New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies

Journal of Medicinal Chemistry

Volumn 49, Issue 3, 2006, Pages 947-954

  De Martino, Gabriella ^a   Edler, Michael C ^d   La Regina, Giuseppe ^a   Coluccia, Antonio ^a   Barbera, Maria Chiara ^b   Barrow, Denise ^b   Nicholson, Robert I ^b   Chiosis, Gabriela ^c   Brancale, Andrea ^b   Hamel, Ernest ^d   Artico, Marino ^a   Silvestri, Romano ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3,4,5 TRIMETHOXYPHENYL)THIOINDOLE DERIVATIVE; 3 METHOXYPHENYLTHIOINDOLE DERIVATIVE; 3,5 DIMETHOXYPHENYLTHIOINDOLE DERIVATIVE; ANTINEOPLASTIC AGENT; COLCHICINE; COMBRETASTATIN A4; EPIDERMAL GROWTH FACTOR RECEPTOR 2; HEAT SHOCK PROTEIN 90; INDOLE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CARCINOMA; CANCER INHIBITION; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; LUNG SMALL CELL CANCER; MICROTUBULE ASSEMBLY; MITOSIS; MOLECULAR MODEL; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

BENZENE DERIVATIVES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; TUBULIN MODULATORS;

EID: 32344432249     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050809s     Document Type: Article

References (35)

1. 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 to colchicine to tubulin. Biochemistry 1989, 28, 6984-6991.
2. Beckers, T.; Mahboobi, S. Natural, semisynthetic and synthetic microtubule inhibitors for cancer therapy. Drugs Future 2003, 28, 767-785.
3. Medina, J. C.; Houze, J.; Clark, D. L.; Schwendner, S.; Beckmann, H.; Shan, B. Selective irreversible tubulin binders with efficacy against multi-drug resistant tumor cells. Abstracts of Papers, 222nd American Chemical Society National Meeting, Chicago, August 26-30, 2001; ACS: Washington, DC.
4. (a) Pellegrini, F.; Budman D. R. Review: tubulin function, action of antitubulin drugs, and new drug development. Cancer Invest. 2005, 23, 264-273.
5. (b) Iyer, S.; Chaplin, D. J.; Rosenthal, D. S.; Boulares, A. H.; Li, L.-Y.; Smulson, M. E. Induction of apoptosis in proliferating human endothelial cells by the tumor-specific antiangiogenesis agent combretastatin A-4. Cancer Res. 1998, 58, 4510-4514.
6. Sridhare, M.; Macapinlac, M. J.; Goel, S.; Verdier-Pinard, D.; Fojo, T.; Rothenberg, M.; Colevas, D. The clinical development of new mitotic inhibitors that stabilize the microtubule. Anticancer Drugs 2004, 15, 553-555.
7. Soltau, J.; Drevs, D. ZD-6126 (AstraZeneca). IDrugs 2004, 7, 380-387.
8. Mcintyre, J. A.; Castaner, J. Vinflunine: antimitotic vinca alkaloid. Drugs Future 2004, 29, 574-580.
9. Bai, R.; Pettit, G. R.; Hamel, E. Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. J. Biol. Chem. 1990, 265, 17141-17149.
10. Hamel, E.; Covell, D. G. Antimitotic peptides and depsipeptides. Curr. Med. Chem. - Anticancer Agents 2002, 2, 19-53.
11. Owa, T.; Yokoi, A.; Yamazaki, K.; Yoshimatsu, K.; Yamori, T.; Nagasu, T. Array based structure and gene expression relationship study of antitumor sulfonamides including N-[2-[(4-hydroxyphenyl)amino]-4-methoxybenzene sulfonamide and N-(3-chloro-7-indolyl)-1,4-benzenenedisulfonamide. J. Med. Chem. 2002, 45, 4913-4922.
12. http://www.baxter-oncology.com/english/projects/index.html.
13. Gastpar, R.; Goldbrunner, M.; Marko, D.; von Angerer, E. Methoxy-substituted 3-formyl-2-phenylindoles inhibit tubulin polymerization. J. Med. Chem. 1998, 41, 4965-4972.
14. Medarde, M.; Ramos, A.; Caballero, E.; Peláz-Lamamié de Clairac, R.; López, J. L.; García Grávalos, D.; San Feliciano, A. Synthesis and antineoplastic activity of combretastatin analogues: heterocombretastatins. Eur. J. Med. Chem. 1998, 33, 71-77.
15. 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.
16. De Martino, G.; La Regina, G.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. Arylthioindoles, potent inhibitors of tubulin polymerization. J. Med. Chem. 2004, 47, 6120-6123.
17. Silvestri, R.; De Martino, G.; Artico, M.; Massa, S.; Marceddu, T.; Loi, A. G.; Musiu, C.; La Colla, C. Indolyl Aryl Sulfones (IASs). Part 1: SAR Studies and in vitro anti-HIV-1 activity against wt RT and related mutants. J. Med. Chem. 2003, 46, 2482-2493.
18. Chiosis, G.; Lucas, B.; Shtil, A.; Huezo, H.; Rosen, N. Development of a purine-scaffold novel class of Hsp90 binders that inhibit the proliferation of cancer cells and induce the degradation of Her2 tyrosine kinase. Bioorg. Med. Chem. 2002, 10, 3555-3564.
19. Tripos SYBYL 7.0; Tripos Inc., 1699 South Hanley Rd, St. Louis, MO 63144, USA. http://www.tripos.com.
20. Molecular Operating Environment (MOE 2004.03). Chemical Computing Group, Inc. Montreal, Quebec, Canada. http://www.chem-comp.com.
21. Bai, R.; Covell, D. G.; Pei, X. F.; Ewell, J. B.; Nguyen, N. Y.; Brossi, A. Hamel, E. Mapping the binding site of colchicinoids on β-tubulin: 2-chloroacety-2-demethylthiocolchicine covalently reacts predominantly with cysteine 239 and secondarily with cysteine 354. J. Biol. Chem. 2000, 275, 40443-40452.
22. For spectral data and elemental analysis of 13, Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates. Org. Lett. 2004, 6, 819-821.
23. Offer, J.; Boddy, C. N. C.; Dawson, P. E. Extending Synthetic Access to Proteins with a Removable Acyl Transfer Auxiliary. J. Am. Chem. Soc. 2002, 124, 4642-4646.
24. Boger, D. L.; Nishi, T. Diastereoselective Dieckmann condensation suitable for introduction of the duocarmycin A C6 center: development of a divergent strategy for the total synthesis of duocarmycins A and SA. Bioorg., Med. Chem. 1995, 3, 67-77.
25. Atkinson, J. G.; Hamel, P.; Girard, Y. A new synthesis of 3-arylthioindoles. Synthesis 1988, 6, 480-481.
26. Arcoria, A.; Scarlata, G. Reactivity of methoxythioanisoles with N-bromosuccinimide and with bromine. Ann. Chim. 1964, 54, 139-155.
27. Savarin, C.; Srogl, J.; Liebeskind, L. S. A Mild, Nonbasic Synthesis of Thioethers. The Copper-Catalyzed Coupling of Boronic Acids with N-Thio(alkyl, aryl, heteroaryl)imides. Org. Lett. 2002, 4, 4309-4312.
28. Ondetti, M. A.; Krapcho, J. Mercaptoacyl derivatives of substituted prolines. US Patent 4316906, 1982.
29. Hamel, E. Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin. Cell Biochem. Biophys. 2003, 38, 1-21.
30. Verdier-Pinard, P.; Lai, J.-Y.; Yoo, H.-D.; Yu, J.; Marquez, B.; Nagle, D. G.; Nambu, M.; White, J. D.; Falck, J. R.; Gerwick, W. H.; Day, B. W.; Hamel, E. Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells. Mol. Pharmacol. 1998, 53, 62-76.
31. Jones, H. E.; Goddard, L.; Gee, J. M. W.; Hiscox, S.; Rubini, M.; Barrow, D.; Knowlden, J. M.; Williams, S.; Wakeling, A. E.; Nicholson, R. I. Insulin- like growth factor-1 receptor signalling and acquired resistance to gefitnib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr. Relat. Cancer 2004, 11, 793-814.
32. Llauger, L.; He, H.; Kim, J.; Aguirre, J.; Rosen, N.; Peters, U.; Davies, P.; Chiosis, G. 8-Arylsulfanyl and 8-arylsulfoxyl adenine derivatives as inhibitors of the heat shock protein 90. J. Med. Chem. 2005, 48, 2892-2905.
33. Llauger, L.; Felts, S.; Huezo, H.; Rosen, N.; Chiosis, G. Synthesis of novel fluorescent probes for the molecular chaperone Hsp90. Bioorg. Med. Chem. Lett. 2003, 13, 3975-3978.
34. 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.
35. Code "scoring.svl" obtained from SLV Exchange website http://svl.chemcomp.com., Chemical Computing Group, Inc., Montreal, Canada.