Discovery of a novel CCR5 antagonist lead compound through fragment assembly

Molecules

Volumn 13, Issue 10, 2008, Pages 2426-2441

  Liu, Yanqing ^a   Zhou, Enkun ^b,c   Yu, Kunqian ^d   Zhu, Jin ^a   Zhang, Yu ^a   Xie, Xin ^b   Li, Jian ^a   Jiang, Hualiang ^a,d  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c SOUTHWEST UNIVERSITY   (China)

^d SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

CCR5 antagonist; Fragment assembly, HIV 1; Molecular modeling

Indexed keywords

ALKANONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CHEMOKINE RECEPTOR CCR5; CYCLOHEXANE DERIVATIVE; MARAVIROC; TRIAZOLE DERIVATIVE;

ARTICLE; CALCIUM SIGNALING; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; DRUG EFFECT; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-HIV AGENTS; BUTANONES; CALCIUM SIGNALING; CYCLOHEXANES; DRUG DESIGN; HUMANS; RECEPTORS, CCR5; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 55249120412     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13102426     Document Type: Article

References (24)

1. Doranz, B. J.; Berson, J. F.; Rucker, J.; Doms, R. W. Chemokine receptors as fusion cofactors for human immunodeficiency virus type 1 (HIV-1). Immunol. Res. 1997, 16, 15-28.
2. Feng, Y.; Broder, C. C.; Kennedy, P. E.; Berger, E. A. HIV-1 entry cofactor: functional cDNA cloning of a seven-transmembrane, G proteincoupled receptor. Science 1996, 272, 872-877.
3. Alkhatib, G.; Combadiere, C.; Broder, C. C.; Feng, Y.; Kennedy, P. E.; Murphy, P. M.; Berger, E. A. CC-CKR5: a RANTES, MIP-1alpha, MIP-1beta receptor as a fusion cofactor for macrophagetropic HIV-1. Science 1996, 272, 1955-1958.
4. Deng, H.; Liu, R.; Ellmeier, W.; Choe, S.; Unutmaz, D.; Burkhart, M.; Marzio, P.; Marmon, S.; Sutton, R. E.; Hill, C. M.; Davis, C. B.; Peiper, S. C.; Schall, T. J.; Littman, D. R.; Landau, N. R. Identification of a major co-receptor for primary isolates of HIV-1. Nature 1996, 381, 661-666.
5. + cells is mediated by the chemokine receptor CC-CKR-5. Nature 1996, 381, 667-673.
6. Wu, L.; Gerard, N. P.; Wyatt, R.; Choe, H.; Parolin, C.; Ruffing, N.; Borsetti, A.; Cardoso, A. A.; Desjardin, E.; Newman, W.; Gerard, C. Sodroski, J. CD4-induced interaction of primary HIV-1 gp120 glycoproteins with the chemokine receptor CCR-5. Nature 1996, 384, 179-183.
7. Kwong, P. D.; Wyatt, R.; Robinson, J.; Sweet, R. W.; Sodroski, J.; Hendricks, W. A. Structure of an HIV gp120 envelope glycoprotein in complex with the CD4 receptor and a neutralizing human antibody. Nature 1998, 393, 648-659.
8. + T cells. Science 1995, 270, 1811-1815.
9. Simmons, G.; Clapham, P. R.; Picard, L.; Offord, R. E.; Rosenkilde, M. M.; Schwartz, T. W.; Buser, R.; Wells, T. N. C.; Proudfoot, A. E. I. Potent inhibition of HIV-1 infectivity in macrophages and lymphocytes by a novel CCR5 antagonist. Science 1997, 276, 276-279.
10. Heveker, N.; Montes, M.; Germeroth, L.; Amara, A.; Trautmann, A.; Alizon, M.; Schneider-Mergener, J. Dissociation of the signalling and antiviral properties of SDF-1-derived small peptides. Curr. Biol. 1998, 8, 369-376.
11. Olson, W. C.; Rabut, G. E.; Nagashima, K. A.; Tran, D. N.; Anselma, D. J.; Monard, S. P.; Segal, J. P.; Thompson, D. A.; Kajumo, F.; Guo, Y.; Moore, J. P.; Maddon, P. J.; Dragic, T. Differential inhibition of human immunodeficiency virus type 1 fusion, gp120 binding, and CC-chemokine activity by monoclonal antibodies to CCR5. J. Virol. 1999, 73, 4145-4155.
12. Liu, R.; Paxton, W. A.; Choe, S.; Ceradini, D.; Martin, S. R.; Horuk, R.; MacDonald, M. E.; Stuhlmann, H.; Koup, R. A.; Landau, N. R. Homozygous defect in HIV-1 coreceptor accounts for resistance of some multiply-exposed individuals to HIV-1 infection. Cell 1996, 86, 367-377.
13. Palani, A.; Tagat, J. R. Discovery and Development of Small-Molecule Chemokine Coreceptor CCR5 Antagonists. J. Med. Chem. 2006, 49, 2851-2857.
14. Dorr, P.; Westby, M.; Dobbs, S.; Griffin, P.; Irvine, B.; Macartney, M.; Mori, J.; Rickett, G.; Smith-Burchnell, C.; Napier, C.; Webster, R.; Armour, D.; Price, D.; Stammen, B.; Wood, A.; Perros, M. Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity. Antimicrob. Agents Chemother. 2005, 49, 4721-4732.
15. Dunning, L.; Jaroch, S.; Kochanny, M. J.; Lee, W.; Lian, X.; Liang, M.; Lu, S.; Qnuffer, J.; Phillips, G.; Wei, G.; Ye, B. [WO Patent 2004002960, 2004].
16. Xu, Y.; Liu, H.; Niu, C.; Luo, C.; Luo, X.; Shen, J.; Chen, K.; Jiang, H. Molecular docking and 3D QSAR studies on 1-amino-2-phenyl-4-(piperidin-1-yl)- butanes based on the structural modeling of human CCR5 receptor. Bioorg. Med. Chem. 2004, 12, 6193-6208.
17. Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Le Trong, I.; Teller, D. C.; Okada, T.; Stenkamp, R. E.; Yamamoto, M.; Miyano, M. Crystal structure of rhodopsin: A G protein-coupled receptor. Science 2000, 289, 739-745.
18. Li, J.; Chen, J.; Gui, C.; Zhang, L.; Qin, Y.; Xu, Q.; Zhang, J.; Liu, H.; Shen, X.; Jiang, H. Discovering novel chemical inhibitors of human cyclophilin A:Virtual screening, synthesis, and bioassay. Bioorg. Med. Chem. 2006, 14, 2209-2224.
19. Ewing, T. J.; Makino, S.; Skillman, A. G.; Kuntz, I. D. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases. J. Comput. Aided Mol. Des. 2001, 15, 411-428.
20. Morris, G. M.; Goodsell, D. S.; Halliday, R.S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated Docking Using a Lamarckian Genetic Algorithm and and Empirical Binding Free Energy Function. J. Comput. Chem. 1998, 19, 1639-1662.
21. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. An all atom force field for simulations of proteins and nucleic acids. J. Comput. Chem. 1986, 7, 230-252.
22. Baba, M.; Takashima, K.; Miyake, H.; Kanzaki, N.; Teshima, K.; Wang, X.; Shiraishi, M.; Iizawa, Y. TAK-652 inhibits CCR5-mediated human immunodeficiency virus type 1 infection in vitro and has favorable pharmacokinetics in humans. Antimicrob. Agents Chemother. 2005, 49, 4584-4591.
23. Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3228.
24. Kuehne, P.; Linden, A.; Hesse, M. Asymmetric Synthesis of the Alkaloids Mayfoline and N(1)-Acetyl-N(1)-Deoxymayfoline. Helv. Chim. Acta 1996, 79, 1085-1094.