancer: a study of 583 patients Int J Cancer 28 1981 677 683 (Pubitemid 12245890)
5. V.C. Jordan, and B.W. O'Malley Selective estrogen-receptor modulators and antihormonal resistance in breast cancer J Clin Oncol 25 2007 5815 5824
6. B. Fisher, J.P. Costantino, C.K. Redmond, E.R. Fisher, D.L. Wickerham, and W.M. Cronin Endometrial cancer in tamoxifen-treated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14 J Nat Cancer Inst 86 1994 527 537 (Pubitemid 24111008)
7. R. Clarke, F. Leonessa, J.N. Welch, and T.C. Skaar Cellular and molecular pharmacology of antiestrogen action and resistance Pharmacol Rev 53 2001 25 71 (Pubitemid 32173107)
8. V. Srivastava, A.S. Negi, J.K. Kumar, M.M. Gupta, and S.P.S. Khanuja Plant based anticancer molecules: a chemical and biological profile of some important molecules Bioorg Med Chem 13 2005 5892 5908 (Pubitemid 41399898)
9. G. Brandi, M. Paiardini, B. Cervasi, C. Fiorucci, P. Filippone, C. De Marco, N. Zaffaroni, and M. MaGnani The chemistry and pharmacology of indole-3-carbinol (indole-3-methanol) and 3-(methoxymethyl)indole Cancer Res 63 2003 4028 4036
10. K. Ohsumi, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, K. Ohishi, Y. Suga, Y. Akiyama, and T. Tsuji Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships J Med Chem 41 1998 3022 3032 (Pubitemid 28359938)
11. N.M. O'Boyle, M. Carr, L.M. Greene, O. Bergin, S.M. Nathwani, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents J Med Chem 53 2010 8569 8584
12. D.W. Siemann, and D.J. Chaplin A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P) Expert Opin Investig Drugs 18 2009 189 197
13. G.R. Pettit, B. Toki, D.L. Herald, P. Verdier-Pinard, M.R. Boyd, H. Hamel, and R.K. Pettit Antineoplastic agents. 379. synthesis of phenstatin phosphate1a J Med Chem 41 1998 1688 1695 (Pubitemid 28221962)
14. G.R. Pettit, M.P. Grealish, D.L. Herald, M.R. Boyd, E. Hamel, and R.K. Pettit Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug J Med Chem 43 2000 2731 2737 (Pubitemid 30463921)
15. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani Medicinal chemistry of combretastatin A4: present and future directions J Med Chem 49 2006 3033 3044 (Pubitemid 43830499)
16. IUPAC. Joint commission on biochemical nomenclature (JCBN). Nomenclature of steroids. Pure Appl Chem 1989;61:1783-1822.
17. S. Kumar, S. Deshpande, V. Chandra, S. Kitchlu, A. Dwivedi, V.L. Nayak, R. Konwar, Y.S. Prabhakar, and D.P. Sahu Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer Bioorg Med Chem 17 2009 6832 6840
18. M.L. Shelanski, F. Gaskin, and C.R. Cantor Microtubule assembly in the absence of added nucleotides Proc Nat Acad Sci 70 1973 765 768
19. J.C. Lee, and S.N. Timassheff In vitro reconstitution of calf brain microtubules: effects of solution variable Biochemistry 16 1977 1754 1762
20. R. Ghosh, V.P. Kamboj, and M.M. Singh Interaction with anti-implantation and estrogen antagonistic activities of dl-ormeloxifene, a selective estrogen receptor modulator, by tetracycline in female Sprague-Dawley rats Contraception 64 2001 261 269 (Pubitemid 34020822)
21. H.O. Saxena, U. Faridi, J.K. Kumar, S. Luqman, M.P. Darokar, K. Shanker, C.S. Chanotiya, M.M. Gupta, and A.S. Negi Synthesis of chalcone derivatives on steroidal framework and their anticancer activities Steroids 72 2007 892 900 (Pubitemid 47422269)
22. H. Gilman, A.H. Blatt, and Organic Syntheses 2nd ed. Collective vol. 1 1941 John Wiley & Sons Inc. New York p 537-38
23. Y.W. Li, J. Liu, N. Liu, D. Shi, X.T. Zhou, J.G. Lv, C.H. Zheng, and Y.J. Zhou Imidazolone-amide bridges and their effects on tubulin polymerisation in cis-locked vinylogous combretastatin-A4 analogues: synthesis and biological evaluation Bioorg Med Chem 19 2011 3579 3584
24. M.N. Ghosh Fundamentals of Experimental Pharmacology 1st ed. 1984 Scientific Book Agency Kolkata p. 156
25. L.G. Wang, X.M. Liu, W. Kreis, and D.R. Budman The effect of antimicrotubule agents on signal transduction pathways of apoptosis: a review Cancer Chemother Pharmacol 44 1999 355 361 (Pubitemid 29455579)
26. M.A. Jordan, and L. Wilson Microtubules as a target for anticancer drugs Nat Rev Cancer 4 2004 253 265 (Pubitemid 38525281)
27. G.M. Tozer, C. Kanthou, and B.C. Baguley Disrupting tumour blood vessels Nat Rev Cancer 5 2005 423 435 (Pubitemid 40791485)
28. J. Griggs, J.C. Metcalfe, and R. Hesketh Targeting tumour vasculature: the development of combretastatin A4 The Lancet Oncol 2 2001 82 87 (Pubitemid 33585919)
29. J.X. Duan, X. Cai, F. Meng, L. Lan, and M. Matteucci Potent antitubulin tumor cell cytotoxins based on 3-aroyl indazoles J Med Chem 50 2007 1001 1006 (Pubitemid 46394002)
30. R. Romagnoli, P.G. Baraldi, T. Sarkar, M.D. Carrion, C.L. Cara, O. Cruz-Lopez, D. Preti, A. Tabrizi, M. Tolomeo, S. Grimaudo, A.D. Cristina, N. Zonta, J. Balzarini, A. Brancale, H.P. Hsieh, and E. Hamel Synthesis and biological evaluation of 1-Methyl-2-(3′,4′,5′- trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors J Med Chem 51 2008 1464 1468 (Pubitemid 351480406)