Application of the phosphoramidate ProTide approach to the antiviral drug ribavirin

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 7, 2010, Pages 2748-2755

  Derudas, Marco ^a   Brancale, Andrea ^a   Naesens, Lieve ^b   Neyts, Johan ^b   Balzarini, Jan ^b   McGuigan, Christopher ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Carboxypeptidase Y; Human hint enzyme; ProTide; Ribavirin

Indexed keywords

PHOSPHORAMIDIC ACID DERIVATIVE; RIBAVIRIN DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

AMIDES; ANTIVIRAL AGENTS; CELL LINE; CYTOPATHOGENIC EFFECT, VIRAL; DRUG DELIVERY SYSTEMS; DRUG DESIGN; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NERVE TISSUE PROTEINS; PEPTIDES; PHOSPHORIC ACIDS; PRODRUGS; RIBAVIRIN; VIRUSES;

EID: 77950047417     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.02.015     Document Type: Article

References (30)

1. Sidwell R.W., Huffman J.H., Khare G.P., Allen L.B., Witkowski J.T., and Robins R.K. Science 177 (1972) 705
2. Snell N.J. Exp. Opin. Pharmacother. 2 (2001) 1317
3. Saracco G., Ciancio A., Olivero A., Smedile A., Roffi L., Croce G., Colletta C., Cariti G., Andreoni M., Biglino A., Calleri G., Maggi G., Tappero G.F., Orsi P.G., Terreni N., Macor A., Di Napoli A., Rinaldi E., Ciccone G., and Rizzetto M. Hepatology 34 (2001) 133
4. Graci J.D., and Cameron C.E. Virology 298 (2002) 175
5. Leyssen P., Balzarini J., De Clercq E., and Neyts J. J. Virol. 79 (2005) 1943
6. Leyssen P., De Clercq E., and Neyts J. Mol. Pharmacol. 69 (2006) 1461
7. Crotty S., Maag D., Arnold J.J., Zhong W., Lau J.Y.N., Hong Z., Andino R., and Cameron C.E. Nat. Med. 6 (2000) 1375
8. Eriksson B., Helgstrand E., Johansson N.G., Larsson A., Misiorny A., Noren J.O., Philipson L., Stenberg K., Stening G., Stridh S., and Öberg B. Antimicrob. Agents Chemother. 11 (1977) 946
9. Benarroch D., Egloff M.P., Mulard L., Guerreiro C., Romette J.L., and Canard B. J. Biol. Chem. 279 (2004) 35638
10. Crotty S., Cameron C.E., and Andino R. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 6895
11. Bergamini A., Bolacchi F., Cepparulo M., Demin F., Uccella I., Bongi ova nni B., Ombres D., Angelico F., Liuti A., Hurtova M., Francioso S., Carvelli C., Cerasari G., Angelico M., and Rocchi G. Clin. Exp. Immunol. 123 (2001) 459
12. Hultgren C., Milich D.R., Weiland O., and Sällberg M. J. Gen. Virol. 79 (1998) 2381
13. Willis R.C., Carson D.A., and Seegmiller J.E. Proc. Natl. Acad. Sci. U.S.A. 75 (1978) 3042
14. McGuigan C., Cahard D., Sheeka H.M., De Clercq E., and Balzarini J. Bioorg. Med. Chem. Lett. 6 (1996) 1183
15. McGuigan C., Cahard D., Sheeka H.M., De Clercq E., and Balzarini J. J. Med. Chem. 39 (1996) 1748
16. Harris S.A., McGuigan C., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Antiviral Chem. Chemother. 12 (2001) 293
17. McGuigan C., Harris S.A., Daluge S.M., Gudmundsson K.S., McLean E.W., Burnette T.C., Marr H., Hazen R., Condreay L.D., Johnson L., De Clercq E., and Balzarini J. J. Med. Chem. 48 (2005) 3504
18. Perrone P., Luoni G.M., Kelleher M.R., Daverio F., Angell A., Mulready S., Congiatu C., Rajyaguru S., Martin J.A., Levêque V., Le Pogam S., Najera I., Klumpp K., Smith D.B., and McGuigan C. J. Med. Chem. 50 (2007) 1840
19. McGuigan C., Derudas M., Bugert J.J., Andrei G., Snoeck R., and Balzarini J. Bioorg. Med. Chem. Lett. 18 (2008) 4364
20. Derudas M., Carta D., Brancale A., Vanpouille C., Lisco A., Margolis L., Balzarini J., and McGuigan C. J. Med. Chem. 52 (2009) 5520
21. Witkowski J.T., Robins R.K., Sidwell R.W., and Simon L.N. J. Med. Chem. 15 (1972) 1150
22. Uchiyama M., Aso Y., Noyori R., and Hayakawa Y. J. Org. Chem. 58 (1993) 373
23. Saboulard D., Naesens L., Cahard D., Salgado A., Pathirana R., Velazquez S., McGuigan C., De Clercq E., and Balzarini J. Mol. Pharmacol. 56 (1999) 693
24. Dang Q., Kasibhatla S.R., Reddy K.R., Jiang T., Reddy M.R., Potter S.C., Fujitaki J.M., van Poelje P.D., Huang J., Lipscomb W.N., and Erion M.D. J. Am. Chem. Soc. 129 (2007) 15491
25. Birkus G., Wang R., Liu X., Kutty N., MacArthur H., Cihlar T., Gibbs C., Swaminathan S., Lee W., and McDermott M. Antimicrob. Agents Chemother. 51 (2007) 543
26. Valente, R. Ph.D. Thesis, Cardiff University, 2009.
27. Brenner C. Biochemistry 41 (2002) 9003
28. Congiatu C., Brancale A., and McGuigan C. Nucleosides, Nucleotides Nucleic Acids 26 (2007) 1121
29. Vrolijk J.M., Kaul A., Hansen B.E., Lohmann V., Haagmans B.L., Schalm S.W., and Bartenschlager R. J. Virol. Methods 110 (2003) 201
30. Paeshuyse J., Coelmont L., Vliegen I., Van hemel J., Vandenkerckhove J., Peys E., Sas B., De Clercq E., and Neyts J. Biochem. Biophys. Res. Commun. 348 (2006) 139