메뉴 건너뛰기




Volumn 92, Issue 2, 2011, Pages 277-291

Application of kinase bypass strategies to nucleoside antivirals

Author keywords

Antiviral; HCV; HIV; Nucleotide; Phosphonate; Prodrug

Indexed keywords

3' DEOXY 3' FLUORO THYMIDINE; 3',5' CYCLIC 3 DEAZAGUANOSINE MONOPHOSPHATE; 3',5' CYCLIC ARA CYTIDINE MONOPHOSPHATE; 3',5, CYCLIC 5 FLUORO CYTIDINE MONOPHOSPHATE; ADEFOVIR; ADEFOVIR DIPIVOXIL; BIS PIVALOYLOXYMETHYL; CIDOFOVIR; CYCLIC 1 ARYL 1,3 PROPANYL ESTER; CYCLIC AMP; ESTER DERIVATIVE; ETOMIDATE; FOSALVUDINE TIDOXIL; IDX 184; INX 08189; NEOGLYCOPROTEIN; NUCLEOSIDE ANALOG; PEPTIDOMIMETIC AGENT; PHOSPHOLIPID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHOTRANSFERASE; PRODRUG; PSI 352938; PSI 353661; PSI 7977; TENOFOVIR; TENOFOVIR 3 HEXADECYLOXYPROPYL ESTER; TENOFOVIR DISOPROXIL; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZIDOVUDINE;

EID: 80054862874     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2011.08.015     Document Type: Article
Times cited : (41)

References (149)
  • 1
    • 0027534661 scopus 로고
    • Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine
    • Balzarini J., Holy A., Jindrich J., Naesens L., Snoeck R., Schols D., De Clercq E. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 1993, 37:332-338.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 332-338
    • Balzarini, J.1    Holy, A.2    Jindrich, J.3    Naesens, L.4    Snoeck, R.5    Schols, D.6    De Clercq, E.7
  • 4
    • 0035991718 scopus 로고    scopus 로고
    • Alkoxyalkyl esters of cidofovir and cyclic cidofovir exhibit multiple-log enhancement of antiviral activity against cytomegalovirus and herpesvirus replication in vitro
    • Beadle J.R., Hartline C., Aldern K.A., Rodriguez N., Harden E., Kern E.R., Hostetler K.Y. Alkoxyalkyl esters of cidofovir and cyclic cidofovir exhibit multiple-log enhancement of antiviral activity against cytomegalovirus and herpesvirus replication in vitro. Antimicrob. Agents Chemother. 2002, 46:2381-2386.
    • (2002) Antimicrob. Agents Chemother. , vol.46 , pp. 2381-2386
    • Beadle, J.R.1    Hartline, C.2    Aldern, K.A.3    Rodriguez, N.4    Harden, E.5    Kern, E.R.6    Hostetler, K.Y.7
  • 6
    • 0029731207 scopus 로고    scopus 로고
    • Synthesis, in vitro antiviral evaluation, and stability studies of bis(S-acyl-2-thioethyl) ester derivatives of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) as potential PMEA prodrugs with improved oral bioavailability
    • Benzaria S., Pelicano H., Johnson R., Maury G., Imbach J.L., Aubertin A.M., Obert G., Gosselin G. Synthesis, in vitro antiviral evaluation, and stability studies of bis(S-acyl-2-thioethyl) ester derivatives of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) as potential PMEA prodrugs with improved oral bioavailability. J. Med. Chem. 1996, 39:4958-4965.
    • (1996) J. Med. Chem. , vol.39 , pp. 4958-4965
    • Benzaria, S.1    Pelicano, H.2    Johnson, R.3    Maury, G.4    Imbach, J.L.5    Aubertin, A.M.6    Obert, G.7    Gosselin, G.8
  • 7
    • 0022545923 scopus 로고
    • Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines, 3',5'-cyclic monophosphates, and neutral cyclic triesters
    • Beres J., Bentrude W.G., Balzarini J., De Clercq E., Otvos L. Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines, 3',5'-cyclic monophosphates, and neutral cyclic triesters. J. Med. Chem. 1986, 29:494-499.
    • (1986) J. Med. Chem. , vol.29 , pp. 494-499
    • Beres, J.1    Bentrude, W.G.2    Balzarini, J.3    De Clercq, E.4    Otvos, L.5
  • 8
    • 0022481853 scopus 로고
    • Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates
    • Beres J., Bentrude W.G., Kalman A., Parkanyi L., Balzarini J., De Clercq E. Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates. J. Med. Chem. 1986, 29:488-493.
    • (1986) J. Med. Chem. , vol.29 , pp. 488-493
    • Beres, J.1    Bentrude, W.G.2    Kalman, A.3    Parkanyi, L.4    Balzarini, J.5    De Clercq, E.6
  • 9
    • 0022452139 scopus 로고
    • Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters
    • Beres J., Sagi G., Bentrude W.G., Balzarini J., De Clercq E., Otvos L. Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters. J. Med. Chem. 1986, 29:1243-1249.
    • (1986) J. Med. Chem. , vol.29 , pp. 1243-1249
    • Beres, J.1    Sagi, G.2    Bentrude, W.G.3    Balzarini, J.4    De Clercq, E.5    Otvos, L.6
  • 10
    • 0026524094 scopus 로고
    • Failure of acyclovir to enhance the antiviral effect of alpha lymphoblastoid interferon on HBe-seroconversion in chronic hepatitis B. A multi-centre randomized controlled trial
    • Berk L., Schalm S.W., de Man R.A., Heytink R.A., Berthelot P., Brechot C., Boboc B., Degos F., Marcellin P., Benhamou J.P., et al. Failure of acyclovir to enhance the antiviral effect of alpha lymphoblastoid interferon on HBe-seroconversion in chronic hepatitis B. A multi-centre randomized controlled trial. J. Hepatol. 1992, 14:305-309.
    • (1992) J. Hepatol. , vol.14 , pp. 305-309
    • Berk, L.1    Schalm, S.W.2    de Man, R.A.3    Heytink, R.A.4    Berthelot, P.5    Brechot, C.6    Boboc, B.7    Degos, F.8    Marcellin, P.9    Benhamou, J.P.10
  • 11
    • 45749091322 scopus 로고    scopus 로고
    • Activation of 9-[(R)-2-[[(S)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino] phenoxyphosphinyl]-methoxy]propyl]adenine (GS-7340) and other tenofovir phosphonoamidate prodrugs by human proteases
    • Birkus G., Kutty N., He G.X., Mulato A., Lee W., McDermott M., Cihlar T. Activation of 9-[(R)-2-[[(S)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino] phenoxyphosphinyl]-methoxy]propyl]adenine (GS-7340) and other tenofovir phosphonoamidate prodrugs by human proteases. Mol. Pharmacol. 2008, 74:92-100.
    • (2008) Mol. Pharmacol. , vol.74 , pp. 92-100
    • Birkus, G.1    Kutty, N.2    He, G.X.3    Mulato, A.4    Lee, W.5    McDermott, M.6    Cihlar, T.7
  • 12
  • 13
    • 0027980318 scopus 로고
    • 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl] cytosine, an intracellular prodrug for (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine with improved therapeutic index in vivo
    • Bischofberger N., Hitchcock M.J., Chen M.S., Barkhimer D.B., Cundy K.C., Kent K.M., Lacy S.A., Lee W.A., Li Z.H., Mendel D.B., et al. 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl] cytosine, an intracellular prodrug for (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine with improved therapeutic index in vivo. Antimicrob. Agents Chemother. 1994, 38:2387-2391.
    • (1994) Antimicrob. Agents Chemother. , vol.38 , pp. 2387-2391
    • Bischofberger, N.1    Hitchcock, M.J.2    Chen, M.S.3    Barkhimer, D.B.4    Cundy, K.C.5    Kent, K.M.6    Lacy, S.A.7    Lee, W.A.8    Li, Z.H.9    Mendel, D.B.10
  • 14
    • 78651110499 scopus 로고    scopus 로고
    • Advances in nucleoside monophosphate prodrugs as anti-HCV agents
    • Bobeck D.R., Schinazi R.F., Coats S.J. Advances in nucleoside monophosphate prodrugs as anti-HCV agents. Antiviral Ther. 2010, 15:935-950.
    • (2010) Antiviral Ther. , vol.15 , pp. 935-950
    • Bobeck, D.R.1    Schinazi, R.F.2    Coats, S.J.3
  • 17
    • 0030049336 scopus 로고    scopus 로고
    • Potential lipophilic nucleotide prodrugs: synthesis, hydrolysis, and antiretroviral activity of AZT and d4T acyl nucleotides
    • Bonnaffe D., Dupraz B., Ughetto-Monfrin J., Namane A., Henin Y., Huynh-Dinh T. Potential lipophilic nucleotide prodrugs: synthesis, hydrolysis, and antiretroviral activity of AZT and d4T acyl nucleotides. J. Org. Chem. 1996, 61:895-902.
    • (1996) J. Org. Chem. , vol.61 , pp. 895-902
    • Bonnaffe, D.1    Dupraz, B.2    Ughetto-Monfrin, J.3    Namane, A.4    Henin, Y.5    Huynh-Dinh, T.6
  • 18
    • 0036890172 scopus 로고    scopus 로고
    • Pivalate-generating prodrugs and carnitine homeostasis in man
    • Brass E.P. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol. Rev. 2002, 54:589-598.
    • (2002) Pharmacol. Rev. , vol.54 , pp. 589-598
    • Brass, E.P.1
  • 19
    • 73549103358 scopus 로고    scopus 로고
    • The development of antiretroviral therapy and its impact on the HIV-1/AIDS pandemic
    • Broder S. The development of antiretroviral therapy and its impact on the HIV-1/AIDS pandemic. Antiviral Res. 2010, 85:1-18.
    • (2010) Antiviral Res. , vol.85 , pp. 1-18
    • Broder, S.1
  • 24
    • 78649937348 scopus 로고    scopus 로고
    • Development of cytarabine prodrugs and delivery systems for leukemia treatment
    • Chhikara B.S., Parang K. Development of cytarabine prodrugs and delivery systems for leukemia treatment. Expert Opin. Drug Deliv. 2010, 7:1399-1414.
    • (2010) Expert Opin. Drug Deliv. , vol.7 , pp. 1399-1414
    • Chhikara, B.S.1    Parang, K.2
  • 25
    • 2442661557 scopus 로고    scopus 로고
    • A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent
    • Choi J.R., Cho D.G., Roh K.Y., Hwang J.T., Ahn S., Jang H.S., Cho W.Y., Kim K.W., Cho Y.G., Kim J., Kim Y.Z. A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent. J. Med. Chem. 2004, 47:2864-2869.
    • (2004) J. Med. Chem. , vol.47 , pp. 2864-2869
    • Choi, J.R.1    Cho, D.G.2    Roh, K.Y.3    Hwang, J.T.4    Ahn, S.5    Jang, H.S.6    Cho, W.Y.7    Kim, K.W.8    Cho, Y.G.9    Kim, J.10    Kim, Y.Z.11
  • 26
    • 34247380394 scopus 로고    scopus 로고
    • Phosphoramidate pronucleotides: a comparison of the phosphoramidase substrate specificity of human and Escherichia coli histidine triad nucleotide binding proteins
    • Chou T.F., Baraniak J., Kaczmarek R., Zhou X., Cheng J., Ghosh B., Wagner C.R. Phosphoramidate pronucleotides: a comparison of the phosphoramidase substrate specificity of human and Escherichia coli histidine triad nucleotide binding proteins. Mol. Pharm. 2007, 4:208-217.
    • (2007) Mol. Pharm. , vol.4 , pp. 208-217
    • Chou, T.F.1    Baraniak, J.2    Kaczmarek, R.3    Zhou, X.4    Cheng, J.5    Ghosh, B.6    Wagner, C.R.7
  • 27
    • 73549088038 scopus 로고    scopus 로고
    • Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine
    • Cihlar T., Ray A.S. Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010, 85:39-58.
    • (2010) Antiviral Res. , vol.85 , pp. 39-58
    • Cihlar, T.1    Ray, A.S.2
  • 30
    • 0033039933 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl]cytosine in human immunodeficiency virus-infected patients
    • Cundy K.C., Barditch-Crovo P., Petty B.G., Ruby A., Redpath M., Jaffe H.S., Lietman P.S. Clinical pharmacokinetics of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl]cytosine in human immunodeficiency virus-infected patients. Antimicrob. Agents Chemother. 1999, 43:271-277.
    • (1999) Antimicrob. Agents Chemother. , vol.43 , pp. 271-277
    • Cundy, K.C.1    Barditch-Crovo, P.2    Petty, B.G.3    Ruby, A.4    Redpath, M.5    Jaffe, H.S.6    Lietman, P.S.7
  • 31
    • 0025609122 scopus 로고
    • Synthesis and anti-HIV evaluation of some phosphoramidate derivatives of AZT: studies on the effect of chain elongation on biological activity
    • Curley D., McGuigan C., Devine K.G., O'Connor T.J., Jeffries D.J., Kinchington D. Synthesis and anti-HIV evaluation of some phosphoramidate derivatives of AZT: studies on the effect of chain elongation on biological activity. Antiviral Res. 1990, 14:345-356.
    • (1990) Antiviral Res. , vol.14 , pp. 345-356
    • Curley, D.1    McGuigan, C.2    Devine, K.G.3    O'Connor, T.J.4    Jeffries, D.J.5    Kinchington, D.6
  • 32
    • 30344486584 scopus 로고    scopus 로고
    • Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy
    • De Clercq E., Field H.J. Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br. J. Pharmacol. 2006, 147:1-11.
    • (2006) Br. J. Pharmacol. , vol.147 , pp. 1-11
    • De Clercq, E.1    Field, H.J.2
  • 35
    • 0031710248 scopus 로고    scopus 로고
    • Safety, pharmacokinetics, and antiretroviral activity of intravenous 9-[2-(R)-(phosphonomethoxy)propyl]adenine, a novel anti-human immunodeficiency virus (HIV) therapy, in HIV-infected adults
    • Deeks S.G., Barditch-Crovo P., Lietman P.S., Hwang F., Cundy K.C., Rooney J.F., Hellmann N.S., Safrin S., Kahn J.O. Safety, pharmacokinetics, and antiretroviral activity of intravenous 9-[2-(R)-(phosphonomethoxy)propyl]adenine, a novel anti-human immunodeficiency virus (HIV) therapy, in HIV-infected adults. Antimicrob. Agents Chemother. 1998, 42:2380-2384.
    • (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 2380-2384
    • Deeks, S.G.1    Barditch-Crovo, P.2    Lietman, P.S.3    Hwang, F.4    Cundy, K.C.5    Rooney, J.F.6    Hellmann, N.S.7    Safrin, S.8    Kahn, J.O.9
  • 38
    • 68249104931 scopus 로고    scopus 로고
    • Nucleotide analogue prodrug tenofovir disoproxil enhances lymphoid cell loading following oral administration in monkeys
    • Durand-Gasselin L., Van Rompay K.K., Vela J.E., Henne I.N., Lee W.A., Rhodes G.R., Ray A.S. Nucleotide analogue prodrug tenofovir disoproxil enhances lymphoid cell loading following oral administration in monkeys. Mol. Pharm. 2009, 6:1145-1151.
    • (2009) Mol. Pharm. , vol.6 , pp. 1145-1151
    • Durand-Gasselin, L.1    Van Rompay, K.K.2    Vela, J.E.3    Henne, I.N.4    Lee, W.A.5    Rhodes, G.R.6    Ray, A.S.7
  • 39
    • 0141923630 scopus 로고    scopus 로고
    • S-Acyl-2-thioethyl phosphoramidate diester derivatives as mononucleotide prodrugs
    • Egron D., Imbach J.L., Gosselin G., Aubertin A.M., Perigaud C. S-Acyl-2-thioethyl phosphoramidate diester derivatives as mononucleotide prodrugs. J. Med. Chem. 2003, 46:4564-4571.
    • (2003) J. Med. Chem. , vol.46 , pp. 4564-4571
    • Egron, D.1    Imbach, J.L.2    Gosselin, G.3    Aubertin, A.M.4    Perigaud, C.5
  • 41
    • 0034852392 scopus 로고    scopus 로고
    • Metabolism of GS-7340, a novel phenyl monophosphoramidate intracellular prodrug of PMPA, in blood
    • Eisenberg E.J., He G.X., Lee W.A. Metabolism of GS-7340, a novel phenyl monophosphoramidate intracellular prodrug of PMPA, in blood. Nucleosides Nucleotides Nucleic Acids 2001, 20:1091-1098.
    • (2001) Nucleosides Nucleotides Nucleic Acids , vol.20 , pp. 1091-1098
    • Eisenberg, E.J.1    He, G.X.2    Lee, W.A.3
  • 43
    • 32544443162 scopus 로고    scopus 로고
    • HepDirect prodrugs for targeting nucleotide-based antiviral drugs to the liver
    • Erion M.D., Bullough D.A., Lin C.C., Hong Z. HepDirect prodrugs for targeting nucleotide-based antiviral drugs to the liver. Curr. Opin. Investig. Drugs 2006, 7:109-117.
    • (2006) Curr. Opin. Investig. Drugs , vol.7 , pp. 109-117
    • Erion, M.D.1    Bullough, D.A.2    Lin, C.C.3    Hong, Z.4
  • 44
    • 11144357250 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of a series of cytochrome P(450) 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)ate-based drugs to the liver
    • Erion M.D., Reddy K.R., Boyer S.H., Matelich M.C., Gomez-Galeno J., Lemus R.H., Ugarkar B.G., Colby T.J., Schanzer J., Van Poelje P.D. Design, synthesis, and characterization of a series of cytochrome P(450) 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)ate-based drugs to the liver. J. Am. Chem. Soc. 2004, 126:5154-5163.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5154-5163
    • Erion, M.D.1    Reddy, K.R.2    Boyer, S.H.3    Matelich, M.C.4    Gomez-Galeno, J.5    Lemus, R.H.6    Ugarkar, B.G.7    Colby, T.J.8    Schanzer, J.9    Van Poelje, P.D.10
  • 46
    • 0022357014 scopus 로고
    • Preparation of a lactosaminated albumin-ara-AMP conjugate which remains soluble after lyophilization
    • Fiume L., Bassi B., Busi C., Mattioli A. Preparation of a lactosaminated albumin-ara-AMP conjugate which remains soluble after lyophilization. Pharm. Acta. Helv. 1985, 60:318-320.
    • (1985) Pharm. Acta. Helv. , vol.60 , pp. 318-320
    • Fiume, L.1    Bassi, B.2    Busi, C.3    Mattioli, A.4
  • 51
    • 34147154785 scopus 로고    scopus 로고
    • Enzymatically activated cycloSal-d4T-monophosphates: the third generation of cycloSal-pronucleotides
    • Gisch N., Balzarini J., Meier C. Enzymatically activated cycloSal-d4T-monophosphates: the third generation of cycloSal-pronucleotides. J. Med. Chem. 2007, 50:1658-1667.
    • (2007) J. Med. Chem. , vol.50 , pp. 1658-1667
    • Gisch, N.1    Balzarini, J.2    Meier, C.3
  • 52
    • 66749116603 scopus 로고    scopus 로고
    • Doubly loaded cycloSaligenyl-pronucleotides - 5,5'-Bis-(cycloSaligenyl-2',3'-dideoxy-2',3'-didehydrothymidine monophosphates)
    • Gisch N., Balzarini J., Meier C. Doubly loaded cycloSaligenyl-pronucleotides - 5,5'-Bis-(cycloSaligenyl-2',3'-dideoxy-2',3'-didehydrothymidine monophosphates). J. Med. Chem. 2009, 52:3464-3473.
    • (2009) J. Med. Chem. , vol.52 , pp. 3464-3473
    • Gisch, N.1    Balzarini, J.2    Meier, C.3
  • 53
    • 0016180458 scopus 로고
    • Synthesis and properties of some cyclic AMP alkyl phosphotriesters
    • Gohil R.N., Gillen R.G., Nagyvary J. Synthesis and properties of some cyclic AMP alkyl phosphotriesters. Nucleic Acids Res. 1974, 1:1691-1701.
    • (1974) Nucleic Acids Res. , vol.1 , pp. 1691-1701
    • Gohil, R.N.1    Gillen, R.G.2    Nagyvary, J.3
  • 55
    • 0024426186 scopus 로고
    • 6- and 1-Substituted mannosyl phosphotryiesters as lipophilic macrophage-targeted carriers of aniviral nucleosides
    • Gouyette C., Neumann J.M., Fauve R., Huynh-Dinh T. 6- and 1-Substituted mannosyl phosphotryiesters as lipophilic macrophage-targeted carriers of aniviral nucleosides. Tetrahedron Lett. 1989, 30:6019-6022.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6019-6022
    • Gouyette, C.1    Neumann, J.M.2    Fauve, R.3    Huynh-Dinh, T.4
  • 57
    • 0021208982 scopus 로고
    • Inhibition of human and woodchuck hepatitis virus DNA polymerase by the triphosphates of acyclovir, 1-(2'-deoxy-2'-fluoro-beta-d-arabinofuranosyl)-5-iodocytosine and E-5-(2-bromovinyl)-2'-deoxyuridine
    • Hantz O., Allaudeen H.S., Ooka T., De Clercq E., Trepo C. Inhibition of human and woodchuck hepatitis virus DNA polymerase by the triphosphates of acyclovir, 1-(2'-deoxy-2'-fluoro-beta-d-arabinofuranosyl)-5-iodocytosine and E-5-(2-bromovinyl)-2'-deoxyuridine. Antiviral Res. 1984, 4:187-199.
    • (1984) Antiviral Res. , vol.4 , pp. 187-199
    • Hantz, O.1    Allaudeen, H.S.2    Ooka, T.3    De Clercq, E.4    Trepo, C.5
  • 58
    • 43049112098 scopus 로고    scopus 로고
    • Prodrugs of phosphates and phosphonates
    • Hecker S.J., Erion M.D. Prodrugs of phosphates and phosphonates. J. Med. Chem. 2008, 51:2328-2345.
    • (2008) J. Med. Chem. , vol.51 , pp. 2328-2345
    • Hecker, S.J.1    Erion, M.D.2
  • 60
    • 0025814856 scopus 로고
    • Lipophilic glycosyl phosphotriester derivatives of AZT: synthesis, NMR transmembrane transport study, and antiviral activity
    • Henin Y., Gouyette C., Schwartz O., Debouzy J.C., Neumann J.M., Huynh-Dinh T. Lipophilic glycosyl phosphotriester derivatives of AZT: synthesis, NMR transmembrane transport study, and antiviral activity. J. Med. Chem. 1991, 34:1830-1837.
    • (1991) J. Med. Chem. , vol.34 , pp. 1830-1837
    • Henin, Y.1    Gouyette, C.2    Schwartz, O.3    Debouzy, J.C.4    Neumann, J.M.5    Huynh-Dinh, T.6
  • 61
    • 0000055156 scopus 로고
    • The cyclic congener of cidofovir has reduced nephrotoxicity in three species
    • Hitchcock M.J.M., Lacy S.A., Lindsey J.R., Kern E.R. The cyclic congener of cidofovir has reduced nephrotoxicity in three species. Antiviral Res. 1995, 26:A358.
    • (1995) Antiviral Res. , vol.26
    • Hitchcock, M.J.M.1    Lacy, S.A.2    Lindsey, J.R.3    Kern, E.R.4
  • 62
    • 67349157073 scopus 로고    scopus 로고
    • Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: current state of the art
    • Hostetler K.Y. Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: current state of the art. Antiviral Res. 2009, 82:A84-A98.
    • (2009) Antiviral Res. , vol.82
    • Hostetler, K.Y.1
  • 63
    • 79952147366 scopus 로고    scopus 로고
    • Synthesis and early development of hexadecyloxypropyl-cidofovir: an oral antipoxvirus nucleoside phosphonate
    • Hostetler K.Y. Synthesis and early development of hexadecyloxypropyl-cidofovir: an oral antipoxvirus nucleoside phosphonate. Viruses 2010, 2:2213-2225.
    • (2010) Viruses , vol.2 , pp. 2213-2225
    • Hostetler, K.Y.1
  • 65
    • 0030786518 scopus 로고    scopus 로고
    • Enhanced oral absorption and antiviral activity of 1-O-octadecyl-sn-glycero-3-phospho-acyclovir and related compounds in hepatitis B virus infection, in vitro
    • Hostetler K.Y., Beadle J.R., Kini G.D., Gardner M.F., Wright K.N., Wu T.H., Korba B.A. Enhanced oral absorption and antiviral activity of 1-O-octadecyl-sn-glycero-3-phospho-acyclovir and related compounds in hepatitis B virus infection, in vitro. Biochem. Pharmacol. 1997, 53:1815-1822.
    • (1997) Biochem. Pharmacol. , vol.53 , pp. 1815-1822
    • Hostetler, K.Y.1    Beadle, J.R.2    Kini, G.D.3    Gardner, M.F.4    Wright, K.N.5    Wu, T.H.6    Korba, B.A.7
  • 66
    • 0025955435 scopus 로고
    • Phosphatidylazidothymidine. Mechanism of antiretroviral action in CEM cells
    • Hostetler K.Y., Carson D.A., Richman D.D. Phosphatidylazidothymidine. Mechanism of antiretroviral action in CEM cells. J. Biol. Chem. 1991, 266:11714-11717.
    • (1991) J. Biol. Chem. , vol.266 , pp. 11714-11717
    • Hostetler, K.Y.1    Carson, D.A.2    Richman, D.D.3
  • 68
    • 0026662054 scopus 로고
    • Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3'-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3'-deoxythymidine
    • Hostetler K.Y., Richman D.D., Carson D.A., Stuhmiller L.M., van Wijk G.M., van den Bosch H. Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3'-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3'-deoxythymidine. Antimicrob. Agents Chemother. 1992, 36:2025-2029.
    • (1992) Antimicrob. Agents Chemother. , vol.36 , pp. 2025-2029
    • Hostetler, K.Y.1    Richman, D.D.2    Carson, D.A.3    Stuhmiller, L.M.4    van Wijk, G.M.5    van den Bosch, H.6
  • 69
    • 0025262446 scopus 로고
    • Synthesis and antiretroviral activity of phospholipid analogs of azidothymidine and other antiviral nucleosides
    • Hostetler K.Y., Stuhmiller L.M., Lenting H.B., van den Bosch H., Richman D.D. Synthesis and antiretroviral activity of phospholipid analogs of azidothymidine and other antiviral nucleosides. J. Biol. Chem. 1990, 265:6112-6117.
    • (1990) J. Biol. Chem. , vol.265 , pp. 6112-6117
    • Hostetler, K.Y.1    Stuhmiller, L.M.2    Lenting, H.B.3    van den Bosch, H.4    Richman, D.D.5
  • 70
    • 0031919066 scopus 로고    scopus 로고
    • Ribavirin uptake by human erythrocytes and the involvement of nitrobenzylthioinosine-sensitive (es)-nucleoside transporters
    • Jarvis S.M., Thorn J.A., Glue P. Ribavirin uptake by human erythrocytes and the involvement of nitrobenzylthioinosine-sensitive (es)-nucleoside transporters. Br. J. Pharmacol. 1998, 123:1587-1592.
    • (1998) Br. J. Pharmacol. , vol.123 , pp. 1587-1592
    • Jarvis, S.M.1    Thorn, J.A.2    Glue, P.3
  • 72
    • 78049256334 scopus 로고    scopus 로고
    • Hexadecyloxypropyl-cidofovir (CMX001) suppresses JC virus replication in human fetal brain SVG cell cultures
    • Jiang Z.G., Cohen J., Marshall L.J., Major E.O. Hexadecyloxypropyl-cidofovir (CMX001) suppresses JC virus replication in human fetal brain SVG cell cultures. Antimicrob. Agents Chemother. 2010, 54:4723-4732.
    • (2010) Antimicrob. Agents Chemother. , vol.54 , pp. 4723-4732
    • Jiang, Z.G.1    Cohen, J.2    Marshall, L.J.3    Major, E.O.4
  • 75
    • 33847689816 scopus 로고    scopus 로고
    • Crystal structures of phosphodiesterases and implications on substrate specificity and inhibitor selectivity
    • Ke H., Wang H. Crystal structures of phosphodiesterases and implications on substrate specificity and inhibitor selectivity. Curr. Top. Med. Chem. 2007, 7:391-403.
    • (2007) Curr. Top. Med. Chem. , vol.7 , pp. 391-403
    • Ke, H.1    Wang, H.2
  • 76
    • 0038312076 scopus 로고    scopus 로고
    • Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication
    • Keith K.A., Hitchcock M.J., Lee W.A., Holy A., Kern E.R. Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication. Antimicrob. Agents Chemother. 2003, 47:2193-2198.
    • (2003) Antimicrob. Agents Chemother. , vol.47 , pp. 2193-2198
    • Keith, K.A.1    Hitchcock, M.J.2    Lee, W.A.3    Holy, A.4    Kern, E.R.5
  • 77
    • 0029796135 scopus 로고    scopus 로고
    • Neighboring group catalysis in the design of nucleotide prodrugs
    • Khamnei S., Torrence P.F. Neighboring group catalysis in the design of nucleotide prodrugs. J. Med. Chem. 1996, 39:4109-4115.
    • (1996) J. Med. Chem. , vol.39 , pp. 4109-4115
    • Khamnei, S.1    Torrence, P.F.2
  • 78
    • 15444363853 scopus 로고    scopus 로고
    • Direct measurement of nucleoside monophosphate delivery from a phosphoramidate pronucleotide by stable isotope labeling and LC-ESI(-)-MS/MS
    • Kim J., Chou T.F., Griesgraber G.W., Wagner C.R. Direct measurement of nucleoside monophosphate delivery from a phosphoramidate pronucleotide by stable isotope labeling and LC-ESI(-)-MS/MS. Mol. Pharm. 2004, 1:102-111.
    • (2004) Mol. Pharm. , vol.1 , pp. 102-111
    • Kim, J.1    Chou, T.F.2    Griesgraber, G.W.3    Wagner, C.R.4
  • 82
    • 18244398917 scopus 로고    scopus 로고
    • Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue
    • Lee W.A., He G.X., Eisenberg E., Cihlar T., Swaminathan S., Mulato A., Cundy K.C. Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue. Antimicrob. Agents Chemother. 2005, 49:1898-1906.
    • (2005) Antimicrob. Agents Chemother. , vol.49 , pp. 1898-1906
    • Lee, W.A.1    He, G.X.2    Eisenberg, E.3    Cihlar, T.4    Swaminathan, S.5    Mulato, A.6    Cundy, K.C.7
  • 83
    • 33747125380 scopus 로고    scopus 로고
    • Perspectives on the development of acyclic nucleotide analogs as antiviral drugs
    • Lee W.A., Martin J.C. Perspectives on the development of acyclic nucleotide analogs as antiviral drugs. Antiviral Res. 2006, 71:254-259.
    • (2006) Antiviral Res. , vol.71 , pp. 254-259
    • Lee, W.A.1    Martin, J.C.2
  • 84
    • 33745031316 scopus 로고    scopus 로고
    • Enzymes involved in the bioconversion of ester-based prodrugs
    • Liederer B.M., Borchardt R.T. Enzymes involved in the bioconversion of ester-based prodrugs. J. Pharm. Sci. 2006, 95:1177-1195.
    • (2006) J. Pharm. Sci. , vol.95 , pp. 1177-1195
    • Liederer, B.M.1    Borchardt, R.T.2
  • 85
    • 0015466351 scopus 로고
    • Synthesis and antitumor and antiviral activities of 1-β-d-arabinofuranosylpyrimidine 3',5'-cyclic phosphates
    • Long R.A., Szekeres G.L., Khwaja T.A., Sidwell R.W., Simon L.N., Robins R.K. Synthesis and antitumor and antiviral activities of 1-β-d-arabinofuranosylpyrimidine 3',5'-cyclic phosphates. J. Med. Chem. 1972, 15:1215-1218.
    • (1972) J. Med. Chem. , vol.15 , pp. 1215-1218
    • Long, R.A.1    Szekeres, G.L.2    Khwaja, T.A.3    Sidwell, R.W.4    Simon, L.N.5    Robins, R.K.6
  • 87
    • 80054857205 scopus 로고    scopus 로고
    • GS-7340 demonstrates greater declines in HIV-1 RNA than TDF during 14 days of monotherapy in HIV-1-infected subjects, In: 18th Conference on Retroviruses and Opportunistic Infections, Abstract 152LB, Boston, MA, USA.
    • Markowitz, M., Zolopa, A., Ruane, P., Squires, K., Zhong, L., Kearney, B.P., Lee, W., 2011. GS-7340 demonstrates greater declines in HIV-1 RNA than TDF during 14 days of monotherapy in HIV-1-infected subjects, In: 18th Conference on Retroviruses and Opportunistic Infections, Abstract 152LB, Boston, MA, USA.
    • (2011)
    • Markowitz, M.1    Zolopa, A.2    Ruane, P.3    Squires, K.4    Zhong, L.5    Kearney, B.P.6    Lee, W.7
  • 88
    • 73549122138 scopus 로고    scopus 로고
    • Early nucleoside reverse transcriptase inhibitors for the treatment of HIV: a brief history of stavudine (D4T) and its comparison with other dideoxynucleosides
    • Martin J.C., Hitchcock M.J., De Clercq E., Prusoff W.H. Early nucleoside reverse transcriptase inhibitors for the treatment of HIV: a brief history of stavudine (D4T) and its comparison with other dideoxynucleosides. Antiviral Res. 2010, 85:34-38.
    • (2010) Antiviral Res. , vol.85 , pp. 34-38
    • Martin, J.C.1    Hitchcock, M.J.2    De Clercq, E.3    Prusoff, W.H.4
  • 89
    • 0028060330 scopus 로고
    • Certain phosphoramidate derivatives of dideoxy uridine (ddU) are active against HIV and successfully by-pass thymidine kinase
    • McGuigan C., Bellevergue P., Sheeka H., Mahmood N., Hay A.J. Certain phosphoramidate derivatives of dideoxy uridine (ddU) are active against HIV and successfully by-pass thymidine kinase. FEBS Lett. 1994, 351:11-14.
    • (1994) FEBS Lett. , vol.351 , pp. 11-14
    • McGuigan, C.1    Bellevergue, P.2    Sheeka, H.3    Mahmood, N.4    Hay, A.J.5
  • 90
    • 0029975897 scopus 로고    scopus 로고
    • Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite
    • McGuigan C., Cahard D., Sheeka H.M., De Clercq E., Balzarini J. Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite. J. Med. Chem. 1996, 39:1748-1753.
    • (1996) J. Med. Chem. , vol.39 , pp. 1748-1753
    • McGuigan, C.1    Cahard, D.2    Sheeka, H.M.3    De Clercq, E.4    Balzarini, J.5
  • 91
    • 0025801734 scopus 로고
    • Synthesis and anti-HIV activity of some haloalkyl phosphoramidate derivatives of 3'-azido-3'-deoxythymidine (AZT): potent activity of the trichloroethyl methoxyalaninyl compound
    • McGuigan C., Devine K.G., O'Connor T.J., Kinchington D. Synthesis and anti-HIV activity of some haloalkyl phosphoramidate derivatives of 3'-azido-3'-deoxythymidine (AZT): potent activity of the trichloroethyl methoxyalaninyl compound. Antiviral Res. 1991, 15:255-263.
    • (1991) Antiviral Res. , vol.15 , pp. 255-263
    • McGuigan, C.1    Devine, K.G.2    O'Connor, T.J.3    Kinchington, D.4
  • 94
    • 67649999890 scopus 로고    scopus 로고
    • The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus
    • McGuigan C., Perrone P., Madela K., Neyts J. The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus. Bioorg. Med. Chem. Lett. 2009, 19:4316-4320.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 4316-4320
    • McGuigan, C.1    Perrone, P.2    Madela, K.3    Neyts, J.4
  • 95
    • 0024337542 scopus 로고
    • Synthesis and biological evaluation of some phosphate triester derivatives of the anti-viral drug AraA
    • McGuigan C., Tollerfield S.M., Riley P.A. Synthesis and biological evaluation of some phosphate triester derivatives of the anti-viral drug AraA. Nucleic Acids Res. 1989, 17:6065-6075.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 6065-6075
    • McGuigan, C.1    Tollerfield, S.M.2    Riley, P.A.3
  • 96
    • 73449119606 scopus 로고    scopus 로고
    • Aryloxy phosphoramidate triesters: a technology for delivering monophosphorylated nucleosides and sugars into cells
    • Mehellou Y., Balzarini J., McGuigan C. Aryloxy phosphoramidate triesters: a technology for delivering monophosphorylated nucleosides and sugars into cells. ChemMedChem 2009, 4:1779-1791.
    • (2009) ChemMedChem , vol.4 , pp. 1779-1791
    • Mehellou, Y.1    Balzarini, J.2    McGuigan, C.3
  • 97
    • 33747093326 scopus 로고    scopus 로고
    • Application of the cycloSal-prodrug approach for improving the biological potential of phosphorylated biomolecules
    • Meier C., Balzarini J. Application of the cycloSal-prodrug approach for improving the biological potential of phosphorylated biomolecules. Antiviral Res. 2006, 71:282-292.
    • (2006) Antiviral Res. , vol.71 , pp. 282-292
    • Meier, C.1    Balzarini, J.2
  • 98
    • 29144464769 scopus 로고    scopus 로고
    • CycloSal-PMEA and cycloAmb-PMEA: potentially new phosphonate prodrugs based on the cycloSal-pronucleotide approach
    • Meier C., Gorbig U., Muller C., Balzarini J. CycloSal-PMEA and cycloAmb-PMEA: potentially new phosphonate prodrugs based on the cycloSal-pronucleotide approach. J. Med. Chem. 2005, 48:8079-8086.
    • (2005) J. Med. Chem. , vol.48 , pp. 8079-8086
    • Meier, C.1    Gorbig, U.2    Muller, C.3    Balzarini, J.4
  • 100
    • 0032560234 scopus 로고    scopus 로고
    • CycloSal-2',3'-dideoxy-2',3'-didehydrothymidine monophosphate (cycloSal-d4TMP): synthesis and antiviral evaluation of a new d4TMP delivery system
    • Meier C., Lorey M., De Clercq E., Balzarini J. CycloSal-2',3'-dideoxy-2',3'-didehydrothymidine monophosphate (cycloSal-d4TMP): synthesis and antiviral evaluation of a new d4TMP delivery system. J. Med. Chem. 1998, 41:1417-1427.
    • (1998) J. Med. Chem. , vol.41 , pp. 1417-1427
    • Meier, C.1    Lorey, M.2    De Clercq, E.3    Balzarini, J.4
  • 101
    • 0031038255 scopus 로고    scopus 로고
    • Conversion of 1-[((S)-2-hydroxy-2-oxo-1, 4, 2-dioxaphosphorinan-5-yl)methyl]cytosine to cidofovir by an intracellular cyclic CMP phosphodiesterase
    • Mendel D.B., Cihlar T., Moon K., Chen M.S. Conversion of 1-[((S)-2-hydroxy-2-oxo-1, 4, 2-dioxaphosphorinan-5-yl)methyl]cytosine to cidofovir by an intracellular cyclic CMP phosphodiesterase. Antimicrob. Agents Chemother. 1997, 41:641-646.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 641-646
    • Mendel, D.B.1    Cihlar, T.2    Moon, K.3    Chen, M.S.4
  • 103
    • 0025605531 scopus 로고
    • Targeting of antiviral drugs to T4-lymphocytes. Anti-HIV activity of neoglycoprotein-AZTMP conjugates in vitro
    • Molema G., Jansen R.W., Pauwels R., de Clercq E., Meijer D.K. Targeting of antiviral drugs to T4-lymphocytes. Anti-HIV activity of neoglycoprotein-AZTMP conjugates in vitro. Biochem. Pharmacol. 1990, 40:2603-2610.
    • (1990) Biochem. Pharmacol. , vol.40 , pp. 2603-2610
    • Molema, G.1    Jansen, R.W.2    Pauwels, R.3    de Clercq, E.4    Meijer, D.K.5
  • 104
    • 67649966294 scopus 로고    scopus 로고
    • Alkoxyalkyl esters of 9-(s)-(3-hydroxy-2-phosphonomethoxypropyl) adenine are potent and selective inhibitors of hepatitis B virus (HBV) replication in vitro and in HBV transgenic mice in vivo
    • Morrey J.D., Korba B.E., Beadle J.R., Wyles D.L., Hostetler K.Y. Alkoxyalkyl esters of 9-(s)-(3-hydroxy-2-phosphonomethoxypropyl) adenine are potent and selective inhibitors of hepatitis B virus (HBV) replication in vitro and in HBV transgenic mice in vivo. Antimicrob. Agents Chemother. 2009, 53:2865-2870.
    • (2009) Antimicrob. Agents Chemother. , vol.53 , pp. 2865-2870
    • Morrey, J.D.1    Korba, B.E.2    Beadle, J.R.3    Wyles, D.L.4    Hostetler, K.Y.5
  • 106
  • 108
    • 0027722026 scopus 로고
    • Rational design for cytosolic delivery of nucleoside monophopshates: " SATE" and " DTE" as enzyme-liabile transient phosphate protecting groups
    • Perigaud C., Gosselin G., Lefebvre I., Giradet J.L., Benzaria S., Barber I., Imbach J.L. Rational design for cytosolic delivery of nucleoside monophopshates: " SATE" and " DTE" as enzyme-liabile transient phosphate protecting groups. Bioorg. Med. Chem. Lett. 1993, 3:2521-2526.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2521-2526
    • Perigaud, C.1    Gosselin, G.2    Lefebvre, I.3    Giradet, J.L.4    Benzaria, S.5    Barber, I.6    Imbach, J.L.7
  • 109
    • 35848930168 scopus 로고    scopus 로고
    • First example of phosphoramidate approach applied to a 4'-substituted purine nucleoside (4'-azidoadenosine): conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus
    • Perrone P., Daverio F., Valente R., Rajyaguru S., Martin J.A., Leveque V., Le Pogam S., Najera I., Klumpp K., Smith D.B., McGuigan C. First example of phosphoramidate approach applied to a 4'-substituted purine nucleoside (4'-azidoadenosine): conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus. J. Med. Chem. 2007, 50:5463-5470.
    • (2007) J. Med. Chem. , vol.50 , pp. 5463-5470
    • Perrone, P.1    Daverio, F.2    Valente, R.3    Rajyaguru, S.4    Martin, J.A.5    Leveque, V.6    Le Pogam, S.7    Najera, I.8    Klumpp, K.9    Smith, D.B.10    McGuigan, C.11
  • 112
    • 0017117688 scopus 로고
    • Studies on nucleotide diphosphate diacylglycerol specificity of acidic phospholipid biosynthesis in rat liver subcellular fractions
    • Poorthuis B.J., Hostetler K.Y. Studies on nucleotide diphosphate diacylglycerol specificity of acidic phospholipid biosynthesis in rat liver subcellular fractions. Biochim. Biophys. Acta 1976, 431:408-415.
    • (1976) Biochim. Biophys. Acta , vol.431 , pp. 408-415
    • Poorthuis, B.J.1    Hostetler, K.Y.2
  • 114
    • 0022461410 scopus 로고
    • Synthesis and antiherpes virus activity of phosphate and phosphonate derivatives of 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
    • Prisbe E.J., Martin J.C., McGee D.P., Barker M.F., Smee D.F., Duke A.E., Matthews T.R., Verheyden J.P. Synthesis and antiherpes virus activity of phosphate and phosphonate derivatives of 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine. J. Med. Chem. 1986, 29:671-675.
    • (1986) J. Med. Chem. , vol.29 , pp. 671-675
    • Prisbe, E.J.1    Martin, J.C.2    McGee, D.P.3    Barker, M.F.4    Smee, D.F.5    Duke, A.E.6    Matthews, T.R.7    Verheyden, J.P.8
  • 115
    • 0027433373 scopus 로고
    • Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process
    • Puech F., Gosselin G., Lefebvre I., Pompon A., Aubertin A.M., Kirn A., Imbach J.L. Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process. Antiviral Res. 1993, 22:155-174.
    • (1993) Antiviral Res. , vol.22 , pp. 155-174
    • Puech, F.1    Gosselin, G.2    Lefebvre, I.3    Pompon, A.4    Aubertin, A.M.5    Kirn, A.6    Imbach, J.L.7
  • 120
    • 0031916651 scopus 로고    scopus 로고
    • Anti-human immunodeficiency virus activity and cellular metabolism of a potential prodrug of the acyclic nucleoside phosphonate 9-R-(2-phosphonomethoxypropyl)adenine (PMPA), bis(isopropyloxymethylcarbonyl)PMPA
    • Robbins B.L., Srinivas R.V., Kim C., Bischofberger N., Fridland A. Anti-human immunodeficiency virus activity and cellular metabolism of a potential prodrug of the acyclic nucleoside phosphonate 9-R-(2-phosphonomethoxypropyl)adenine (PMPA), bis(isopropyloxymethylcarbonyl)PMPA. Antimicrob. Agents Chemother. 1998, 42:612-617.
    • (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 612-617
    • Robbins, B.L.1    Srinivas, R.V.2    Kim, C.3    Bischofberger, N.4    Fridland, A.5
  • 121
    • 0029155592 scopus 로고
    • Synthesis, bioactivation and anti-HIV activity of 4-acyloxybenzyl bis(Nucleosid-5'-yl) phosphates
    • Routledge A., Walker I., Freeman S., Hay A., Mahmood N. Synthesis, bioactivation and anti-HIV activity of 4-acyloxybenzyl bis(Nucleosid-5'-yl) phosphates. Nucleosides Nucleotides Nucleic Acids 1995, 14:1545-1558.
    • (1995) Nucleosides Nucleotides Nucleic Acids , vol.14 , pp. 1545-1558
    • Routledge, A.1    Walker, I.2    Freeman, S.3    Hay, A.4    Mahmood, N.5
  • 127
    • 0037333460 scopus 로고    scopus 로고
    • Prodrugs of biologically active phosphate esters
    • Schultz C. Prodrugs of biologically active phosphate esters. Bioorg. Med. Chem. 2003, 11:885-898.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 885-898
    • Schultz, C.1
  • 129
    • 0031430945 scopus 로고    scopus 로고
    • Metabolism and pharmacokinetics of novel oral prodrugs of 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA) in dogs
    • Shaw J.P., Sueoko C.M., Oliyai R., Lee W.A., Arimilli M.N., Kim C.U., Cundy K.C. Metabolism and pharmacokinetics of novel oral prodrugs of 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA) in dogs. Pharm. Res. 1997, 14:1824-1829.
    • (1997) Pharm. Res. , vol.14 , pp. 1824-1829
    • Shaw, J.P.1    Sueoko, C.M.2    Oliyai, R.3    Lee, W.A.4    Arimilli, M.N.5    Kim, C.U.6    Cundy, K.C.7
  • 132
    • 0026739035 scopus 로고
    • Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine
    • Starrett J.E., Tortolani D.R., Hitchcock M.J., Martin J.C., Mansuri M.M. Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine. Antiviral Res. 1992, 19:267-273.
    • (1992) Antiviral Res. , vol.19 , pp. 267-273
    • Starrett, J.E.1    Tortolani, D.R.2    Hitchcock, M.J.3    Martin, J.C.4    Mansuri, M.M.5
  • 133
    • 0019276096 scopus 로고
    • Prodrugs and site-specific drug delivery
    • Stella V.J., Himmelstein K.J. Prodrugs and site-specific drug delivery. J. Med. Chem. 1980, 23:1275-1282.
    • (1980) J. Med. Chem. , vol.23 , pp. 1275-1282
    • Stella, V.J.1    Himmelstein, K.J.2
  • 134
    • 0032823876 scopus 로고    scopus 로고
    • Development and optimization of anti-HIV nucleoside analogs and prodrugs: a review of their cellular pharmacology, structure-activity relationships and pharmacokinetics
    • Tan X., Chu C.K., Boudinot F.D. Development and optimization of anti-HIV nucleoside analogs and prodrugs: a review of their cellular pharmacology, structure-activity relationships and pharmacokinetics. Adv. Drug Deliv. Rev. 1999, 39:117-151.
    • (1999) Adv. Drug Deliv. Rev. , vol.39 , pp. 117-151
    • Tan, X.1    Chu, C.K.2    Boudinot, F.D.3
  • 135
    • 0029761595 scopus 로고    scopus 로고
    • Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine
    • Tsotinis A., Calogeropoulou T., Koufaki M., Souli C., Balzarini J., De Clercq E., Makriyannis A. Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine. J. Med. Chem. 1996, 39:3418-3422.
    • (1996) J. Med. Chem. , vol.39 , pp. 3418-3422
    • Tsotinis, A.1    Calogeropoulou, T.2    Koufaki, M.3    Souli, C.4    Balzarini, J.5    De Clercq, E.6    Makriyannis, A.7
  • 136
    • 79960559670 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of 9-(S)-[3-Alkoxy-2-(phosphonomethoxy)propyl] nucleoside alkoxyalkyl esters: inhibitors of hepatitis C virus and HIV-1 replication
    • Valiaeva N., Wyles D.L., Schooley R.T., Hwu J.B., Beadle J.R., Prichard M.N., Hostetler K.Y. Synthesis and antiviral evaluation of 9-(S)-[3-Alkoxy-2-(phosphonomethoxy)propyl] nucleoside alkoxyalkyl esters: inhibitors of hepatitis C virus and HIV-1 replication. Bioorg. Med. Chem. 2011, 19:4616-4625.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 4616-4625
    • Valiaeva, N.1    Wyles, D.L.2    Schooley, R.T.3    Hwu, J.B.4    Beadle, J.R.5    Prichard, M.N.6    Hostetler, K.Y.7
  • 137
    • 0033796942 scopus 로고    scopus 로고
    • Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases
    • Van Rompay A.R., Johansson M., Karlsson A. Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases. Pharmacol. Ther. 2000, 87:189-198.
    • (2000) Pharmacol. Ther. , vol.87 , pp. 189-198
    • Van Rompay, A.R.1    Johansson, M.2    Karlsson, A.3
  • 138
    • 0028220406 scopus 로고
    • Synthesis and antiviral activity of 3'-azido-3'-deoxythymidine triphosphate distearoylglycerol: a novel phospholipid conjugate of the anti-HIV agent AZT
    • van Wijk G.M., Hostetler K.Y., Kroneman E., Richman D.D., Sridhar C.N., Kumar R., van den Bosch H. Synthesis and antiviral activity of 3'-azido-3'-deoxythymidine triphosphate distearoylglycerol: a novel phospholipid conjugate of the anti-HIV agent AZT. Chem. Phys. Lipids 1994, 70:213-222.
    • (1994) Chem. Phys. Lipids , vol.70 , pp. 213-222
    • van Wijk, G.M.1    Hostetler, K.Y.2    Kroneman, E.3    Richman, D.D.4    Sridhar, C.N.5    Kumar, R.6    van den Bosch, H.7
  • 141
    • 0029118114 scopus 로고
    • Aromatic amino acid phosphoramidate di- and triesters of 3'-azido-3'-deoxythymidine (AZT) are non-toxic inhibitors of HIV-1 replication
    • Wagner C.R., McIntee E.J., Schinazi R.F., Abraham T.W. Aromatic amino acid phosphoramidate di- and triesters of 3'-azido-3'-deoxythymidine (AZT) are non-toxic inhibitors of HIV-1 replication. Bioorg. Med. Chem. Lett. 1995, 5:1809-1824.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1809-1824
    • Wagner, C.R.1    McIntee, E.J.2    Schinazi, R.F.3    Abraham, T.W.4
  • 143
    • 77952303898 scopus 로고    scopus 로고
    • Understanding specificity in metabolic pathways - structural biology of human nucleotide metabolism
    • Welin M., Nordlund P. Understanding specificity in metabolic pathways - structural biology of human nucleotide metabolism. Biochem. Biophys. Res. Commun. 2010, 396:157-163.
    • (2010) Biochem. Biophys. Res. Commun. , vol.396 , pp. 157-163
    • Welin, M.1    Nordlund, P.2
  • 144
    • 0034956253 scopus 로고    scopus 로고
    • Mitochondrial toxicity and HIV therapy
    • White A.J. Mitochondrial toxicity and HIV therapy. Sex Transm. Infect. 2001, 77:158-173.
    • (2001) Sex Transm. Infect. , vol.77 , pp. 158-173
    • White, A.J.1
  • 145
    • 67650003697 scopus 로고    scopus 로고
    • GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions
    • Wolfgang G.H., Shibata R., Wang J., Ray A.S., Wu S., Doerrfler E., Reiser H., Lee W.A., Birkus G., Christensen N.D., Andrei G., Snoeck R. GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions. Antimicrob. Agents Chemother. 2009, 53:2777-2784.
    • (2009) Antimicrob. Agents Chemother. , vol.53 , pp. 2777-2784
    • Wolfgang, G.H.1    Shibata, R.2    Wang, J.3    Ray, A.S.4    Wu, S.5    Doerrfler, E.6    Reiser, H.7    Lee, W.A.8    Birkus, G.9    Christensen, N.D.10    Andrei, G.11    Snoeck, R.12
  • 146
    • 80054846702 scopus 로고    scopus 로고
    • Enhanced cellular penetration of ODE-(S)-MPMPA accounts for its prolonged post-exposure anti-HCV activity, In: 24th International Conference on Antiviral Research, Sofia, Bulgaria.
    • Wyles, D.L., Jones, K.A., Valiaeva, N., Beadle, J.R., Schooley, R.T., Hostetler, K.Y., 2011. Enhanced cellular penetration of ODE-(S)-MPMPA accounts for its prolonged post-exposure anti-HCV activity, In: 24th International Conference on Antiviral Research, Sofia, Bulgaria.
    • (2011)
    • Wyles, D.L.1    Jones, K.A.2    Valiaeva, N.3    Beadle, J.R.4    Schooley, R.T.5    Hostetler, K.Y.6
  • 147
    • 67049086876 scopus 로고    scopus 로고
    • The octadecyloxyethyl ester of (S)-9-[3-hydroxy-2-(phosphonomethoxy) propyl]adenine is a potent and selective inhibitor of hepatitis C virus replication in genotype 1A, 1B, and 2A replicons
    • Wyles D.L., Kaihara K.A., Korba B.E., Schooley R.T., Beadle J.R., Hostetler K.Y. The octadecyloxyethyl ester of (S)-9-[3-hydroxy-2-(phosphonomethoxy) propyl]adenine is a potent and selective inhibitor of hepatitis C virus replication in genotype 1A, 1B, and 2A replicons. Antimicrob. Agents Chemother. 2009, 53:2660-2662.
    • (2009) Antimicrob. Agents Chemother. , vol.53 , pp. 2660-2662
    • Wyles, D.L.1    Kaihara, K.A.2    Korba, B.E.3    Schooley, R.T.4    Beadle, J.R.5    Hostetler, K.Y.6
  • 148
    • 12144255999 scopus 로고    scopus 로고
    • Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity
    • Yan Z., Kern E.R., Gullen E., Cheng Y.C., Drach J.C., Zemlicka J. Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity. J. Med. Chem. 2005, 48:91-99.
    • (2005) J. Med. Chem. , vol.48 , pp. 91-99
    • Yan, Z.1    Kern, E.R.2    Gullen, E.3    Cheng, Y.C.4    Drach, J.C.5    Zemlicka, J.6
  • 149
    • 78650674078 scopus 로고    scopus 로고
    • Safety and pharmacokinetics of IDX184, a liver-targeted nucleotide polymerase inhibitor of hepatitis C virus, in healthy subjects
    • Zhou X.J., Pietropaolo K., Chen J., Khan S., Sullivan-Bolyai J., Mayers D. Safety and pharmacokinetics of IDX184, a liver-targeted nucleotide polymerase inhibitor of hepatitis C virus, in healthy subjects. Antimicrob. Agents Chemother. 2011, 55:76-81.
    • (2011) Antimicrob. Agents Chemother. , vol.55 , pp. 76-81
    • Zhou, X.J.1    Pietropaolo, K.2    Chen, J.3    Khan, S.4    Sullivan-Bolyai, J.5    Mayers, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.