Dipeptide monoester ganciclovir prodrugs for transscleral drug delivery: Targeting the oligopeptide transporter on rabbit retina

Journal of Ocular Pharmacology and Therapeutics

Volumn 23, Issue 4, 2007, Pages 321-334

  Kansara, Viral ^a   Hao, Y I ^a   Mitra, Ashim K ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; CAPTOPRIL; CEFALEXIN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENALAPRIL; GANCICLOVIR DERIVATIVE; GLYCYLSARCOSINE; GLYCYLVALYLGANCICLOVIR; PRODRUG; TYROSYLVALYLGANCICLOVIR; UNCLASSIFIED DRUG; VALYLGANCICLOVIR; VALYLVALYLGANCICLOVIR; ANTIVIRUS AGENT; CARRIER PROTEIN; DIPEPTIDE; DRUG DERIVATIVE; GANCICLOVIR; OLIGOPEPTIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG TARGETING; ENZYME SPECIFICITY; ENZYME STABILITY; HYDROLYSIS; MALE; NONHUMAN; PH; PROTEIN TRANSPORT; RABBIT; RETINA; TEMPERATURE SENSITIVITY; ANIMAL; CHOROID; IN VITRO STUDY; METABOLISM; PIGMENT EPITHELIUM; SCLERA; STRUCTURE ACTIVITY RELATION; TRANSPORT AT THE CELLULAR LEVEL;

ANIMALS; ANTIVIRAL AGENTS; BIOLOGICAL TRANSPORT; CARRIER PROTEINS; CHOROID; DIPEPTIDES; DRUG DELIVERY SYSTEMS; GANCICLOVIR; MALE; OLIGOPEPTIDES; PIGMENT EPITHELIUM OF EYE; PRODRUGS; RABBITS; RETINA; SCLERA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35848953208     PISSN: 10807683     EISSN: None     Source Type: Journal    
DOI: 10.1089/jop.2006.0150     Document Type: Article

References (36)

1. Cunningham, E.T., Jr., and Margolis, T.P. Ocular manifestations of HIV infection. N. Engl. J. Med. 339:236-244, 1998.
2. Cheung, T.W., and Teich, S.A. Cytomegalovirus infection in patients with HIV infection. Mt. Sinai J. Med. 66:113-124, 1999.
3. Burd, E.M., Pulido, J.S., Puro, D.G., et al. Replication of human cytomegalovirus in human retinal glial cells. Invest. Ophthalmol. Vis. Sci. 37:1957-1966, 1996.
4. Whitley, R.J., Jacobson, M.A., Friedberg, D.N., et al. Guidelines for the treatment of cytomegalovirus diseases in patients with AIDS in the era of potent antiretroviral therapy: Recommendations of an international panel. International AIDS Society - USA. Arch. Intern. Med. 158:957-969, 1998.
5. Duvvuri, S., Majumdar, S., and Mitra, A.K. Drug delivery to the retina: Challenges and opportunities. Exp. Opin. Biol. Ther. 3:45-56, 2003.
6. Spector, S. A., McKinley, G.F., Lalezari, J.P., et al. Oral ganciclovir for the prevention of cytomegalovirus disease in persons with AIDS: Roche Cooperative Oral Ganciclovir Study Group. N. Engl. J. Med. 334:1491-1497, 1996.
7. Cundy, K.C., Lynch, G., Shaw, J.P., et al. Distribution and metabolism of intravitreal cidofovir and cyclic HPMPC in rabbits. Curr. Eye Res. 15:569-576, 1996.
8. Lopez-Cortes, L.F., Pastor-Ramos, M.T., Ruiz-Valderas, R., et al. Intravitreal pharmacokinetics and retinal concentrations of ganciclovir and foscarnet after intravitreal administration in rabbits. Invest. Ophthalmol. Vis. Sci. 42:1024-1028, 2001.
9. Baudouin, C., Chassain, C., Caujolle, C., et al. Treatment of cytomegalovirus retinitis in AIDS patients using intravitreal injections of highly concentrated ganciclovir. Ophthalmologica 210:329-335, 1996.
10. Stone, T.W., and Jaffe, G.J. Reversible bull's-eye maculopathy associated with intravitreal fomivirsen therapy for cytomegalovirus retinitis. Am. J. Ophthalmol. 130:242-243, 2000.
11. Sanborn, G.E., Anand, R., Torti, R.E., et al. Sustained-release ganciclovir therapy for treatment of cytomegalovirus retinitis: Use of an intravitreal device. Arch. Ophthalmol. 110:188-195, 1992.
12. Virata, S.R., and Kylstra, J.A. Delayed vitreous hemorrhage after placement of a ganciclovir implant for cytomegalovirus retinitis. Am. J. Ophthalmol. 124:557-558, 1997.
13. Guembel, H.O., Krieglsteiner, S., Rosenkranz, C., et al. Complications after implantation of intraocular devices in patients with cytomegalovirus retinitis. Graefe's Arch. Clin. Exp. Ophthalmol. 237:824-829, 1999.
14. Geroski, D.H., and Edelhauser, H.F. Transscleral drug delivery for posterior segment disease. Adv. Drug Deliv. Rev. 52:37-48, 2001.
15. Weijtens, O., van der Sluijs, F.A., Schoemaker, R.C., et al. Peribulbar corticosteroid injection: Vitreal and serum concentrations after dexamethasone disodium phosphate injection. Am. J. Ophthalmol. 123:358-363, 1997.
16. Weijtens, O., Feron, E.J., Schoemaker, R.C., et al. High concentration of dexamethasone in aqueous and vitreous after subconjunctival injection. Am. J. Ophthalmol. 128:192-197, 1999.
17. Ambati, J., Canakis, C.S., Miller, J.W., et al. Diffusion of high molecular weight compounds through sclera. Invest. Ophthalmol. Vis. Sci. 41:1181-1185, 2000.
18. Ambati, J., Gragoudas, E.S., Miller, J.W., et al. Transscleral delivery of bioactive protein to the choroid and retina. Invest. Ophthalmol. Vis. Sci. 41:1186-1191, 2000.
19. Majumdar, S., Duvvuri, S., and Mitra, A.K. Membrane transporter/receptor- targeted prodrug design: Strategies for human and veterinary drug development. Adv. Drug Deliv. Rev. 56:1437-1452, 2004.
20. Balimane, P.V., Tamai, I., Guo, A., et al. Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem. Biophys. Res. Commun. 250:246-251, 1998.
21. Majumdar, S., Nashed, Y.E., Patel, K., et al. 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, 2005.
22. Steingrimsdottir, H., Gruber, A., Palm, C., et al. Bioavailability of aciclovir after oral administration of aciclovir and its prodrug valaciclovir to patients with leukopenia after chemotherapy. Antimicrob. Agents Chemother. 44:207-209, 2000.
23. Brown, F., Banken, L., Saywell, K., et al. Pharmacokinetics of valganciclovir and ganciclovir following multiple oral dosages of valganciclovir in HIV- and CMV-seropositive volunteers. Clin. Pharmacokinet. 37:167-176, 1999.
24. Han, H., de Vrueh, R.L., Rhie, J.K., et al. 5′-amino acid esters of antiviral nucleosides, acyclovir and AZT, are absorbed by the intestinal PEPT1 peptide transporter. Pharm. Res. 15:1154-1159, 1998.
25. Yamashita, T., Shimada, S., Guo, W., et al. Cloning and functional expression of a brain peptide/histidine transporter. J. Biol. Chem. 272:10205-10211, 1997.
26. Majumdar, S., Macha, S., Nashed, Y., et al. Expresiion of peptide transporter on the rabbit retina: A strategy to improve retinal delivery of ganciclovir. Lett. Drug Des. Discov. 1:73-77, 2004.
27. Ocheltree, S.M., Keep, R.F., Shen, H., et al. Preliminary investigation into the expression of proton-coupled oligopeptide transporters in neural retina and retinal pigment epithelium (RPE): Lack of functional activity in RPE plasma membranes. Pharm Res. 20:1364-1372, 2003.
28. Atluri, H., Anand, B.S., Patel, J., et al. Mechanism of a model dipeptide transport across blood-ocular barriers following systemic administration. Exp. Eye Res. 78:815-522, 2004.
29. Kansara, V., and Mitra, A.K. Evaluation of an ex vivo model implication for carrier-mediated retinal drug delivery. Curr. Eye Res. 31:415-426, 2006.
30. Andrei, G., Snoeck, R., Schols, D., et al. Comparative activity of selected antiviral compounds against clinical isolates of human cytomegalovirus. Eur. J. Clin. Microbiol. Infect. Dis. 10:1026-1033, 1991.
31. Hamalainen, K.M., Kananen, K., Auriola, S., et al. Characterization of paracellular and aqueous penetration routes in cornea, conjunctiva, and sclera. Invest. Ophthalmol. Vis. Sci. 38:627-634, 1997.
32. Majumdar, S., Macha, S., Pal, D., et al. Mechanism of ganciclovir uptake by rabbit retina and human retinal pigmented epithelium cell line, ARPE-19. Curr. Eye Res. 29:127-136, 2004.
33. Atluri, H., and Mitra, A.K. Disposition of short-chain aliphatic alcohols in rabbit vitreous by ocular microdialysis. Exp. Eye Res. 76:315-320, 2003.
34. Kyte, J., and Doolittle, R.F. A simple method for displaying the hydropathic character of a protein. J. Mol. Biol. 157:105-132, 1982.
35. Lister, N., Bailey, P.D., Collier, I.D., et al. The influence of luminal pH on transport of neutral and charged dipeptides by rat small intestine, in vitro. Biochim. Biophys. Acta. 1324:245-250, 1997.
36. Cheruvu, N.P., and Kompella, U.B. Bovine and porcine transscleral solute transport: Influence of lipophilicity and the Choroid-Bruch's layer. Invest. Ophthalmol. Vis. Sci. 47:4513-4522, 2006.