Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety

Journal of Medicinal Chemistry

Volumn 48, Issue 2, 2005, Pages 556-568

  Maya, Ana B S ^a   Pérez Melero, Concepción ^a   Mateo, Carmen ^a   Alonso, Dulce ^a   Fernández, José Luis ^b   Gajate, Consuelo ^a   Mollinedo, Faustino ^a   Peláez, Rafael ^a   Caballero, Esther ^a   Medarde, Manuel ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b Instituto Biomar SA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMBRETASTATIN; COMBRETASTATIN A4; DRUG RESIDUE; ISOVANILLIN; NAPHTHALENE DERIVATIVE; NAPHTHYLCOMBRETASTATIN DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CELL CYCLE G2 PHASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; MITOSIS INHIBITION;

ANILINE COMPOUNDS; ANTINEOPLASTIC AGENTS; BIOPOLYMERS; CELL CYCLE; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICROTUBULES; NAPHTHALENES; STEREOISOMERISM; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN;

EID: 19944433930     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0310737     Document Type: Article

References (57)

1. Hyams, J.; Lloyd, C. W. Microtubules; Wiley-Liss: New York, 1994.
2. Shi, Q.; Chen, K.; MorrisNatschke, S. L.; Lee, K. H. Recent progress in the development of tubulin inhibitors as antimitotic antitumor agents. Curr. Pharm. Des. 1998, 4, 219-248.
3. ter Haar, E.; Rosenkranz, H. S.; Hamel, E.; Day, B. W. Computational and molecular modeling evaluation of the structural basis for tubulin polymerization inhibition by colchicine site agents. Bioorg. Med. Chem. 1996, 4, 1659-1671.
4. Zhang, S. X.; Feng, J.; Kuo, S. C.; Brossi, A.; Hamel, E.; Tropsha, A.; Lee, K. H. Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis. J. Med. Chem. 2000, 43, 167-176.
5. Rai, S. S.; Wolff, J. Localization of the vinblastine-binding site on beta-tubulin. J. Biol. Chem. 1996, 271, 14707-14711.
6. Andreu, J. M.; Barasoain, I. The interaction of baccatin III with the Taxol binding site of microtubules determined by a homogeneous assay with fluorescent taxoid. Biochemistry 2001, 40, 11975-11984.
7. Diaz, J. F.; Barasoain, I.; Andreu, J. M. Fast kinetics of Taxol binding to microtubules. Effects of solution variables and microtubule-associated proteins. J. Biol. Chem. 2003, 278, 8407-8419.
8. Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGown, A. T. Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle. Med. Res. Rev. 1998, 18, 259-296.
9. Ravelli, R. B. G.; Gigant, B.; Curmi, P. A.; Jourdain, I.; Lachkar, S.; Sobel, A.; Knossow, M. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 2004, 428, 198-202.
10. Nam, N. H. Combretastatin A-4 Analogues as Antimitotic Antitumor Agents. Curr. Med. Chem. 2003, 10, 1697-1722.
11. Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem. 1991, 34, 2579-2588.
12. Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H. M.; Lin, C. M.; 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, 2293-2306.
13. Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. J. Med. Chem. 1995, 38, 1666-1672.
14. Liekens, S.; De Clercq, E.; Neyts, J. Angiogenesis: regulators and clinical applications. Biochem. Pharmacol. 2001, 61, 253-270.
15. Dark, G. G.; Hill, S. A.; Prise, V. E.; Tozer, G. M.; Pettit, G. R.; Chaplin, D. J. Combretastatin A-4, an agent that displays potent and selective toxicity toward tumor vasculature. Cancer Res. 1997, 57, 1829-1834.
16. Brown, R. T.; Fox, B. W.; Hadfield, J. A.; McGown, A. T.; Mayalarp, S. P.; Pettit, G. R.; Woods, J. A. Synthesis of Water-soluble Sugar Derivatives of Combretastatin A-4. J. Chem. Soc., Perkin Trans. 1 1995, 577-581.
17. Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series). Carbohydr. Res. 1997, 301, 95-109.
18. Ohsumi, K; Hatanaka, T.; Nakagawa, R.; Fukuda, Y.; Morinaga, Y.; Suga, Y.; Nihei, Y.; Ohishi, K.; Akiyama, Y.; Tsuji, T. Synthesis and antitumor activities of amino acid prodrugs of amino-combretastatins. Anticancer Drug Des. 1999, 14, 539-548.
19. Bedford, S. B.; Quarterman, C. P.; Rathbone, D. L.; Slack, J. A.; Griffin, R. J.; Stevens, M. F. G. Synthesis of water-soluble prodrugs of the cytotoxic agent combretastatin A4. Bioorg. Med. Chem. Lett. 1998, 6, 157-160.
20. Pettit, G. R.; Temple, C., Jr.; Narayanan, V. L.; Varma, R.; Simpson, M. J.; Boyd, M. R.; Rener, G. A.; Bansal, N. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs. Anticancer Drug Des. 1995, 10, 299-309.
21. Pettit, G. R.; Cragg, G. M.; Herald, D. L.; Schmidt, J. M.; Lohavanijaya, P. Isolation and structure of combretastatin. Can. J. Chem. 1982, 60, 1374-1376.
22. Nandy, P.; Banerjee, S.; Gao, H.; Hui, M. B.; Lien, E. J. Quantitative structure-activity relationship analysis of combretastatins: a class of novel antimitotic agents. Pharm. Res. 1991, 8, 776-781.
23. Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: a structure-activity study. Mol. Pharmacol. 1988, 34, 200-208,
24. Brown, M. L.; Rieger, J. M.; Macdonald, T. L. Comparative molecular field analysis of colchicine inhibition and tubulin polymerization for combretastatins binding to the colchicine binding site on beta-tubulin. Bioorg. Med. Chem. 2000, 8, 1433-1441.
25. Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 28, 6984-6991.
26. Ohsumi, K.; Nakagawa, R.; Fukuda, Y.; Hatanaka, T.; Morinaga, Y.; Nihei, Y.; Ohishi, K.; Suga, Y.; Akiyama, Y.; Tsuji, T. Novel combretastatin analogues effective against murine solid tumors: Design and structure-activity relationships. J. Med. Chem. 1998, 41, 3022-3032.
27. Rubenstein, S. M.; Baichwal, V.; Beckmann, H.; Clark, D. L.; Frankmoelle, W.; Roche, D.; Santha, E.; Schwender, S.; Thoolen, M.; Ye, Q. P.; Jaen, J. C. Hydrophilic, pro-drug analogues of T138067 are efficacious in controlling tumor growth in vivo and show a decreased ability to cross the blood brain barrier. J. Med. Chem. 2001, 44, 3599-3605.
28. Shan, B.; Medina, J. C.; Santha, E.; Frankmoelle, W. P.; Chou, T. C.; Learned, R. M.; Narbut, M. R.; Stott, D.; Wu, P. G.; Jaen, J. C.; Rosen, T.; Timmermans, P.; Beckmann, H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 5686-5691.
29. Medina, J. C.; Shan, B.; Beckmann, H.; Farrell, R. P.; Clark, D. L.; Learned, R. M.; Roche, D.; Li, A.; Baichwal, V.; Case, C.; Baeuerle, P. A.; Rosen, T.; Jaen, J. C. Novel antineoplastic agents with efficacy against multidrug resistant tumor cells. Bioorg. Med. Chem. Lett. 1998, 8, 2653-2656.
30. Medina, J. C.; Roche, D.; Shan, B.; Learned, R. M.; Frankmoelle, W. P.; Clark, D. L.; Rosen, T.; Jaen, J. C. Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells. Bioorg. Med. Chem. Lett. 1999, 9, 1843-1846.
31. Gwaltney, S. L.; Imade, H. M.; Barr, K. J.; Li, Q.; Gehrke, L.; Credo, R. B.; Warner, R. B.; Lee, J. Y.; Kovar, P.; Wang, J. Y.; Nukkala, M. A.; Zielinski, N. A.; Frost, D.; Ng, S. C.; Sham, H. L. Novel sulfonate analogues of combretastatin A-4: Potent antimitotic agents. Bioorg. Med. Chem. Lett. 2001, 11, 871-874.
32. Gwaltney, S. L.; Imade, H. M.; Li, Q.; Gehrke, L.; Credo, R. B.; Warner, R. B.; Lee, J. Y.; Kovar, P.; Frost, D.; Ng, S. C.; Sham, H. L. Novel sulfonate derivatives: Potent antimitotic agents. Bioorg. Med. Chem. Lett. 2001, 11, 1671-1673.
33. Cushman, M.; He, H. M.; Lin, C. M.; Hamel, E. Synthesis and evaluation of a series of benzylaniline hydrochlorides as potential cytotoxic and antimitotic agents acting by inhibition of tubulin polymerization. J. Med. Chem. 1993, 36, 2817-2821.
34. Mu, F.; Hamel, E.; Lee, D. J.; Pryor, D. E.; Cushman, M. Synthesis, anticancer activity, and inhibition of tubulin polymerization by conformationally restricted analogues of lavendustin A. J. Med. Chem. 2003, 46, 1670-1682.
35. Shirai, R.; Tokuda, K.; Koiso, Y.; Iwasaki, S. Synthesis and anti-Tubulin activity of aza-Combretastatins. Bioorg. Med. Chem. Lett. 1994, 4, 699-704.
36. Lawrence, N. J.; Rennison, D.; Woo, M.; McGown, A. T.; Hadfield, J. A. Antimitotic and cell growth inhibitory properties of combretastatin A-4-like ethers. Bioorg. Med. Chem. Lett. 2001, 11, 51-54.
37. Nam, N. H.; Kim, Y.; You, Y. J.; Hong, D. H.; Kim, H. M.; Ahn, B. Z. Synthesis and anti-tumor activity of novel combretastatins: Combretocyclopentenones and related analogues. Bioorg. Med. Chem. Lett. 2002, 12, 1955-1958.
38. Westwell, A. D. Novel antitumour molecules. Drug Discovery Today 2003, 8, 421-422.
39. Ohsumi, K.; Hatanaka, T.; Fujita, K.; Nakagawa, R.; Fukuda, Y.; Nihei, Y.; Suga, Y.; Morinaga, Y.; Akiyama, Y.; Tsuji, T. Syntheses and antitumor activity of cis-restricted combretastatins: 5-membered heterocyclic analogues. Bioorg. Med. Chem. Lett. 1998, 8, 3153-3158.
40. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y. H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Potent, orally active heterocycle-based combretastatin A-4 analogues: Synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J. Med. Chem. 2002, 45, 1697-1711.
41. Nam, N. H.; Kim, Y.; You, Y. J.; Hong, D. H.; Kim, H. M.; Ahn, B. Z. Combretoxazolones: Synthesis, cytotoxicity and antitumor activity. Bioorg. Med. Chem. Lett. 2001, 11, 3073-3076.
42. Flynn, B. L.; Flynn, G. P.; Hamel, E.; Jung, M. K. The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. Bioorg. Med. Chem. Lett. 2001, 11, 2341-2343.
43. Chen, Z.; Mocharla, V. P.; Farmer, J. M.; Pettit, G. R.; Hamel, E.; Pinney, K. G. Preparation of new anti-tubulin ligands through a dual-mode, addition-elimination reaction to a bromo-substituted alpha,beta-unsaturated sulfoxide. J. Org. Chem. 2000, 65, 8811-8815.
44. Shirai, R.; Okabe, T.; Iwasaki, S. Synthesis of conformationary restricted combretastatins. Heterocycles 1997, 46, 145-148.
45. Shirai, R.; Takayama, H.; Nishikawa, A.; Koiso, Y.; Hashimoto, Y. Asymmetric synthesis of antimitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells. Bioorg. Med. Chem. Lett. 1998, 8, 1997-2000.
46. Kim, Y.; Nam, N. H.; You, Y. J.; Ahn, B. Z. Synthesis and cytotoxicity of 3,4-diaryl-2(5H)-furanones. Bioorg. Med. Chem. Lett. 2002, 12, 719-722.
47. Flynn, B. L.; Hamel, E.; Jung, M. K. One-pot synthesis of benzo-[b]furan and indole inhibitors of tubulin polymerization. J. Med. Chem. 2002, 45, 2670-2673.
48. Medarde, M.; Ramos, A.; Caballero, E.; deClairac, R. P. L.; Lopez, J. L.; Gravalos, D. G.; SanFeliciano, A. Synthesis and antineoplastic activity of combretastatin analogues: Heterocombretastatins. Eur. J. Med. Chem. 1998, 33, 71-77.
49. Medarde, M.; Ramos, A. C.; Caballero, E.; de Clairac, R. P. L.; Lopez, J. L.; Gravalos, D. G.; Feliciano, A. S. Synthesis and pharmacological activity of diarylindole derivatives. Cytotoxic agents based on combretastatins. Bioorg. Med. Chem. Lett. 1999, 9, 2303-2308.
50. del Rey, B.; Ramos, A. C.; Caballero, E.; Inchaustti, A.; Yaluff, G.; Medarde, M.; de Arias, A. R.; San Feliciano, A. Leishmanicidal activity of combretastin analogues and heteroanalogues. Bioorg. Med. Chem. Lett. 1999, 9, 2711-2714.
51. Maya, A. B. S.; del Rey, B.; de Clairac, R. P. L.; Caballero, E.; Barasoain, I.; Andreu, J. M.; Medarde, M. Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4. Bioorg. Med. Chem. Lett. 2000, 10, 2549-2551.
52. Shelanski, M. L.; Gaskin, F.; Cantor, C. R. Microtubule assembly in the absence of added nucleotides. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 765-768.
53. Dumortier, C.; Gorbunoff, M.; Andreu, J. M.; Engelborghs, Y. Different kinetic pathways of the binding of two biphenyl analogues of colchicine to tubulin. Biochemistry 1998, 35, 4387-4395.
54. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quntities of protein using the principle of protein-binding dye. Anal. Biochem. 1976, 72, 248-254.
55. Han, Y.; Chaudhary, A. G.; Chordia, M. D.; Sackett, D. L.; Perez-Ramirez, B.; Kingston, D. G. I.; Bane, S. Interaction of a fluorescent derivative of paclitaxel (Taxol) with microtubules and tubulin-colchicine. Biochemistry 1998, 35, 14173-14183.
56. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
57. Gajate, C.; Barasoain, I.; Andreu, J. M.; Mollinedo, F. Induction of apoptosis in leukemic cells by the reversible microtubule-disrupting agent 2-methoxy-5-(2′,3′,4′-trimethoxyphenyl)-2,4, 6-cycloheptatrien-1-one: protection by Bcl-2 and BcI-X(L) and cell cycle arrest. Cancer Res. 2000, 60, 2651-2659.