Involvement of multiple transporters in the oral absorption of nucleoside analogues

Advanced Drug Delivery Reviews

Volumn 39, Issue 1-3, 1999, Pages 183-209

  Balimane, Praveen V ^a   Sinko, Patrick J ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Carrier mediated transport; Cloning; Equilibrative transporters; HIV; Intestinal absorption; Nucleoside transporters; Prodrugs; Reverse transcriptase inhibitors

Indexed keywords

ABSORPTION; CLONING; DRUG INTERACTIONS; ENZYME INHIBITION; PHARMACOKINETICS; VIRUSES;

HUMAN IMMUNODEFICIENCY VIRUS (HIV);

CONTROLLED DRUG DELIVERY;

ABACAVIR; ACICLOVIR; CARRIER PROTEIN; DIDANOSINE; FAMCICLOVIR; GANCICLOVIR; LAMIVUDINE; NUCLEOSIDE ANALOG; PRODRUG; RIBAVIRIN; SODIUM ION; STAVUDINE; VALACICLOVIR; VIDARABINE; ZALCITABINE; ZIDOVUDINE;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; DIFFUSION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GASTROINTESTINAL TRACT; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; INTESTINE ABSORPTION; MOLECULAR CLONING; NONHUMAN; NUCLEOSIDE TRANSPORT; OPPORTUNISTIC INFECTION; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW; TISSUE DISTRIBUTION;

EID: 0032846316     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(99)00026-5     Document Type: Article

References (95)

1. Kolb V.M. Novel and unusual nucleosides as drugs. Prog. Drug Res. 48:1997;195-232.
2. Dolin R. Antiviral chemotherapy and chemoprophylaxis. Science. 227:1985;1296-1303.
3. Larder B.A., Kohli A., Bloor S., Kemp S.D., Harrigan P.R., Schooley R.T., Lange J.M., Pennington K., Clair M.H.S. Human immunodeficiency virus type I drug susceptibility during zidovudine (AZT) monotherapy compared with AZT plus 2′-3′-dideoxyinosine or AZT plus 2′-3′-dideoxycytidine combination therapy. J. Virol. 70:1996;5922-5929.
4. Yarchoan R., Mitsutya H., Meyers C.E., Broder S. Clinical pharmacology of 3′-azido-2′-3′-dideoxythymidine (zidovudine) and related dideoxynucleosides. N. Engl. J. Med. 11:1989;726-738.
5. Saven A., Piro L.D. The newer purine analogues. Cancer. 72:1993;3470-3483.
6. Tucker A.L., Linden J. Cloned receptors and cardiovascular responses to adenosine. Cardiovasc. Res. 27:1993;62-67.
7. Clercq E.D. HIV inhibitors targeted at the reverse transcriptase. AIDS Res. Hum. Retroviruses. 8:1992;119-134.
8. Belt J.A., Marina N.M., Phelps D.A., Crawford C.R. Nucleoside transport in normal and neoplastic cells. Adv. Enzyme Regul. 33:1993;235-252.
9. Plagemann P.G., Wohlhueter R. Permeation of nucleosides, nucleic acid bases and nucleotides in animal cells. Curr. Topics Membr. Transp. 14:1980;225-313.
10. +-independent nucleoside transporters in Xenopus laevis oocytes. Biochem. Pharmacol. 53:1997;1909-1918.
11. Wang J., Schaner M.E., Thomassen S., Su S.F., Piquette-Miller M., Giacomini K.M. Functional and molecular characteristics of Na(+)-dependent nucleoside transporters. Pharm. Res. 14:1997;1524-1532.
12. Huang Q.Q., Harvey C.M., Paterson A.R., Cass C.E., Young J.D. Functional expression of Na(+)-dependent nucleoside transport systems of rat intestine in isolated oocytes of Xenopus laevis. Demonstration that rat jejunum expresses the purine-selective system N1 (cif) and a second, novel system N3 having broad specificity for purine and pyrimidine nucleosides. J. Biol. Chem. 268:(cif):1993;20613-20619.
13. Williams T.C., Jarvis S.M. Multiple sodium-dependent nucleoside transport systems in bovine renal brush-border membrane vesicles. Biochem. J. 274:1991;27-33.
14. Vijayalakshmi D., Belt J.A. Sodium-dependent nucleoside transport in mouse intestinal epithelial cells. Two transport systems with differing substrate specificities. J. Biol. Chem. 263:1988;19419-19423.
15. Plagemann P.G., Wohlhueter R., Woffendin C. Nucleoside and nucleobase transport in animal cells. Biochim. Biophys. Acta. 947:1988;405-443.
16. Gutierrez M.M., Brett C.M., Ott R.J., Hui A.C., Giacomini K.M. Nucleoside transport in brush border membrane vesicles from human kidney. Biochim. Biophys. Acta. 1105:1992;1-9.
17. Wu X., Yuan G., Brett C.M., Hui A.C., Giacomini K.M. Sodium dependent nucleoside transport in choroid plexus from rabbit. J. Biol. Chem. 167:1992;8813-8818.
18. Patil S.D., Unadkat J.D. Sodium-dependent nucleoside transport in the human intestinal brush-border membrane. Am. J. Physiol. 272:1997;G1314-G1320.
19. Cass C.E. Nucleoside transport in drug transport. Antimicrobial and Anticancer Chemotherapy. 1995;403 Marcel Dekker, New York.
20. Plagemann P.G., Wohlhueter R. Nucleoside transport in cultured mammalian cells. Multiple forms with different sensitivity to inhibition by nitrobezylthioinosine or hypoxanthine. Biochim. Biophys. Acta. 773:1984;39-52.
21. Jarvis S.M., Young J.D. Nucleoside transport in rat erythrocytes: Two components with differences in sensitivity to inhibition by nitrobenzylthioinosine and p-chloromercuriphenyl sulfonate. J. Membr. Biol. 93:1986;1-10.
22. Lee C.W., Jarvis S.M. Nucleoside transport in rat cerebral-cortical synaptosomes. Evidence for two types of nucleoside transporters. Biochem. J. 249:1988;557-564.
23. Thorn J.A., Jarvis S.M. Adenosine transporters. Gen. Pharmacol. 27:1996;613-620.
24. Young J.D., Jarvis S.M. Nucleoside transport in mammalian cells. Biosci. Rep. 3:1983;309-322.
25. Jakobs E.S., Paterson A.R. Sodium-dependent, concentrative nucleoside transport in cultured intestinal epithelial cells. Biochem. Biophys. Res. Commun. 140:1986;1028-1035.
26. Brett C.M., Washington C.B., Ott R.J., Gutierrez M.M., Giacomini K.M. Interaction of nucleoside analogues with the sodium nucleoside - Nucleoside transport system in brush border membrane vesicles from human kidney. Pharm. Res. 10:1993;423-426.
27. Huang Q.Q., Yao S.Y., Ritzel M.W., Paterson A.R., Cass C.E., Young J.D. Cloning and functional expression of a complementary DNA encoding a mammalian nucleoside transporter protein. J. Biol. Chem. 269:1994;17757-17760.
28. + nucleoside transporter. J. Biol. Chem. 270:1995;13596-13599.
29. +-nucleoside cotransporter (hCNT1). Am. J. Physiol. 272:1997;C707-C714.
30. Wang J., Su S.F., Dresser M.J., Schaner M.E., Washington C.B., Giacomini K.M. Na(+)-dependent purine nucleoside transporter from human kidney: cloning and functional characterization. Am. J. Physiol. 273:1997;F1058-F1065.
31. Griffiths M., Beaumont N., Yao S.Y., Sundaram M., Boumah C.E., Davies A., Kwong F.Y., Coe I., Cass C.E., Young J.D., Baldwin S.A. Cloning of a human nucleoside transporter implicated in the cellular uptake of adenosine and chemotherapeutic drugs. Nat. Med. 3:1997;89-93.
32. Crawford C.R., Patel D.H., Naeve C., Belt J.A. Cloning of the human equilibrative, nitrobenzylmercaptopurine riboside (NBMPR)-insensitive nucleoside transporter ei by functional expression in a transport-deficient cell line. J. Biol. Chem. 273:1998;5288-5293.
33. Schaner M.E., Wang J., Zevin S., Gerstin K.M., Giacomini K.M. Transient expression of a purine-selective nucleoside transporter (SPNTint) in a human cell line (HeLa). Pharm. Res. 14:1997;1316-1321.
34. Yao S.Y., Cass C.E., Young J.D. Transport of the antiviral nucleoside analogs 3′-azido-3′-deoxythymidine and 2′,3′-dideoxycytidine by a recombinant nucleoside transporter (rCNT) expressed in Xenopus laevis oocytes. Mol. Pharmacol. 50:1996;388-393.
35. Anderson C.M., Xiong W., Young J.D., Cass C.E., Parkinson F.E. Demonstration of the existence of mRNAs encoding N1/cif and N2/cit sodium/nucleoside cotransporters in rat brain. Brain Res. Mol. Brain Res. 42:1996;358-361.
36. +-dependent, guanosine-specific, nitrobenzylthioinosine-sensitive transporter in acute promyelocytic leukemia cells. J. Biol. Chem. 272:1997;18026-18032.
37. Griffith D.A., Jarvis S.M. Nucleoside and nucleobase transport systems of mammalian cells. Biochim. Biophys. Acta. 1286:1996;153-181.
38. Sundaram M., Yao S.Y., Ng A.M., Griffiths M., Cass C.E., Baldwin S.A., Young J.D. Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs. J. Biol. Chem. 273:1998;21519-21525.
39. Griffiths M., Yao S.Y., Abidi F., Phillips S.E., Cass C.E., Young J.D., Baldwin S.A. Molecular cloning and characterization of a nitrobenzylthioinosine-insensitive (ei) equilibrative nucleoside transporter from human placenta. Biochem. J. 328:1997;739-743.
40. Williams J.B., Lanahan A.A. A mammalian delayed early response gene encodes HNP36, a novel, conserved nucleolar protein. Biochem. Biophys. Res. Commun. 213:1995;325-333.
41. Yao S.Y., Ng A.M., Muzyka W.R., Griffiths M., Cass C.E., Baldwin S.A., Young J.D. Molecular cloning and functional characterization of nitrobenzylthioinosine (NBMPR)-sensitive (es) and NBMPR-insensitive (ei) equilibrative nucleoside transporter proteins (rENT1 and rENT2) from rat tissues. J. Biol. Chem. 272:1997;28423-28430.
42. Creamer B. The turnover of the epithelium of the small intestine. Br. Med. Bull. 23:1967;226-230.
43. Zollner N. Purine and pyrimidine metabolism. Proc. Nutr. Soc. 41:1982;329-342.
44. Sonoda T., Tatibana M. Metabolic fate of pyrimidines and purines in dietary nucleic acids ingested by mice. Biochim. Biophys. Acta. 521:1978;55-56.
45. Jacobson M.A. Valaciclovir (BW256U87): the L-valyl ester of acyclovir. J. Med. Virol. Suppl. 1:1993;150-153.
46. Sinko P.J., Balimane P.V. Carrier-mediated intestinal absorption of valacyclovir, the L-valyl ester prodrug of acyclovir: 1. Interactions with peptides, organic anions and organic cations in rats. Biopharm. Drug Dispos. 19:1998;209-217.
47. Ganapathy M.E., Huang W., Wang H., Ganapathy V., Leibach F.H. Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem. Biophys. Res. Commun. 246:1998;470-475.
48. Balimane P.V., Tamai I., Guo A., Nakanishi T., Kitada H., Leibach F.H., Tsuji A., Sinko P.J. Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem. Biophys. Res. Commun. 250:1998;246-251.
49. Han H.-K., Vrueh R., Rhie J.K., Covitz K.-M., Smith P.L., Lee C.-P., Oh D.-M., Amidon G.L. 5′-Amino acid ester of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm. Res. 15:1998;1154-1159.
50. Han H.-K., Oh D.-M., Amidon G.L. Cellular uptake mechanism of amino acid ester prodrugs in Caco-2/hPEPT1 cells overexpressing a human peptide transporter. Pharm. Res. 15:1998;1382-1386.
51. Morse G.D., Shelton M.J., O'Donnell A.M. Comparative pharmacokinetic of antiviral nucleoside analogues. Clin. Pharmacokinet. 24:1993;101-123.
52. Lea A.P., Faulds D. Stavudine: A review of its pharmacodynamic and pharmacokinetic properties and clinical potential in HIV infection. Drugs. 51:1996;846-864.
53. Perry C.M., Faulds D. Lamivudine: A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in the management of HIV infection. Drugs. 53:1997;657-680.
54. Perry C.M., Faulds D. Valaciclovir. A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in herpesvirus infections. Drugs. 52:1996;754-772.
55. Foster R.H., Faulds D. Abacavir. Drugs. 55:1998;729-738.
56. Blum M.R., Liao S.H.T., Good S.S., deMiranda P. Pharmacokinetics and bioavailability of zidovudine in humans. Am. J. Med. 85:1988;189-194.
57. Gustavson L., Fukuda E.K., Rubio F.A., Dunton A.W. A pilot study of the bioavailability and pharmacokinetics of 2′-3′-dideoxycytidine in patients with AIDS or AIDS related complexes. J. Acquired Immune Defic. Syndr. 3:1990;28-31.
58. Hartman N.R., Yarchoan R., Pluda J.M., Thomas R.V., Marczyk K.S., Broder S., Johns D.G. Pharmacokinetics of 2′-3′-dideoxyadenosine and 2′-3′-dideoxyinosine in patients with severe HIV infection. Clin. Pharmacol. Ther. 47:1990;647-654.
59. Kaul S., Mummaneni V., Barbhaiya R.H. Dose proportionality of stavudine in HIV seropositive asymptomatic subjects: application to bioequivalence assessment of various capsule formulations. Biopharm. Drug Dispos. 16:1995;125-136.
60. VanLeeuwen R., Lange J.M., Hussey E.K., Donn K.H., Hall S.T., Harker A.J., Jonker P., Danner S.A. The safety and pharmacokinetics of a reverse transcriptase inhibitor, 3TC, in patients with HIV infection.: A phase I study. AIDS. 6:1992;1471-1475.
61. Pue M.A., Pratt S.K., Fairless A.J., Fowles S., Laroche J., Georgiou P., Prince W. Linear pharmacokinetics of penciclovir following administration of single oral doses of famciclovir 125, 250, 500 and 750 mg to healthy volunteers. J. Antimicrob. Chemother. 33:1994;119-127.
62. Hasegawa T., Juni K., Saneyoshi M., Kawaguchi T. Intestinal absorption and first-pass elimination of 2′,3′-dideoxynucleosides following oral administration in rats. Biol. Pharm. Bull. 19:1996;599-603.
63. Cline J.J., Garrett A.D. Combination antiviral therapy for cytomegalovirus disease in patients with AIDS. Ann. Pharmacother. 31:1997;1080-1082.
64. Solder B., Wintergerst U., Notheis G., Eberle J., Gurtler L., Belohradsky B.H. Effect of antiretroviral combination therapy (zidovudine/dianosine or zidovudine/lamivudine) on quantitative plasma human immunodeficiency virus-ribonucleic acid in children and adolescents with human immunodeficiency virus. J. Pediatr. 130:1997;293-299.
65. Englund J.A., Baker C.J., Raskino C., McKinney R.E., Petrie B., Fowler M.G., Pearson D., Gershon A., McSherry G.D., Abrams E.J., Schliozberg J., Sullivan J. Zidovudine, didanosine, or both as the initial treatment for symptomatic HIV-infected children. AIDS clinical trials group (ACTG) study 152 team. N. Engl. J. Med. 336:1997;1704-1712.
66. Hammer S.M., Katzenstein D.A., Hughes M.D., Gundacker H., Schooley R.T., Haubrich R.H., Henry W.K., Lederman M.M., Phair J.P., Niu M., Hirch M.S., Merigan T.C. A trial comparing nucleoside monotherapy with combination therapy in HIV-infected adults with CD4 cell counts from 200 to 500 per cubic millimeter. AIDS clinical trials group study 175 study team. N. Engl. J. Med. 335:1996;1081-1090.
67. Clumeck N. Current use of anti-HIV drugs in AIDS. J. Antimicrob. Chemother. 32:1993;133-138.
68. Mitsuya H., Weinhold K.J., Furman P.A., St. Clair M.H., Lehrman S.N., Gallo R.C., Bolognesi D., Barry D.W., Broder S. 3′-Azido-3′-deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc. Natl. Acad. Sci. USA. 82:1985;7096-7100.
69. Langtry H.D., Campoli-Richards D.M. Zidovudine - A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 37:1989;408-450.
70. Furman P.A., Fyfe J.A., Clair M.H., Weinhold K., Rideout J.L., Freeman G.A., Lehrman S.N., Bolognesi D.P., Broder S., Mitsuya H., Barry D.W. Phosphorylation of 3′-azido-3′-deoxythymidine and selective interaction of the 5′-triphosphate with human HIV reverse transcriptase. Proc. Natl. Acad. Sci. USA. 83:1986;8333-8337.
71. Zimmerman T.P., Mahony W.B., Prus K.L. AZT, an unusual nucleoside analogue that permeates the membrane of human erythrocytes and lymphocytes by non-facilitated diffusion. J. Biol. Chem. 262:1987;5748-5754.
72. Klecker R.W.J., Collins J.M., Yarchoan R., Thomas R., Jenkins J.F., Broder S., Myers C.E. Plasma and cerebrospinal fluid pharmacokinetics of AZT: A novel pyrimidine analog with potential application for the treatment of patients with AIDS and related diseases. Clin. Pharmacol. Ther. 41:1987;407-412.
73. Boudinot F.D., Schinazi R.F., Gallo J.M., McClure H.M., Anderson D.C., Doshi K.J., Kambhampathi P.C., Chu C.K. 3′-Azido-2′,3′-dideoxyuridine (AzddU): comparative pharmacokinetics with 3′-azido-3′-deoxythymidine (AZT) in monkeys. AIDS Res. Hum. Retroviruses. 6:1990;219-228.
74. Zimmerman T.P., Domin B.A., Mahony W.B. Inhibition of thymidine transport by 3′-azido-3′-deoxythymidine and its metabolites. Oncol. Res. 5:1993;483-487.
75. Hu M. Comparison of uptake characteristics of thymidine and zidovudine in a human intestinal epithelial model system. J. Pharm. Sci. 82:1993;829-833.
76. Fang X., Parkinson F.E., Mowles D.A., Young J.D., Cass C.E. Functional characterization of a recombinant sodium-dependent nucleoside transporter with selectivity for pyrimidine nucleosides (cNT1rat) by transient expression in cultured mammalian cells. Biochem. J. 317:1996;457-465.
77. Hu P., Frost C.E., Sinko P.J. Intestinal transport and metabolism of zidovudine in rat. Pharm. Res. 11:1994;S-254.
78. Hu P., Sinko P.J. Carrier mediated intestinal transport of zidovudine in rabbit brush border membrane vesicles (BBMV). Pharm. Res. 12:1995;S-304.
79. Hu P., Sinko P.J. Carrier mediated transport of zidovudine in rabbit basolateral intestinal membrane vesicles (BLMV). Pharm. Res. 13:1996;S-247.
80. Bendayan R., Georgis W., Rafi-Tari S. Interaction of 3′-azido-3′-deoxythymidine with the organic base transporter in a cultured renal epithelium. Pharmacotherapy. 15:1995;338-344.
81. Griffith D.A., Hall S.D., Sokol P.P. Interaction of AZT with organic ion transport in rat renal basolateral membrane vesicles. J. Pharmacol. Exp. Ther. 257:1991;149155.
82. Katlama C., Havlir D.V. Newer nucleosides: lamivudine and stavudine. AIDS. 10:(Suppl A):1996;S135-S143.
83. Beach J.W. Chemotherapeutic agents for human immunodeficiency virus infection: mechanism of action, pharmacokinetics, metabolism, and adverse reactions. Clin. Ther. 20:1998;2-25.
84. Cammack N., Rouse P., Marr C.L., Reid P.J., Boehme R.E., Coates J.A., Penn C.R., Cameron J.M. Cellular metabolism of (-) enantiomeric 2′-deoxy-3′-thiacytidine. Biochem. Pharmacol. 43:1992;2059-2064.
85. Johnson M.A., Ahluwalia G., Connelly M.C., Cooney D.A., John D.G., Fridland A. Metabolic pathways for activation of the antiretroviral agent 2′-3′-dideoxyadenosine in human lymphoid cells. J. Biol. Chem. 263:1988;15354-15357.
86. Drusano G. L, Yuen G.J., Morse G.D., Cooley T.P., Seidlin M., Lambert J.S., Liebman H.A., Valentine F.T., Dolin R. Impact of bioavailability on determination of the maximal tolerated dose of 2′-3′-dideoxyinosine in phase I trials. Antimicrob. Agents Chemother. 36:1992;1280-1283.
87. Sinko P.J., Hu P., Waclawski A.P., Patel N.R. Oral absorption of anti-AIDS nucleoside analogues. 1. Intestinal transport of didanosine in rat and rabbit preparations. J. Pharm. Sci. 84:1995;959-965.
88. Sinko P.J., Patel N.R., Hu P. Site-specific oral absorption of didanosine: in situ characterization and correlation with extent of absorption in vivo. Int. J. Pharm. 109:1994;125-133.
89. Sinko P.J., Sutyak J.P., Leesman G.D., Hu P., Makhey V.D., Yu H., Smith C.L. Oral absorption of anti-AIDS nucleoside analogues: 3. Regional absorption and in vivo permeability of 2′-3′-dideoxyinosine in an intestinal-vascular access port (IVAP) dog model. Biopharm. Drug Dispos. 18:1997;697-710.
90. Klecker R.W. Jr., Collins J.M., Yarchoan R.C., Thomas R., Mcatee N., Broder S., Myers C.E. Pharmacokinetics of 2′-3′-dideoxycytidine in patients with AIDS and related disorders. J. Clin. Pharmacol. 28:1988;837-842.
91. Starnes M.C., Cheng Y.C. Cellular metabolism of 2′-3′-dideoxycytidine, a compound active against HIV in vitro. J. Biol. Chem. 262:1998;988-991.
92. Waclawski A.P., Sinko P.J. Oral absorption of anti-acquired immune deficiency syndrome nucleoside analogues. 2. Carrier-mediated intestinal transport of stavudine in rat and rabbit preparations. J. Pharm. Sci. 85:1996;478-484.
93. Beauchamp L.M., Orr G.F., deMiranda P., Doucette M., Burnette T., Krenitsky T.A. Amino acid ester prodrugs of acyclovir. Antivir. Chem. Chemother. 3:1992;157-164.
94. Smith C., Klein A., Zimmerman T. Influx of valacyclovir into cynomologous monkey intestinal brush border membranes is transporter mediated and enhanced over acyclovir. 33rd Interscience Conference on Antimicrobial Agents and Chemotherapy :1993.
95. Guo A., Hu P., Balimane P.V., Leibach F.H., Sinko P.J. Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPepT1). J. Pharmacol. Exp. Ther. 289:1999;448-454.