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Volumn 71, Issue 1, 2006, Pages 15-23

Discovery of TSAO derivatives with an unusual HIV-1 activity/resistance profile

Author keywords

Deaminated TSAO; Non nucleoside HIV 1 RT inhibitors; Spironucleosides; TSAO compounds

Indexed keywords

[1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N METHYLTHYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE)NUCLEOSIDE; ANTIVIRUS AGENT; DELAVIRDINE; EFAVIRENZ; EMIVIRINE; LAMIVUDINE; NEVIRAPINE; NUCLEOSIDE DERIVATIVE; QUINOXALINE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG; ZIDOVUDINE;

EID: 33746974786     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.antiviral.2006.02.009     Document Type: Article
Times cited : (9)

References (39)
  • 1
    • 3142698606 scopus 로고    scopus 로고
    • The phenylmethylthiazolylthiourea nonnucleoside reverse transcriptase (RT) inhibitor MSK-076 selects for a resistance mutation in the active site of human immunodeficiency virus type 2 RT
    • Auwerx J., Stevens M., Van Rompay A.R., Bird L.E., Ren J., De Clercq E., Öberg B., Stammers D.K., Karlsson A., and Balzarini J. The phenylmethylthiazolylthiourea nonnucleoside reverse transcriptase (RT) inhibitor MSK-076 selects for a resistance mutation in the active site of human immunodeficiency virus type 2 RT. J. Virol. 78 (2004) 7427-7437
    • (2004) J. Virol. , vol.78 , pp. 7427-7437
    • Auwerx, J.1    Stevens, M.2    Van Rompay, A.R.3    Bird, L.E.4    Ren, J.5    De Clercq, E.6    Öberg, B.7    Stammers, D.K.8    Karlsson, A.9    Balzarini, J.10
  • 2
    • 0026606044 scopus 로고
    • 2′,5′-Bis-O-(tert-butyldimethylsilyl)-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine (TSAO) nucleoside analogues: highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase
    • Balzarini J., Pérez-Pérez M.J., San-Félix A., Schols D., Perno C.F., Vandamme A.M., Camarasa M.J., and De Clercq E. 2′,5′-Bis-O-(tert-butyldimethylsilyl)-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine (TSAO) nucleoside analogues: highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 4392-4396
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 4392-4396
    • Balzarini, J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Schols, D.4    Perno, C.F.5    Vandamme, A.M.6    Camarasa, M.J.7    De Clercq, E.8
  • 3
    • 0027214433 scopus 로고
    • Treatment of human immunodeficiency virus type 1 (HIV-1)-infected cells with combinations of HIV-1-specific inhibitors results in a different resistance pattern than does treatment with single-drug therapy
    • Balzarini J., Karlsson A., Pérez-Pérez M.-J., Camarasa M.-J., Tarpley W.G., and De Clercq E. Treatment of human immunodeficiency virus type 1 (HIV-1)-infected cells with combinations of HIV-1-specific inhibitors results in a different resistance pattern than does treatment with single-drug therapy. J. Virol. 67 (1993) 5353-5359
    • (1993) J. Virol. , vol.67 , pp. 5353-5359
    • Balzarini, J.1    Karlsson, A.2    Pérez-Pérez, M.-J.3    Camarasa, M.-J.4    Tarpley, W.G.5    De Clercq, E.6
  • 4
    • 0027202617 scopus 로고
    • Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specific [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro-5 ″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide )]-β-d-pentofuranosyl (TSAO) nucleoside analogues retain sensitivity to HIV-1-specific nonnucleoside inhibitors
    • Balzarini J., Karlsson A., Vandamme A.M., Pérez-Pérez M.J., Zhang H., Vrang L., Öberg B., Backbro K., Unge T., San-Félix A., Velázquez S., Camarasa M.J., and De Clercq E. Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specific [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″ -dioxide)]-β-d-pentofuranosyl (TSAO) nucleoside analogues retain sensitivity to HIV-1-specific nonnucleoside inhibitors. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 6952-6956
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 6952-6956
    • Balzarini, J.1    Karlsson, A.2    Vandamme, A.M.3    Pérez-Pérez, M.J.4    Zhang, H.5    Vrang, L.6    Öberg, B.7    Backbro, K.8    Unge, T.9    San-Félix, A.10    Velázquez, S.11    Camarasa, M.J.12    De Clercq, E.13
  • 5
    • 0027524005 scopus 로고
    • The HIV-l-specific TSAO-purine analogues show a resistance spectrum that is different from that of the HIV-l-specific non-nucleoside analogues
    • Balzarini J., Velázquez S., San-Félix A., Karlsson A., Pérez-Pérez M.J., Camarasa M.J., and De Clercq E. The HIV-l-specific TSAO-purine analogues show a resistance spectrum that is different from that of the HIV-l-specific non-nucleoside analogues. Mol. Pharmacol. 43 (1993) 109-114
    • (1993) Mol. Pharmacol. , vol.43 , pp. 109-114
    • Balzarini, J.1    Velázquez, S.2    San-Félix, A.3    Karlsson, A.4    Pérez-Pérez, M.J.5    Camarasa, M.J.6    De Clercq, E.7
  • 6
    • 0028068907 scopus 로고
    • Sensitivity of (138 Glu → Lys) mutated human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) to HIV-1-specific RT inhibitors
    • Balzarini J., Kleim J.-P., Riess G., Camarasa M.-J., De Clercq E., and Karlsson A. Sensitivity of (138 Glu → Lys) mutated human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) to HIV-1-specific RT inhibitors. Biochem. Biophys. Res. Commun. 201 (1994) 1305-1312
    • (1994) Biochem. Biophys. Res. Commun. , vol.201 , pp. 1305-1312
    • Balzarini, J.1    Kleim, J.-P.2    Riess, G.3    Camarasa, M.-J.4    De Clercq, E.5    Karlsson, A.6
  • 7
    • 0033169086 scopus 로고    scopus 로고
    • Suppression of resistance to drug targeted to human immunodeficiency virus reverse transcriptase by combination therapy
    • Balzarini J. Suppression of resistance to drug targeted to human immunodeficiency virus reverse transcriptase by combination therapy. Biochem. Pharmacol. 58 (1999) 1-27
    • (1999) Biochem. Pharmacol. , vol.58 , pp. 1-27
    • Balzarini, J.1
  • 8
    • 2942524068 scopus 로고    scopus 로고
    • Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1
    • Balzarini J. Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1. Curr. Top. Med. Chem. 4 (2004) 921-944
    • (2004) Curr. Top. Med. Chem. , vol.4 , pp. 921-944
    • Balzarini, J.1
  • 9
    • 37049127147 scopus 로고
    • A simple and convenient deamination of aromatic amines
    • Cadogan J.I.G., and Molina G.A. A simple and convenient deamination of aromatic amines. J. Chem. Soc., Perkin I (1973) 541-542
    • (1973) J. Chem. Soc., Perkin I , pp. 541-542
    • Cadogan, J.I.G.1    Molina, G.A.2
  • 10
    • 0026771409 scopus 로고
    • 3′-Spironucleosides a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-xylo and ribofuranose]-3′-spiro-5″-[4″-amino-1″,2″- oxathiole-2″,2″-dioxide] (TSAO) pyrimidine nucleosides
    • Camarasa M.J., Pérez-Pérez M.J., San-Félix A., Balzarini J., and De Clercq E. 3′-Spironucleosides a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-xylo and ribofuranose]-3′-spiro-5″-[4″-amino-1″,2″- oxathiole-2″,2″-dioxide] (TSAO) pyrimidine nucleosides. J. Med. Chem. 35 (1992) 2721-2727
    • (1992) J. Med. Chem. , vol.35 , pp. 2721-2727
    • Camarasa, M.J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Balzarini, J.4    De Clercq, E.5
  • 16
    • 0032437454 scopus 로고    scopus 로고
    • The role of nonnucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E. The role of nonnucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Antiviral Res. 38 (1998) 153-179
    • (1998) Antiviral Res. , vol.38 , pp. 153-179
    • De Clercq, E.1
  • 17
    • 0032918170 scopus 로고    scopus 로고
    • Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E. Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Il Farmaco 54 (1999) 26-45
    • (1999) Il Farmaco , vol.54 , pp. 26-45
    • De Clercq, E.1
  • 18
    • 0034109049 scopus 로고    scopus 로고
    • NNRTIs-a new class of drugs for HIV
    • Drake S.M. NNRTIs-a new class of drugs for HIV. J. Antimicrob. Chemoth. 45 (2000) 615-657
    • (2000) J. Antimicrob. Chemoth. , vol.45 , pp. 615-657
    • Drake, S.M.1
  • 19
    • 0029975891 scopus 로고    scopus 로고
    • Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 6-Amino prodrugs of 2′-β-fluoro-2′,3′-dideoxyinosine
    • Driscoll J.S., Siddiqui M.A., Ford Jr. H., Kelley J.A., Roth J.S., Mitsuya H., Tanaka M., and Marquez V.E. Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 6-Amino prodrugs of 2′-β-fluoro-2′,3′-dideoxyinosine. J. Med. Chem. 36 (1996) 1619-1625
    • (1996) J. Med. Chem. , vol.36 , pp. 1619-1625
    • Driscoll, J.S.1    Siddiqui, M.A.2    Ford Jr., H.3    Kelley, J.A.4    Roth, J.S.5    Mitsuya, H.6    Tanaka, M.7    Marquez, V.E.8
  • 21
    • 0030935265 scopus 로고    scopus 로고
    • Unique features in the structure of the complex between HIV-1 reverse transcriptase and the bis(heteroaryl)piperazine (BHAP) U-90152 explain resistance mutations for this nonnucleoside inhibitor
    • Esnouf R.M., Ren J., Hopkins A.L., Ross C.K., Jones E.Y., Stammers D.K., and Stuart D.I. Unique features in the structure of the complex between HIV-1 reverse transcriptase and the bis(heteroaryl)piperazine (BHAP) U-90152 explain resistance mutations for this nonnucleoside inhibitor. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 3984-3989
    • (1997) Proc. Natl. Acad. Sci. U.S.A. , vol.94 , pp. 3984-3989
    • Esnouf, R.M.1    Ren, J.2    Hopkins, A.L.3    Ross, C.K.4    Jones, E.Y.5    Stammers, D.K.6    Stuart, D.I.7
  • 23
    • 0028099251 scopus 로고
    • Resistance of HIV-1 reverse transcriptase against [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″ -dioxide)] (TSAO) derivatives is determined by the mutation Glu138 → Lys on the p51 subunit
    • Jonckheere H., Taymans J.M., Balzarini J., Velázquez S., Camarasa M.J., Desmyter J., De Clercq E., and Anne J. Resistance of HIV-1 reverse transcriptase against [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″ -dioxide)] (TSAO) derivatives is determined by the mutation Glu138 → Lys on the p51 subunit. J. Biol. Chem. 269 (1994) 25255-25258
    • (1994) J. Biol. Chem. , vol.269 , pp. 25255-25258
    • Jonckheere, H.1    Taymans, J.M.2    Balzarini, J.3    Velázquez, S.4    Camarasa, M.J.5    Desmyter, J.6    De Clercq, E.7    Anne, J.8
  • 24
    • 0034059835 scopus 로고    scopus 로고
    • The HIV-1 reverse transcription (RT) process as target for RT inhibitors
    • Jonckheere H., Anné J., and De Clercq E. The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Med. Res. Rev. (2000) 129-154
    • (2000) Med. Res. Rev. , pp. 129-154
    • Jonckheere, H.1    Anné, J.2    De Clercq, E.3
  • 25
    • 0037194544 scopus 로고    scopus 로고
    • Synthesis of 3″-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach
    • Lobatón E., Rodríguez-Barrios F., Gago F., Pérez-Pérez M.J., De Clercq E., Balzarini J., Camarasa M.J., and Velázquez S. Synthesis of 3″-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach. J. Med. Chem. 45 (2002) 3934-3945
    • (2002) J. Med. Chem. , vol.45 , pp. 3934-3945
    • Lobatón, E.1    Rodríguez-Barrios, F.2    Gago, F.3    Pérez-Pérez, M.J.4    De Clercq, E.5    Balzarini, J.6    Camarasa, M.J.7    Velázquez, S.8
  • 26
    • 0019196854 scopus 로고
    • Utility of purinyl radicals in the synthesis of base-modified nucleosides and alkylpurines: 6-amino group replacement by H, Cl, Br and I.
    • Nair V., and Richardson S.G. Utility of purinyl radicals in the synthesis of base-modified nucleosides and alkylpurines: 6-amino group replacement by H, Cl, Br and I. J. Org. Chem. 45 (1980) 3969-3974
    • (1980) J. Org. Chem. , vol.45 , pp. 3969-3974
    • Nair, V.1    Richardson, S.G.2
  • 27
    • 0035859690 scopus 로고    scopus 로고
    • The beta7-beta8 loop of the p51 subunit in the heterodimeric (p66/p51) human immunodeficency virus type 1 reverse transcriptase is essential for the catalytic function of the p66 subunit
    • Pandey P.K., Kaushik N., Talele T.T., Yadav P.N., and Pandey V.N. The beta7-beta8 loop of the p51 subunit in the heterodimeric (p66/p51) human immunodeficency virus type 1 reverse transcriptase is essential for the catalytic function of the p66 subunit. Biochemistry 40 (2001) 9505-9512
    • (2001) Biochemistry , vol.40 , pp. 9505-9512
    • Pandey, P.K.1    Kaushik, N.2    Talele, T.T.3    Yadav, P.N.4    Pandey, V.N.5
  • 28
    • 34248393491 scopus 로고    scopus 로고
    • Insertion of a small peptide of six amino acids into the beta7-beta8 loop of the p51 subunit of HIV-1 reverse transcriptase perturbs the heterodimer and affects its activities
    • Pandey P.K., Kaushik N., Singh K., Sharma B., Upadhyay A.K., Kumar S., Harris D., and Pandey V.N. Insertion of a small peptide of six amino acids into the beta7-beta8 loop of the p51 subunit of HIV-1 reverse transcriptase perturbs the heterodimer and affects its activities. BMC Biochem. 3 (2002) 18-31
    • (2002) BMC Biochem. , vol.3 , pp. 18-31
    • Pandey, P.K.1    Kaushik, N.2    Singh, K.3    Sharma, B.4    Upadhyay, A.K.5    Kumar, S.6    Harris, D.7    Pandey, V.N.8
  • 30
    • 0026737678 scopus 로고
    • TSAO Analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-ribofurano syl]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole -2″,2″-dioxide) pyrimidine and pyrimidine-modified nucleosides
    • Pérez-Pérez M.J., San-Félix A., Balzarini J., De Clercq E., and Camarasa M.J. TSAO Analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-ribofurano syl]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole -2″,2″-dioxide) pyrimidine and pyrimidine-modified nucleosides. J. Med. Chem. 35 (1992) 2988-2995
    • (1992) J. Med. Chem. , vol.35 , pp. 2988-2995
    • Pérez-Pérez, M.J.1    San-Félix, A.2    Balzarini, J.3    De Clercq, E.4    Camarasa, M.J.5
  • 31
    • 0025297454 scopus 로고
    • Dimerization of human immunodeficiency virus type 1 reverse transcriptase. A target for chemotherapeutic intervention
    • Restle T., Müller B., and Goody R.S. Dimerization of human immunodeficiency virus type 1 reverse transcriptase. A target for chemotherapeutic intervention. J. Biol. Chem. 265 (1990) 8986-8988
    • (1990) J. Biol. Chem. , vol.265 , pp. 8986-8988
    • Restle, T.1    Müller, B.2    Goody, R.S.3
  • 32
    • 0026503970 scopus 로고
    • RNase H activity of HIV reverse transcriptases is confined exclusively to the dimeric forms
    • Restle T., Müller B., and Goody R.S. RNase H activity of HIV reverse transcriptases is confined exclusively to the dimeric forms. FEBS Lett. 300 (1992) 97-100
    • (1992) FEBS Lett. , vol.300 , pp. 97-100
    • Restle, T.1    Müller, B.2    Goody, R.S.3
  • 33
    • 0035821586 scopus 로고    scopus 로고
    • Identification of a putative binding site for [2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-ribofuranosy l]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole-2 ″,2″-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase
    • Rodríguez-Barrios F., Pérez C., Lobatón E., Velázquez S., Chamorro C., San-Félix A., Pérez-Pérez M.J., Camarasa M.J., Pelemans H., Balzarini J., and Gago F. Identification of a putative binding site for [2′,5′-bis-O-(tert-butyldimethylsilyl)-β-d-ribofuranosy l]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole-2 ″,2″-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase. J. Med. Chem. 44 (2001) 1853-1865
    • (2001) J. Med. Chem. , vol.44 , pp. 1853-1865
    • Rodríguez-Barrios, F.1    Pérez, C.2    Lobatón, E.3    Velázquez, S.4    Chamorro, C.5    San-Félix, A.6    Pérez-Pérez, M.J.7    Camarasa, M.J.8    Pelemans, H.9    Balzarini, J.10    Gago, F.11
  • 35
    • 0034673154 scopus 로고    scopus 로고
    • Human immunodeficiency virus type 1 reverse transcriptase dimer destabilization by 1-[spiro[4″-amino-2″,2″-dioxo-1″,2″-oxathi ole-5″,3′-[2′,5′-bis-O-(tert-butyldimethylsilyl) -β-d-ribofuranosyl]]]-3-ethylthymine
    • Sluis-Cremer N., Dmitrienko G.I., Balzarini J., Camarasa M.J., and Parniak M.A. Human immunodeficiency virus type 1 reverse transcriptase dimer destabilization by 1-[spiro[4″-amino-2″,2″-dioxo-1″,2″-oxathi ole-5″,3′-[2′,5′-bis-O-(tert-butyldimethylsilyl) -β-d-ribofuranosyl]]]-3-ethylthymine. Biochemistry 39 (2000) 1427-1433
    • (2000) Biochemistry , vol.39 , pp. 1427-1433
    • Sluis-Cremer, N.1    Dmitrienko, G.I.2    Balzarini, J.3    Camarasa, M.J.4    Parniak, M.A.5
  • 36
    • 0033014605 scopus 로고    scopus 로고
    • Guide to major clinical trials of antiretroviral therapy in human inmunodeficiency virus-infected patients: protease inhibitors, non-nucleoside reverse transcriptase inhibitors and nucleoside reverse transcriptase inhibitors
    • Tavel J.A., Miller K.D., and Masur H. Guide to major clinical trials of antiretroviral therapy in human inmunodeficiency virus-infected patients: protease inhibitors, non-nucleoside reverse transcriptase inhibitors and nucleoside reverse transcriptase inhibitors. Clin. Infect. Dis. 28 (1999) 643-676
    • (1999) Clin. Infect. Dis. , vol.28 , pp. 643-676
    • Tavel, J.A.1    Miller, K.D.2    Masur, H.3
  • 39
    • 84982068675 scopus 로고
    • Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts
    • Vorbrüggen H., Krolikiewicz K., and Bennua B. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ver. 114 (1981) 1234-1256
    • (1981) Chem. Ver. , vol.114 , pp. 1234-1256
    • Vorbrüggen, H.1    Krolikiewicz, K.2    Bennua, B.3


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