Characterization of HIV-1 enzyme reverse transcriptase inhibition by the compound 6-chloro-1,4-dihydro-4-oxo-1-(β-D-ribofuranosyl) quinoline-3-carboxylic acid through kinetic and in silico studies

Current HIV Research

Volumn 7, Issue 3, 2009, Pages 327-335

  Souza, Thiago Moreno L ^a   Rodriguez, Diego Q ^a   Ferreira, Vitor F ^b   Marquez, Isakelly Pereira ^b   Santos, Fernando da Costa ^b   Cunha, Anna Claudia ^b   Vieira de Souza, Maria Cecilia Bastos ^b   Frugulhetti, Izabel Christina de Palmer Paixão ^b   Bou Habib, Dumith Chequer ^a   Fontes, Carlos Frederico Leite ^c  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

AUDS; Chloroxoquinolinic acid; HIV 1; Reverse transcriptase

Indexed keywords

6 CHLORO 1,4 DIHYDRO 4 OXO 1 (BETA DEXTRO RIBOFURANOSYL)QUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 1,4 DIHYDRO 4 OXO 1H QUINOLINE 3 CARBOXYLIC ACID; ACICLOVIR TRIPHOSPHATE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CARBOXYLIC ACID; DNA DIRECTED DNA POLYMERASE; EFAVIRENZ; NEVIRAPINE; NUCLEOTIDYLTRANSFERASE INHIBITOR; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THYMIDINE TRIPHOSPHATE; TYROSINE; UNCLASSIFIED DRUG; ZIDOVUDINE 5' TRIPHOSPHATE; 6 CHLORO 1,4 DIHYDRO 4 OXO 1 (BETA D RIBOFURANOSYL)QUINOLINE 3 CARBOXYLIC ACID; 6-CHLORO-1,4-DIHYDRO-4-OXO-1-(BETA-D-RIBOFURANOSYL)QUINOLINE-3-CARBOXYLIC ACID; QUINOLINE DERIVATIVE; REVERSE TRANSCRIPTASE, HUMAN IMMUNODEFICIENCY VIRUS 1; RIBONUCLEOSIDE;

ALLOSTERISM; BINDING AFFINITY; COMPETITIVE INHIBITION; COMPUTER MODEL; CONTROLLED STUDY; CRYSTAL STRUCTURE; DISSOCIATION; DNA TEMPLATE; DRUG MECHANISM; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; HUMAN IMMUNODEFICIENCY VIRUS 1; INHIBITION KINETICS; MOLECULAR DOCKING; NONHUMAN; NUCLEOTIDE SEQUENCE; REVIEW; ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; COMPUTER SIMULATION; DRUG ANTAGONISM; DRUG EFFECT; HUMAN; KINETICS; PROTEIN BINDING;

BINDING SITES; COMPUTER SIMULATION; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; KINETICS; MODELS, MOLECULAR; PROTEIN BINDING; QUINOLINES; REVERSE TRANSCRIPTASE INHIBITORS; RIBONUCLEOSIDES;

EID: 67649101419     PISSN: 1570162X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016209788347958     Document Type: Review

References (24)

1. Braithwaite DK, Ito J. Compilation, "alignment and phylogenetic relationships of DNA polymerases. Nucleic Acids Res 1993; 25: 787-802
2. Arts EJ, Ma J, Kleiman L, Wainberg MA. Mature reverse transcriptase (p66/ p51) is responsible for low levels of viral DNA found in human immunodeficiency virus type I (HIV-1). Leukemia 1994; 1: S175-S178.
3. Hottiger M, Hubscher U. Human Immunodeficiency Virus type 1 reverse transcriptase. Biol Chem Hoppe Seyler 1996; 377: 97-120.
4. Telesnitsky A, Goff SP. Reverse transcriptase and the generation of retroviral DNA. In: Coffin JW, Hughes SH, Varmus HE, Eds. Retroviruses. Plainview. Cold Spring Harbor Laboratory Press. 1997; pp. 121-60.
5. Butler SL, Johnson EP, Bushman FD. Human immunodeficiency virus cDNA metabolism: notable stability of two-long terminal repeat circles. J Virol 2002; 76: 3739-47.
6. Maga G, Ubiali D, Salvetti R, Pregnolato M. Spadari S. Selective interaction of the human immunodeficiency virus type 1 reverse transcriptase nonnucleoside inhibitor efavirenz; and its thiosubstituted analog with different enzyme-substrate complexes. Antimicrob Agents Chemother 2000; 44: 1186-94.
7. Westby M, Nakayama G, Butler SL, Blair WS. Cell-based and biochemical screening approaches for the discovery of novel HTV-1 inhibitors. Antiviral Res 2005; 67: 12140.
8. White K, Margot NA, Wrin T, Petropoulos CJ, Miller MD, Naeger LK. Molecular mechanisms of resistance to human immunodeficiency virus type 1 with reverse transcriptase mutations K65R and K65R+MI84V and their effects on enzyme function and viral replication capacity. Antimicrob Agents Chemother 2002; 46: 3437-46.
9. Zhou Z, Lin X, Madura JD. HIV-1 RT nonnucleuside inhibitors, and their interaction with RT for antiviral drug development. Infect Disord Drug Targets 2006; 6: 391-413.
10. Richman DD. AZT resistance in isolates of HIV. Immunodefic Rev 1991; 2: 315-8.
11. Ren J, Esnouf RM, Hopkins AL, et al. 3′-Azido-3′ -deoxythymidine drug resistance mutations in HIV-1 reverse transcriptase can induce long range conformational changes. Proc Natl Acad Sci USA 1998; 95: 9518-23.
12. Zhang, Z, Walker M, Xu W, et al. Novel nonnucleoside inhibitors that select nucleoside inhibitor resistance mutations in human immunodeficiency virus type-1 reverse transcriptase. Antimicrob-Agents Chemother 2006; 50: 2772-81.
13. De Clercq E. Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. Chem Biodivers 2004; 1: 44-64.
14. Souza TML, Cirne-Santos CC, Fontes-CFL, et al. the compound 6-chloro-1,4-dihydro-oxo-1-(β-D-ribofuranosyl) quinoline-3-carboxylic acid inhibits HIV-1 replication by targeting the enzyme Reverse Transcriptase. Curr HIV Res 2008; 6: 209-17.
15. Matta AD, Santos CVB, Pereira HS, et al. Synthesis of novel nucleosides of 4-oxoquinoline-3-carboxylic acid analogues. Heteroatom Chem 1999; 10: 197-202.
16. Dixon M, Webb EC. Enzymes. 3rd ed. Academic Press, NY 1979.
17. Greco WH. Bravo G. Parsons JC. The search for synergy: a critical review from a response surface perspective. Pharmacol Rev 1995; 47: 331-85.
18. Souza TML, Santos MCV, Ferreira VF, et al. Inhibition of HSV-1 replication and HSV DNA polymerase by the chloroxoquinolinic ribonucleoside 6-chloro-1,4-dihydro-4-oxo-1-(β-d-ribofuranosyl) quinoline-3-carboxylic acid and its aglycone. Antiviral Res 2008; 77: 20-7.
19. Podzamczer D, Fumero E. The role of nevirapine in the treatment of HIV-1 disease. Expert Opin Pharmacother. 2001; 2: 2065-78.
20. Castro HC, Loureiro NI, Pujol-Luz M, et al. HIV-1 reverse transcriptase: a therapeutical target in the spotlight. Curr Med Chem 2006; 13: 313-24.
21. Huang H, Chopra R, Verdine GL, Harrison SC. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: implications for drug resistance. Science 1998; 27: 1669-75.
22. Squires KE. An introduction to nucleoside and nucleotide analogues. Antivir Ther 2001; 6: 1-14.
23. Cases-González CE, Menéndez-Axias L. Nucleotide specificity of HIV-1 reverse transcriptases with amino acid substitutions affecting Ala-114. Biochem J 2005; 387: 221-9.
24. Vandamme AM, Van Vaerenbergh K, De Clercq E. Anti-human immunodeficiency virus drug combination strategies. Antivir Chem Chemother 1998; 9: 187-203.