Transcorneal permeation of l- and d-aspartate ester prodrugs of acyclovir: Delineation of passive diffusion versus transporter involvement

Pharmaceutical Research

Volumn 26, Issue 5, 2009, Pages 1261-1269

  Majumdar, Soumyajit ^a,b   Hingorani, Tushar ^a   Srirangam, Ramesh ^a   Gadepalli, Rama Sarma ^c   Rimoldi, John M ^b,c   Repka, Michael A ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Amino acid transporter; Asp ACV; Cornea; Permeability; Prodrug

Indexed keywords

ACICLOVIR; AMINO ACID TRANSPORTER; ASPARTIC ACID; ASPARTIC ACID ACICLOVIR; DEXTRO ASPARTIC ACID; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; DRUG DIFFUSION; DRUG SOLUBILITY; DRUG STABILITY; NONHUMAN; PKA; PRIORITY JOURNAL; RABBIT;

ACYCLOVIR; AMINO ACID TRANSPORT SYSTEMS; ANIMALS; ASPARTIC ACID; BIOLOGICAL TRANSPORT; CORNEA; DRUG STABILITY; ESTERS; PRODRUGS; RABBITS; SOLUBILITY;

EID: 63949087764     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9730-0     Document Type: Article

References (35)

1. I. P. Kaur R. Smitha 2002 Penetration enhancers and ocular bioadhesives: two new avenues for ophthalmic drug delivery Drug Dev. Ind. Pharm. 28 353 369
2. E. Mannermaa K. S. Vellonen A. Urtti 2006 Drug transport in corneal epithelium and blood-retina barrier: emerging role of transporters in ocular pharmacokinetics Adv. Drug Deliv. Rev. 58 1136 1163
3. D. A. Jabs 1998 Acyclovir for recurrent herpes simplex virus ocular disease N. Engl. J. Med. 339 340 341
4. S. Guess D. U. Stone J. Chodosh 2007 Evidence-based treatment of herpes simplex virus keratitis: a systematic review Ocul. Surf. 5 240 250
5. K. R. Wilhelmus 2000 The treatment of herpes simplex virus epithelial keratitis Trans. Am. Ophthalmol. Soc. 98 505 532
6. K. R. Wilhelmus. Therapeutic interventions for herpes simplex virus epithelial keratitis. Cochrane Database Syst. Rev. CD002898 (2007).
7. P. Chetoni S. Rossi S. Burgalassi D. Monti S. Mariotti M. F. Saettone 2004 Comparison of liposome-encapsulated acyclovir with acyclovir ointment: ocular pharmacokinetics in rabbits J Ocul Pharmacol Ther 20 169 177
8. S. Ghosh V. Jhanji E. Lamoureux H. R. Taylor R. B. Vajpayee 2008 Acyclovir therapy in prevention of recurrent herpetic keratitis following penetrating keratoplasty Am. J. Ophthalmol. 145 198 202
9. S. Majumdar Y. E. Nashed K. Patel R. Jain M. Itahashi D. M. Neumann J. M. Hill A. K. Mitra 2005 Dipeptide monoester ganciclovir prodrugs for treating HSV-1-induced corneal epithelial and stromal keratitis: in vitro and in vivo evaluations J. Ocul. Pharmacol. Ther. 21 463 474
10. S. Y. Lee 1998 Herpes simplex virus ocular infections Drugs Today (Barc) 34 241 249
11. A. Simmons 2002 Clinical manifestations and treatment considerations of herpes simplex virus infection J. Infect Dis. 186 Suppl 1 S71 S77
12. M. Fresta G. Fontana C. Bucolo G. Cavallaro G. Giammona G. Puglisi 2001 Ocular tolerability and in vivo bioavailability of poly(ethylene glycol) (PEG)-coated polyethyl-2-cyanoacrylate nanosphere-encapsulated acyclovir J. Pharm. Sci. 90 288 97
13. S. L. Law K. J. Huang C. H. Chiang 2000 Acyclovir-containing liposomes for potential ocular delivery. Corneal penetration and absorption J. Control Release 63 135 140
14. B. Wang W. Teng X. Han 2000 An experimental study of a new route for acyclovir administration for anti-keratitis therapeutic treatment Zhonghua Shi Yan He Lin Chuang Bing Du Xue Za Zhi 14 379 381
15. S. Majumdar K. Hippalgaonkar M. A. Repka 2008 Effect of chitosan, benzalkonium chloride and ethylenediaminetetraacetic acid on permeation of acyclovir across isolated rabbit cornea Int. J. Pharm. 348 175 178
16. S. Majumdar S. Duvvuri A. K. Mitra 2004 Membrane transporter/receptor- targeted prodrug design: strategies for human and veterinary drug development Adv. Drug Deliv. Rev. 56 1437 1452
17. M. Palacin R. Estevez J. Bertran A. Zorzano 1998 Molecular biology of mammalian plasma membrane amino acid transporters Physiol. Rev. 78 969 1054
18. B. Anand Y. Nashed A. Mitra 2003 Novel dipeptide prodrugs of acyclovir for ocular herpes infections: Bioreversion, antiviral activity and transport across rabbit cornea Curr Eye Res 26 151 163
19. B. S. Anand A. K. Mitra 2002 Mechanism of corneal permeation of l-valyl ester of acyclovir: targeting the oligopeptide transporter on the rabbit cornea Pharm. Res. 19 1194 1202
20. M. E. Ganapathy V. Ganapathy 2005 Amino acid transporter ATB0,+ as a delivery system for drugs and prodrugs Curr. Drug Targets Immune. Endocr. Metabol. Disord. 5 357 364
21. T. Hatanaka M. Haramura Y. J. Fei S. Miyauchi C. C. Bridges P. S. Ganapathy S. B. Smith V. Ganapathy M. E. Ganapathy 2004 Transport of amino acid-based prodrugs by the Na+- and Cl(-) -coupled amino acid transporter ATB0,+ and expression of the transporter in tissues amenable for drug delivery J. Pharmacol. Exp. Ther. 308 1138 1147
22. K. Patel S. Trivedi S. Luo X. Zhu D. Pal E. R. Kern A. K. Mitra 2005 Synthesis, physicochemical properties and antiviral activities of ester prodrugs of ganciclovir Int. J. Pharm. 305 75 89
23. C. Santos J. Morais L. Gouveia E. de Clercq C. Pannecouque C. U. Nielsen B. Steffansen R. Moreira P. Gomes 2008 Dipeptide derivatives of AZT: synthesis, chemical stability, activation in human plasma, hPEPT1 affinity, and antiviral activity ChemMedChem 3 970 978
24. B. S. Anand S. Katragadda Y. E. Nashed A. K. Mitra 2004 Amino acid prodrugs of acyclovir as possible antiviral agents against ocular HSV-1 infections: interactions with the neutral and cationic amino acid transporter on the corneal epithelium Curr. Eye Res. 29 153 166
25. L. M. Beauchamp G. F. Orr P. de Miranda T. Burnette T. A. Krenitsky 1992 Amino acid ester prodrugs of acyclovir Antivir. Chem. Chemother. 3 157 164
26. United States Pharmacopeial Commission. The United States Pharmacopoeia XXX, NF XXV, United States Pharmacopeial Commission, Inc., Rockville, MD, 2006, 806-807.
27. M. M. Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 248 254
28. B. Garre K. Shebany A. Gryspeerdt K. Baert K. van der Meulen H. Nauwynck P. Deprez P. De Backer S. Croubels 2007 Pharmacokinetics of acyclovir after intravenous infusion of acyclovir and after oral administration of acyclovir and its prodrug valacyclovir in healthy adult horses Antimicrob. Agents Chemother. 51 4308 4314
29. B. Jain-Vakkalagadda S. Dey D. Pal A. K. Mitra 2003 Identification and functional characterization of a Na+-independent large neutral amino acid transporter, LAT1, in human and rabbit cornea Invest. Ophthalmol. Vis. Sci. 44 2919 2927
30. B. Jain-Vakkalagadda D. Pal S. Gunda Y. Nashed V. Ganapathy A. K. Mitra 2004 Identification of a Na+-dependent cationic and neutral amino acid transporter, B(0,+), in human and rabbit cornea Mol. Pharm. 1 338 346
31. C. Yang H. Gao A. K. Mitra 2001 Chemical stability, enzymatic hydrolysis, and nasal uptake of amino acid ester prodrugs of acyclovir J. Pharm. Sci. 90 617 624
32. H. Bundgaard E. Jensen E. Falch 1991 Water-soluble, solution-stable, and biolabile N-substituted (aminomethyl)benzoate ester prodrugs of acyclovir Pharm. Res. 8 1087 1093
33. C. G. Jordan 1998 How an increase in the carbon chain length of the ester moiety affects the stability of a homologous series of oxprenolol esters in the presence of biological enzymes J. Pharm. Sci. 87 880 885
34. S. C. Chang V. H. Lee 1982 Influence of chain length on the in vitro hydrolysis of model ester prodrugs by ocular esterases Curr. Eye Res. 2 651 656
35. D. S. Chien H. Sasaki H. Bundgaard A. Buur V. H. Lee 1991 Role of enzymatic lability in the corneal and conjunctival penetration of timolol ester prodrugs in the pigmented rabbit Pharm. Res. 8 728 733