New anthraquinone derivatives as inhibitors of the HIV-1 reverse transcriptase-associated ribonuclease H function

Chemotherapy

Volumn 58, Issue 4, 2012, Pages 299-307

  Esposito, Francesca ^a   Corona, Angela ^a   Zinzula, Luca ^a   Kharlamova, Tatyana ^a   Tramontano, Enzo ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Anthraquinone derivatives; HIV 1; Reverse transcriptase; Ribonuclease H; RNase H

Indexed keywords

ALIZARIN; ANTHRAQUINONE DERIVATIVE; RIBONUCLEASE H; RNA DIRECTED DNA POLYMERASE;

ARTICLE; DRUG DETERMINATION; DRUG INHIBITION; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; VIRUS INHIBITION;

ANTHRAQUINONES; HIV-1; HUMANS; KINETICS; PROTEIN BINDING; RECOMBINANT PROTEINS; REVERSE TRANSCRIPTASE INHIBITORS; RIBONUCLEASE H;

EID: 84868261918     PISSN: 00093157     EISSN: 14219794     Source Type: Journal    
DOI: 10.1159/000343101     Document Type: Article

References (28)

1. Engelman A, Cherepanov P: The structural biology of HIV-1: mechanistic and therapeutic insights. Nat Rev Microbiol 2012; 10: 279-290.
2. Esposito F, Corona A, Tramontano E: HIV-1 reverse transcriptase still remains a new drug target: structure, function, classical inhibitors and new inhibitors with innovative mechanisms of actions. Mol Biol Int 2012; 2012: 586401.
3. Tramontano, E: HIV-1 RNase H: Recent progress in an exciting, yet little explored, drug target. Mini Rev Med Chem 2006; 6: 727-737.
4. Tramontano E, Di Santo R: HIV-1 RT-associated RNase H function inhibitors: recent advances in drug development. Curr Med Chem 2010; 17: 2837-2853.
5. Huang HS, Chiou JF, Fong Y, Hou CC, Lu YC, Wang JY, Shih JW, Pan YR, Lin JJ: Activation of human telomerase reverse transcriptase expression by some new symmetrical bis-substituted derivatives of the anthraquinone. J Med Chem 2003; 46: 3300-3307.
6. Tan JH, Zhang QX, Huang ZS, Chen Y, Wang XD, Gu LQ, Wu JY: Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives. Eur J Med Chem 2006; 41: 1041-1047.
7. Wheate NJ, Brodie CR, Collins JG, Kemp S, Aldrivch-Wright JR: DNA intercalators in cancer therapy: organic and inorganic drugs and their spectroscopic tools of analysis. Mini Rev Med Chem 2007; 6: 627-648.
8. Huang Q, Lu G, Shen HM, Chung MC, Onq CN: Anticancer properties of anthraquinones from rhubarb. Med Res Rev 2007; 27: 609-630.
9. Bernard DL, Huffman JH, Morris JLB, Wood SG, Huges BG, Sidwell RW: Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus. Antiviral Res 1992; 17: 63-77.
10. Bernard DL, Firbairn DW, O'Neill KL, Gage TL, Sidwell RW: Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives. Antiviral Res 1995; 28: 317-329.
11. Semple SJ, Pyke SM, Reynolds GD, Flower FLP: In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus. Antiviral Res 2001; 49: 169-178.
12. Shuangsuo D, Zhengguo Z, Yunru C, Xin Z, Baofeng W, Lichao Y, Yan'an C: Inhibition of the replication of hepatitis B virus in vitro by emodin. Med Sci Monit 2006; 12: 302-306.
13. Li Z, Li LJ, Sun Y, Li J: Identification of natural compounds with anti-hepatitis B virus activity from Rheum palmatum L. ethanol extract. Chemotheraphy 2007; 53: 320-326.
14. Esimone CO, Grunwald T, Nworu CS, Kuate S, Proksch P, Überla K: Broad spectrum antiviral fractions from the lichen Ramalina farinacea (L.) Ach. Chemotherapy 2009; 55: 119-126.
15. Schinazi RF, Chu CK, Babu JR, Oswald BJ, Saalmann V, Cannon DL, Eriksson BF, Nasr M: Anthraquinones as a new class of antiviral agents against human immunodeficiency virus. Antiviral Res 1990; 13: 265-272.
16. Higuchi H, Mori K, Kato A, Ohkuma T, Endo T, Kaji H, Kaji A: Antiretroviral activities of anthraquinones and their inhibitory effects on reverse transcriptase. Antiviral Res 1991; 15: 205-216.
17. Esposito F, Kharlamova T, Distinto S, Zinzula L, Cheng YC, Dutschman G, Floris G, Markt P, Corona A, Tramontano E: Alizarine derivatives as new dual inhibitors of the HIV-1 reverse transcriptase-associated DNA polymerase and RNase H activities effective also on the RNase H activity of nonnucleoside resistant reverse transcriptases. FEBS J 2011; 278: 1444-1457.
18. Kharlamova T, Esposito F, Zinzula L, Floris G, Cheng Y-C, Dutschman GE, Tramontano E: Inhibition of HIV-1 ribonuclease H activity by novel frangula-emodine derivatives. Med Chem 2009; 5: 398-410.
19. Farnet CM, Wang B, Lipford JR, Bushman FD: Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. Proc Natl Acad Sci USA 1996; 93: 9742-9747.
20. Tramontano E, Esposito F, Badas R, Di Santo R, Costi R, La Colla P: 6-[1-(4-Fluorophenyl) methyl-1H-pyrrol-2-yl)]-2,4-dioxo-5-hexenoic acid ethyl ester a novel diketo acid derivative which selectively inhibits the HIV-1 viral replication in cell culture and the ribonuclease H activity in vitro. Antiviral Res 2005; 65: 117-124.
21. Tramontano E, Kharlamova T, Zinzula L, Esposito F: Effects of new quinizarin derivatives on both HCV NS5B RNA polymerase and HIV-1 reverse transcriptase associated ribonuclease H activities. J Chemother 2011; 23: 273-276.
22. Tramontano E, Cheng YC: HIV-1 reverse transcriptase inhibition by a dipyridodiazepinone derivative: BI-RG-587. Biochem Pharmacol 1992; 43: 1371-1376.
23. Artico M, Massa S, Mai A, Marongiu ME, Piras G, Tramontano E, La Colla P: 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs): a new class of specific inhibitors of human immunodeficiency virus type 1. Antiviral Chem Chemother 1993; 4: 361-368.
24. Mellors J, Im GJ, Tramontano E, Winkler SR, Medina DJ, Dutschman GE, Bazmi HZ, Piras G, Gonzales CJ, Cheng YC: A single conservative amino acid substitution in the reverse transcriptase of human immunodeficiency virus-1 confers resistance to (+)-(5S)-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2- butenyl)imidazo[4, 5, 1-jk][1, 4] benzodiazepin-2(1H)-thione (TIBO R82150). Mol Pharmacol 1993; 43: 11-16.
25. Suchaud V, Bailly F, Lion C, Tramontano E, Esposito F, Corona A, Christ F, Debyser Z, Cotelle P: Development of a series of 3-hydroxyquinolin-2(1 H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity. Bioorg Med Chem Lett 2012; 22: 3988-3992.
26. Distinto S, Esposito F, Kirchmair J, Cardia MC, Gaspari M, Maccioni E, Alcaro S, Markt P, Wolber G, Zinzula L, Tramontano E: Identification of HIV-1 reverse transcriptase dual inhibitors by a combined shape-, 2D-fingerprint-and pharmacophore-based virtual screening approach. Eur J Med Chem 2012; 50: 1-14.
27. Starnes MC, Cheng YC: Human immunodeficiency virus reverse transcriptase-associated RNase H activity. J Biol Chem 1989; 264: 7073-7077.
28. Himmel DM, Sarafinos SG, Dharmasena S, Hossain MM, McCoy-Simandle K, Ilina T, Clark AD, Knight JL, Julias JG, Clark PK, Krogh-Jespersen K, Levy RM, Hughes SH, Parniak MA, Arnold E: HIV-1 reverse transcriptase structure with RNase H inhibitor dihydroxy benzoyl naphtyl hydrazone bound at a novel site. ACS Chem Biol 2006; 1: 702-712.