Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase

Antimicrobial Agents and Chemotherapy

Volumn 42, Issue 1, 1998, Pages 140-146

  Mcdougall, Brenda ^a   King, Peter J ^a   Wu, Bor Wen ^b   Hostomsky, Zdenek ^b   Reinecke, Manfred G ^c   Robinson Jr , W Edward ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b AGOURON PHARMACEUTICALS INC   (United States)

^c TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CD4 ANTIGEN; DICAFFEOYLQUINIC ACID DERIVATIVE; DICAFFEOYLTARTARIC ACID DERIVATIVE; GLYCOPROTEIN GP 120; INTEGRASE; INTEGRASE INHIBITOR; RIBONUCLEASE H; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG SPECIFICITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL;

EID: 0031973575     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.42.1.140     Document Type: Article

References (55)

1. Aboulker, J., and A. M. Swart. 1993. Preliminary analysis of the Concorde trial. Lancet 341:889-890.
2. Albert, J., J. Wahlberg, J. Lundeberg, S. Cox, E. Sandstrom, B. Wahren, and M. Uhlen. 1992. Persistence of azidothymidine-resistant human immunodeficiency virus type 1 RNA genotypes in posttreatment sera. J. Virol. 66:5627-5630.
3. Baldwin, E. T., T. N. Bhat, B. Liu, N. Pattabiraman, and J. W. Erickson. 1995. Structural basis of drug resistance for the V82A mutant of HIV-1 proteinase. Nat. Struct. Biol. 2:244-249.
4. Brinkworth, R. I., and D. P. Fairlie. 1992. Non-peptidic anti-AIDS agents: inhibition of HIV-1 proteinase by disulfonates. Biochem. Biophys. Res. Commun. 188:624-630.
5. Brinkworth, R. I., T. C. Woon, and D. P. Fairlie. 1991. Inhibition of HIV-1 proteinase by non-peptide carboxylates. Biochem. Biophys. Res. Commun. 176:241-246.
6. Carteau, S., J. F. Mouscadet, H. Goulaouic, F. Subra, and C. Auclair. 1993. Effect of topoisomerase inhibitors on the in vitro HIV DNA integration reaction. Biochem. Biophys. Res. Commun. 192:1409-1414.
7. Carteau, S., J. F. Mouscadet, H. Goulaouic, F. Subra, and C. Auclair. 1993. Inhibitory effect of the polyanionic drug suramin on the in vitro HIV DNA integration reaction. Arch. Biochem. Biophys. 305:606-610.
8. Chow, S. A., K. A. Vincent, V. Ellison, and P. O. Brown. 1992. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus. Science 255:723-726.
9. Collier, A. C., R. W. Coombs, D. A. Schoenfeld, R. L. Bassett, J. Timpone, A. Baruch, M. Jones, K. Facey, C. Whitacre, V. J. McAuliffe, H. M. Friedman, T. C. Merigan, R. C. Reichman, C. Hooper, and L. Corey. 1996. Treatment of human immunodeficiency virus infection with saquinavir, zidovudine, and zalcitabine. N. Engl. J. Med. 334:1011-1017.
10. Craig, J. C., I. B. Duncan, D. Hockley, C. Grief, N. A. Roberts, and J. S. Mills. 1991. Antiviral properties of Ro 31-8959, an inhibitor of human immunodeficiency virus (HIV) proteinase. Antivir. Res. 16:295-305.
11. Culberson, J. C., B. L. Bush, and V. V. Sardana. 1994. Qualitative study of drug resistance in retroviral protease using structural modeling and site-directed mutagenesis. Methods Enzymol. 241:285-394.
12. Cushman, M., W. M. Golebiewski, Y. Pommier, A. Mazumder, D. Reymen, E. De Clercq, L. Graham, and W. G. Rice. 1995. Cosalane analogues with enhanced potencies as inhibitors of HIV-1 protease and integrase. J. Med. Chem. 38:443-452.
13. Cushman, M., and P. Sherman. 1992. Inhibition of HIV-1 integration protein by aurintricarboxylic acid monomers, monomer analogs, and polymer fractions. Biochem. Biophys. Res. Commun. 185:85-90.
14. Davies, J. F., II, Z. Hostomska, Z. Hostomsky, S. R. Jordan, and D. A. Matthews. 1991. Crystal structure of the ribonuclease H domain of HIV-1 reverse transcriptase. Science 252:88-95.
15. Dyda, F., A. B. Hickman, T. M. Jenkins, A. Engelman, R. Craigie, and D. R. Davies. 1994. Crystal structure of the catalytic domain of HIV-1 integrase: similarity to other polynucleotidyl transferases. Science 266:1981-1986.
16. Farnet, C., B. Wang, J. R. Lipford, and F. D. Bushman. 1996. Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. Proc. Natl. Acad. Sci. USA 93:9742-9747.
17. Fesen, M. R., K. W. Kohn, F. Leteurtre, and Y. Pommier. 1993. Inhibitors of human immunodeficiency virus integrase. Proc. Natl. Acad. Sci. USA 90: 2399-2403.
18. Fesen, M. R., Y. Pommier, F. Leteurtre, S. Hiroguchi, J. Yung, and K. W. Kohn. 1994. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem. Pharmacol. 48:595-608.
19. Gao, Q., Z. Gu, M. A. Parniak, X. Li, and M. A. Wainberg. 1992. In vitro selection of variants of human immunodeficiency virus type 1 resistant to 3′-azido-3′-deoxythymidine and 2′,3′-dideoxyinosine. J. Virol. 66:12-19.
20. Gu, Z., Q. Gao, H. Fang, M. A. Parniak, B. G. Brenner, and M. A. Wainberg. 1994. Identification of novel mutations that confer drug resistance in the human immunodeficiency virus polymerase gene. Leukemia 8(Suppl. 1): S166-S169.
21. Gulick, R. M., J. W. Mellors, D. Havlir, J. J. Eron, C. Gonzalez, D. McMahon, D. D. Richman, F. T. Valentine, L. Jonas, A. Meibohm, E. A. Emini, and J. A. Chodakewitz. 1997. Treatment with indinavir, zidovudine, and lamivudine in adults with human immunodeficiency virus infection and prior anti-retroviral therapy. N. Engl. J. Med. 337:734-739.
22. Gulnik, S. V., L. I. Suvorov, B. Liu, B. Yu, B. Anderson, H. Mitsuya, and J. W. Erickson. 1995. Kinetic characterization and cross-resistance patterns of HIV-1 protease mutants selected under drug pressure. Biochemistry 34: 9282-9287.
23. Hammer, S. M., K. E. Squires, M. D. Hughes, J. M. Grimes, L. M. Demeter, J. S. Currier, J. J. Eron, J. E. Feinberg, H. H. Balfour, Jr., L. R. Deyton, J. A. Chodakewitz, M. A. Fischl, and ACTG. 1997. A controlled trial of two nucleoside analogues plus indinavir in persons with human immunodeficiency virus infection and CD4 cell counts of 200 per cubic millimeter or less. N. Engl. J. Med. 337:725-733.
24. 2-symmetric protease inhibitor. J. Virol. 68:2016-2020.
25. Hong, H., N. Neamati, S. Wang, M. C. Nicklaus, A. Mazumder, H. Zhao, T. R. Burke, Jr., Y. Pommier, and G. W. A. Milne. 1997. Discovery of HIV-1 integrase inhibitors by pharmacophore searching. J. Med. Chem. 40:930-936.
26. Hostomsky, Z., Z. Hostomska, G. O. Hudson, E. W. Moomaw, and B. O. Nodes. 1991. Reconstitution in vitro of RNase H activity by using purified N-terminal and C-terminal domains of human immunodeficiency virus type 1 reverse transcriptase. Proc. Natl. Acad. Sci. USA 88:1148-1152.
27. 2 symmetry-based HIV protease inhibitors as single agents or in combinations. Antimicrob. Agents Chemother. 36:926-933.
28. LaFemina, R. L., P. L. Graham, K. LeGrow, J. C. Hastings, A. Wolfe, S. D. Young, E. A. Emini, and D. J. Hazuda. 1995. Inhibition of human immunodeficiency virus integrase by bis-catechols. Antimicrob. Agents Chemother. 39:320-324.
29. Mahmood, N., P. S. Moore, N. De Tommasi, F. De Simone, S. Colman, A. J. Hay, and C. Pizza. 1993. Inhibition of HIV infection by caffeoylquinic acid derivatives. Antivir. Chem. Chemother. 4:235-240.
30. Martin, J. L., J. E. Wilson, R. L. Haynes, and P. A. Furman. 1993. Mechanism of resistance of human immunodeficiency virus type 1 to 2′,3′-dideoxyinosine. Proc. Natl. Acad. Sci. USA 90:6135-6139.
31. Mazumder, A., K. Raghavan, J. Weinstein, K. W. Kohn, and Y. Pommier. 1995. Inhibition of human immunodeficiency virus type-1 integrase by curcumin. Biochem. Pharmacol. 49:1165-1170.
32. Merigan, T. C., G. Skowron, and SG-ACTG-NIAID. 1990. Safety and tolerance of dideoxycytidine as a single agent. Results of early phase studies in patients with acquired immunodeficiency syndrome (AIDS) or advanced AIDS-related complex. Am. J. Med. 88:11S-15S.
33. Mitsuya, H., K. J. Weinhold, P. A. Furman, M. H. St. Clair, S. Nusinoff-Lehrman, R. C. Gallo, D. Bolognesi, D. W. Barry, and S. Broder. 1985. 3′-Azido-3-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc. Natl. Acad. Sci. USA 82: 7096-7100.
34. Mizrahi, V. 1989. Analysis of ribonuclease H activity of HIV-1 reverse transcriptase using RNA-DNA hybrid substrates derived from the gag region of HIV-1. Biochemistry 28:9088-9094.
35. Montefiori, D. C., W. E. Robinson, Jr., S. S. Schuffman, and W. M. Mitchell. 1988. Evaluation of antiviral drugs and neutralizing antibodies against human immunodeficiency virus by a rapid and sensitive microtiter infection assay. J. Clin. Microbiol. 26:231-235.
36. Neamati, N., H. Hong, A. Mazumder, S. Wang, S. Sunder, M. C. Nicklaus, G. W. A. Milne, B. Proksa, and Y. Pommier. 1997. Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. J. Med. Chem. 40:942-951.
37. Nicklaus, M. C., N. Neamati, H. Hong, A. Mazumder, S. Sunder, J. Chen, G. W. A. Milne, and Y. Pommier. 1997. HIV-1 integrase pharmacophore: discovery of inhibitors through three-dimensional database searching. J. Med. Chem. 40:920-929.
38. Nishizawa, M., T. Yamagishi, G. E. Dutschman, W. B. Parker, A. J. Bonder, R. E. Kilkuskie, Y.-C. Cheng, and K.-H. Lee. 1989. Anti-AIDS agents. 1. Isolation and characterization of four new tetragalloylquinic acids as a new class of HIV reverse transcriptase inhibitors from tannic acid. J. Nat. Prod. 52:762-768.
39. Nonaka, G.-I., I. Nishioka, M. Nishizawa, T. Yamagishi, Y. Kashiwada, G. E. Dutschman, A. Bonder, R. E. Kilkuskie, Y.-C. Cheng, and K.-H. Lee. 1990. Anti-AIDS agents. 2. Inhibitory effect of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells. J. Nat. Prod. 53:589-595.
40. Otto, M. J., S. Garber, D. L. Winslow, C. D. Reid, P. Aldrich, P. K. Jadhav, C. E. Patterson, C. N. Hodge, and Y. S. Cheng. 1993. In vitro isolation and identification of human immunodeficiency virus (HIV) variants with reduced sensitivity to C-2 symmetrical inhibitors of HIV type 1 protease. Proc. Natl. Acad. Sci. USA 90:7543-7547.
41. Poiesz, B. J., F. W. Ruscetti, A. F. Gazder, B. A. Bunn, J. D. Minna, and R. C. Gallo. 1980. Detection and isolation of type C retrovirus particles from fresh and cultured lymphocytes of a patient with cutaneous T-cell lymphoma. Proc. Natl. Acad. Sci. USA 77:7415-7419.
42. Ratner, L., W. Haseltine, R. Patarca, K. J. Livak, B. Starcich, S. F. Josephs, E. R. Doran, J. A. Rafalski, E. A. Whitehorn, K. Baumeister, L. Ivanoff, S. R. Petteway, M. L. Person, J. A. Lautenberger, T. S. Papas, J. Ghrayeb, N. T. Chang, R. C. Gallo, and F. Wong-Staal. 1985. Complete nucleotide sequence of the AIDS virus, HTLV III. Nature 313:277-284.
43. Richman, D. D. 1992. HIV drug resistance. AIDS Res. Hum. Retroviruses 8:1065-1071.
44. Robinson, W. E., Jr., M. Cordeiro, S. Abdel-Malek, Q. Jia, S. A. Chow, M. G. Reinecke, and W. M. Mitchell. 1996. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus (HIV) integrase: inhibition of the core catalytic domain of HIV integrase. Mol. Pharmacol. 50:846-855.
45. Robinson, W. E., Jr., D. C. Montefiori, D. H. Gillespie, and W. M. Mitchell. 1989. Complement-mediated, antibody-dependent enhancement of human immunodeficiency virus type 1 (HIV-1) infection in vitro increases HIV-1 RNA and protein synthesis and infectious virus production. J. Acquired Immune Defic. Syndr. 2:33-42.
46. Robinson, W. E., Jr., M. G. Reinecke, S. Abdel-Malek, Q. Jia, and S. A. Chow. 1996. Inhibitors of HIV-1 replication that inhibit HIV integrase. Proc. Natl. Acad. Sci. USA 93:6326-6331.
47. Rooke, R., M. A. Parniak, M. Tremblay, H. Soudeyns, X. Li, Q. Gao, X.-J. Yao, and M. A. Wainberg. 1991. Biological comparison of wild-type and zidovudine-resistant isolates of human immunodeficiency virus type 1 from the same subjects: susceptibility and resistance to other drugs. Antimicrob. Agents Chemother. 35:988-991.
48. Swanstrom, R. 1994. Characterization of HIV-1 protease mutants: random, directed selected. Curr. Opin. Biotechnol. 5:409-413.
49. Tisdale, M., R. E. Myers, B. Maschera, N. R. Parry, N. M. Oliver, and E. D. Blair. 1995. Cross-resistance analysis of human immunodeficiency virus type 1 variants individually selected for resistance to five different protease inhibitors. Antimicrob. Agents Chemother. 39:1704-1710.
50. Yarchoan, R., H. Mitsuya, R. V. Thomas, J. M. Pluda, N. R. Hartman, C.-F. Perno, K. S. Marczyk, J.-P. Allain, D. G. Johns, and S. Broder. 1989. In vivo activity against HIV and favorable toxicity profile of 2′,3′-dideoxyinosine. Science 245:412-415.
51. Yarchoan, R., C. F. Perno, R. V. Thomas, R. W. Klecker, J.-P. Allain, R. J. Wills, N. McAtee, M. A. Fischl, R. Dubinsky, M. C. McNeely, H. Mitsuya, J. M. Pluda, T. J. Lawley, M. Leuther, B. Safai, J. M. Collins, C. E. Myers, and S. Broder. 1988. Phase I studies of 2′,3′-dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudine (AZT). Lancet i:76-81.
52. Zack, J. A., S. J. Arrigo, S. R. Weitsman, A. S. Go, A. Haislip, and I. S. Y. Chen. 1990. HIV-1 entry into quiescent primary lymphocytes: molecular analysis reveals a labile, latent viral structure. Cell 61:213-222.
53. Zhao, H., N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G. W. A. Milne, Y. Pommier, and T. R. Burke, Jr. 1997. Coumarin-based inhibitors of HIV integrase. J. Med. Chem. 40:242-249.
54. Zhao, H., N. Neamati, A. Mazumder, S. Sunder, Y. Pommier, and T. R. Burke, Jr. 1997. Arylamide inhibitors of HIV-1 integrase. J. Med. Chem. 40:1186-1194.
55. Zhao, H., N. Neamati, S. Sunder, H. Hong, S. Wang, G. W. A. Milne, Y. Pommier, and T. R. Burke, Jr. 1997. Hydrazide-containing inhibitors of HIV-1 integrase. J. Med. Chem. 40:937-941.