Dicaffeoyltartaric Acid and Dicaffeoylquinic Acid HIV Integrase Inhibitors

HIV-1 Integrase: Mechanism and Inhibitor Design

Volumn , Issue , 2011, Pages 341-362

  Crosby, David C ^a   Robinson, W Edward ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Dicaffeoyltartaric acid, and HIV IN inhibitors; L CA, antiviral and anti IN activity; L CA, partner antiretroviral therapy

Indexed keywords

EID: 84886216010     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118015377.ch23     Document Type: Chapter

References (39)

1. Robinson, W. E., Jr.; Reinecke, M.; Abdel-Malek, S.; Jia, Q.; Chow, S. Inhibitors of HIV-1 replication that inhibit HIV integrase. Proc. Natl. Acad. Sci. USA 1996, 93, 6326_6331.
2. King, P.; Lee, D.; Reinke, R.; Victoria, J.; Beale, K.; Robinson, W. E., Jr., Human immunodeficiency virus type-1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors. Virology 2003, 306, 147_161.
3. King, P.; Robinson, W. E., Jr., 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. 1998, 72, 8420_8424.
4. Abdel-Malek, S.; Bastien, J.; Mahler, W.; Jia, Q.; Reinecke, M.; Robinson, W. E., Jr.; Shu, Y.; Zalles-Asin, J. Drug leads from the Kallawaya herbalists of Bolivia. 1. Background, rationale, protocol and anti-HIV activity. J. Ethnopharmacol. 1996, 50, 157_166.
5. Tamura, H.; Akioka, T.; Ueno, K.; Chujyo, T.; Okazaki, K.; King, P. J.; Robinson, W. E., Jr., Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves. Mol. Nutr. Food Res. 2006, 50, 396_400.
6. Kim, H. J.; Kim, E. J.; Seo, S. H.; Shin, C. G.; Jin, C.; Lee, Y. S. Vanillic acid glycoside and quinic acid derivatives from gardeniae fructus. J. Nat. Prod. 2006, 69, 600_603.
7. Robinson, W. E., Jr.; Cordeiro, M.; Abdel-Malek, S.; Jia, Q.; Chow, S. A.; Reinecke, M. G.; Mitchell, W. M. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 1996, 50, 846_855.
8. McDougall, B.; King, P.; Wu, B.; Hostomsky, Z.; Reinecke, M.; Robinson, W. E., Jr., Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrob. Agents Chemother. 1998, 42, 140_146.
9. Reinke, R.; King, P. J.; Victoria, J. G.; McDougall, B. R.; Ma, G.; Mao, Y.; Reinecke, M. G.; Robinson, W. E., Jr., Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations. J. Med. Chem. 2002, 45, 3669_3683.
10. Davies, D. R.; Craigie, R.; Engelman, A.; Jenkins, T. M.; Hickman, A. B.; Dyda, F. Crystal structure of the catalytic domain of HIV-1 integrase: Similarity to other polynucleotidyl transferases. Science 1994, 266, 1981_1986.
11. Yang, W.; Steitz, T. Recombining the structures of HIV integrase, RuvC and RNaseH. Structure 1995, 3, 131_134.
12. Zhu, K.; Cordeiro, M.; Atienza, J.; Robinson,W. E., Jr.; Chow, S. Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids. J. Virol. 1999, 73, 3309_3316.
13. Reinke, R.; Lee, D.; McDougall, B.; King, P.; Victoria, J.; Mao, Y.; Lei, X.; Reinecke, M.; Robinson, W. E., Jr., L-Chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology 2004, 326, 203_219.
14. Pluymers, W.; Neamati, N.; Pannecouque, C.; Fikkert, V.; Marchand, C.; Burke, T., Jr.; Pommier, Y.; Schols, D.; De-Clercq, E.; Debyser, Z.; Witvrouw, M. Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters. Mol. Pharmacol. 2000, 58, 641_648.
15. Reinke, R.; Lee, D.; Robinson, W. E., Jr., Inhibition of human immunodeficiency virus type 1 isolates by the integrase inhibitor L-731,988, a diketo acid. Antimicrob. Agents Chemother. 2002, 46, 3301_3303.
16. Greenwald, J.; Le, V.; Butler, S. L.; Bushman, F.; Choe, S. The mobility of an HIV-1 integrase active site loop is correlated with catalytic activity. Biochemistry 1999, 38, 8892_8898.
17. Lee, D.; Robinson, W. E., Jr., Human immunodeficiency virus type 1 (HIV-1) integrase: Resistance to diketo acid integrase inhibitors impairs HIV-1 replication and integration and confers cross-resistance to L-chicoric acid. J. Virol. 2004, 78, 5835_5847.
18. Hazuda, D.; Felock, P.; Witmer, M.; Wolfe, A.; Stillmock, K.; Grobler, J.; Espeseth, A.; Gabryelski, L.; Schleif,W.; Blau, C.; Miller, M. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells. Science 2000, 287, 646_650.
19. Brigo, A.; Lee, K. W.; Iurcu Mustata, G.; Briggs, J. M. Comparison of multiple molecular dynamics trajectories calculated for the drug-resistant HIV-1 integrase T66I/M154I catalytic domain. Biophys. J. 2005, 88, 3072_3082.
20. Lins, R. D.; Briggs, J. M.; Straatsma, T. P.; Carlson, H. A.; Greenwald, J.; Choe, S.; McCammon, J. A. Molecular dynamics studies on the HIV-1 integrase catalytic domain. Biophys. J. 1999, 76, 2999_3011.
21. Sotriffer, C. A.; Ni, H. H.; McCammon, J. A. Active site binding modes of HIV-1 integrase inhibitors. J. Med. Chem. 2000, 43, 4109_4117.
22. Lee, D.; Robinson, W. E., Jr., Preliminary mapping of a putative inhibitor-binding pocket for human immunodeficiency virus type 1 integrase inhibitors. Antimicrob. Agents Chemother. 2006, 50, 134_142.
23. 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. 1999, 96, 13040_13043.
24. Hwang, D. J.; Kim, S. N.; Choi, J. H.; Lee, Y. S. Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors. Bioorg. Med. Chem., 2001, 9, 1429_1437.
25. King, P.; 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. 1999, 42, 497_509.
26. Charvat, T.; Lee, D.; Robinson, W. E. Jr.; Chamberlin, A. R. Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase. Bioorg. Med. Chem. 2006, 14, 4552_4567.
27. Kim, S. N.; Lee, J. Y.; Kim, H. J.; Shin, C.; Park, H.; Lee, Y. S. Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides. Bioorg. Med. Chem. Lett., 2000, 10, 1879_1882.
28. Lin, Z.; Neamati, N.; Zhao, H.; Kiryu, Y.; Turpin, J. A.; Aberham, C.; Strebel, K.; Kohn, K.; Witvrouw, M.; Pannecouque, C.; Debyser, Z.; DeClercq, E.; Rice, W. G.; Pommier, Y.; Burke, T. R. Chicoric acid analogues as HIV-1 integrase inhibitors. J. Med. Chem. 1999, 42, 1401_1414.
29. Xu, Y.; Zhao, G.; Shin, C.; Zang, H.; Lee, C.; Lee, Y. S. Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors. Bioorg. Med. Chem., 2003, 11, 3589_3593.
30. Meadows, D. C.; Mathews, T. B.; North, T. W.; Hadd, M. J.; Kuo, C. L.; Neamati, N.; Gervay-Hague, J. Synthesis and biological evaluation of geminal disulfones as HIV-1 integrase inhibitors. J. Med. Chem. 2005, 48, 4526_4534.
31. Sakai, H.; Kawamura, M.; Sakuragi, J.; Sakuragi, S.; Shibata, R.; Ishimoto, A.; Ono, N.; Ueda, S.; Adachi, A. Integration is essential for efficient gene expression of human immunodeficiency virus type 1. J. Virol. 1993, 67, 1169_1174.
32. Robinson, W. E., Jr., 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. 1998, 39, 101_111.
33. Beale, K.; Robinson, W. E., Jr., Combinations of reverse transcriptase, protease, and integrase inhibitors can be synergistic in vitro against drug-sensitive and RT inhibitor-resistant molecular clones of HIV-1. Antiviral Res. 2000, 46, 223_232.
34. Chou, J.; Chou, T. C. Dose-effect analysis with microcomputers: Quantitation of ED50, LD50, synergism, and antagonism, low-dose risk, receptor binding and enzyme kinetics. In A Computer Software for Apple II Series or IBM PC and Manual. Elsevier Science Publishers, Cambridge, 1985.
35. Chou, T. C. Relationships between inhibition constants and fractional inhibitions in enzyme-catalyzed reactions with different numbers of reactants, different reaction mechanisms, and different types of mechanisms of inhibition. Pharmacology. 1974, 10, 235_247.
36. Chou, T. C. The median-effect principle and the combination index for quantitation of synergism and antagonism. In Synergism and Antagonism in Chemotherapy (T. C. Chou, and D. C. Rideout, Eds.). Academic, San Diego, 1991, pp. 61_102.
37. Chou, T. C.; Talalay, P. Quantitative analysis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors. Adv. Enzyme Regul. 1984, 22, 27_55.
38. Chou, T. C.; Talalay, P. Generalized equations for the analysis of Michaelis-Menten and higher order kinetic systems with two or more mutually exclusive and nonexclusive inhibitors. Eur. J. Biochem. 1981, 115, 207_216.
39. Reinke, R.; Steffen, N.; Robinson, W. E., Jr., Natural selection results in conservation of HIV-1 integrase activity despite sequence variability. AIDS 2001, 15, 823.