Amino acid prodrugs: An approach to improve the absorption of HIV-1 protease inhibitor, lopinavir

Pharmaceuticals

Volumn 7, Issue 4, 2014, Pages 433-452

  Patel, Mitesh ^a   Mandava, Nanda ^a   Gokulgandhi, Mitan ^a   Pal, Dhananjay ^a   Mitra, Ashim K ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

Efflux; Lopinavir; LPV; MRP2; P gp; Permeability; Prodrug; Transport; Uptake

Indexed keywords

ISOLEUCINE; LOPINAVIR; METHIONINE; MULTIDRUG RESISTANCE ASSOCIATED PROTEIN 2; MULTIDRUG RESISTANCE PROTEIN; PRODRUG; TRYPTOPHAN;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; DRUG ABSORPTION; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DETERMINATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG TRANSPORT; ENDOTHELIUM CELL; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MICROSOME; NONHUMAN; PH MEASUREMENT; RAT; TANDEM MASS SPECTROMETRY;

EID: 84898648516     PISSN: None     EISSN: 14248247     Source Type: Journal    
DOI: 10.3390/ph7040433     Document Type: Article

References (26)

1. Agarwal, S.; Pal, D.; Mitra, A.K. Both P-gp and MRP2 mediate transport of Lopinavir, a protease inhibitor. Int. J. Pharm. 2007, 339, 139-147.
2. Kumar, G.N.; Jayanti, V.K.; Johnson, M.K.; Uchic, J.; Thomas, S.; Lee, R.D.; Grabowski, B.A.; Sham, H.L.; Kempf, D.J.; Denissen, J.F., et al. Metabolism and disposition of the HIV-1 protease inhibitor lopinavir (ABT-378) given in combination with ritonavir in rats, dogs, and humans. Pharm. Res. 2004, 21, 1622-1630.
3. Kumar, G.N.; Dykstra, J.; Roberts, E.M.; Jayanti, V.K.; Hickman, D.; Uchic, J.; Yao, Y.; Surber, B.; Thomas, S.; Granneman, G.R. Potent inhibition of the cytochrome P-450 3A-mediated human liver microsomal metabolism of a novel HIV protease inhibitor by ritonavir: A positive drug-drug interaction. Drug Metab. Dispos. Biol. Fate Chem. 1999, 27, 902-908.
4. Patel, M.; Mandava, N.K.; Vadlapatla, R.K.; Mitra, A.K. Recent patents and emerging therapeutics for HIV infections: A focus on protease inhibitors. Pharm. Patent Anal. 2013, 2, 513-538.
5. Gupta, D.; Varghese Gupta, S.; Dahan, A.; Tsume, Y.; Hilfinger, J.; Lee, K.D.; Amidon, G.L. Increasing oral absorption of polar neuraminidase inhibitors: A prodrug transporter approach applied to oseltamivir analogue. Mol. Pharm. 2013, 10, 512-522.
6. Landowski, C.P.; Song, X.; Lorenzi, P.L.; Hilfinger, J.M.; Amidon, G.L. Floxuridine amino acid ester prodrugs: Enhancing Caco-2 permeability and resistance to glycosidic bond metabolism. Pharm. Res. 2005, 22, 1510-1518.
7. Gupta, S.V.; Gupta, D.; Sun, J.; Dahan, A.; Tsume, Y.; Hilfinger, J.; Lee, K.D.; Amidon, G.L. Enhancing the intestinal membrane permeability of zanamivir: A carrier mediated prodrug approach. Mol. Pharm. 2011, 8, 2358-2367.
8. Dias, C.; Nashed, Y.; Atluri, H.; Mitra, A. Ocular penetration of acyclovir and its peptide prodrugs valacyclovir and val-valacyclovir following systemic administration in rabbits: An evaluation using ocular microdialysis and LC-MS. Curr. Eye Res. 2002, 25, 243-252.
9. Majumdar, S.; Nashed, Y.E.; Patel, K.; Jain, R.; Itahashi, M.; Neumann, D.M.; Hill, J.M.; Mitra, A.K. Dipeptide monoester ganciclovir prodrugs for treating HSV-1-induced corneal epithelial and stromal keratitis: In vitro and in vivo evaluations. J. Ocular Pharm. Ther. Off. J. Assoc. Ocular Pharm. Ther. 2005, 21, 463-474.
10. Patel, K.; Trivedi, S.; Luo, S.; Zhu, X.; Pal, D.; Kern, E.R.; Mitra, A.K. Synthesis, physicochemical properties and antiviral activities of ester prodrugs of ganciclovir. Int. J. Pharm. 2005, 305, 75-89.
11. Gunda, S.; Hariharan, S.; Mitra, A.K. Corneal absorption and anterior chamber pharmacokinetics of dipeptide monoester prodrugs of ganciclovir (GCV): In vivo comparative evaluation of these prodrugs with Val-GCV and GCV in rabbits. J. Ocular Pharm. Ther. Off. J. Assoc. Ocular Pharm. Ther. 2006, 22, 465-476.
12. Majumdar, S.; Kansara, V.; Mitra, A.K. Vitreal pharmacokinetics of dipeptide monoester prodrugs of ganciclovir. J. Ocular Pharm. Ther. Off. J. Assoc. Ocular Pharm. Ther. 2006, 22, 231-241.
13. Agarwal, S.; Boddu, S.H.; Jain, R.; Samanta, S.; Pal, D.; Mitra, A.K. Peptide prodrugs: Improved oral absorption of lopinavir, a HIV protease inhibitor. Int. J. Pharm. 2008, 359, 7-14.
14. Jain, R.; Duvvuri, S.; Kansara, V.; Mandava, N.K.; Mitra, A.K. Intestinal absorption of novel-dipeptide prodrugs of saquinavir in rats. Int. J. Pharm. 2007, 336, 233-240.
15. Katragadda, S.; Talluri, R.S.; Mitra, A.K. Modulation of P-glycoprotein-mediated efflux by prodrug derivatization: An approach involving peptide transporter-mediated influx across rabbit cornea. J. Ocular Pharm. Ther. Off. J. Assoc. Ocular Pharm. Ther. 2006, 22, 110-120.
16. Patel, M.; Mandava, N.K.; Pal, D.; Mitra, A.K. Amino Acid Prodrug of Quinidine: An Approach to Circumvent P-glycoprotein Mediated Cellular Efflux. Int. J. Pharm. 2014, 464, 196-204.
17. Santos, C.; Morais, J.; Gouveia, L.; de Clercq, E.; Pannecouque, C.; Nielsen, C.U.; Steffansen, B.; Moreira, R.; Gomes, P. Dipeptide derivatives of AZT: Synthesis, chemical stability, activation in human plasma, hPEPT1 affinity, and antiviral activity. ChemMedChem 2008, 3, 970-978.
18. Kwatra, D.; Vadlapatla, R.K.; Vadlapudi, A.D.; Pal, D.; Mitra, A.K. Interaction of gatifloxacin with efflux transporters: A possible mechanism for drug resistance. Int. J. Pharm. 2010, 395, 114-121.
19. Luo, S.; Wang, Z.; Patel, M.; Khurana, V.; Zhu, X.; Pal, D.; Mitra, A.K. Targeting SVCT for enhanced drug absorption: Synthesis and in vitro evaluation of a novel vitamin C conjugated prodrug of saquinavir. Int. J. Pharm. 2011, 414, 77-85.
20. Patel, M.; Vadlapatla, R.K.; Pal, D.; Mitra, A.K. Molecular and functional characterization of riboflavin specific transport system in rat brain capillary endothelial cells. Brain Res. 2012, 1468, 1-10.
21. Patel, M.; Vadlapatla, R.K.; Shah, S.; Mitra, A.K. Molecular expression and functional activity of sodium dependent multivitamin transporter in human prostate cancer cells. Int. J. Pharm. 2012, 436, 324-331.
22. Patel, M.; Dalvi, P.; Gokulgandhi, M.; Kesh, S.; Kohli, T.; Pal, D.; Mitra, A.K. Functional characterization and molecular expression of large neutral amino acid transporter (LAT1) in human prostate cancer cells. Int. J. Pharm. 2013, 443, 245-253.
23. Feierman, D.E.; Melinkov, Z.; Nanji, A.A. Induction of CYP3A by ethanol in multiple in vitro and in vivo models. Alcohol. Clin. Exp. Res. 2003, 27, 981-988.
24. Tang, F.; Horie, K.; Borchardt, R.T. Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm. Res. 2002, 19, 765-772.
25. Tang, F.; Horie, K.; Borchardt, R.T. Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm. Res. 2002, 19, 773-779.
26. Wang, Z.; Pal, D.; Mitra, A.K. Stereoselective evasion of P-glycoprotein, cytochrome P450 3A, and hydrolases by peptide prodrug modification of saquinavir. J. Pharm. Sci. 2012, 101, 3199-3213.