메뉴 건너뛰기




Volumn 99, Issue 1, 2013, Pages 18-26

Synthesis and evaluation of a new phosphorylated ribavirin prodrug

Author keywords

Antiviral drug; Cellular uptake; Hepatitis C virus; Prodrug; Red blood cell; Ribavirin

Indexed keywords

ADENOSINE TRIPHOSPHATE; PRODRUG; RIBAVIRIN;

EID: 84878144500     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2013.04.014     Document Type: Article
Times cited : (10)

References (35)
  • 1
    • 77949656148 scopus 로고    scopus 로고
    • Ribavirin ante portas: uptake transporters into hepatocytes dissected
    • Bengsch, B., Thimme, R., 2010. Ribavirin ante portas: uptake transporters into hepatocytes dissected. J. Hepatol. 52, 469-471.
    • (2010) J. Hepatol. , vol.52 , pp. 469-471
    • Bengsch, B.1    Thimme, R.2
  • 2
    • 0034623816 scopus 로고    scopus 로고
    • Efficient initiation of HCV RNA replication in cell culture
    • Blight, K.J., Kolykhalov, A.A., Rice, C.M., 2000. Efficient initiation of HCV RNA replication in cell culture. Science 290, 1972-1974.
    • (2000) Science , vol.290 , pp. 1972-1974
    • Blight, K.J.1    Kolykhalov, A.A.2    Rice, C.M.3
  • 3
    • 0036182633 scopus 로고    scopus 로고
    • Ribavirin's antiviral mechanism of action: lethal mutagenesis
    • Crotty, S., Cameron, C., Andino, R., 2002. Ribavirin's antiviral mechanism of action: lethal mutagenesis? J. Mol. Med 80, 86-95.
    • (2002) J. Mol. Med , vol.80 , pp. 86-95
    • Crotty, S.1    Cameron, C.2    Andino, R.3
  • 4
    • 4544386821 scopus 로고    scopus 로고
    • Viramidine demonstrates better safety than ribavirin in monkeys but not rats
    • Dadgostari, S., Xu, C., Yeh, L.-T., Lin, C.C., Vitarella, D., 2004. Viramidine demonstrates better safety than ribavirin in monkeys but not rats. Drug. Chem. Toxicol. 27, 191-211.
    • (2004) Drug. Chem. Toxicol. , vol.27 , pp. 191-211
    • Dadgostari, S.1    Xu, C.2    Yeh, L.-T.3    Lin, C.C.4    Vitarella, D.5
  • 6
    • 0028794108 scopus 로고
    • An ion-pairing high-performance liquid chromatographic method for the direct simultaneous determination of nucleotides
    • deoxynucleotides, nicotinic coenzymes, oxypurines, nucleosides, and bases in perchloric acid cell extracts
    • Di Pierro, D., Tavazzi, B., Perno, C.F., Bartolini, M., Balestra, E., Calió, R., Giardina, B., Lazzarino, G., 1995. An ion-pairing high-performance liquid chromatographic method for the direct simultaneous determination of nucleotides, deoxynucleotides, nicotinic coenzymes, oxypurines, nucleosides, and bases in perchloric acid cell extracts. Anal. Biochem. 231, 407-412.
    • (1995) Anal. Biochem. , vol.231 , pp. 407-412
    • DiPierro, D.1    Tavazzi, B.2    Perno, C.F.3    Bartolini, M.4    Balestra, E.5    Calió, R.6    Giardina, B.7    Lazzarino, G.8
  • 7
    • 33646560284 scopus 로고    scopus 로고
    • The metabolism, pharmacokinetics and mechanisms of antiviral activity of ribavirin against hepatitis C virus
    • Dixit, N.M., Perelson, A.S., 2006. The metabolism, pharmacokinetics and mechanisms of antiviral activity of ribavirin against hepatitis C virus. Cell. Mol. Life Sci. 63, 832-842.
    • (2006) Cell. Mol. Life Sci. , vol.63 , pp. 832-842
    • Dixit, N.M.1    Perelson, A.S.2
  • 8
    • 84860311258 scopus 로고    scopus 로고
    • Is there a role for ribavirin in the era of hepatitis C virus direct-acting antivirals
    • Feld, J.J., 2012. Is there a role for ribavirin in the era of hepatitis C virus direct-acting antivirals? Gastroenterology 142, 1356-1359.
    • (2012) Gastroenterology , vol.142 , pp. 1356-1359
    • Feld, J.J.1
  • 9
    • 85030412539 scopus 로고    scopus 로고
    • A HTS system for screening antiviral compounds using the cell Titer® 96 aqueous one solution assay
    • Fletcher, T., Ptak, R., Bartram, S., Halliday, S., Buckheit, R., Moravec, R., Riss, T., 2000. A HTS system for screening antiviral compounds using the cell Titer® 96 aqueous one solution assay. Promega Notes 75, 13-16.
    • (2000) Promega Notes , vol.75 , pp. 13-16
    • Fletcher, T.1    Ptak, R.2    Bartram, S.3    Halliday, S.4    Buckheit, R.5    Moravec, R.6    Riss, T.7
  • 10
    • 77949657465 scopus 로고    scopus 로고
    • Characterization of ribavirin uptake systems in human hepatocytes
    • Fukuchi, Y., Furihata, T., Hashizume, M., Iikura, M., Chiba, K., 2010. Characterization of ribavirin uptake systems in human hepatocytes. J. Hepatol. 52, 486-492.
    • (2010) J. Hepatol. , vol.52 , pp. 486-492
    • Fukuchi, Y.1    Furihata, T.2    Hashizume, M.3    Iikura, M.4    Chiba, K.5
  • 11
    • 84888129361 scopus 로고    scopus 로고
    • Prodrugs of phosphonates, phosphinates, and phosphates
    • In: Stella, V.J., Borchardt, R.T., Hageman, M.J., Oliyai, R., Maag, H., Tilley, J.W. (Eds.), Prodrugs. Springer, New York, NY
    • He, G.-X., Krise, J.P., Oliyai, R., 2007. Prodrugs of phosphonates, phosphinates, and phosphates. In: Stella, V.J., Borchardt, R.T., Hageman, M.J., Oliyai, R., Maag, H., Tilley, J.W. (Eds.), Prodrugs. Springer, New York, NY, pp. 923-964.
    • (2007) , pp. 923-964
    • He, G.-X.1    Krise, J.P.2    Oliyai, R.3
  • 13
    • 0034973557 scopus 로고    scopus 로고
    • In vitro and in vivo activity of 1-O-hexadecylpropanediol-3-phosphoganciclovir and 1-O-hexadecylpropanediol-3-phospho-penciclovir in cytomegalovirus and herpes simplex virus infections
    • Hostetler, K.Y., Rybak, R.J., Beadle, J.R., Gardner, M.F., Aldern, K.A., Wright, K.N., Kern, E.R., 2001. In vitro and in vivo activity of 1-O-hexadecylpropanediol-3-phosphoganciclovir and 1-O-hexadecylpropanediol-3-phospho-penciclovir in cytomegalovirus and herpes simplex virus infections. Antivir. Chem. Chemother. 12, 61-70.
    • (2001) Antivir. Chem. Chemother. , vol.12 , pp. 61-70
    • Hostetler, K.Y.1    Rybak, R.J.2    Beadle, J.R.3    Gardner, M.F.4    Aldern, K.A.5    Wright, K.N.6    Kern, E.R.7
  • 14
    • 67349157073 scopus 로고    scopus 로고
    • Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: current state of the art
    • Hostetler, Karl Y., 2009. Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: current state of the art. Antiviral Res. 82, A84-98.
    • (2009) Antiviral Res. , vol.82
    • Hostetler Karl, Y.1
  • 15
    • 79952147366 scopus 로고    scopus 로고
    • Synthesis and early development of hexadecyloxypropylcidofovir: an oral antipoxvirus nucleoside phosphonate
    • Hostetler, Karl Y., 2010. Synthesis and early development of hexadecyloxypropylcidofovir: an oral antipoxvirus nucleoside phosphonate. Viruses 2, 2213- 2225.
    • (2010) Viruses , vol.2 , pp. 2213-2225
    • Hostetler Karl, Y.1
  • 16
    • 66149132168 scopus 로고    scopus 로고
    • Reduced ribavirin antiviral efficacy via nucleoside transporter-mediated drug resistance
    • Ibarra, K.D., Pfeiffer, J.K., 2009. Reduced ribavirin antiviral efficacy via nucleoside transporter-mediated drug resistance. J. Virol. 83, 4538-4547.
    • (2009) J. Virol. , vol.83 , pp. 4538-4547
    • Ibarra, K.D.1    Pfeiffer, J.K.2
  • 17
    • 84857172274 scopus 로고    scopus 로고
    • ENT1, a ribavirin transporter, plays a pivotal role in antiviral efficacy of ribavirin in a hepatitis C virus replication cell system
    • Iikura, M., Furihata, T., Mizuguchi, M., Nagai, M., Ikeda, M., Kato, N., Tsubota, A., Chiba, K., 2012. ENT1, a ribavirin transporter, plays a pivotal role in antiviral efficacy of ribavirin in a hepatitis C virus replication cell system. Antimicrob. Agents Chemother. 56, 1407-1413.
    • (2012) Antimicrob. Agents Chemother. , vol.56 , pp. 1407-1413
    • Iikura, M.1    Furihata, T.2    Mizuguchi, M.3    Nagai, M.4    Ikeda, M.5    Kato, N.6    Tsubota, A.7    Chiba, K.8
  • 18
    • 30744469345 scopus 로고    scopus 로고
    • Erythrocyte ribavirin concentration for assessing hemoglobin reduction in interferon and ribavirin combination therapy
    • Inoue, Y., Homma, M., Matsuzaki, Y., Shibata, M., Matsumura, T., Ito, T., Kohda, Y., 2006. Erythrocyte ribavirin concentration for assessing hemoglobin reduction in interferon and ribavirin combination therapy. Hepatol. Res. 34, 23-27.
    • (2006) Hepatol. Res. , vol.34 , pp. 23-27
    • Inoue, Y.1    Homma, M.2    Matsuzaki, Y.3    Shibata, M.4    Matsumura, T.5    Ito, T.6    Kohda, Y.7
  • 19
    • 0026663576 scopus 로고
    • Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication
    • Korba, B.E., Gerin, J.L., 1992. Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral Res. 19, 55-70.
    • (1992) Antiviral Res. , vol.19 , pp. 55-70
    • Korba, B.E.1    Gerin, J.L.2
  • 20
    • 84881546293 scopus 로고    scopus 로고
    • Methods of drug delivery to hepatocytes and treatment of flaviviridae infections [WWW Document]
    • (accessed 5.23.12)
    • Lau, J., Hong, Z., 2004. Methods of drug delivery to hepatocytes and treatment of flaviviridae infections [WWW Document]. http://patentscope.wipo.int/search/en/WO2002015904 (accessed 5.23.12).
    • (2004)
    • Lau, J.1    Hong, Z.2
  • 21
    • 0041736493 scopus 로고    scopus 로고
    • Viramidine, a prodrug of ribavirin, shows better liver-targeting properties and safety profiles than ribavirin in animals
    • Lin, C., Yeh, L.-T., Vitarella, D., Hong, Z., 2003a. Viramidine, a prodrug of ribavirin, shows better liver-targeting properties and safety profiles than ribavirin in animals. Antivir. Chem. Chemother. 14, 145-152.
    • (2003) Antivir. Chem. Chemother. , vol.14 , pp. 145-152
    • Lin, C.1    Yeh, L.-T.2    Vitarella, D.3    Hong, Z.4
  • 22
    • 0042675191 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of [14C]viramidine in rats and cynomolgus monkeys
    • Lin, C.-C., Luu, K., Lourenco, D., Yeh, L.-T., 2003b. Pharmacokinetics and metabolism of [14C]viramidine in rats and cynomolgus monkeys. Antimicrob. Agents Chemother. 47, 2458-2463.
    • (2003) Antimicrob. Agents Chemother. , vol.47 , pp. 2458-2463
    • Lin, C.-C.1    Luu, K.2    Lourenco, D.3    Yeh, L.-T.4
  • 23
    • 65549117967 scopus 로고    scopus 로고
    • The mouse model for influenza
    • In: Coico, R., Kowalik, T., Quarles, J., Stevenson, B., Taylor, R. (Eds.), Current Protocols in Microbiology. John Wiley and Sons, Inc., Hoboken, NJ, USA
    • Matsuoka, Y., Lamirande, E.W., Subbarao, K., 2009. The mouse model for influenza. In: Coico, R., Kowalik, T., Quarles, J., Stevenson, B., Taylor, R. (Eds.), Current Protocols in Microbiology. John Wiley & Sons, Inc., Hoboken, NJ, USA.
    • (2009)
    • Matsuoka, Y.1    Lamirande, E.W.2    Subbarao, K.3
  • 24
    • 11844269964 scopus 로고    scopus 로고
    • Enhancement of antiviral activity against hepatitis C virus in vitro by interferon combination therapy
    • Okuse, C., Rinaudo, J.A., Farrar, K., Wells, F., Korba, Brent.E., 2005. Enhancement of antiviral activity against hepatitis C virus in vitro by interferon combination therapy. Antiviral Res. 65, 23-34.
    • (2005) Antiviral Res. , vol.65 , pp. 23-34
    • Okuse, C.1    Rinaudo, J.A.2    Farrar, K.3    Wells, F.4    Korba Brent, E.5
  • 25
    • 82955163230 scopus 로고    scopus 로고
    • Ribavirin for the treatment of chronic hepatitis C virus infection: a review of the proposed mechanisms of action
    • Paeshuyse, J., Dallmeier, K., Neyts, J., 2011. Ribavirin for the treatment of chronic hepatitis C virus infection: a review of the proposed mechanisms of action. Curr. Opin. Virol. 1, 590-598.
    • (2011) Curr. Opin. Virol. , vol.1 , pp. 590-598
    • Paeshuyse, J.1    Dallmeier, K.2    Neyts, J.3
  • 26
    • 0025236704 scopus 로고
    • The metabolism of ribavirin in erythrocytes and nucleated cells
    • Page, T., Connor, J.D., 1990. The metabolism of ribavirin in erythrocytes and nucleated cells. Int. J. Biochem. 22, 379-383.
    • (1990) Int. J. Biochem. , vol.22 , pp. 379-383
    • Page, T.1    Connor, J.D.2
  • 27
    • 11844282166 scopus 로고    scopus 로고
    • Metabolism and antiviral activity of ribavirin
    • Parker, W.B., 2005. Metabolism and antiviral activity of ribavirin. Virus Res. 107, 165-171.
    • (2005) Virus Res. , vol.107 , pp. 165-171
    • Parker, W.B.1
  • 28
    • 77953416889 scopus 로고    scopus 로고
    • New direct-acting antivirals in the development for hepatitis C virus infection
    • Pockros, P.J., 2010. New direct-acting antivirals in the development for hepatitis C virus infection. Therap. Adv. Gastroenterol. 3, 191-202.
    • (2010) Therap. Adv. Gastroenterol. , vol.3 , pp. 191-202
    • Pockros, P.J.1
  • 29
    • 0037422607 scopus 로고    scopus 로고
    • Clearance of replicating hepatitis C virus replicon RNAs in cell culture by small interfering RNAs
    • Randall, G., Grakoui, A., Rice, Charles M., 2003. Clearance of replicating hepatitis C virus replicon RNAs in cell culture by small interfering RNAs. PNAS 100, 235-240.
    • (2003) PNAS , vol.100 , pp. 235-240
    • Randall, G.1    Grakoui, A.2    Rice Charles, M.3
  • 30
    • 33750571888 scopus 로고    scopus 로고
    • Ribavirin-induced anemia: mechanisms, risk factors and related targets for future research
    • Russmann, S., Grattagliano, I., Portincasa, P., Palmieri, V.O., Palasciano, G., 2006. Ribavirin-induced anemia: mechanisms, risk factors and related targets for future research. Curr. Med. Chem. 13, 3351-3357.
    • (2006) Curr. Med. Chem. , vol.13 , pp. 3351-3357
    • Russmann, S.1    Grattagliano, I.2    Portincasa, P.3    Palmieri, V.O.4    Palasciano, G.5
  • 31
    • 0026594620 scopus 로고
    • Release of choline by phospholipase D and a related phosphoric diester hydrolase in human erythrocytes
    • Selle, H., Chapman, B.E., Kuchel, P.W., 1992. Release of choline by phospholipase D and a related phosphoric diester hydrolase in human erythrocytes. 1H spin-echo n.m.r. studies. Biochem. J. 284 (Pt. 1), 61-65.
    • (1992) 1H spin-echo n.m.r. studies. Biochem. J. , vol.284 , Issue.1 PT , pp. 61-65
    • Selle, H.1    Chapman, B.E.2    Kuchel, P.W.3
  • 32
    • 59149106172 scopus 로고    scopus 로고
    • What future for ribavirin
    • Shiffman, M.L., 2009. What future for ribavirin? Liver Int. 29 (Suppl. 1), 68-73.
    • (2009) Liver Int. , vol.29 SUPPL , Issue.1 , pp. 68-73
    • Shiffman, M.L.1
  • 33
    • 0015523596 scopus 로고
    • Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide
    • Sidwell, R.W., Huffman, J.H., Khare, G.P., Allen, L.B., Witkowski, J.T., Robins, R.K., 1972. Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science 177, 705-706.
    • (1972) Science , vol.177 , pp. 705-706
    • Sidwell, R.W.1    Huffman, J.H.2    Khare, G.P.3    Allen, L.B.4    Witkowski, J.T.5    Robins, R.K.6
  • 35
    • 19444363846 scopus 로고    scopus 로고
    • A sensitive and specific method for the determination of total ribavirin in monkey liver by high-performance liquid chromatography with tandem mass spectrometry
    • Yeh, L.-T., Nguyen, M., Lourenco, D., Lin, C.-C., 2005. A sensitive and specific method for the determination of total ribavirin in monkey liver by high-performance liquid chromatography with tandem mass spectrometry. J. Pharm. Biomed. Anal. 38, 34-40.
    • (2005) J. Pharm. Biomed. Anal. , vol.38 , pp. 34-40
    • Yeh, L.-T.1    Nguyen, M.2    Lourenco, D.3    Lin, C.-C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.