Molecular Interactions of CCR5 with Major Classes of Small-Molecule Anti-HIV CCR5 Antagonists

Molecular Pharmacology - Tập 73 Số 3 - Trang 789-800 - 2008
Rama K. Kondru1, Jun Zhang, Changhua Ji, Tara Mirzadegan, David S. Rotstein, Surya Sankuratri, Marianna Dioszegi
1Department of Medicinal Chemistry, Roche Palo Alto, 3431 Hillview Avenue, Palo Alto, CA 94304, USA

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Baba, 1999, A small-molecule, nonpeptide CCR5 antagonist with highly potent and selective anti-HIV-1 activity, Proc Natl Acad Sci U S A, 96, 5698, 10.1073/pnas.96.10.5698

Berman, 2000, The Protein Data Bank, Nucleic Acids Res, 28, 235, 10.1093/nar/28.1.235

Blanpain, 1999, Multiple charged and aromatic residues in CCR5 amino-terminal domain are involved in high affinity binding of both chemokines and HIV-1 Env protein, J Biol Chem, 274, 34719, 10.1074/jbc.274.49.34719

Bower, 1997, Prediction of protein side-chain rotamers from a backbone-dependent rotamer library: a new homology modeling tool, J Mol Biol, 267, 1268, 10.1006/jmbi.1997.0926

Crabb, 2006, GlaxoSmithKline ends aplaviroc trials, AIDS, 20, 641, 10.1097/01.aids.0000216362.59657.96

Doranz, 1997, Two distinct CCR5 domains can mediate coreceptor usage by human immunodeficiency virus type 1, J Virol, 71, 6305, 10.1128/jvi.71.9.6305-6314.1997

Dorr, 2005, 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, 49, 4721, 10.1128/AAC.49.11.4721-4732.2005

Dragic, 2001, An overview of the determinants of CCR5 and CXCR4 co-receptor function, J Gen Virol, 82, 1807, 10.1099/0022-1317-82-8-1807

Dragic, 1998, Amino-terminal substitutions in the CCR5 coreceptor impair gp120 binding and human immunodeficiency virus type 1 entry, J Virol, 72, 279, 10.1128/JVI.72.1.279-285.1998

Dragic, 2000, A binding pocket for a small molecule inhibitor of HIV-1 entry within the transmembrane helices of CCR5, Proc Natl Acad Sci U S A, 97, 5639, 10.1073/pnas.090576697

Farzan, 1998, A tyrosine-rich region in the N terminus of CCR5 is important for human immunodeficiency virus type 1 entry and mediates an association between gp120 and CCR5, J Virol, 72, 1160, 10.1128/JVI.72.2.1160-1164.1998

Fätkenheuer, 2005, Efficacy of short-term monotherapy with maraviroc, a new CCR5 antagonist, in patients infected with HIV-1, Nat Med, 11, 1170, 10.1038/nm1319

Fechteler, 1995, Prediction of protein three-dimensional structures in insertion and deletion regions: a procedure for searching data bases of representative protein fragments using geometric scoring criteria, J Mol Biol, 253, 114, 10.1006/jmbi.1995.0540

Howard, 1999, Naturally occurring CCR5 extracellular and transmembrane domain variants affect HIV-1 Co-receptor and ligand binding function, J Biol Chem, 274, 16228, 10.1074/jbc.274.23.16228

Imamura, 2006, Discovery of a piperidine-4-carboxamide CCR5 antagonist (TAK-220) with highly potent Anti-HIV-1 activity, J Med Chem, 49, 2784, 10.1021/jm051034q

Ji, 2006, Development of a novel dual CCR5-dependent and CXCR4-dependent cell-cell fusion assay system with inducible gp160 expression, J Biomol Screen, 11, 65, 10.1177/1087057105282959

Jones, 1986, Using known substructures in protein model building and crystallography, EMBO J, 5, 819, 10.1002/j.1460-2075.1986.tb04287.x

Laskowski, 1993, Main-chain bond lengths and bond angles in protein structures, J Mol Biol, 231, 1049, 10.1006/jmbi.1993.1351

Levitt, 1992, Accurate modeling of protein conformation by automatic segment matching, J Mol Biol, 226, 507, 10.1016/0022-2836(92)90964-L

Maeda, 2006, Structural and molecular interactions of CCR5 inhibitors with CCR5, J Biol Chem, 281, 12688, 10.1074/jbc.M512688200

Maeda, 2004, Spirodiketopiperazine-based CCR5 inhibitor which preserves CC-chemokine/CCR5 interactions and exerts potent activity against R5 human immunodeficiency virus type 1 in vitro, J Virol, 78, 8654, 10.1128/JVI.78.16.8654-8662.2004

Marozsan, 2005, Generation and properties of a human immunodeficiency virus type 1 isolate resistant to the small molecule CCR5 inhibitor, SCH-417690 (SCH-D), Virology, 338, 182, 10.1016/j.virol.2005.04.035

Mirzadegan, 2000, Identification of the binding site for a novel class of CCR2b chemokine receptor antagonists: binding to a common chemokine receptor motif within the helical bundle, J Biol Chem, 275, 25562, 10.1074/jbc.M000692200

Morris, 1992, Stereochemical quality of protein structure coordinates, Proteins, 12, 345, 10.1002/prot.340120407

Nakata, 2005, Potent anti-R5 human immunodeficiency virus type 1 effects of a CCR5 antagonist, AK602/ONO4128/GW873140, in a novel human peripheral blood mononuclear cell nonobese diabetic-SCID, interleukin-2 receptor gamma-chain-knocked-out AIDS mouse model, J Virol, 79, 2087, 10.1128/JVI.79.4.2087-2096.2005

Nishikawa, 2005, Analysis of binding sites for the new small-molecule CCR5 antagonist TAK-220 on human CCR5, Antimicrob Agents Chemother, 49, 4708, 10.1128/AAC.49.11.4708-4715.2005

Palani, 2002, Synthesis, SAR, and biological evaluation of oximinopiperidino-piperidine amides. 1. Orally bioavailable CCR5 receptor antagonists with potent anti-HIV activity, J Med Chem, 45, 3143, 10.1021/jm0200815

Rabut, 1998, Alanine substitutions of polar and nonpolar residues in the amino-terminal domain of CCR5 differently impair entry of macrophage- and dualtropic isolates of human immunodeficiency virus type 1, J Virol, 72, 3464, 10.1128/JVI.72.4.3464-3468.1998

Ross, 1998, Multiple residues contribute to the inability of murine CCR-5 to function as a coreceptor for macrophage-tropic human immunodeficiency virus type 1 isolates, J Virol, 72, 1918, 10.1128/JVI.72.3.1918-1924.1998

Rucker, 1996, Regions in beta-chemokine receptors CCR5 and CCR2b that determine HIV-1 cofactor specificity, Cell, 87, 437, 10.1016/S0092-8674(00)81364-1

Seibert, 2006, Interaction of small molecule inhibitors of HIV-1 entry with CCR5, Virology, 349, 41, 10.1016/j.virol.2006.01.018

Seto, 2006, Highly potent and orally active CCR5 antagonists as anti-HIV-1 agents: synthesis and biological activities of 1-benzazocine derivatives containing a sulfoxide moiety, J Med Chem, 49, 2037, 10.1021/jm0509703

Strizki, 2005, Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1, Antimicrob Agents Chemother, 49, 4911, 10.1128/AAC.49.12.4911-4919.2005

Tagat, 2004, J Med Chem, 47, 2405, 10.1021/jm0304515

Thompson, 1994, CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice, Nucleic Acids Res, 22, 4673, 10.1093/nar/22.22.4673

Tsamis, 2003, Analysis of the mechanism by which the small-molecule CCR5 antagonists SCH-351125 and SCH-350581 inhibit human immunodeficiency virus type 1 entry, J Virol, 77, 5201, 10.1128/JVI.77.9.5201-5208.2003

Watson, 2005, The CCR5 receptor-based mechanism of action of 873140, a potent allosteric noncompetitive HIV entry inhibitor, Mol Pharmacol, 67, 1268, 10.1124/mol.104.008565

Westby, 2007, Reduced maximal inhibition in phenotypic susceptibility assays indicates that viral strains resistant to the CCR5 antagonist maraviroc utilize inhibitor-bound receptor for entry, J Virol, 81, 2359, 10.1128/JVI.02006-06

Wood, 2005, The discovery of the CCR5 receptor antagonist, UK-427,857, a new agent for the treatment of HIV infection and AIDS, Prog Med Chem, 43, 239, 10.1016/S0079-6468(05)43007-6