Calculation procedures and HPLC method for analysis of the lipophilicity of acyclovir esters

References

• Bernstein DI, Bellamy AR, Hook III EW, et al. Epidemiology, clinical presentation, and antibody response to primary infection with herpes simplex virus type 1 and type 2 in young women. Clin Infect Dis 2013;56:344–51
   PubMed Web of Science ®Google Scholar
• Dzieciątkowski T, Rola A, Majewska A, et al. Drugs used in antiherpesviral therapy in humans. Adv Microbiol (in Polish) 2007;46:211–21
   Google Scholar
• Erlich KS. Management of herpes simplex and varicella-zoster virus infections. Western J Med 1997;166:211–15
   PubMedGoogle Scholar
• Janiec W. Pharmacodynamics: handbook for students of pharmacy (in Polish). PZWL Warszawa 2009;2:1193–4
   Google Scholar
• Fletcher C, Bean B. Evaluation of oral acyclovir therapy. Drug Intell Clin Pharm 1985;19:518–24
   PubMedGoogle Scholar
• Beutner KR. Valacyclovir: a revive of its antiviral activity, pharmacokinetics properties, and clinical efficacy. Antiviral Res 1995;28:281–90
   PubMed Web of Science ®Google Scholar
• Katragadda S, Jain R, Kwatra D, et al. Pharmacokinetics of amino acid ester prodrugs of acyclovir after oral administration: interaction with the transporters on Caco-2 cells. Int J Pharm 2008;362:93–101
   PubMed Web of Science ®Google Scholar
• Santos CR, Capela R, Pereira CS, et al. Structure–activity relationships for dipeptide prodrugs of acyclovir: implications for prodrug design. Eur J Med Chem 2009;44:2339–46
   PubMed Web of Science ®Google Scholar
• Talluri RS, Gaudana R, Hariharan S, et al. Disposition kinetics of a dipeptide ester prodrug of acyclovir and its metabolites following intravenous and oral administrations in rat. Clin Res Regul Aff 2009;26:65–72
   Google Scholar
• Talluri RS, Samanta SK, Gaudana R, Mitra AK. Synthesis, metabolism and cellular permeability of enzymatically stable dipeptide prodrugs of acyclovir. Int J Pharm 2008;361:118–24
   PubMed Web of Science ®Google Scholar
• Bundgaard H, Jensen E, Falch E. Water-soluble, solution-stable, and biolabile N-substituted (aminomethyl)benzoate ester prodrugs of acyclovir. Pharmaceut Res 1991;8:1087–93
   PubMed Web of Science ®Google Scholar
• Zacchigna M, Di Luca G, Maurich V, Boccù E. Synthesis, chemical and enzymatic stability of new poly(ethylene glycol)-acyclovir prodrugs. Farmaco 2002;57:207–14
   PubMedGoogle Scholar
• Stankova I, Dzimbova T, Shishko S. Synthesis and biological activity of amino acid esters of acyclovir. Adv Exp Med Biol 2007;611:169–70
   Web of Science ®Google Scholar
• Hristov G, Stankova I. Chemical stability of new acyclovir analogues with peptidomimetics. Sci Pharm 2011;79:259–64
   PubMedGoogle Scholar
• Shao Z, Park GB, Krishnamoorthy R, Mitra AK. The physicochemical properties, plasma enzymatic hydrolysis and nasal absorption of acyclovir and it’s 2′-ester prodrugs. Pharmaceut Res 1994;11:237–42
   PubMed Web of Science ®Google Scholar
• Gao H, Mitra AK. NMR spectral data for acyclovir prodrugs. Magn Reson Chem 1999;37:687–9
   Web of Science ®Google Scholar
• Gao H, Mitra AK. Synthesis of acyclovir, ganciclovir and their prodrugs: a review. Synthesis 2000;3:329–51
   Google Scholar
• Bando H, Takagi T, Yamashita F, et al. Theoretical design of prodrug-enhancer combination based on a skin diffusion model: prediction of permeation of acyclovir prodrugs treated with 1-geranylazacycloheptan-2-one. Pharm Res 1996;19:427–32
   Web of Science ®Google Scholar
• De Regil-Hernández R, Martinez-Lagos F, Rodrigez-Bayón A, Sinisterra JV. New green synthesis and formulations of acyclovir prodrugs. Chem Pharm Bull 2011;59:1089–93
   PubMed Web of Science ®Google Scholar
• MnGuigan C, Derudas M, Bugert JJ, et al. Successful kinase bypass with new acyclovir phosphroamidate prodrugs. Bioorg Med Chem Lett 2008;18:4364–7
   PubMed Web of Science ®Google Scholar
• Haky JE, Young AM. Evaluation of a simple HPLC correlation method for the estimation of the octanol-water partition coefficients of organic compounds. J Liq Chromatogr 1984;7:675–89
   Web of Science ®Google Scholar
• Fei X, Zheng QH. Lipophilicity coefficients of [11C]MeHalo-CGS 27023A analogs determined by HPLC. J Liq Chromatogr Relat Technol 2005;28:939–45
   Web of Science ®Google Scholar
• OECD Guideline for Testing of Chemicals – Partition coefficient (n-octanol/water), High Performance Liquid Chromatography (HPLC) method. Draft Guideline 117, [Online: DOI:10.1787/9789264069824-en] 2004. Available from: http://www.oecd-library.org/content/book/9789264069824-en [last accessed 4 Nov 2013]
   Google Scholar
• Moffat AC, Osselton MD, Widdop B, Watts J. Clarke’s analysis of drugs and poisons. 4th ed. [Online] 2011. Available from: http://www.medicinescomplete.com/mc/clarke/current/d1e579315.htm [last accessed 4 Nov 2013]
   Google Scholar
• Hansch C, Leo A, Hoekman D. Exploring QSAR: hydrophobic, electronic, and steric constants. Washington, DC: American Chemical Society; 1995
   Google Scholar