메뉴 건너뛰기




Volumn 278, Issue 9, 2011, Pages 1444-1457

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 non-nucleoside resistant reverse transcriptases

Author keywords

anthraquinones; HIV 1 ribonuclease H; NNRTI resistant; RNase H; RT inhibitors

Indexed keywords

2,2 DICHLORO 12 (4 CHLOROPHENYL)DODECANOIC ACID; ALIZARIN; ALIZARINE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIVIRUS AGENT; DELAVIRDINE; DNA POLYMERASE; EFAVIRENZ; EMODIN; ETRAVIRINE; K 126; K 45; K 49; K 52; K 53; K 54; K 56; K 57; K 61; KNA 26; KNA 53; MAGNESIUM ION; NEVIRAPINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; RIBONUCLEASE H; RNA; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 79955072485     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2011.08057.x     Document Type: Article
Times cited : (38)

References (49)
  • 1
    • 77249134151 scopus 로고    scopus 로고
    • Twenty-six years of anti-HIV drug discovery: Where do we stand and where do we go?
    • Mehellou Y, &, De Clercq E, (2010) Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J Med Chem 53, 521-538.
    • (2010) J Med Chem , vol.53 , pp. 521-538
    • Mehellou, Y.1    De Clercq, E.2
  • 2
    • 0002615512 scopus 로고    scopus 로고
    • RNase H of retroviral reverse transcriptases
    • (Crouch R.J. & Toulme J.J. eds) Les Editions INSERM, Paris.
    • Hughes SH, Arnold E, &, Hostomsky Z, (1998) RNase H of retroviral reverse transcriptases. In Ribonucleases H (, Crouch RJ, &, Toulme JJ, eds), pp 195-224. Les Editions INSERM, Paris.
    • (1998) Ribonucleases H , pp. 195-224
    • Hughes, S.H.1    Arnold, E.2    Hostomsky, Z.3
  • 3
    • 0036822181 scopus 로고    scopus 로고
    • Uncovering the complexities of retroviral ribonuclease H reveals its potential as a therapeutic target
    • Klarmann GJ, Hawkins ME, &, Le Grice SF, (2002) Uncovering the complexities of retroviral ribonuclease H reveals its potential as a therapeutic target. AIDS Rev 4, 183-194. (Pubitemid 36104230)
    • (2002) AIDS Reviews , vol.4 , Issue.4 , pp. 183-194
    • Klarmann, G.J.1    Hawkins, M.E.2    Le Grice, S.F.J.3
  • 4
    • 0035343895 scopus 로고    scopus 로고
    • Comparative architecture of transposase and integrase complexes
    • DOI 10.1038/86166
    • Rice PA, &, Baker TA, (2001) Comparative architecture of transposase and integrase complexes. Nat Struct Biol 8, 302-307. (Pubitemid 32275012)
    • (2001) Nature Structural Biology , vol.8 , Issue.4 , pp. 302-307
    • Rice, P.A.1    Baker, T.A.2
  • 5
    • 33745107517 scopus 로고    scopus 로고
    • HIV-1 RNase H: Recent progress in an exciting, yet little explored, drug target
    • DOI 10.2174/138955706777435733
    • Tramontano E, (2006) HIV-1 RNase H: recent progress in an exciting, yet little explored, drug target. Mini Rev Med Chem 6, 727-737. (Pubitemid 43881124)
    • (2006) Mini-Reviews in Medicinal Chemistry , vol.6 , Issue.6 , pp. 727-737
    • Tramontano, E.1
  • 6
    • 77955648999 scopus 로고    scopus 로고
    • HIV-1 RT-associated RNase H function inhibitors: Recent advances in drug development
    • Tramontano E, &, Di Santo R, (2010) HIV-1 RT-associated RNase H function inhibitors: recent advances in drug development. Curr Med Chem 17, 2837-2853.
    • (2010) Curr Med Chem , vol.17 , pp. 2837-2853
    • Tramontano, E.1    Di Santo, R.2
  • 7
    • 27444442274 scopus 로고    scopus 로고
    • 9,10-Anthraquinones and other biologically active compounds from the genus Rubia
    • Singh R, Geetanjali R, &, Chauhan SMS, (2004) 9,10-Anthraquinones and other biologically active compounds from the genus Rubia. Chem Biodivers 1, 1241-1264.
    • (2004) Chem Biodivers , vol.1 , pp. 1241-1264
    • Singh, R.1    Geetanjali, R.2    Chauhan, S.M.S.3
  • 8
    • 0038155211 scopus 로고    scopus 로고
    • Activation of human telomerase reverse transcriptase expression by some new symmetrical bis-substituted derivatives of the anthraquinone
    • DOI 10.1021/jm020492l
    • Huang HS, Chiou JF, Fong Y, Hou CC, Lu YC, Wang JY, Shih JW, Pan YR, &, Lin JJ, (2003) Activation of human telomerase reverse transcriptase expression by some new symmetrical bis-substituted derivatives of the anthraquinone. J Med Chem 46, 3300-3307. (Pubitemid 36842414)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.15 , pp. 3300-3307
    • Huang, H.-S.1    Chiou, J.-F.2    Fong, Y.3    Hou, C.-C.4    Lu, Y.-C.5    Wang, J.-Y.6    Shih, J.-W.7    Pan, Y.-R.8    Lin, J.-J.9
  • 10
    • 34447137400 scopus 로고    scopus 로고
    • DNA intercalators in cancer therapy: Organic and inorganic drugs and their spectroscopic tools of analysis
    • DOI 10.2174/138955707780859413
    • Wheate NJ, Brodie CR, Collins JG, Kemp S, &, Aldrivch-Wright JR, (2007) DNA intercalators in cancer therapy: organic and inorganic drugs and their spectroscopic tools of analysis. Mini Rev Med Chem 6, 627-648. (Pubitemid 47099183)
    • (2007) Mini-Reviews in Medicinal Chemistry , vol.7 , Issue.6 , pp. 627-648
    • Wheate, N.J.1    Brodie, C.R.2    Collins, J.G.3    Kemp, S.4    Aldrich-Wright, J.R.5
  • 11
    • 34548047015 scopus 로고    scopus 로고
    • Anticancer properties of anthraquinones from rhubarb
    • Huang Q, Lu G, Shen HM, Chung MC, &, Onq CN, (2007) Anticancer properties of anthraquinones from rhubarb. Med Res Rev 27, 609-630.
    • (2007) Med Res Rev , vol.27 , pp. 609-630
    • Huang, Q.1    Lu, G.2    Shen, H.M.3    Chung, M.C.4    Onq, C.N.5
  • 12
    • 0016175071 scopus 로고
    • Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. Bis-basic ethers of anthraquinone and bisalkamine esters of anthraquinonedicarboxylic acids
    • Sill AD, Andrews ER, Sweet FW, Hoffman JW, Tiernan PL, Grisar JM, Fleming RW, &, Mayer GD, (1974) Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. Bis-basic ethers of anthraquinone and bisalkamine esters of anthraquinonedicarboxylic acids. J Med Chem 17, 965-968.
    • (1974) J Med Chem , vol.17 , pp. 965-968
    • Sill, A.D.1    Andrews, E.R.2    Sweet, F.W.3    Hoffman, J.W.4    Tiernan, P.L.5    Grisar, J.M.6    Fleming, R.W.7    Mayer, G.D.8
  • 14
    • 0026595816 scopus 로고
    • Evaluation of antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cyromegalovirus
    • Barnard DL, Huffman JH, Morris JLB, Wood SG, Hughes BG, &, Sidwell RW, (1992) Evaluation of antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cyromegalovirus. Antiviral Res 17, 63-77.
    • (1992) Antiviral Res , vol.17 , pp. 63-77
    • Barnard, D.L.1    Huffman, J.H.2    Morris, J.L.B.3    Wood, S.G.4    Hughes, B.G.5    Sidwell, R.W.6
  • 15
    • 0028834462 scopus 로고
    • Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives
    • Bamard DL, Fairbaim DW, O'Neill KL, Gage TL, &, Sidwell RW, (1995) Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives. Antiviral Res 28, 317-329.
    • (1995) Antiviral Res , vol.28 , pp. 317-329
    • Bamard, D.L.1    Fairbaim, D.W.2    O'Neill, K.L.3    Gage, T.L.4    Sidwell, R.W.5
  • 16
    • 0035046141 scopus 로고    scopus 로고
    • In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus
    • DOI 10.1016/S0166-3542(01)00125-5, PII S0166354201001255
    • Semple SJ, Pyke SM, Reynolds GD, &, Flower FLP, (2001) In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus. Antiviral Res 49, 169-178. (Pubitemid 32322470)
    • (2001) Antiviral Research , vol.49 , Issue.3 , pp. 169-178
    • Semple, S.J.1    Pyke, S.M.2    Reynolds, G.D.3    Flower, R.L.P.4
  • 17
  • 18
    • 0025829325 scopus 로고
    • Antiretroviral activities of anthraquinones and their inhibitory effects on reverse transcriptase
    • Higuchi H, Mori K, Kato A, Ohkuma T, Endo T, Kaji H, &, Kaji A, (1991) Antiretroviral activities of anthraquinones and their inhibitory effects on reverse transcriptase. Antiviral Res 15, 205-216.
    • (1991) Antiviral Res , vol.15 , pp. 205-216
    • Higuchi, H.1    Mori, K.2    Kato, A.3    Ohkuma, T.4    Endo, T.5    Kaji, H.6    Kaji, A.7
  • 22
    • 13544276913 scopus 로고    scopus 로고
    • 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
    • DOI 10.1016/j.antiviral.2004.11.002
    • Tramontano E, Esposito F, Badas R, Di Santo R, Costi R, &, La Colla P, (2005) 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 65, 117-124. (Pubitemid 40222288)
    • (2005) Antiviral Research , vol.65 , Issue.2 , pp. 117-124
    • Tramontano, E.1    Esposito, F.2    Badas, R.3    Di Santo, R.4    Costi, R.5    La Colla, P.6
  • 24
    • 33751538895 scopus 로고    scopus 로고
    • Substrate-dependent inhibition or stimulation of HIV RNase H activity by non-nucleoside reverse transcriptase inhibitors (NNRTIs)
    • DOI 10.1016/j.bbrc.2006.11.018, PII S0006291X06024818
    • Hang QL, Li Y, Yang Y, Cammack N, Mirzadegan T, &, Klumpp K, (2007) Substrate-dependent inhibition or stimulation of HIV RNase H activity by non-nucleoside reverse transcriptase inhibitors (NNRTIs). Biochem Biophys Res Commun 352, 341-350. (Pubitemid 44838494)
    • (2007) Biochemical and Biophysical Research Communications , vol.352 , Issue.2 , pp. 341-350
    • Hang, J.Q.1    Li, Y.2    Yang, Y.3    Cammack, N.4    Mirzadegan, T.5    Klumpp, K.6
  • 25
    • 0020346411 scopus 로고
    • The Yonetani-Theorell graphical method for examining overlapping subsite of enzyme centers
    • Yonetani T, (1982) The Yonetani-Theorell graphical method for examining overlapping subsite of enzyme centers. Methods Enzymol 87, 500-509.
    • (1982) Methods Enzymol , vol.87 , pp. 500-509
    • Yonetani, T.1
  • 26
    • 13444257639 scopus 로고    scopus 로고
    • Dissecting the effects of DNA polymerase and ribonuclease H inhibitor combinations on HIV-1 reverse-transcriptase activities
    • DOI 10.1021/bi0486740
    • Shaw-Reid CA, Feuston B, Munshi V, Getty K, Jrueger J, Hazuda DJ, Parniak MA, Miller MD, &, Lewis D, (2005) Dissecting the effects of DNA polymerase and ribonuclease H inhibitor combinations on HIV-1 reverse-transcriptase activities. Biochemistry 44, 1595-1606. (Pubitemid 40204402)
    • (2005) Biochemistry , vol.44 , Issue.5 , pp. 1595-1606
    • Shaw-Reid, C.A.1    Feuston, B.2    Munshi, V.3    Getty, K.4    Krueger, J.5    Hazuda, D.J.6    Parniak, M.A.7    Miller, M.D.8    Lewis, D.9
  • 28
    • 70350501156 scopus 로고    scopus 로고
    • Correlation between performance of QM/MM docking and simple classification of binding sites
    • Chung JY, Hah J-M, &, Cho AE, (2009) Correlation between performance of QM/MM docking and simple classification of binding sites. J Chem Inf Model 49, 2382-2387.
    • (2009) J Chem Inf Model , vol.49 , pp. 2382-2387
    • Chung, J.Y.1    Hah, J.-M.2    Cho, A.E.3
  • 29
    • 4544265135 scopus 로고    scopus 로고
    • Conformational changes in HIV-1 reverse transcriptase induced by nonnucleoside reverse transcriptase inhibitor binding
    • DOI 10.2174/1570162043351093
    • Sluis-Cremer N, Temiz NA, &, Bahar I, (2004) Conformational changes in HIV-1 reverse transcriptase induced by nonnucleoside reverse transcriptase inhibitor binding. Curr HIV Res 2, 323-332. (Pubitemid 39242962)
    • (2004) Current HIV Research , vol.2 , Issue.4 , pp. 323-332
    • Sluis-Cremer, N.1    Temiz, N.A.2    Bahar, I.3
  • 32
    • 0028926938 scopus 로고
    • Nevirapine alters the cleavage specificity of ribonuclease H of human immunodeficiency virus 1 reverse transcriptase
    • Palaniappan C, Fay PJ, &, Bambara RA, (1995) Nevirapine alters the cleavage specificity of ribonuclease H of human immunodeficiency virus 1 reverse transcriptase. J Biol Chem 270, 4861-4869.
    • (1995) J Biol Chem , vol.270 , pp. 4861-4869
    • Palaniappan, C.1    Fay, P.J.2    Bambara, R.A.3
  • 34
    • 0037117744 scopus 로고    scopus 로고
    • Altering the RNase H primer grip of human immunodeficiency virus reverse transcriptase modifies cleavage specificity
    • DOI 10.1021/bi015970t
    • Rausch JW, Lener D, Miller JT, Julias JG, Hughes SH, &, Le Grice SF, (2002) Altering the RNase H primer grip of human immunodeficiency virus reverse transcriptase modifies cleavage specificity. Biochemistry 41, 4856-4865. (Pubitemid 34298652)
    • (2002) Biochemistry , vol.41 , Issue.15 , pp. 4856-4865
    • Rausch, J.W.1    Lener, D.2    Miller, J.T.3    Julias, J.G.4    Hughes, S.H.5    Le Grice, S.F.J.6
  • 36
    • 0038107748 scopus 로고    scopus 로고
    • Mutation of amino acids in the connection domain of human immunodeficiency virus type 1 reverse transcriptase that contact the template-primer affects RNase H activity
    • DOI 10.1128/JVI.77.15.8548-8554.2003
    • Julias JG, McWilliams MJ, Sarafianos SG, Alvord WG, Arnold E, &, Hughes SH, (2003) Mutation of amino acids in the connection domain of human immunodeficiency virus type 1 reverse transcriptase that contact the template-primer affects RNase H activity. J Virol 77, 8548-8554. (Pubitemid 36871483)
    • (2003) Journal of Virology , vol.77 , Issue.15 , pp. 8548-8554
    • Julias, J.G.1    McWilliams, M.J.2    Sarafianos, S.G.3    Alvord, W.G.4    Arnold, E.5    Hughes, S.H.6
  • 37
    • 0033863784 scopus 로고    scopus 로고
    • Mutants of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase resistant to nonnucleoside reverse transcriptase inhibitors demonstrate altered rates of RNase H cleavage that correlate with HIV-1 replication fitness in cell culture
    • DOI 10.1128/JVI.74.18.8390-8401.2000
    • Archer RH, Dykes C, Gerondelis P, Lloyd A, Fay P, Reichman RC, Bambara RA, &, Demeter LM, (2000) Mutants of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase resistant to nonnucleoside reverse transcriptase inhibitors demonstrate altered rates of RNase H cleavage that correlate with HIV-1 replication fitness in cell culture. J Virol 74, 8390-8401. (Pubitemid 30666690)
    • (2000) Journal of Virology , vol.74 , Issue.18 , pp. 8390-8401
    • Archer, R.H.1    Dykes, C.2    Gerondelis, P.3    Lloyd, A.4    Fay, P.5    Reichman, R.C.6    Bambara, R.A.7    Demeter, L.M.8
  • 38
    • 0035799358 scopus 로고    scopus 로고
    • The Y181C mutant of HIV-1 reverse transcriptase resistant to nonnucleoside reverse transcriptase inhibitors alters the size distribution of RNase H cleavages
    • DOI 10.1021/bi002328a
    • Archer RH, Wisniewski M, Bambara RA, &, Demeter LM, (2001) The Y181C mutant of HIV-1 reverse transcriptase resistant to nonnucleoside reverse transcriptase inhibitors alters the size distribution of RNase H cleavages. Biochemistry 40, 4087-4095. (Pubitemid 32280446)
    • (2001) Biochemistry , vol.40 , Issue.13 , pp. 4087-4095
    • Archer, R.H.1    Wisniewski, M.2    Bambara, R.A.3    Demeter, L.M.4
  • 40
    • 0026540533 scopus 로고
    • HIV-1 reverse transcriptase inhibition by dipyridodiazepinone derivative: BI-RG-587
    • Tramontano E, &, Cheng Y-C, (1992) HIV-1 reverse transcriptase inhibition by dipyridodiazepinone derivative: BI-RG-587. Biochem Pharmacol 43, 1371.
    • (1992) Biochem Pharmacol , vol.43 , pp. 1371
    • Tramontano, E.1    Cheng, Y.-C.2
  • 41
    • 0026579394 scopus 로고
    • In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase
    • Mellors JW, Dutschman GE, Im GJ, Tramontano E, Winkler SR, &, Cheng Y-C, (1992) In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase. Mol Pharmacol 41, 446-451.
    • (1992) Mol Pharmacol , vol.41 , pp. 446-451
    • Mellors, J.W.1    Dutschman, G.E.2    Im, G.J.3    Tramontano, E.4    Winkler, S.R.5    Cheng, Y.-C.6
  • 45
    • 0000530285 scopus 로고
    • Time-reversible multiple time scale ab initio molecular dynamics
    • Gibson DA, &, Carter EA, (1993) Time-reversible multiple time scale ab initio molecular dynamics. J Phys Chem 97, 13429.
    • (1993) J Phys Chem , vol.97 , pp. 13429
    • Gibson, D.A.1    Carter, E.A.2
  • 46
    • 33646940952 scopus 로고
    • Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckaert JP, Ciccotti G, &, Berendsen HJC, (1977) Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 23, 327-341.
    • (1977) J Comput Phys , vol.23 , pp. 327-341
    • Ryckaert, J.P.1    Ciccotti, G.2    Berendsen, H.J.C.3
  • 47
    • 33846823909 scopus 로고
    • Particle mesh Ewald: An N.log(N) method for Ewald sums in large systems
    • Darden T, York D, &, Pedersen L, (1993) Particle mesh Ewald: an N.log(N) method for Ewald sums in large systems. J Chem Phys 98, 10089.
    • (1993) J Chem Phys , vol.98 , pp. 10089
    • Darden, T.1    York, D.2    Pedersen, L.3
  • 49
    • 13844320566 scopus 로고    scopus 로고
    • LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters
    • Wolber G, &, Langer T, (2005) LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J Chem Inf Model 45, 160.
    • (2005) J Chem Inf Model , vol.45 , pp. 160
    • Wolber, G.1    Langer, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.