Circumvention of P-gp and MRP2 mediated efflux of lopinavir by a histidine based dipeptide prodrug

International Journal of Pharmaceutics

Volumn 512, Issue 1, 2016, Pages 49-60

  Mandal, Abhirup ^a   Pal, Dhananjay ^a   Mitra, Ashim K ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

HIV 1; MRP2; P gp; PepT1; PHT1; Protease inhibitor; Transport; Uptake

Indexed keywords

CARRIER PROTEINS AND BINDING PROTEINS; DIPEPTIDE DERIVATIVE; ESTERASE; HISTIDINE; HISTIDINE TRANSPORTER 1; HISTIDYLLEUCINE LOPINAVIR DIPEPTIDE; LOPINAVIR; MULTIDRUG RESISTANCE ASSOCIATED PROTEIN 2; MULTIDRUG RESISTANCE PROTEIN; PEPTIDASE; PEPTIDE TRANSPORTER 1; PRODRUG; UNCLASSIFIED DRUG; CARRIER PROTEIN; COTRANSPORTER; DIPEPTIDE; HISTIDYLLEUCINE; MULTIDRUG RESISTANCE-ASSOCIATED PROTEIN 2; NERVE PROTEIN; SLC15A4 PROTEIN, HUMAN;

AQUEOUS SOLUTION; ARTICLE; CACO 2 CELL LINE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; DRUG TRANSPORT; DRUG UPTAKE; ESTERIFICATION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; HYDROLYSIS; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY; CELL CULTURE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; GENETIC TRANSFECTION; METABOLISM; SOLUBILITY; SYNTHESIS;

CARRIER PROTEINS; CELL SURVIVAL; CELLS, CULTURED; DIPEPTIDES; DRUG STABILITY; HUMANS; LOPINAVIR; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NERVE TISSUE PROTEINS; P-GLYCOPROTEIN; PRODRUGS; SOLUBILITY; SYMPORTERS; TRANSFECTION;

EID: 84983233442     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2016.08.027     Document Type: Article

References (26)

1. 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. 359 (2008), 7–14.
2. Amin, M.L., P-glycoprotein inhibition for optimal drug delivery. Drug Target Insights 7 (2013), 27–34.
3. Bertrand, Y., Capdeville, R., Balduck, N., Philippe, N., Cyclosporin A used to reverse drug resistance increases vincristine neurotoxicity. Am. J. Hematol. 40 (1992), 158–159.
4. Bhardwaj, R.K., Herrera-Ruiz, D., Eltoukhy, N., Saad, M., Knipp, G.T., The functional evaluation of human peptide/histidine transporter 1 (hPHT1) in transiently transfected COS-7 cells. Eur. J. Pharm. Sci. 27 (2006), 533–542.
5. Chandwani, A., Shuter, J., Lopinavir/ritonavir in the treatment of HIV-1 infection: a review. Ther. Clin. Risk Manage. 4 (2008), 1023–1033.
6. Christians, U., Transport proteins and intestinal metabolism: P-glycoprotein and cytochrome P4503A. Ther. Drug Monit. 26 (2004), 104–106.
7. Cvetkovic, R.S., Goa, K.L., Lopinavir/ritonavir: a review of its use in the management of HIV infection. Drugs 63 (2003), 769–802.
8. Herrera-Ruiz, D., Wang, Q., Gudmundsson, O.S., Cook, T.J., Smith, R.L., Faria, T.N., Knipp, G.T., Spatial expression patterns of peptide transporters in the human and rat gastrointestinal tracts, Caco-2 in vitro cell culture model, and multiple human tissues. AAPS PharmSci, 3, 2001, E9.
9. Hu, Y., Xie, Y., Keep, R.F., Smith, D.E., Divergent developmental expression and function of the proton-coupled oligopeptide transporters PepT2 and PhT1 in regional brain slices of mouse and rat. J. Neurochem. 129 (2014), 955–965.
10. Hughes, P.J., Cretton-Scott, E., Teague, A., Wensel, T.M., Protease inhibitors for patients with HIV-1 infection: a comparative overview. P & T: Peer-Rev. J. Formul. Manage. 36 (2011), 332–345.
11. Kansara, V., Hao, Y., Mitra, A.K., Dipeptide monoester ganciclovir prodrugs for transscleral drug delivery: targeting the oligopeptide transporter on rabbit retina. J. Ocul. Pharmacol. Ther. 23 (2007), 321–334.
12. Kerr, D.J., Graham, J., Cummings, J., Morrison, J.G., Thompson, G.G., Brodie, M.J., Kaye, S.B., The effect of verapamil on the pharmacokinetics of adriamycin. Cancer Chemother. Pharmacol. 18 (1986), 239–242.
13. Kis, O., Robillard, K., Chan, G.N., Bendayan, R., The complexities of antiretroviral drug–drug interactions: role of ABC and SLC transporters. Trends Pharmacol. Sci. 31 (2010), 22–35.
14. 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. 414 (2011), 77–85.
15. Mahato, R., Tai, W., Cheng, K., Prodrugs for improving tumor targetability and efficiency. Adv. Drug Deliv. Rev. 63 (2011), 659–670.
16. Mandal, A., Patel, M., Sheng, Y., Mitra, A.K., Design of lipophilic prodrugs to improve drug delivery and efficacy. Curr. Drug Targets, 2015.
17. Murakami, T., Takano, M., Intestinal efflux transporters and drug absorption. Expert Opin. Drug Metab. Toxicol. 4 (2008), 923–939.
18. 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. 436 (2012), 324–331.
19. Patel, M., 2014. title. Ph.D. Dissertation, University of Missouri-Kansas City, Kansas City, MO.
20. Rautio, J., Kumpulainen, H., Heimbach, T., Oliyai, R., Oh, D., Jarvinen, T., Savolainen, J., Prodrugs: design and clinical applications. Nat. Rev. Drug Discov. 7 (2008), 255–270.
21. Senise, J.F., Castelo, A., Martinez, M., Current treatment strategies, complications and considerations for the use of HIV antiretroviral therapy during pregnancy. AIDS Rev. 13 (2011), 198–213.
22. Takano, M., Yumoto, R., Murakami, T., Expression and function of efflux drug transporters in the intestine. Pharmacol. Ther. 109 (2006), 137–161.
23. Talluri, R.S., Gaudana, R., Hariharan, S., Mitra, A.K., Pharmacokinetics of stereoisomeric dipeptide prodrugs of acyclovir following intravenous and oral administrations in rats: a study involving In vivo corneal uptake of acyclovir following oral dosing. Ophthalmol. Eye Dis. 1 (2009), 21–31.
24. 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. 101 (2012), 3199–3213.
25. Wang, Z., Pal, D., Patel, A., Kwatra, D., Mitra, A.K., Influence of overexpression of efflux proteins on the function and gene expression of endogenous peptide transporters in MDR-transfected MDCKII cell lines. Int. J. Pharm. 441 (2013), 40–49.
26. Zwarycz, B., Wong, E.A., Expression of the peptide transporters PepT1, PepT2, and PHT1 in the embryonic and posthatch chick. Poult. Sci. 92 (2013), 1314–1321.