Rigid analogues of antimitotic indolobenzazepinones: New insights into tubulin binding via molecular modeling

ACS Medicinal Chemistry Letters

Volumn 2, Issue 8, 2011, Pages 565-570

  Pons, Valérie ^a   Beaumont, Stéphane ^a   Tran Huu Dau, Marie Elise ^a   Iorga, Bogdan I ^a   Dodd, Robert H ^a  

^a CNRS   (France)

Author keywords

atropoisomers; cytotoxicity; Indolobenzazepinone; molecular docking; tubulin polymerization

Indexed keywords

5 ETHYLINDOLOBENZAZEPINONE; ANTIMITOTIC AGENT; COLCHICINE; INDAN DERIVATIVE; INDOLOBENZAZEPINONE DERIVATIVE; NITROGEN; PYRROLIDINE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CANCER CELL CULTURE; CANCER INHIBITION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; MICROTUBULE ASSEMBLY; MOLECULAR DOCKING; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN BINDING;

EID: 80051771482     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200024y     Document Type: Article

References (18)

1. Jordan, M. A.; Wilson, L. Microtubules as a target for anticancer drugs Nat. Rev. Cancer 2004, 4, 253-265 (Pubitemid 38525281)
2. Guéritte, F.; Fahy, J. The Vinca Alkaloids. In Anticancer Agents from Natural Products; Cragg, G. M.; Kingston, D. G. I.; Newman, D. J., Eds.; CRC Press: Boca Raton, FL, 2005; pp 123-135.
3. Kingston, D. G. I. Taxol and Its Analogs. In Anticancer Agents from Natural Products; Cragg, G. M.; Kingston, D. G. I.; Newman, D. J., Eds.; CRC Press: Boca Raton, FL, 2005; pp 89-122.
4. Davis, P. D.; Dougherty, G. J.; Blakey, D. C.; Galbraith, S. M.; Tozer, G. M.; Holder, A. L.; Naylor, M. A.; Nolan, J.; Stratford, M. R. L.; Chaplin, D. J.; Hill, S. A. ZD6126: A novel vascular-targeting agent that causes selective destruction of tumor vasculature Cancer Res. 2002, 62, 7247-7253 (Pubitemid 36025246)
5. 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 (Pubitemid 38374318)
6. Tron, G. C.; Pirali, T.; Sorba, G.; Pagliai, F.; Busacca, S.; Genazzani, A. A. Medicinal chemistry of combretastatin A4: Present and future directions J. Med. Chem. 2006, 49, 3033-3044 (Pubitemid 43830499)
7. Keller, L; Beaumont, S; Liu, J.-M.; Thoret, S.; Bignon, J. S.; Wdzieczak-Bakala, J.; Dauban, P.; Dodd, R. H. New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: Cytotoxic and antitumor activities J. Med. Chem. 2008, 51, 3414-3421 (Pubitemid 351874998)
8. Phong, N.; Corpuz, E.; Heidelbaugh, T. M.; Chow, K.; Garst, M. E. A convenient synthesis of 7-halo-1-indanones and 8-halo-1-tetralones J. Org. Chem. 2003, 68, 10195-10198 (Pubitemid 38017886)
9. Baudoin, O.; Cesario, M.; Guénard, D.; Guéritte, F. Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl-lactams J. Org. Chem. 2002, 67, 1199-1207 (Pubitemid 34178204)
10. Wu, S.; Lee, S.; Beak, P. Asymmetric deprotonation by BuLi/(-)-sparteine: Convenient and highly enantioselective syntheses of (S)-2-aryl-Boc-pyrrolidines J. Am. Chem. Soc. 1996, 118, 715-721 (Pubitemid 26052040)
11. Putey, A.; Joucla, L.; Picot, L.; Besson, T.; Joseph, B. Synthesis of latonduine derivatives via intramolecular Heck reaction Tetrahedron 2007, 63, 867-879 (Pubitemid 44920335)
12. Putey, A.; Popowycz, F.; Do, Q.-T.; Bernard, P.; Talapatra, S. K.; Kozielski, F.; Galmarini, C. K.; Joseph, B. Indolobenzazepino-7-ones and 6-, 8, and 9-membered ring derivatives as tubulin polymerization inhibitors: Synthesis and structure-activity relationship studies J. Med. Chem. 2009, 52, 5916-5925
13. http://www.schrodinger.com/.
14. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr. ; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2003.
15. Verdonk, M. L.; Cole, J. C.; Hartshorn, M. J.; Murray, C. W.; Taylor, R. D. Improved protein-ligand docking using GOLD Proteins 2003, 52, 609-623 (Pubitemid 37034158)
16. Ravelli, R. B.; 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). The 3D structures of ligands were constructed with CORINA 3.44 (Molecular Networks GmbH) (Pubitemid 38374318)
17. Images were created with the Chimera software (Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera-A visualization system for exploratory research and analysis. J. Comput. Chem. 2004, 25, 1605-1612) and the PovRay module (http://www.povray. org/).
18. Herrbach, A.; Marinetti, A.; Baudoin, O.; Guénard, D.; Guéritte, F. Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling J. Org. Chem. 2003, 68, 4897-4905 (Pubitemid 36682717)