Retroviral integrase inhibitors year 2000: Update and perspectives

Antiviral Research

Volumn 47, Issue 3, 2000, Pages 139-148

  Pommier, Yves ^a   Marchand, Christophe ^a   Neamati, Nouri ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Integrase inhibitors; Resistance; Retroviruses; Structure of integrases

Indexed keywords

(1 (5 CHLOROINDOL 3 YL) 3 HYDROXY 3 (2H TETRAZOL 5 YL) PROPENONE; ALKALOID; ANTIRETROVIRUS AGENT; ANTIVIRUS AGENT; CICHORIC ACID; COSALANE; COUMARIN DERIVATIVE; DICAFFEOYLQUINIC ACID; EQUISETIN; FLAVONE DERIVATIVE; GRANULATINE; GUANOSINE DERIVATIVE; HYPERICIN; INTEGRASE INHIBITOR; LAMELLARIN ALPHA 20 SULFATE; LEXITROPSIN; LUFFIN; NUCLEOTIDE DERIVATIVE; OXOACID; PHOMASETIN; QUINOLINE DERIVATIVE; SAPORIN; STYRYLQUINOLINE; SULFONAMIDE; TEMACRIZINE; TETRACYCLINE DERIVATIVE; THIAZOLOTHIAZEPINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS DNA;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTIVIRAL ACTIVITY; DRUG DNA BINDING; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PRIORITY JOURNAL; RETROVIRUS; REVIEW; VIRUS INFECTION; VIRUS INHIBITION;

ANTI-HIV AGENTS; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS;

EID: 0033813928     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(00)00112-1     Document Type: Review

References (57)

1. Au T.K., Collins R.A., Lam T.L., Ng T.B., Fong W.P., Wan D.C. The plant ribosome inactivating proteins luffin and saporin are potent inhibitors of HIV-1 integrase. FEBS Lett. 471:2000;169-172.
2. Bouziane M., Cherny D.I., Mouscadet J.F., Auclair C. Alternate strand DNA triple helix-mediated inhibition of HIV-1 U5 long terminal repeat integration in vitro. J. Biol. Chem. 271:1996;10359-10364.
3. Brodin P., Pinskaya M., Volkov E., Romanova E., Leh H., Auclair C., Mouscadet J., Gottikh M. Branched oligonucleotide-intercalator conjugate forming a parallel stranded structure inhibits HIV-1 integrase. FEBS Lett. 460:1999;270-274.
4. Carroll S.S., Geib J., Olsen D.B., Stahlhut M., Shafer J.A., Kuo L.C. Sensitivity of HIV-1 reverse transcriptase and its mutants to inhibition by azidothymidine triphosphate. Biochemistry. 33:1994;2113-2120.
5. Caumont A., Jamieson G., de Soultrait V.R., Parissi V., Fournier M., Zakharova O.D., Bayandin R., Litvak S., Tarrago-Litvak L., Nevinsky G.A. High affinity interaction of HIV-1 integrase with specific and non-specific single-stranded short oligonucleotides. FEBS Lett. 455:1999;154-158.
6. Chen Z., Yan Y., Munshi S., Li Y., Zugay-Murphy J., Xu B., Witmer M., Felock P., Wolfe A., Sardana V., Emini E.A., Hazuda D., Kuo L.C. X-ray structure of Simian immunodeficiency virus integrase containing the core and C-terminal domain (residues 50-293) - an initial glance of the viral DNA-binding platform. J. Mol. Biol. 296:2000;521-533.
7. Cushman M., Golebiewski W.M., Pommier Y., Mazumder A., Reymen D., De Clerq E., Grahm L., Rice W.G. Cosalane analogues with enhanced potencies as inhibitors of HIV-1 protease and integrase. J. Med. Chem. 38:1995;443-452.
8. Drake R., Neamati N., Hong H., Pilon A.A., Sunthankar P., Hume S.D., Milne G.W.A., Pommier Y. Identification of a nucleotide binding site in HIV-1 integrase. Proc. Natl. Acad. Sci. USA. 95:1998;4170-4175.
9. Esposito D., Craigie R. Sequence selectivity of viral end DNA binding by HIV-1 integrase reveals critical regions for protein-DNA interactions. EMBO J. 17:1998;5832-5843.
10. Esposito D., Craigie R. HIV integrase structure and function. Skalka A.M. Advances in Virus Research. 52:1999;319-333 Academic Press, San Diego.
11. Este J.A., Cabrera C., Schols D., Cherepanov P., Gutierrez A., Witvrouw M., Pannecouque C., Debyser Z., Rando R.F., Clotet B., Desmyter J., De Clercq E. Human immunodeficiency virus glycoprotein Gp120 as the primary target for the antiviral action of AR177 (Zintevir). Mol. Pharmacol. 53:1998;340-345.
12. Farnet C.M., Wang B., Hansen M., Lipford J.R., Zalkow L., Robinson W.E., Siegel J., Bushman F. Human immunodeficiency virus type 1 cDNA integration: new aromatic hydroxylated inhibitors and studies of the inhibition mechanism. Antimicrob. Agents Chemother. 42:1998;2245-2253.
13. Fesen M.R., Kohn K.W., Leteurtre F., Pommier Y. Inhibitors of human immunodeficiency virus integrase. Proc. Natl. Acad. Sci. USA. 90:1993;2399-2403.
14. Fesen M.R., Pommier Y., Leteurtre F., Hiroguchi S., Yung J., Kohn K.W. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem. Pharmacol. 48:1994;595-608.
15. Filipowsky M.E., Kopka M.L., Brazil-Zison M., Lown J.W., Dickerson R.E. Linked lexitropsins and the in vitro inhibition of HIV-1 reverse transcriptase RNA-directed DNA polymerization: a novel induced-fit of 3,5 m-pyridyl bisdistamycin to enzyme-associated template-primer. Biochemistry. 35:1996;15397-15410.
16. Goldgur Y., Craigie R., Cohen G.H., Fujiwara T., Yoshinaga T., Fujishita T., Sugimoto H., Endo T., Murai H., Davies D.R. Structure of the HIV-1 integrase catalytic domain complexed with an inhibitor: a platform for antiviral drug design. Proc. Natl. Acad. Sci. USA. 96:1999;13040-13043.
17. Hansen M.S.T., Smith G.J.I., Kafri T., Molteni V., Siegel J.S., Bushman F.D. Integration complexes derived from HIV vectors for rapid assays in vitro. Nat. Biotechnol. 17:1999;578-582.
18. Hazuda D.J., Felock P.J., Hastings J.C., Pramanik B., Wolfe A.L. Differential divalent cation requirements uncouple the assembly and catalytic reactions of human immunodeficiency virus type 1 integrase. J. Virol. 71:1997;7005-7011.
19. Hazuda D., UncapherBlau C., Felock P., Hastings J., Pramanik B., Wolfe A., Bushman R., Farnet C., Goetz M., Williams M., Silverman K., Lingham R., Singh S. Isolation and characterization of novel human immunodeficiency virus integrase inhibitors from fungal metabolites. Antiviral Chem. Chemother. 10:1999;63-70.
20. Hazuda D.J., Felock P., Witmer M., Wolfe A., Stillmock K., Grobler J.A., Espesath A., Gabryelski L., Schlelf W., Blau C., Miller M.D. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells. Science. 287:2000;646-650.
21. Jing, N., Marchand, C., Liu, J., Mitra, R., Hogan, M.E., Pommier, Y., 2000a. Mechanism of inhibition of HIV-1 integrase by G-tetra forming oligonucleotides. J. Biol. Chem. 275, 21460-21467.
22. Jing N., de Clercq E., Rando R.F., Pallansch L., Lackman-Smith C., Lee S., Hogan M.E. Stability-activity relationships of a family of G-tetrad forming oligonucleotides as potent HIV inhibitors: a basis for anti-HIV drug design. J. Biol. Chem. 275:2000;3421-3430.
23. King P.J., Robinson W.E. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. J. Virol. 72:1998;8420-8424.
24. King P.J., Ma G., Miao W., Jia Q., McDougall B.R., Reinecke M.G., Cornell C., Kuan J., Kim T.R., Robinson W.E. Jr Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. J. Med. Chem. 42:1999;497-509.
25. Lin Z., Neamati N., Zhao H., Kiryu Y., Turpin J.A., Aberham C., Strebel K., Kohn K., Witvrouw M., Pannecouque C., Debyser Z., De Clercq E., Rice W.G., Pommier Y., Burke T.R. Jr Chicoric acid analogues as HIV-1 integrase inhibitors. J. Med. Chem. 42:1999;1401-1414.
26. Lubkowski J., Yang F., Alexandratos J., Wlodawer A., Zhao H., Burke T.R., Neamati N., Pommier Y., Merkel G., Skalka A.M. Structure of the catalytic domain of avian sarcoma virus integrase with a bound HIV-1 integrase-targeted inhibitor. Proc. Natl. Acad. Sci. USA. 95:1998;4831-4836.
27. Mazumder A., Wang S., Neamati N., Nicklaus M., Sunder S., Chen J., Milne G., Rice W.G., Burke T.R., Pommier Y. Antiretroviral agent as inhibitors of both human immunodeficiency virus type 1 integrase and protease. J. Med. Chem. 39:1996;2472-2481.
28. Mekouar K., Mouscadet J.F., Desmaele D., Subra F., Leh H., Savoure D., Auclair C., d'Angelo J. Styrylquinoline derivatives: a new class of potent HIV-1 integrase inhibitors that block HIV-1 replication in CEM cells. J. Med. Chem. 41:1998;2846-2857.
29. Mouscadet J.F., Carteau S., Goulaouic H., Subra F., Auclair C. Triplex-mediated inhibition of HIV DNA integration in vitro. J. Biol. Chem. 269:1994;21634-21638.
30. Neamati N., Hong H., Mazumder A., Wang S., Sunder S., Nicklaus M.C., Milne G.W.A., Proska B., Pommier Y. Depside and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3-D database searching. J. Med. Chem. 40:1997;942-951.
31. Neamati N., Hong H., Sunder S., Milne G.W.A., Pommier Y. Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors. Mol. Pharmacol. 52:1997;1041-1055.
32. Neamati N., Mazumder A., Sunder S., Owen J.M., Schultz R.J., Pommier Y. 2-Mercaptobenzenesulfonamides as novel inhibitors of human immunodeficiency virus type 1 integrase and replication. Antiviral Chem. Chemother. 8:1997;485-495.
33. Neamati N., Sunder S., Pommier Y. Design and discovery of HIV-1 integrase inhibitors. Drug Discovery Today. 11:1997;487-498.
34. Neamati N., Mazumder A., Sunder S., Owen J.M., Tandon M., Lown J.W., Pommier Y. Highly potent synthetic polyamines, bis-distamycins and lexitropsins as inhibitors of human immunodeficiency virus type 1 integrase. Mol. Pharmacol. 54:1998;280-290.
35. Neamati N., Hong H., Owen J.M., Sunder S., Winslow H.E., Christensen J.L., Zhao H., Burke T.R., Milne G.W.A., Pommier Y. Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site. J. Med. Chem. 41:1998;3202-3209.
36. Neamati N., Turpin J.A., Winslow H.E., Christensen J.L., Williamson K., Orr A., Rice W.G., Pommier Y., Garofalo A., Brizzi A., Campiani G., Fiorini I., Nacci V. Thiazolothiazepine inhibitors of HIV-1 integrase. J. Med. Chem. 42:1999;3334-3341.
37. Neamati N., Marchand C., Pommier Y. HIV-1 integrase inhibitors: past, present and future. Adv. Pharmacol. 49:2000;147-165.
38. Nicklaus M., Neamati N., Hong H., Mazumder A., Sunder Y., Chen J., Milne G.W.A., Pommier Y. HIV-1 integrase pharmacophore: discovery of inhibitors through 3-D database searching. J. Med. Chem. 40:1997;920-929.
39. Parissi V., Caumont A.B., deSoultrait V.R., Calmels C., Pichuantes S., Litvak S., Dupont C.H. Selection of amino acid substitutions restoring activity of HIV-1 integrase mutated in its catalytic site using the yeast Saccharomyces cerevisiae. J. Mol. Biol. 295:2000;755-765.
40. Pluymers, W., Pannecouque, C., Fikkert, V., Neamati, N., Marchand, C., Burke Jr., T.R., Pommier, Y., Schols, D., De Clercq, E., Debyser, Z., Witvrouw, M., 2000. Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters. Mol. Pharmacol., submitted for publication.
41. Pommier Y., Neamati N. Inhibitors of human immunodeficiency virus integrase. Adv. Virus Res. 52:1999;427-458.
42. Pommier Y., Pilon A.A., Bajaj K., Mazumder A., Neamati N. HIV-1 integrase as a target for antiviral drugs. Antiviral Chem. Chemother. 8:1997;463-483.
43. Reddy M.V., Rao M.R., Rhodes D., Hansen M.S., Rubins K., Bushman F.D., Venkateswarlu Y., Faulkner D.J. Lamellarin α-20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture. J. Med. Chem. 42:1999;1901-1907.
44. Reddy B.S.P., Sondhi S.M., Lown J.W. Synthetic DNA minor groove-binding drugs. Pharmacol. Ther. 84:1999;1-111.
45. Robinson W.E. L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of zidovudine plus a protease inhibitor (AG1350). Antiviral Res. 39:1998;101-111.
46. Singh S.B., Zink D., Polishook J., Valentino D., Shafiee A., Silverman K., Felock P., Teran A., Vilella D., Hazuda D.J., Lingham R.B. Structure and absolute stereochemistry of HIV-1 integrase inhibitor integric acid. A novel eremophilane sesquiterpenoid produced by a Xylariai sp. Tetrahedron Lett. 40:1999;8775-8779.
47. Skalka A.M. Retroviral integration. Maramorosh K., Murphy F., Shatkin A.J. Advances in Virus Research. 52:1999;271-475 Academic Press, San Diego.
48. Stanwell C., Ye B., Yuspa S.H., Burke T.R. Cell protein-rosslinking by erbstatin and related compounds. Biochem. Pharmacol. 52:1996;475-480.
49. Taktakishivli M., Neamati N., Pommier Y., Nair V. Recognition and inhibition of HIV integrase by novel dinucleotides. J. Am. Chem. Soc. 122:2000;5671-5677.
50. Turpin J.A., Buckheit R.W. Jr, Derse D., Hollingshead M., Williamson K., Palamone C., Osterling M.C., Hill S.A., Graham L., Schaeffer C.A., Bu M., Huang M., Cholody W.M., Michejda C.J., Rice W.G. Inhibition of acute-, latent-, and chronic-phase human immunodeficiency virus type 1 (HIV-1) replication by a bistriazoloacridone analog that selectively inhibits HIV-1 transcription. Antimicrob. Agents Chemother. 42:1998;487-494.
51. Wang Y.X., Neamati N., Jacob J., Palmer I., Stahl S.J., Kaufman J.D., Huang P.L., Winslow H.E., Pommier Y., Wingfield P.T., Lee-Huang S., Bax A., Torchia D.A. Solution structure of anti-HIV-1 and anti-tumor protein MAP30: structural insights into its multiple functions. Cell. 99:1999;433-442.
52. White S., Szewczyk J.W., Turner J.M., Baird E.E., Dervan P.B. Recognition of the four Watson-Crick base pairs in the DNA minor groove by synthetic ligands. Nature. 391:1998;468-470.
53. Wlodawer A. Crystal structure of catalytic core domains of retroviral integrases and role of divalent cations in enzymatic activity. Skalka A.M. Advances in Virus Research. 52:1999;335-350 Academic Press, San Diego.
54. Yang Z.N., Mueser T.C., Bushman F.D., Hyde C.C. Crystal structure of an active two-domain derivative of Rous Sarcoma virus integrase. J. Mol. Biol. 296:2000;535-548.
55. Zhang J., Neamati N., Nair V. Inhibition of HIV integrase by novel nucleotides bearing tricyclic bases. Biorg. Med. Chem. Lett. 8:1998;1887-1890.
56. Zhu K., Cordeiro M.L., Atienza J., Robinson W.E. Jr, Chow S.A. Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids. J. Virol. 73:1999;3309-3316.
57. Zouhiri F., Mouscadet J.F., Mekouar K., Desmaele D., Savoure D., Leh H., Subra F., Le Bret M., Auclair C., d'Angelo J. Structure-activity relationships and binding mode of styrylquinolines as potent inhibitors of HIV-1 integrase and replication of HIV-1 in cell culture. J. Med. Chem. 43:2000;1533-1540.