Small-molecule HIV-1 entry inhibitors targeting gp120 and gp41: a patent review (2010-2015)

References

• Rife B, Salemi M. On the early dynamics and spread of HIV-1. Trends Microbiol. 2015;23:3–4.
   PubMed Web of Science ®Google Scholar
• Fauci AS, Marston HD. Ending the HIV–AIDS Pandemic—Follow the Science. New Engl J Med. 2015;373:2197–2199.
   PubMed Web of Science ®Google Scholar
• Barré-Sinoussi F, Ross AL, Delfraissy J-F. Past, present and future: 30 years of HIV research. Nat Rev Microbio. 2013;11:877–883.
   PubMed Web of Science ®Google Scholar
• Brook I. Approval of zidovudine (AZT) for acquired immunodeficiency syndrome: a challenge to the medical and pharmaceutical communities. JAMA. 1987;258:1517.
   PubMed Web of Science ®Google Scholar
• Fischl MA, Richman DD, Grieco MH, et al. The efficacy of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. New Engl J Med. 1987;317:185–191.
   PubMed Web of Science ®Google Scholar
• Engelman A, Cherepanov P. The structural biology of HIV-1: mechanistic and therapeutic insights. Nat Rev Microbiol. 2012;10:279–290.
   PubMed Web of Science ®Google Scholar
• Goodsell DS. Illustrations of the HIV Life Cycle. The Future of HIV-1 Therapeutics. Curr Top Microbiol Immunol. 2015;389:243–252.
   PubMed Web of Science ®Google Scholar
• Perelson AS, Essunger P, Cao Y, et al. Decay characteristics of HIV-1-infected compartments during combination therapy. Nature. 1997;387:188–191.
   PubMed Web of Science ®Google Scholar
• Gulick RM, Mellors JW, Havlir D, et al. Treatment with indinavir, zidovudine, and lamivudine in adults with human immunodeficiency virus infection and prior antiretroviral therapy. New Engl J Med. 1997;337:734–739.
   PubMed Web of Science ®Google Scholar
• Aberg JA, Gallant JE, Ghanem KG, et al. Primary care guidelines for the management of persons infected with HIV: 2013 update by the HIV Medicine Association of the Infectious Diseases Society of America. Clin Infect Dis. 2014;58:1–10.
   Web of Science ®Google Scholar
• Fellay J, Ledergerber B, Bernasconi E, et al. Prevalence of adverse events associated with potent antiretroviral treatment: Swiss HIV Cohort Study. The Lancet. 2001;358:1322–1327.
   PubMed Web of Science ®Google Scholar
• Wegner SA, Brodine SK, Mascola JR, et al. Prevalence of genotypic and phenotypic resistance to anti-retroviral drugs in a cohort of therapy-naive HIV-1 infected US military personnel. AIDS. 2000;14:1009–1015.
   PubMed Web of Science ®Google Scholar
• Chan DC, Fass D, Berger JM, et al. Core structure of gp41 from the HIV envelope glycoprotein. Cell. 1997;89:263–273.
   PubMed Web of Science ®Google Scholar
• Lu L, Pan C, Li Y, et al. A bivalent recombinant protein inactivates HIV-1 by targeting the gp41 prehairpin fusion intermediate induced by CD4 D1D2 domains. Retrovirology. 2012;9:1–14.
   PubMed Web of Science ®Google Scholar
• Liu S, Wu S, Jiang S. HIV entry inhibitors targeting gp41: from polypeptides to small-molecule compounds. Curr Pharm Des. 2007;13:143–162.
   PubMed Web of Science ®Google Scholar
• Jiang S, Lin K, Strick N, et al. HIV-1 inhibition by a peptide. Nature. 1993;365:113.
   PubMed Web of Science ®Google Scholar
• Jiang S, Lin K, Strick N, et al. Inhibition of HIV-1 infection by a fusion domain binding peptide from the HIV-1 envelope glycoprotein GP41. Biochem Biophys Res Commun. 1993;195:533–538.
   PubMed Web of Science ®Google Scholar
• Poveda E, Briz V, Soriano V. Enfuvirtide, the first fusion inhibitor to treat HIV infection. AIDS Rev. 2004;7:139–147.
   Web of Science ®Google Scholar
• Rimsky LT, Shugars DC, Matthews TJ. Determinants of human immunodeficiency virus type 1 resistance to gp41-derived inhibitory peptides. J Virol. 1998;72:986–993.
   PubMed Web of Science ®Google Scholar
• Lu J, Deeks SG, Hoh R, et al. Rapid emergence of enfuvirtide resistance in HIV-1-infected patients: results of a clonal analysis. JAIDS J Acquir Immune Defic Syndr. 2006;43:60–64.
   PubMed Web of Science ®Google Scholar
• Dorr P, Westby M, Dobbs S, et al. 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.
   PubMed Web of Science ®Google Scholar
• Fätkenheuer G, Pozniak AL, Johnson MA, et al. Efficacy of short-term monotherapy with maraviroc, a new CCR5 antagonist, in patients infected with HIV-1. Nature Med. 2005;11:1170–1172.
   PubMed Web of Science ®Google Scholar
• Kromdijk W, Huitema AD, Mulder JW. Treatment of HIV infection with the CCR5 antagonist maraviroc. Expert Opin Pharmacother. 2010;11:1215–1223.
   PubMed Web of Science ®Google Scholar
• Tan Q, Zhu Y, Li J, et al. Structure of the CCR5 chemokine receptor–HIV entry inhibitor maraviroc complex. Science. 2013;341:1387–1390.
   PubMed Web of Science ®Google Scholar
• Biswas P, Tambussi G, Lazzarin A. Access denied? The status of co-receptor inhibition to counter HIV entry. Expert Opin Pharmacother. 2007;8:923–933.
   PubMed Web of Science ®Google Scholar
• Jiang X, Feyertag F, Meehan CJ, et al. Characterizing the Diverse Mutational Pathways Associated with R5-Tropic Maraviroc Resistance: HIV-1 That Uses the Drug-Bound CCR5 Coreceptor. J Virol. 2015;89:11457–11472.
   PubMed Web of Science ®Google Scholar
• Zhao Q, Ma L, Jiang S, et al. Identification of N-phenyl-N′-(2, 2, 6, 6-tetramethyl-piperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4. Virology. 2005;339:213–225.
   PubMed Web of Science ®Google Scholar
• BMS. Alkyl amides as HIV attachment inhibitors. US8912195 B2. 2013.
   Google Scholar
• Wang T, Zhang Z, Wallace OB, et al. Discovery of 4-benzoyl-1-[(4-methoxy-1 H-pyrrolo [2, 3-b] pyridin-3-yl) oxoacetyl]-2-(R)-methylpiperazine (BMS-378806): a novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions. J Med Chem. 2003;46:4236–4239.
   PubMed Web of Science ®Google Scholar
• Virocarb Inc. Small molecule inhibitors of gp120-mediated HIV infection and methods of use. WO 2015/143535 A1. 2015.
   Google Scholar
• Julien J-P, Cupo A, Sok D, et al. Crystal structure of a soluble cleaved HIV-1 envelope trimer. Science. 2013;342:1477–1483.
   PubMed Web of Science ®Google Scholar
• Herschhorn A, Gu C, Espy N, et al. A broad HIV-1 inhibitor blocks envelope glycoprotein transitions critical for entry. Nat Chem Biol. 2014;10:845–852.
   PubMed Web of Science ®Google Scholar
• Courter JR, Madani N, Sodroski J, et al. Structure-based design, synthesis and validation of CD4-mimetic small molecule inhibitors of HIV-1 entry: conversion of a viral entry agonist to an antagonist. Acc Chem Res. 2014;47:1228–1237.
   PubMed Web of Science ®Google Scholar
• BMS. Diketopiperidine derivatives as HIV attachment inhibitors. EP2313408 B1. 2012.
   Google Scholar
• Rothemund PW. Folding DNA to create nanoscale shapes and patterns. Nature. 2006;440:297–302.
   PubMed Web of Science ®Google Scholar
• BMS. Diketo azolopiperidines and azolopiperazines as anti-hiv agents. EP2303876 A1. 2011.
   Google Scholar
• BMS. Spiro bicyclic diamine derivatives as HIV attachment inhibitors. US8664213 B2. 2012.
   Google Scholar
• BMS. Cyclic hydrazine derivatives as HIV attachment inhibitors. US9193725 B2. 2014.
   Google Scholar
• BMS. Alkene piperidine derivatives as antiviral agents. US7745463 B2. 2010.
   Google Scholar
• BMS. Methods of treating HIV infection. US7776863 B2. 2010.
   Google Scholar
• BMS. Thioamide, amidoxime and amidrazone derivatives as HIV attachment inhibitors. US20130102615 A1. 2013.
   Google Scholar
• Lingwood CA. Glycosphingolipid functions. Cold Spring Harb Perspect Biol. 2011;3:a004788.
   PubMed Web of Science ®Google Scholar
• Huang -C-CE, Lam SN, Acharya P, et al. Structures of the CCR5 N terminus and of a tyrosine-sulfated antibody with HIV-1 gp120 and CD4. Science. 2007;317:1930–1934.
   PubMed Web of Science ®Google Scholar
• Munro JB, Gorman J, Ma X, et al. Conformational dynamics of single HIV-1 envelope trimers on the surface of native virions. Science. 2014;346:759–763.
   PubMed Web of Science ®Google Scholar
• Langley DR, Roy Kimura S, Sivaprakasam P, et al. Homology models of the HIV‐1 attachment inhibitor BMS‐626529 bound to gp120 suggest a unique mechanism of action. Proteins Struct Funct Bioinform. 2015;83:331–350.
   PubMed Web of Science ®Google Scholar
• Do Kwon Y, LaLonde JM, Yang Y, et al. Crystal structures of HIV-1 gp120 envelope glycoprotein in complex with NBD analogues that target the CD4-binding site. PloS one. 2014;9:e85940.
   PubMed Web of Science ®Google Scholar
• Curreli F, Do Kwon Y, Zhang H, et al. Binding mode characterization of NBD series CD4-mimetic HIV-1 entry inhibitors by X-ray structure and resistance study. Antimicrob Agents Chemother. 2014;58:5478–5491.
   PubMed Web of Science ®Google Scholar
• Falkowska E, Ramos A, Feng Y, et al. PGV04, an HIV-1 gp120 CD4 binding site antibody, is broad and potent in neutralization but does not induce conformational changes characteristic of CD4. J Virol. 2012;86:4394–4403.
   PubMed Web of Science ®Google Scholar
• Madani N, Schön A, Princiotto AM, et al. Small-molecule CD4 mimics interact with a highly conserved pocket on HIV-1 gp120. Structure. 2008;16:1689–1701.
   PubMed Web of Science ®Google Scholar
• New York Blood Center. HIV inhibitors. WO2013036676 A1. 2013.
   Google Scholar
• Curreli F, Choudhury S, Pyatkin I, et al. Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1. J Med Chem. 2012;55:4764–4775.
   PubMed Web of Science ®Google Scholar
• Curreli F, Kwon YD, Zhang H, et al. Structure-based design of a small molecule CD4-antagonist with broad spectrum anti-HIV-1 activity. J Med Chem. 2015;58:6909–6927.
   PubMed Web of Science ®Google Scholar
• Dana-Farber Cancer Institute. Small molecule inhibitors of HIV-1 entry and methods of use thereof. WO 2015/171995 A1. 2015.
   Google Scholar
• University of Pennsylvania. Inhibitors of HIV-1 entry and methods of use thereof. WO2016025681. 2016.
   Google Scholar
• University of Pennsylvania. CD4-mimetic small molecules sensitize human immunodeficiency virus to vaccine-elited antibodies. WO2015120440 A2. 2015.
   Google Scholar
• University of Pennsylvania. CD4-mimetic inhibitors of HIV-1 entey and methods of use thereof. WO2013090696. 2013.
   Google Scholar
• University of Pennsylvania. Small molecule CD4 mimetics and uses thereof. WO2010053538. 2010.
   Google Scholar
• Chan DC, Chutkowski CT, Kim PS. Evidence that a prominent cavity in the coiled coil of HIV type 1 gp41 is an attractive drug target. Proc Natl Acad Sci USA. 1998;95:15613–15617.
   PubMed Web of Science ®Google Scholar
• Debnath AK, Radigan L, Jiang S. Structure-based identification of small molecule antiviral compounds targeted to the gp41 core structure of the human immunodeficiency virus type 1. J Med Chem. 1999;42:3203–3209.
   PubMed Web of Science ®Google Scholar
• Jiang S, Lin K, Lu M. A conformation-specific monoclonal antibody reacting with fusion-active gp41 from the human immunodeficiency virus type 1 envelope glycoprotein. J Virol. 1998;72:10213–10217.
   PubMed Web of Science ®Google Scholar
• Jiang S, Lin K, Zhang L, et al. A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody. J Virol Methods. 1999;80:85–96.
   PubMed Web of Science ®Google Scholar
• Liu S, Boyer-Chatenet L, Lu H, et al. Rapid and automated fluorescence-linked immunosorbent assay for high-throughput screening of HIV-1 fusion inhibitors targeting gp41. J Biomol Screen. 2003;8:685–693.
   PubMed Web of Science ®Google Scholar
• Jiang S, Lu H, Liu S, et al. N-substituted pyrrole derivatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 six-helix bundle formation and block virus fusion. Antimicrob Agents Chemother. 2004;48:4349–4359.
   PubMed Web of Science ®Google Scholar
• Liu K, Lu H, Hou L, et al. Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41. J Med Chem. 2008;51:7843–7854.
   PubMed Web of Science ®Google Scholar
• Wang Y, Lu H, Zhu Q, et al. Structure-based design, synthesis and biological evaluation of new N-carboxyphenylpyrrole derivatives as HIV fusion inhibitors targeting gp41. Bioorg Med Chem Lett. 2010;20:189–192.
   PubMed Web of Science ®Google Scholar
• Katritzky AR, Tala SR, Lu H, et al. Design, Synthesis, and Structure− Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl) furans as HIV-1 Entry Inhibitors. J Med Chem. 2009;52:7631–7639.
   PubMed Web of Science ®Google Scholar
• Jiang S, Tala SR, Lu H, et al. Design, synthesis, and biological activity of novel 5-((arylfuran/1 H-pyrrol-2-yl) methylene)-2-thioxo-3-(3-(trifluoromethyl) phenyl) thiazolidin-4-ones as HIV-1 fusion inhibitors targeting gp41. J Med Chem. 2010;54:572–579.
   PubMed Web of Science ®Google Scholar
• Janssen R&D Ireland Eastgate. Small molecule entry inhibitors. EP1485079 B1. 2014.
   Google Scholar
• Balata G, Mahdi M, Bakera RA. Improvement of solubility and dissolution properties of ketoconazole by solid dispersions and inclusion complexes. Asian J Pharm Sci. 2010;5:1–12.
   Google Scholar
• Siebert X, Hummer G. Hydrophobicity maps of the N-peptide coiled coil of HIV-1 gp41. Biochemistry. 2002;41:2956–2961.
   PubMed Web of Science ®Google Scholar
• Tuoro University. HIV-1 fusion inhibitors and methods. US8455516 B2. 2011.
   Google Scholar
• Tuoro University. HIV-1 fusion inhibitors and methods. US2011/0190343 A1. 2013.
   Google Scholar
• Zhou G, Wu D, Hermel E, et al. Design, synthesis, and evaluation of indole compounds as novel inhibitors targeting Gp41. Bioorg Med Chem Lett. 2010;20:1500–1503.
   PubMed Web of Science ®Google Scholar
• Gochin M, Zhou G, Phillips AH. Paramagnetic relaxation assisted docking of a small indole compound in the HIV-1 gp41 hydrophobic pocket. ACS Chem Biol. 2011;6:267–274.
   PubMed Web of Science ®Google Scholar
• Li W, Wang Q, Li Y, et al. A Nanoparticle-Encapsulated Non-Nucleoside Reverse-Transcriptase Inhibitor with Enhanced Anti-HIV-1 Activity and Prolonged Circulation Time in Plasma. Curr Pharm Des. 2015;21:925–935.
   PubMed Web of Science ®Google Scholar