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Phosphoramidate ProTides of 2'-C-methylguanosine as highly potent inhibitors of hepatitis C virus. Study of their in vitro and in vivo properties.
McGuigan C, Gilles A, Madela K, Aljarah M, Holl S, Jones S, Vernachio J, Hutchins J, Ames B, Bryant KD, Gorovits E, Ganguly B, Hunley D, Hall A, Kolykhalov A, Liu Y, Muhammad J, Raja N, Walters R, Wang J, Chamberlain S, Henson G. McGuigan C, et al. J Med Chem. 2010 Jul 8;53(13):4949-57. doi: 10.1021/jm1003792. J Med Chem. 2010. PMID: 20527890
Design, synthesis and evaluation of a novel double pro-drug: INX-08189. A new clinical candidate for hepatitis C virus.
McGuigan C, Madela K, Aljarah M, Gilles A, Brancale A, Zonta N, Chamberlain S, Vernachio J, Hutchins J, Hall A, Ames B, Gorovits E, Ganguly B, Kolykhalov A, Wang J, Muhammad J, Patti JM, Henson G. McGuigan C, et al. Bioorg Med Chem Lett. 2010 Aug 15;20(16):4850-4. doi: 10.1016/j.bmcl.2010.06.094. Epub 2010 Jun 20. Bioorg Med Chem Lett. 2010. PMID: 20637609
Phosphorodiamidates as a promising new phosphate prodrug motif for antiviral drug discovery: application to anti-HCV agents.
McGuigan C, Madela K, Aljarah M, Bourdin C, Arrica M, Barrett E, Jones S, Kolykhalov A, Bleiman B, Bryant KD, Ganguly B, Gorovits E, Henson G, Hunley D, Hutchins J, Muhammad J, Obikhod A, Patti J, Walters CR, Wang J, Vernachio J, Ramamurty CV, Battina SK, Chamberlain S. McGuigan C, et al. J Med Chem. 2011 Dec 22;54(24):8632-45. doi: 10.1021/jm2011673. Epub 2011 Nov 16. J Med Chem. 2011. PMID: 22039920
Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
McGuigan C, Bourdin C, Derudas M, Hamon N, Hinsinger K, Kandil S, Madela K, Meneghesso S, Pertusati F, Serpi M, Slusarczyk M, Chamberlain S, Kolykhalov A, Vernachio J, Vanpouille C, Introini A, Margolis L, Balzarini J. McGuigan C, et al. Eur J Med Chem. 2013;70:326-40. doi: 10.1016/j.ejmech.2013.09.047. Epub 2013 Oct 9. Eur J Med Chem. 2013. PMID: 24177359 Free PMC article.
INX-08189, a phosphoramidate prodrug of 6-O-methyl-2'-C-methyl guanosine, is a potent inhibitor of hepatitis C virus replication with excellent pharmacokinetic and pharmacodynamic properties.
Vernachio JH, Bleiman B, Bryant KD, Chamberlain S, Hunley D, Hutchins J, Ames B, Gorovits E, Ganguly B, Hall A, Kolykhalov A, Liu Y, Muhammad J, Raja N, Walters CR, Wang J, Williams K, Patti JM, Henson G, Madela K, Aljarah M, Gilles A, McGuigan C. Vernachio JH, et al. Among authors: mcguigan c. Antimicrob Agents Chemother. 2011 May;55(5):1843-51. doi: 10.1128/AAC.01335-10. Epub 2011 Feb 28. Antimicrob Agents Chemother. 2011. PMID: 21357300 Free PMC article.
Application of the phosphoramidate ProTide approach to 4'-azidouridine confers sub-micromolar potency versus hepatitis C virus on an inactive nucleoside.
Perrone P, Luoni GM, Kelleher MR, Daverio F, Angell A, Mulready S, Congiatu C, Rajyaguru S, Martin JA, Levêque V, Le Pogam S, Najera I, Klumpp K, Smith DB, McGuigan C. Perrone P, et al. Among authors: mcguigan c. J Med Chem. 2007 Apr 19;50(8):1840-9. doi: 10.1021/jm0613370. Epub 2007 Mar 17. J Med Chem. 2007. PMID: 17367121
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 JA, Lévêque V, Le Pogam S, Najera I, Klumpp K, Smith DB, McGuigan C. Perrone P, et al. Among authors: mcguigan c. J Med Chem. 2007 Nov 1;50(22):5463-70. doi: 10.1021/jm070362i. Epub 2007 Oct 3. J Med Chem. 2007. PMID: 17914786
347 results