메뉴 건너뛰기




Volumn 78, Issue 3, 2011, Pages 418-426

3D-QSAR and Docking Studies on the HEPT Derivatives of HIV-1 Reverse Transcriptase

Author keywords

Comparative molecular field analysis; Docking; HEPT; HIV 1 RT; Quantitative structure activity relationship

Indexed keywords

1 (2 HYDROXYETHYLOXYMETHYL) 6 PHENYLTHIOTHYMINE DERIVATIVE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

EID: 80051581507     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01162.x     Document Type: Article
Times cited : (14)

References (54)
  • 1
    • 0023852121 scopus 로고    scopus 로고
    • The human immunodeficiency virus: infectivity and mechanisms of pathogenesis
    • Fauci S. (1998) The human immunodeficiency virus: infectivity and mechanisms of pathogenesis. Science;239:617-622.
    • (1998) Science , vol.239 , pp. 617-622
    • Fauci, S.1
  • 2
    • 0029011730 scopus 로고
    • Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections
    • De Clercq E. (1995) Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J Med Chem;38:2491-2517.
    • (1995) J Med Chem , vol.38 , pp. 2491-2517
    • De Clercq, E.1
  • 3
    • 0034304841 scopus 로고    scopus 로고
    • New targets for inhibitors of HIV-1 replication
    • Moore J.P., Stevenson M. (2000) New targets for inhibitors of HIV-1 replication. Nat Rev Mol Cell Biol;1:40-49.
    • (2000) Nat Rev Mol Cell Biol , vol.1 , pp. 40-49
    • Moore, J.P.1    Stevenson, M.2
  • 6
    • 0001707601 scopus 로고
    • 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro
    • Mitsuya H., Weinhold K.J., Furman P.A., St Clair M.H., Nusinoff-Lehrman S., Gallo R.C., Bolognesi D., Barry D.W., Broder S. (1985) 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci USA;82:7096-7100.
    • (1985) Proc Natl Acad Sci USA , vol.82 , pp. 7096-7100
    • Mitsuya, H.1    Weinhold, K.J.2    Furman, P.A.3    St Clair, M.H.4    Nusinoff-Lehrman, S.5    Gallo, R.C.6    Bolognesi, D.7    Barry, D.W.8    Broder, S.9
  • 7
    • 0001587762 scopus 로고
    • Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides
    • Mitsuya H., Broder S. (1986) Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2', 3'-dideoxynucleosides. Proc Natl Acad Sci USA;83:1911-1915.
    • (1986) Proc Natl Acad Sci USA , vol.83 , pp. 1911-1915
    • Mitsuya, H.1    Broder, S.2
  • 14
    • 0026606044 scopus 로고
    • 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5″-(4″-amino-1″,2″-oxathiole-2″,2'-dioxide)pyrimidine (TSAO) nucleoside analogues: highlyselective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase
    • Balzarini J., Pe' rez-Pe' rez M.J., San-Felix A., Schols D., Perno D.C.F., Vandamme A., Camarasa M.J., De Clercq E. (1992) 2', 5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5″-(4″-amino-1″, 2″-oxathiole-2″, 2'-dioxide)pyrimidine (TSAO) nucleoside analogues: highlyselective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proc Natl Acad Sci USA;89:4392-4396.
    • (1992) Proc Natl Acad Sci USA , vol.89 , pp. 4392-4396
    • Balzarini, J.1    Pe' rez-Pe' rez, M.J.2    San-Felix, A.3    Schols, D.4    Perno, D.C.F.5    Vandamme, A.6    Camarasa, M.J.7    De Clercq, E.8
  • 19
    • 0026341962 scopus 로고
    • Kinetic interaction of human immunodeficiency virus type 1 reverse transcriptase with the antiviral tetrahydroimidazo[4,5,1-jk]-[1,4]-benzodiazepine-2-(1H)-thione compound, R82150
    • Frank K.B., Noll G.J., Connell E.V., Sim I.S. (1991) Kinetic interaction of human immunodeficiency virus type 1 reverse transcriptase with the antiviral tetrahydroimidazo[4, 5, 1-jk]-[1, 4]-benzodiazepine-2-(1H)-thione compound, R82150. J Biol Chem;266:14232-14236.
    • (1991) J Biol Chem , vol.266 , pp. 14232-14236
    • Frank, K.B.1    Noll, G.J.2    Connell, E.V.3    Sim, I.S.4
  • 21
    • 0028925773 scopus 로고
    • Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors
    • Spence R.A., Kati W.M., Anderson K.S., Johnson K.A. (1995) Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors. Science;267:988-993.
    • (1995) Science , vol.267 , pp. 988-993
    • Spence, R.A.1    Kati, W.M.2    Anderson, K.S.3    Johnson, K.A.4
  • 22
    • 0026693137 scopus 로고
    • Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor
    • Kohlstaedt L.A., Wang J., Friedman J.M., Rice P.A., Steitz T.A. (1992) Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science;256:1783-1790.
    • (1992) Science , vol.256 , pp. 1783-1790
    • Kohlstaedt, L.A.1    Wang, J.2    Friedman, J.M.3    Rice, P.A.4    Steitz, T.A.5
  • 25
    • 0029644484 scopus 로고
    • Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor α-APA R 95845 at 2.8 å resolution
    • Ding J., Das K., Tantillo C., Zhang W., Clark A.D.J., Jessen S., Lu X. et al. (1995) Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor α-APA R 95845 at 2.8 å resolution. Structure;3:365-379.
    • (1995) Structure , vol.3 , pp. 365-379
    • Ding, J.1    Das, K.2    Tantillo, C.3    Zhang, W.4    Clark, A.D.J.5    Jessen, S.6    Lu, X.7
  • 26
  • 27
    • 0029645409 scopus 로고
    • The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: lessons for inhibitor design
    • Ren J.S., Esnouf R., Hopkins A., Ross C., Jones Y., Stammers D., Stuart D. (1995) The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: lessons for inhibitor design. Structure;3:915-926.
    • (1995) Structure , vol.3 , pp. 915-926
    • Ren, J.S.1    Esnouf, R.2    Hopkins, A.3    Ross, C.4    Jones, Y.5    Stammers, D.6    Stuart, D.7
  • 28
    • 0023489903 scopus 로고
    • Resumption of virus production after human immunodeficiency virus infection of T lymphocytes in the presence of azidothymidine
    • Smith M.S., Brian E.L., Pagano J.S. (1987) Resumption of virus production after human immunodeficiency virus infection of T lymphocytes in the presence of azidothymidine. J Virol;61:3769-3773.
    • (1987) J Virol , vol.61 , pp. 3769-3773
    • Smith, M.S.1    Brian, E.L.2    Pagano, J.S.3
  • 30
    • 0027363224 scopus 로고
    • Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus
    • Balzarini J., Karlsson A., Pe'rez-Pe'rez M.J., Camarasa M.J., De Clercq E. (1993) Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus. Virology;196:576-585.
    • (1993) Virology , vol.196 , pp. 576-585
    • Balzarini, J.1    Karlsson, A.2    Pe'rez-Pe'rez, M.J.3    Camarasa, M.J.4    De Clercq, E.5
  • 32
    • 19744364217 scopus 로고    scopus 로고
    • The molecular basis of resilience to the effect of the Lys103Asn mutation in non-nucleoside HIV-1 reverse transcriptase inhibitors studied by targeted molecular dynamics simulations
    • Rodriguez-Barrios F., Balzarini J., Gago F. (2005) The molecular basis of resilience to the effect of the Lys103Asn mutation in non-nucleoside HIV-1 reverse transcriptase inhibitors studied by targeted molecular dynamics simulations. J Am Chem Soc;127:7570-7578.
    • (2005) J Am Chem Soc , vol.127 , pp. 7570-7578
    • Rodriguez-Barrios, F.1    Balzarini, J.2    Gago, F.3
  • 33
  • 34
    • 0032741707 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships and comparative molecular field analysis of TIBO derivatised HIV-1 reverse transcriptase inhibitors
    • Hannongbuaa S., Pungpoa P., Limtrakula J., Wolschann P. (1999) Quantitative structure-activity relationships and comparative molecular field analysis of TIBO derivatised HIV-1 reverse transcriptase inhibitors. J Comput Aided Mol Des;13:563-577.
    • (1999) J Comput Aided Mol Des , vol.13 , pp. 563-577
    • Hannongbuaa, S.1    Pungpoa, P.2    Limtrakula, J.3    Wolschann, P.4
  • 35
    • 0346207528 scopus 로고    scopus 로고
    • Comparative quantitative structure-activity relationship studies on anti-HIV drugs
    • Garg R., Gupta S.P., Gao H., Babu M.K., Debnath A.K., Hansch C. (1999) Comparative quantitative structure-activity relationship studies on anti-HIV drugs. Chem Rev;99:3525-3601.
    • (1999) Chem Rev , vol.99 , pp. 3525-3601
    • Garg, R.1    Gupta, S.P.2    Gao, H.3    Babu, M.K.4    Debnath, A.K.5    Hansch, C.6
  • 36
    • 0842283490 scopus 로고    scopus 로고
    • QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners using molecular connectivity and E-sate parameters
    • Roy K., Leonard J.T. (2004) QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners using molecular connectivity and E-sate parameters. Bioorg Med Chem;12:745-754.
    • (2004) Bioorg Med Chem , vol.12 , pp. 745-754
    • Roy, K.1    Leonard, J.T.2
  • 37
    • 1542301644 scopus 로고    scopus 로고
    • QSAR study on some anti-HIV HEPT analogues using physicochemical and topological parameters
    • Gayen S., Debnath B., Samanta S., Jha T. (2004) QSAR study on some anti-HIV HEPT analogues using physicochemical and topological parameters. Bioorg Med Chem;12:1493-1503.
    • (2004) Bioorg Med Chem , vol.12 , pp. 1493-1503
    • Gayen, S.1    Debnath, B.2    Samanta, S.3    Jha, T.4
  • 38
    • 38749146863 scopus 로고    scopus 로고
    • 3D-QSAR models on clinically relevant K103N mutant HIV-1 reverse transcriptase obtained from two strategic considerations
    • Juan A.A.S. (2008) 3D-QSAR models on clinically relevant K103N mutant HIV-1 reverse transcriptase obtained from two strategic considerations. Bioorg Med Chem Lett;18:1181-1194.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 1181-1194
    • Juan, A.A.S.1
  • 39
    • 62749144448 scopus 로고    scopus 로고
    • QSAR models for 2-amino-6-arylsulfonylbenzonitriles and congeners HIV-1 reverse transcriptase inhibitors based on linear and nonlinear regression methods
    • Hua R., Doucet J.P., Delamar M., Zhang R. (2009) QSAR models for 2-amino-6-arylsulfonylbenzonitriles and congeners HIV-1 reverse transcriptase inhibitors based on linear and nonlinear regression methods. Eur J Med Chem;44:2158-2171.
    • (2009) Eur J Med Chem , vol.44 , pp. 2158-2171
    • Hua, R.1    Doucet, J.P.2    Delamar, M.3    Zhang, R.4
  • 40
    • 70349323049 scopus 로고    scopus 로고
    • QSAR study of PETT derivatives as potent HIV-1 reverse transcriptase inhibitors
    • Sabet R., Fassihi A., Moeinifard B. (2009) QSAR study of PETT derivatives as potent HIV-1 reverse transcriptase inhibitors. J Mol Graph Model;28:146-155.
    • (2009) J Mol Graph Model , vol.28 , pp. 146-155
    • Sabet, R.1    Fassihi, A.2    Moeinifard, B.3
  • 41
    • 62549102032 scopus 로고    scopus 로고
    • Receptor- and ligand-based 3D-QSAR study for a series of non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Hu R., Barbault F., Delamar M., Zhang R. (2009) Receptor- and ligand-based 3D-QSAR study for a series of non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem;17:2400-2409.
    • (2009) Bioorg Med Chem , vol.17 , pp. 2400-2409
    • Hu, R.1    Barbault, F.2    Delamar, M.3    Zhang, R.4
  • 42
    • 62549150308 scopus 로고    scopus 로고
    • Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors: docking-based CoMFA and CoMSIA analyses
    • Cichero E., Cesarini S., Fossa P., Spallarossa A., Mosti L. (2009) Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors: docking-based CoMFA and CoMSIA analyses. Eur J Med Chem;44:2059-2070.
    • (2009) Eur J Med Chem , vol.44 , pp. 2059-2070
    • Cichero, E.1    Cesarini, S.2    Fossa, P.3    Spallarossa, A.4    Mosti, L.5
  • 43
    • 1542426115 scopus 로고    scopus 로고
    • Development of neural network QSPR models for hansch substituent constants. 2. applications in QSAR studies of HIV-1 reverse transcriptase and dihydrofolate reductase inhibitors
    • Chiu T.-L., So S.-S. (2004) Development of neural network QSPR models for hansch substituent constants. 2. applications in QSAR studies of HIV-1 reverse transcriptase and dihydrofolate reductase inhibitors. J Chem Inf Comput Sci;44:154-160.
    • (2004) J Chem Inf Comput Sci , vol.44 , pp. 154-160
    • Chiu, T.-L.1    So, S.-S.2
  • 44
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer R.D. III, Patterson D.E., Bunce J.D. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc;110:5959-5967.
    • (1988) J Am Chem Soc , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 45
    • 0030897299 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship studies on some acyclouridine derivatives acting as anti-HIV-1 drugs
    • Garg R., Kurup A., Gupta S.P. (1997) Quantitative structure-activity relationship studies on some acyclouridine derivatives acting as anti-HIV-1 drugs. Quant Struct-Act Rel;16:20-24.
    • (1997) Quant Struct-Act Rel , vol.16 , pp. 20-24
    • Garg, R.1    Kurup, A.2    Gupta, S.P.3
  • 46
    • 0031085412 scopus 로고    scopus 로고
    • QSAR based on multiple linear regression and PLS methods for the anti-HIV activity of a large group of hept derivatives
    • Luco J.M., Ferretti F.H. (1997) QSAR based on multiple linear regression and PLS methods for the anti-HIV activity of a large group of hept derivatives. J Chem Inf Comput Sci;37:392-401.
    • (1997) J Chem Inf Comput Sci , vol.37 , pp. 392-401
    • Luco, J.M.1    Ferretti, F.H.2
  • 47
    • 0029705324 scopus 로고    scopus 로고
    • Automated docking of flexible ligands: applications of autodock
    • Goodsell D.S., Morris G.M., Olson A.J. (1996) Automated docking of flexible ligands: applications of autodock. J Mol Recognit;9:1-5.
    • (1996) J Mol Recognit , vol.9 , pp. 1-5
    • Goodsell, D.S.1    Morris, G.M.2    Olson, A.J.3
  • 49
    • 76149120388 scopus 로고    scopus 로고
    • AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
    • Trott O., Olson A.J. (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem;31:455-461.
    • (2010) J Comput Chem , vol.31 , pp. 455-461
    • Trott, O.1    Olson, A.J.2
  • 51
    • 0001681052 scopus 로고
    • The collinearity problem in linear regression. the partial least squares (PLS) approach to generalized inverses
    • Wold S., Rhue A., Wold H., Dunn W.J. III (1984) The collinearity problem in linear regression. the partial least squares (PLS) approach to generalized inverses. SIAM J Sci Stat Comput;5:735-743.
    • (1984) SIAM J Sci Stat Comput , vol.5 , pp. 735-743
    • Wold, S.1    Rhue, A.2    Wold, H.3    Dunn III, W.J.4
  • 52
    • 84987083710 scopus 로고
    • Validation of QSAR's
    • Wold S. (1991) Validation of QSAR's. Quant Struct-Act Rel;10:191-193.
    • (1991) Quant Struct-Act Rel , vol.10 , pp. 191-193
    • Wold, S.1
  • 53
    • 0027209171 scopus 로고
    • The probability of chance correlation using partial least squares (PLS)
    • Clark M., Cramer R.D. III (1993) The probability of chance correlation using partial least squares (PLS). Quant Struct-Act Rel;12:137-145.
    • (1993) Quant Struct-Act Rel , vol.12 , pp. 137-145
    • Clark, M.1    Cramer III, R.D.2
  • 54
    • 0027094782 scopus 로고
    • Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents
    • Tanaka H., Takashima H., Ubasawa M., Sekiya K., Nitta I., Baba M., Shigeta S., Walker R.T., De Clercq E., Miyasaka T. (1992) Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents. J Med Chem;35:4713-4719.
    • (1992) J Med Chem , vol.35 , pp. 4713-4719
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Nitta, I.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.