Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and hiv-1 replication at nontoxic concentrations

Journal of Medicinal Chemistry

Volumn 45, Issue 17, 2002, Pages 3669-3683

  Reinke, Ryan A ^a   King, Peter J ^a   Victoria, Joseph G ^a   McDougall, Brenda R ^b   Ma, Guoxiang ^c   Mao, Yingqun ^c   Reinecke, Manfred G ^c   Robinson Jr , W Edward ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; CARBOXYLIC ACID; CATECHOL; CHOLIC ACID; CICHORIC ACID; ESTER; INTEGRASE; INTEGRASE INHIBITOR; TARTARIC ACID DERIVATIVE;

ARTICLE; CYTOTOXICITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TISSUE CULTURE; VIRUS REPLICATION;

BENZOIC ACIDS; CAFFEIC ACIDS; CELL SURVIVAL; CHLOROGENIC ACID; DOSE-RESPONSE RELATIONSHIP, DRUG; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; HYDROLYSIS; STRUCTURE-ACTIVITY RELATIONSHIP; SUCCINATES; TARTRATES; VIRUS REPLICATION;

EID: 0037103344     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010359d     Document Type: Article

References (52)

1. A trial comparing nucleoside monotherapy with combination therapy in HIV-infected adults with CD4 cell counts from 200 to 500 per cubic millimeter
2. ACTG. 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
3. Treatment of human immunodeficiency virus infection with saquinavir, zidovudine, and zalcitabine
4. Human immunodeficiency virus type 1 integrase: Effect on viral replication of mutations at highly conserved residues
5. Residues critical for retroviral integrative recombination in a region that is highly conserved among retroviral/retrotransposon integrases and bacterial insertion sequence transposases
6. Requirement of active human immunodeficiency virus type 1 integrase enzyme for productive infection of human T-lymphoid cells
7. Integration is not necessary for expression of human immunodeficiency virus type 1 protein products
8. Integrase mutants of human immunodeficiency virus type 1 with a specific defect in integration
9. Effect of HIV integrase inhibitors on the RAG1/2 recombinase
10. 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)
11. 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
12. Retroviruses
13. Genetics of retroviral integration
14. Molecular mechanisms in retrovirus DNA integration
15. Retroviral integration: Structure of the initial covalent product and its precursor, and a role for the viral IN protein
16. Retroviral DNA integration: Structure of an integration intermediate
17. Analysis of mutations in the integration function of Moloney murine leukemia virus: Effect on DNA binding and cutting
18. Activities of human immunodeficiency virus (HIV) integration protein in vitro: Specific cleavage and integration of HIV DNA
19. A role for DNA-PK in retroviral DNA integration
20. Human immunodeficiency virus type 1 preintegration complexes containing discontinuous plus strands are competent to integrate in vitro
21. Human immunodeficiency virus integration protein expressed in Escherichia coli possesses selective DNA cleaving activity
22. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus
23. In vitro assays for activities of retroviral integrase
24. Substrate features important for recognition and catalysis by human immunodeficiency virus type 1 integrase identified by using novel DNA substrates
25. Human immunodeficiency virus type 1 integration protein: DNA sequence requirements for cleaving and joining reactions
26. Characterization of human immunodeficiency virus type 1 integrase expressed in Escherichia coli and analysis of variants with amino-terminal mutations
27. Inhibitors of human immunodeficiency virus integrase
28. HIV integrase: The next target?
29. Inhibitors of HIV-1 replication that inhibit HIV integrase
30. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integrase
31. Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase
32. Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids
33. Structure-activity relationships: Analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication
34. Chicoric acid analogues as HIV-1 integrase inhibitors
35. Active site binding modes of HIV-1 integrase inhibitors
36. Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: Synthesis, biological evaluation, and molecular modeling
37. Meso dihydroguaietic acid and its derivatives
38. The constituents of natural phenolic resins. Part XIV. The synthesis of dl, d, and l matairesinol dimethyl ether
39. Evaluation of antiviral drugs and neutralizing antibodies against human immunodeficiency virus by a rapid and sensitive microtiter infection assay
40. 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
41. Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters
42. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells
43. A quantitative assay for HIV DNA integration in vivo
44. Human immunodeficiency virus type 1 cDNA integration: New aromatic hydroxylated inhibitors and studies of the inhibition mechanism
45. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase
46. Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules
47. Differential divalent cation requirements uncouple the assembly and catalytic reactions of human immunodeficiency virus type 1 integrase
48. Structure of the HIV-1 integrase catalytic domain complexed with an inhibitor: A platform for antiviral drug design
49. A convenient synthesis of (+)-albicanol based on enzymatic function: Total synthesis of (+)-albicanyl acetate, (-)-albicanyl 3,4-dihydroxy-cinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox
50. Facile synthesis of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids
51. Detection of human immunodeficiency virus
52. HIV-1 entry into quiescent primary lymphocytes: Molecular analysis reveals a labile, latent viral structure