메뉴 건너뛰기




Volumn 76, Issue 8, 2008, Pages 997-1005

Intracellular metabolism of the new antiviral compound 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine

Author keywords

Acyclic nucleoside phosphonate; Cidofovir; HPMP 5 azaC; HPMPC

Indexed keywords

1 [3 HYDROXY 2 (PHOSPHONOMETHOXY)PROPYL] 5 AZACYTOSINE; ANTIVIRUS AGENT; CIDOFOVIR; DEOXYCYTIDINE PHOSPHATE DEAMINASE; DRUG METABOLITE; UNCLASSIFIED DRUG;

EID: 52949088625     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.08.009     Document Type: Article
Times cited : (23)

References (26)
  • 1
    • 0027172325 scopus 로고
    • Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in Vero cells
    • Connelly M.C., Robbins B.L., and Fridland A. Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in Vero cells. Biochem Pharmacol 46 (1993) 1053-1057
    • (1993) Biochem Pharmacol , vol.46 , pp. 1053-1057
    • Connelly, M.C.1    Robbins, B.L.2    Fridland, A.3
  • 2
    • 0030480275 scopus 로고    scopus 로고
    • Identification of enzymes catalyzing two-step phosphorylation of cidofovir and the effect of cytomegalovirus infection on their activities in host cells
    • Cihlar T., and Chen M.S. Identification of enzymes catalyzing two-step phosphorylation of cidofovir and the effect of cytomegalovirus infection on their activities in host cells. Mol Pharmacol 50 (1996) 1502-1510
    • (1996) Mol Pharmacol , vol.50 , pp. 1502-1510
    • Cihlar, T.1    Chen, M.S.2
  • 4
    • 33847772580 scopus 로고    scopus 로고
    • Antiviral activity of triazine analogues of 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (cidofovir) and related compounds
    • Krecmerová M., Holý A., Pískala A., Masojídková M., Andrei G., Naesens L., et al. Antiviral activity of triazine analogues of 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (cidofovir) and related compounds. J Med Chem 50 (2007) 1069-1077
    • (2007) J Med Chem , vol.50 , pp. 1069-1077
    • Krecmerová, M.1    Holý, A.2    Pískala, A.3    Masojídková, M.4    Andrei, G.5    Naesens, L.6
  • 5
    • 36749040780 scopus 로고    scopus 로고
    • Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models
    • Duraffour S., Snoeck R., Krecmerová M., van Den Oord J., De Vos R., Holý A., et al. Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models. Antimicrob Agents Chemother 51 (2007) 4410-4419
    • (2007) Antimicrob Agents Chemother , vol.51 , pp. 4410-4419
    • Duraffour, S.1    Snoeck, R.2    Krecmerová, M.3    van Den Oord, J.4    De Vos, R.5    Holý, A.6
  • 6
    • 34250188092 scopus 로고    scopus 로고
    • Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains
    • Lebeau I., Andrei G., Krecmerová M., De Clercq E., Holý A., and Snoeck R. Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains. Antimicrob Agents Chemother 51 (2007) 2268-2273
    • (2007) Antimicrob Agents Chemother , vol.51 , pp. 2268-2273
    • Lebeau, I.1    Andrei, G.2    Krecmerová, M.3    De Clercq, E.4    Holý, A.5    Snoeck, R.6
  • 7
    • 36148947861 scopus 로고    scopus 로고
    • Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine: synthesis and antiviral activity
    • Krecmerová M., Holý A., Pohl R., Masojídková M., Andrei G., Naesens L., et al. Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine: synthesis and antiviral activity. J Med Chem 50 (2007) 5765-5772
    • (2007) J Med Chem , vol.50 , pp. 5765-5772
    • Krecmerová, M.1    Holý, A.2    Pohl, R.3    Masojídková, M.4    Andrei, G.5    Naesens, L.6
  • 8
    • 2942574415 scopus 로고    scopus 로고
    • Oral activity of ether lipid ester prodrugs of cidofovir against experimental human cytomegalovirus infection
    • Bidanset D.J., Beadle J.R., Wan W.B., Hostetler K.Y., and Kern E.R. Oral activity of ether lipid ester prodrugs of cidofovir against experimental human cytomegalovirus infection. J Infect Dis 190 (2004) 499-503
    • (2004) J Infect Dis , vol.190 , pp. 499-503
    • Bidanset, D.J.1    Beadle, J.R.2    Wan, W.B.3    Hostetler, K.Y.4    Kern, E.R.5
  • 9
    • 0022395151 scopus 로고
    • The effects of exogenous thymidine on endogenous deoxynucleotides and mutagenesis in mammalian cells
    • Weinberg G.L., Ullman B., Wright C.M., and Martin Jr. D.W. The effects of exogenous thymidine on endogenous deoxynucleotides and mutagenesis in mammalian cells. Somat Cell Mol Genet 11 (1985) 413-419
    • (1985) Somat Cell Mol Genet , vol.11 , pp. 413-419
    • Weinberg, G.L.1    Ullman, B.2    Wright, C.M.3    Martin Jr., D.W.4
  • 10
    • 0019856151 scopus 로고
    • High-performance liquid chromatographic analysis of chemical stability of 5-aza-2′-deoxycytidine
    • Lin K.T., Momparler R.L., and Rivard G.E. High-performance liquid chromatographic analysis of chemical stability of 5-aza-2′-deoxycytidine. J Pharm Sci 70 (1981) 1228-1232
    • (1981) J Pharm Sci , vol.70 , pp. 1228-1232
    • Lin, K.T.1    Momparler, R.L.2    Rivard, G.E.3
  • 11
    • 47349115510 scopus 로고    scopus 로고
    • Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy
    • Dracínský M., Krecmerová M., and Holý A. Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy. Bioorg Med Chem 16 (2008) 6778-6782
    • (2008) Bioorg Med Chem , vol.16 , pp. 6778-6782
    • Dracínský, M.1    Krecmerová, M.2    Holý, A.3
  • 12
    • 0019522434 scopus 로고
    • Mutator phenotypes in mammalian cell mutants with distinct biochemical defects and abnormal deoxyribonucleoside triphosphate pools
    • Weinberg G., Ullman B., and Martin D.W. Mutator phenotypes in mammalian cell mutants with distinct biochemical defects and abnormal deoxyribonucleoside triphosphate pools. Proc Natl Acad Sci U S A 78 (1981) 2447-2451
    • (1981) Proc Natl Acad Sci U S A , vol.78 , pp. 2447-2451
    • Weinberg, G.1    Ullman, B.2    Martin, D.W.3
  • 13
    • 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., and 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 41 (1997) 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
  • 14
    • 0030988373 scopus 로고    scopus 로고
    • (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) inhibits HIV-1 replication in epithelial cells, but not T-lymphocytes
    • Srinivas R.V., Connely M., and Fridland A. (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) inhibits HIV-1 replication in epithelial cells, but not T-lymphocytes. Antiviral Res 35 (1997) 23-27
    • (1997) Antiviral Res , vol.35 , pp. 23-27
    • Srinivas, R.V.1    Connely, M.2    Fridland, A.3
  • 15
    • 0027289725 scopus 로고
    • Primary structure of human deoxycytidylate deaminase and overexpression of its functional protein in Escherichia coli
    • Weiner K.X., Weiner R.S., Maley F., and Maley G.F. Primary structure of human deoxycytidylate deaminase and overexpression of its functional protein in Escherichia coli. J Biol Chem 268 (1993) 12983-12989
    • (1993) J Biol Chem , vol.268 , pp. 12983-12989
    • Weiner, K.X.1    Weiner, R.S.2    Maley, F.3    Maley, G.F.4
  • 16
    • 0038315265 scopus 로고    scopus 로고
    • Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells
    • Gribaudo G., Riera L., Caposio P., Maley F., and Landolfo S. Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells. J Gen Virol 84 (2003) 1437-1441
    • (2003) J Gen Virol , vol.84 , pp. 1437-1441
    • Gribaudo, G.1    Riera, L.2    Caposio, P.3    Maley, F.4    Landolfo, S.5
  • 17
    • 0031036704 scopus 로고    scopus 로고
    • HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues: a review of their pharmacology and clinical potential in the treatment of viral infections
    • Naesens L., Snoeck R., Andrei G., Balzarini J., Neyts J., and De Clercq E. HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues: a review of their pharmacology and clinical potential in the treatment of viral infections. Antivir Chem Chemother 8 (1997) 1-23
    • (1997) Antivir Chem Chemother , vol.8 , pp. 1-23
    • Naesens, L.1    Snoeck, R.2    Andrei, G.3    Balzarini, J.4    Neyts, J.5    De Clercq, E.6
  • 20
    • 0033909539 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of nucleoside analogues: focus on haematological malignancies
    • Johnson S.A. Clinical pharmacokinetics of nucleoside analogues: focus on haematological malignancies. Clin Pharmacokinet 39 (2000) 5-26
    • (2000) Clin Pharmacokinet , vol.39 , pp. 5-26
    • Johnson, S.A.1
  • 21
    • 21844466446 scopus 로고    scopus 로고
    • Pharmacology of 5-aza-2′-deoxycytidine (decitabine)
    • Momparler R.L. Pharmacology of 5-aza-2′-deoxycytidine (decitabine). Semin Hematol 42 (2005) S9-S16
    • (2005) Semin Hematol , vol.42
    • Momparler, R.L.1
  • 22
    • 0031020664 scopus 로고    scopus 로고
    • Effect of incorporation of cidofovir into DNA by human cytomegalovirus DNA polymerase on DNA elongation
    • Xiong X., Smith J.L., and Chen M.S. Effect of incorporation of cidofovir into DNA by human cytomegalovirus DNA polymerase on DNA elongation. Antimicrob Agents Chemother 41 (1997) 594-599
    • (1997) Antimicrob Agents Chemother , vol.41 , pp. 594-599
    • Xiong, X.1    Smith, J.L.2    Chen, M.S.3
  • 23
    • 23044457366 scopus 로고    scopus 로고
    • Mechanism of inhibition of vaccinia virus DNA polymerase by cidofovir diphosphate
    • Magee W.C., Hostetler K.Y., and Evans D.H. Mechanism of inhibition of vaccinia virus DNA polymerase by cidofovir diphosphate. Antimicrob Agents Chemother 49 (2005) 3153-3162
    • (2005) Antimicrob Agents Chemother , vol.49 , pp. 3153-3162
    • Magee, W.C.1    Hostetler, K.Y.2    Evans, D.H.3
  • 24
    • 38649102173 scopus 로고    scopus 로고
    • Cidofovir and (S)-9-[3-hydroxy-(2-phosphonomethoxy)propyl]adenine are highly effective inhibitors of vaccinia virus DNA polymerase when incorporated into the template strand
    • Magee W.C., Aldern K.A., Hostetler K.Y., and Evans D.H. Cidofovir and (S)-9-[3-hydroxy-(2-phosphonomethoxy)propyl]adenine are highly effective inhibitors of vaccinia virus DNA polymerase when incorporated into the template strand. Antimicrob Agents Chemother 52 (2008) 586-597
    • (2008) Antimicrob Agents Chemother , vol.52 , pp. 586-597
    • Magee, W.C.1    Aldern, K.A.2    Hostetler, K.Y.3    Evans, D.H.4
  • 25
    • 38749144011 scopus 로고    scopus 로고
    • Alpha anomer of 5-aza-2′-deoxycytidine down-regulates hTERT mRNA expression in human leukemia HL-60 cells
    • Hájek M., Votruba I., Holý A., Krecmerová M., and Tloust'ová E. Alpha anomer of 5-aza-2′-deoxycytidine down-regulates hTERT mRNA expression in human leukemia HL-60 cells. Biochem Pharmacol 75 (2008) 965-972
    • (2008) Biochem Pharmacol , vol.75 , pp. 965-972
    • Hájek, M.1    Votruba, I.2    Holý, A.3    Krecmerová, M.4    Tloust'ová, E.5
  • 26
    • 0032997095 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir
    • Cundy K.C. Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir. Clin Pharmacokinet 36 (1999) 127-143
    • (1999) Clin Pharmacokinet , vol.36 , pp. 127-143
    • Cundy, K.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.