메뉴 건너뛰기




Volumn 29, Issue 2-3, 2004, Pages 153-166

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

Author keywords

Acyclovir; Cornea; Prodrug; Transporter

Indexed keywords

2 AMINOBICYCLO[2.2.1]HEPTANE 2 CARBOXYLIC ACID; ACICLOVIR; AMINO ACID TRANSPORTER; ANTIVIRUS AGENT; GAMMA GLUTAMATE ACICLOVIR; ORNITHINE; PRODRUG; TYROSINE ACICLOVIR; UNCLASSIFIED DRUG;

EID: 9344267216     PISSN: 02713683     EISSN: None     Source Type: Journal    
DOI: 10.1080/02713680490504614     Document Type: Conference Paper
Times cited : (42)

References (40)
  • 1
    • 0016430387 scopus 로고
    • Rationale for design of biologically reversible drug derivatives: Prodrugs
    • Sinkula AA, Yalkowsky SH. Rationale for design of biologically reversible drug derivatives: Prodrugs. J Pharm Sci. 1975;64:181-210.
    • (1975) J Pharm Sci , vol.64 , pp. 181-210
    • Sinkula, A.A.1    Yalkowsky, S.H.2
  • 2
    • 0021800252 scopus 로고
    • Prodrugs. Do they have advantages in clinical practice?
    • Stella VJ, Charman WN, Naringrekar VH. Prodrugs. Do they have advantages in clinical practice? Drugs. 1985;29:455-473.
    • (1985) Drugs , vol.29 , pp. 455-473
    • Stella, V.J.1    Charman, W.N.2    Naringrekar, V.H.3
  • 3
    • 0025046860 scopus 로고
    • Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2
    • Dantzig AH, Bergin L. Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2. Biochim Biophys Acta. 1990;1027:211-217.
    • (1990) Biochim Biophys Acta , vol.1027 , pp. 211-217
    • Dantzig, A.H.1    Bergin, L.2
  • 4
    • 0026769788 scopus 로고
    • Transepithelial transport of oral cephalosporins by monolayers of intestinal epithelial cell line Caco-2: Specific transport systems in apical and basolateral membranes
    • Inui K, Yamamoto M, Saito H. Transepithelial transport of oral cephalosporins by monolayers of intestinal epithelial cell line Caco-2: Specific transport systems in apical and basolateral membranes. J Pharmacol Exp Ther. 1992;261:195-201.
    • (1992) J Pharmacol Exp Ther , vol.261 , pp. 195-201
    • Inui, K.1    Yamamoto, M.2    Saito, H.3
  • 5
    • 0028020775 scopus 로고
    • Renin inhibitor: Transport mechanism in rat small intestinal brush-border membrane vesicles
    • Hashimoto N, Fujioka T, Toyoda T, Muranushi N, Hirano K. Renin inhibitor: Transport mechanism in rat small intestinal brush-border membrane vesicles. Pharm Res. 1994;11:1448-1451.
    • (1994) Pharm Res , vol.11 , pp. 1448-1451
    • Hashimoto, N.1    Fujioka, T.2    Toyoda, T.3    Muranushi, N.4    Hirano, K.5
  • 6
    • 0031662109 scopus 로고    scopus 로고
    • 5′-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter
    • Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL. 5′-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998;15:1154-1159.
    • (1998) Pharm Res , vol.15 , pp. 1154-1159
    • Han, H.1    De Vrueh, R.L.2    Rhie, J.K.3    Covitz, K.M.4    Smith, P.L.5    Lee, C.P.6    Oh, D.M.7    Sadee, W.8    Amidon, G.L.9
  • 7
    • 0034533226 scopus 로고    scopus 로고
    • Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain
    • Kiss A, Farah K, Kim J, Garriock RJ, Drysdale TA, Hammond JR. Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain. Biochem J. 2000;352(Pt 2):363-372.
    • (2000) Biochem J , vol.352 , Issue.PART 2 , pp. 363-372
    • Kiss, A.1    Farah, K.2    Kim, J.3    Garriock, R.J.4    Drysdale, T.A.5    Hammond, J.R.6
  • 8
    • 0025095302 scopus 로고
    • Role of amino acid transport and countertransport in nutrition and metabolism
    • Christensen HN. Role of amino acid transport and countertransport in nutrition and metabolism. Physiol Rev. 1990;70:43-77.
    • (1990) Physiol Rev , vol.70 , pp. 43-77
    • Christensen, H.N.1
  • 9
    • 0000284020 scopus 로고
    • Blood-brain barrier amino acid transport
    • W. M. Pardridge, editor. Cambridge: Cambridge University Press
    • Smith QR, Stoll J. Blood-brain barrier amino acid transport. In: Introduction to the Blood-Brain Barrier. W. M. Pardridge, editor. Cambridge: Cambridge University Press; 1988:188-197.
    • (1988) Introduction to the Blood-Brain Barrier , pp. 188-197
    • Smith, Q.R.1    Stoll, J.2
  • 10
    • 0029552114 scopus 로고
    • Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney
    • Saito H, Okuda M, Terada T, Sasaki S, Inui K. Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995;275:1631-1637.
    • (1995) J Pharmacol Exp Ther , vol.275 , pp. 1631-1637
    • Saito, H.1    Okuda, M.2    Terada, T.3    Sasaki, S.4    Inui, K.5
  • 11
    • 0029782485 scopus 로고    scopus 로고
    • Carrier-mediated intestinal transport of drugs
    • Tsuji A, Tamai I. Carrier-mediated intestinal transport of drugs. Pharm Res. 1996;13:963-977.
    • (1996) Pharm Res , vol.13 , pp. 963-977
    • Tsuji, A.1    Tamai, I.2
  • 12
    • 0033254582 scopus 로고    scopus 로고
    • Drug transport and targeting. Intestinal transport
    • Oh DM, Han HK, Amidon GL. Drug transport and targeting. Intestinal transport. Pharm Biotechnol. 1999;12:59-88.
    • (1999) Pharm Biotechnol , vol.12 , pp. 59-88
    • Oh, D.M.1    Han, H.K.2    Amidon, G.L.3
  • 13
    • 0033801280 scopus 로고    scopus 로고
    • Membrane transporters
    • Lee VH. Membrane transporters. Eur J Pharm Sci. 2000;11(Suppl 2):S41-50.
    • (2000) Eur J Pharm Sci , vol.11 , Issue.SUPPL. 2
    • Lee, V.H.1
  • 14
    • 0033756459 scopus 로고    scopus 로고
    • Transporter-mediated permeation of drugs across the blood-brain barrier
    • Tamai I, Tsuji A. Transporter-mediated permeation of drugs across the blood-brain barrier. J Pharm Sci. 2000;89:1371-1388.
    • (2000) J Pharm Sci , vol.89 , pp. 1371-1388
    • Tamai, I.1    Tsuji, A.2
  • 16
    • 0036678569 scopus 로고    scopus 로고
    • Current prodrug strategies via membrane transporters/receptors
    • Anand BS, Dey S, Mitra AK. Current prodrug strategies via membrane transporters/receptors. Expert Opin Biol Ther. 2002;2:607-620.
    • (2002) Expert Opin Biol Ther , vol.2 , pp. 607-620
    • Anand, B.S.1    Dey, S.2    Mitra, A.K.3
  • 17
    • 0037319376 scopus 로고    scopus 로고
    • Transporters/receptors in the anterior chamber: Pathways to explore ocular drug delivery strategies
    • Dey S, Anand BS, Patel J, Mitra AK. Transporters/receptors in the anterior chamber: pathways to explore ocular drug delivery strategies. Exp Opin Biol Ther. 2003;3:23-44.
    • (2003) Exp Opin Biol Ther , vol.3 , pp. 23-44
    • Dey, S.1    Anand, B.S.2    Patel, J.3    Mitra, A.K.4
  • 18
    • 0036689265 scopus 로고    scopus 로고
    • Mechanism of corneal permeation of L-valyl ester of acyclovir: Targeting the oligopeptide transporter on the rabbit cornea
    • Anand BS, Mitra AK. Mechanism of corneal permeation of L-valyl ester of acyclovir: targeting the oligopeptide transporter on the rabbit cornea. Pharm Res. 2002;19:1194-1202.
    • (2002) Pharm Res , vol.19 , pp. 1194-1202
    • Anand, B.S.1    Mitra, A.K.2
  • 19
    • 0038577060 scopus 로고    scopus 로고
    • Identification and functional characterization of a Na+ independent large neutral amino acid transporter LAT1 on rabbit cornea
    • Jain-Vakkalagadda B, Dey S, Pal D, Mitra AK. Identification and functional characterization of a Na+ independent large neutral amino acid transporter LAT1 on rabbit cornea. Inv Ophthalmol Vis Sci. 2003;44:2919-2927.
    • (2003) Inv Ophthalmol Vis Sci , vol.44 , pp. 2919-2927
    • Jain-Vakkalagadda, B.1    Dey, S.2    Pal, D.3    Mitra, A.K.4
  • 21
    • 0035525669 scopus 로고    scopus 로고
    • Differential expression of Na:K:2Cl cotransporter, glucose transporter 1, and aquaporin 1 in freshly isolated and cultured bovine corneal tissues
    • Bildin VN, Iserovich P, Fischbarg J, Reinach PS. Differential expression of Na:K:2Cl cotransporter, glucose transporter 1, and aquaporin 1 in freshly isolated and cultured bovine corneal tissues. Exp Biol Med (Maywood). 2001;226:919-926.
    • (2001) Exp Biol Med (Maywood) , vol.226 , pp. 919-926
    • Bildin, V.N.1    Iserovich, P.2    Fischbarg, J.3    Reinach, P.S.4
  • 22
    • 0028889350 scopus 로고
    • Regulation of glucose transporter 1 (GLUT1) gene expression by epidermal growth factor in bovine corneal endothelial cells
    • Ishida K, Yamashita H, Katagiri H, Oka Y. Regulation of glucose transporter 1 (GLUT1) gene expression by epidermal growth factor in bovine corneal endothelial cells. Jpn J Ophthalmol. 1995;39:225-232.
    • (1995) Jpn J Ophthalmol , vol.39 , pp. 225-232
    • Ishida, K.1    Yamashita, H.2    Katagiri, H.3    Oka, Y.4
  • 23
    • 0030464606 scopus 로고    scopus 로고
    • Glucose transporter 1 expression is enhanced during corneal epithelial wound repair
    • Takahashi H, Kaminski AE, Zieske JD. Glucose transporter 1 expression is enhanced during corneal epithelial wound repair. Exp Eye Res. 1996;63:649-659.
    • (1996) Exp Eye Res , vol.63 , pp. 649-659
    • Takahashi, H.1    Kaminski, A.E.2    Zieske, J.D.3
  • 24
    • 0033772186 scopus 로고    scopus 로고
    • Glucose transporter 1 expression in corneal wound repair under high serum glucose level
    • Takahashi H, Ohara K, Ohmura T, Takahashi R, Zieske JD. Glucose transporter 1 expression in corneal wound repair under high serum glucose level. Jpn J Ophthalmol. 2000;44:470-474.
    • (2000) Jpn J Ophthalmol , vol.44 , pp. 470-474
    • Takahashi, H.1    Ohara, K.2    Ohmura, T.3    Takahashi, R.4    Zieske, J.D.5
  • 25
    • 0038300781 scopus 로고    scopus 로고
    • Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of Acyclovir and Idoxuridne
    • Majumdar S, Gunda S, Mitra AK. Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of Acyclovir and Idoxuridne. Curr Eye Res. 2003;26:175-183.
    • (2003) Curr Eye Res , vol.26 , pp. 175-183
    • Majumdar, S.1    Gunda, S.2    Mitra, A.K.3
  • 26
    • 55449102594 scopus 로고    scopus 로고
    • Functional differences in nucleoside and nucleobase transporters expressed on the rabbit corneal epithelial cell line (SIRC) and isolated rabbit cornea
    • Majumdar S, Tirucherai GS, Pal D, Mitra AK. Functional differences in nucleoside and nucleobase transporters expressed on the rabbit corneal epithelial cell line (SIRC) and isolated rabbit cornea. AAPS Pharm Sci. 2003;5:145-158.
    • (2003) AAPS Pharm Sci , vol.5 , pp. 145-158
    • Majumdar, S.1    Tirucherai, G.S.2    Pal, D.3    Mitra, A.K.4
  • 27
    • 0027768811 scopus 로고
    • Effect of acylation on the ocular disposition of acyclovir. I: Synthesis, physicochemical properties, and antiviral activity of 2′-esters
    • Hughes PM, Krishnamoorthy R, Mitra AK. Effect of acylation on the ocular disposition of acyclovir. I: Synthesis, physicochemical properties, and antiviral activity of 2′-esters. J Ocul Pharmacol. 1993;9:287-297.
    • (1993) J Ocul Pharmacol , vol.9 , pp. 287-297
    • Hughes, P.M.1    Krishnamoorthy, R.2    Mitra, A.K.3
  • 28
    • 0013298520 scopus 로고    scopus 로고
    • Novel dipeptide prodrugs of acyclovir for ocular herpes infections: Bioreversion, antiviral activity and transport across rabbit cornea
    • Anand BS, Nashed YE, Mitra AK. Novel dipeptide prodrugs of acyclovir for ocular herpes infections: Bioreversion, antiviral activity and transport across rabbit cornea. Curr Eye Res. 2003;26:151-163.
    • (2003) Curr Eye Res , vol.26 , pp. 151-163
    • Anand, B.S.1    Nashed, Y.E.2    Mitra, A.K.3
  • 29
    • 0038823800 scopus 로고    scopus 로고
    • In vivo antiviral efficacy of a dipeptide acyclovir prodrug, Val-Val-acyclovir against HSV-1 epithelial and stromal keratitis in the rabbit eye model
    • Anand BS, Hill JM, Dey S, Maruyama K, Bhattacharjee PS, Myles ME, Nashed YE, Mitra AK. In vivo antiviral efficacy of a dipeptide acyclovir prodrug, Val-Val-acyclovir against HSV-1 epithelial and stromal keratitis in the rabbit eye model. Inv Ophthalmol Vis Sci. 2003;44:2529-2534.
    • (2003) Inv Ophthalmol Vis Sci , vol.44 , pp. 2529-2534
    • Anand, B.S.1    Hill, J.M.2    Dey, S.3    Maruyama, K.4    Bhattacharjee, P.S.5    Myles, M.E.6    Nashed, Y.E.7    Mitra, A.K.8
  • 30
    • 0038017245 scopus 로고    scopus 로고
    • Synthesis and characterization of novel dipeptide ester prodrugs of acyclovir
    • Nashed YE, Mitra AK. Synthesis and characterization of novel dipeptide ester prodrugs of acyclovir. Spectrochim Acta A Mol Biomol Spectrosc. 2003;59:2033-2039.
    • (2003) Spectrochim Acta A Mol Biomol Spectrosc , vol.59 , pp. 2033-2039
    • Nashed, Y.E.1    Mitra, A.K.2
  • 31
    • 0034763155 scopus 로고    scopus 로고
    • Transport of acyclovir ester prodrugs through rabbit cornea and SIRC-rabbit corneal epithelial cell line
    • Tak RV, Pal D, Gao H, Dey S, Mitra AK. Transport of acyclovir ester prodrugs through rabbit cornea and SIRC-rabbit corneal epithelial cell line. J Pharm Sci. 2001;90:1505-1515.
    • (2001) J Pharm Sci , vol.90 , pp. 1505-1515
    • Tak, R.V.1    Pal, D.2    Gao, H.3    Dey, S.4    Mitra, A.K.5
  • 32
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (150) of an enzymatic reaction
    • Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (150) of an enzymatic reaction. Biochem Pharmacol. 1973;22:3099-3108.
    • (1973) Biochem Pharmacol , vol.22 , pp. 3099-3108
    • Cheng, Y.1    Prusoff, W.H.2
  • 33
    • 0033588179 scopus 로고    scopus 로고
    • Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+)
    • Sloan JL, Mager S. Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+). J Biol Chem. 1999;274:23740-23745.
    • (1999) J Biol Chem , vol.274 , pp. 23740-23745
    • Sloan, J.L.1    Mager, S.2
  • 34
    • 0031916983 scopus 로고    scopus 로고
    • Transporters for cationic amino acids in animal cells: Discovery, structure, and function
    • Deves R, Boyd CA. Transporters for cationic amino acids in animal cells: Discovery, structure, and function. Physiol Rev. 1998;78:487-545.
    • (1998) Physiol Rev , vol.78 , pp. 487-545
    • Deves, R.1    Boyd, C.A.2
  • 35
    • 0020317553 scopus 로고
    • Cationic amino acid transport into cultured animal cells. I. Influx into cultured human fibroblasts
    • White MF, Gazzola GC, Christensen HN. Cationic amino acid transport into cultured animal cells. I. Influx into cultured human fibroblasts. J Biol Chem. 1982;257:4443-4449.
    • (1982) J Biol Chem , vol.257 , pp. 4443-4449
    • White, M.F.1    Gazzola, G.C.2    Christensen, H.N.3
  • 36
    • 0014690238 scopus 로고
    • Cationic amino acid transport in the rabbit reticulocyte. Na+-dependent inhibition of Na+-independent transport
    • Christensen HN, Antonioli JA. Cationic amino acid transport in the rabbit reticulocyte. Na+-dependent inhibition of Na+-independent transport. J Biol Chem. 1969;244:1497-1504.
    • (1969) J Biol Chem , vol.244 , pp. 1497-1504
    • Christensen, H.N.1    Antonioli, J.A.2
  • 37
    • 0022386480 scopus 로고
    • Na+-dependent transport of basic, zwitterionic, and bicyclic amino acids by a broad-scope system in mouse blastocysts
    • Van Winkle LJ, Christensen HN, Campione AL. Na+-dependent transport of basic, zwitterionic, and bicyclic amino acids by a broad-scope system in mouse blastocysts. J Biol Chem. 1985;260:12118-12123.
    • (1985) J Biol Chem , vol.260 , pp. 12118-12123
    • Van Winkle, L.J.1    Christensen, H.N.2    Campione, A.L.3
  • 38
    • 0023850572 scopus 로고
    • Na+-independent transport of basic and zwitterionic amino acids in mouse blastocysts by a shared system and by processes which distinguish between these substrates
    • Van Winkle LJ, Campione AL, German JM. Na+-independent transport of basic and zwitterionic amino acids in mouse blastocysts by a shared system and by processes which distinguish between these substrates. J Biol Chem. 1988;263:3150-3163.
    • (1988) J Biol Chem , vol.263 , pp. 3150-3163
    • Van Winkle, L.J.1    Campione, A.L.2    German, J.M.3
  • 39
    • 0026699334 scopus 로고
    • Identification of a new transport system (y + L) in human erythrocytes that recognizes lysine and leucine with high affinity
    • Deves R, Chavez P, Boyd CA. Identification of a new transport system (y + L) in human erythrocytes that recognizes lysine and leucine with high affinity. J Physiol. 1992;454:491-501.
    • (1992) J Physiol , vol.454 , pp. 491-501
    • Deves, R.1    Chavez, P.2    Boyd, C.A.3
  • 40
    • 0035210660 scopus 로고    scopus 로고
    • Heterodimeric amino acid transporters: Molecular biology and pathological and pharmacological relevance
    • Kanai Y, Endou H. Heterodimeric amino acid transporters: Molecular biology and pathological and pharmacological relevance. Curr Drug Metab. 2001;2:339-354.
    • (2001) Curr Drug Metab , vol.2 , pp. 339-354
    • Kanai, Y.1    Endou, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.