Intestinal permeability of lamivudine (3TC) and two novel 3TC prodrugs. Experimental and theoretical analyses

European Journal of Pharmaceutical Sciences

Volumn 47, Issue 5, 2012, Pages 965-978

  Gualdesi, María S ^a   Briñón, Margarita C ^a   Quevedo, Mario A ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Intestinal absorption; Lamivudine; Molecular modeling; P glycoprotein; Prodrugs

Indexed keywords

LAMIVUDINE; LAMIVUDINE BUTA; LAMIVUDINE ETHA; PRODRUG; UNCLASSIFIED DRUG; VERAPAMIL; ZIDOVUDINE;

ARTICLE; DIFFUSION; DRUG STRUCTURE; HYDROLYSIS; IN VITRO STUDY; INTESTINE CELL; INTESTINE MUCOSA PERMEABILITY; MALE; MOLECULAR DOCKING; MOLECULAR DYNAMICS; NONHUMAN; PASSIVE DIFFUSION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RAT; THEORETICAL STUDY;

ANIMALS; ANTI-HIV AGENTS; INTESTINAL ABSORPTION; JEJUNUM; LAMIVUDINE; MALE; MODELS, MOLECULAR; P-GLYCOPROTEIN; PERMEABILITY; PRODRUGS; RATS; RATS, WISTAR;

EID: 84868701796     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.10.002     Document Type: Article

References (34)

1. S.G. Aller, J. Yu, A. Ward, Y. Weng, S. Chittaboina, R. Zhuo, P.M. Harrell, Y.T. Trinh, Q. Zhang, I.L. Urbatsch, and G. Chang Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding Science 323 2009 1718 1722
2. A.R. Allouche Gabedita - a graphical user interface for computational chemistry softwares J. Comput. Chem. 32 2011 174 182
3. C. Anastasi, P. Vlieghe, O. Hantz, O. Schorr, C. Pannecouque, M. Witvrouw, E. De Clercq, P. Clayette, N. Dereuddre-Bosquet, D. Dormont, F. Gondois-Rey, I. Hirsch, and J.-L. Kraus Are 5′-O-Carbamate-2′, 3′-dideoxythiacytidine new anti-HIV and anti-HBV nucleoside drugs or prodrugs? Bioorg. Med. Chem. Lett. 13 2003 2459 2463 (Pubitemid 36830750)
4. R.Z. Andrew The evolution of HIV treatment guidelines: current state-of-the-art of ART Antiviral Res. 85 2010 241 244
5. P.V. Balimane, S. Chong, and R.A. Morrison Current methodologies used for evaluation of intestinal permeability and absorption J. Pharmacol. Toxicol. Methods 44 2000 301 312 (Pubitemid 32239482)
6. P. Breedveld, J.H. Beijnen, and J.H.M. Schellens Use of P-glycoprotein and BCRP inhibitors to improve oral bioavailability and CNS penetration of anticancer drugs Trends Pharmacol. Sci. 27 2006 17 24 (Pubitemid 43063120)
7. D.A. Case, T.E. Cheatham Iii, T. Darden, H. Gohlke, R. Luo, K.M. Merz Jr., A. Onufriev, C. Simmerling, B. Wang, and R.J. Woods The Amber biomolecular simulation programs J. Comput. Chem. 26 2005 1668 1688 (Pubitemid 43076180)
8. K.C. Chimalakonda, H.K. Agarwal, A. Kumar, K. Parang, and R. Mehvar Synthesis, analysis, in vitro characterization, and in vivo disposition of a lamivudine-dextran conjugate for selective antiviral delivery to the liver Bioconjug. Chem. 18 2007 2097 2108 (Pubitemid 350220014)
9. T. Cihlar, and A.S. Ray Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine Antiviral Res. 85 2010 39 58
10. A. Dahan, and G.L. Amidon Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting Am. J. Physiol. Gastrointest. Liver Physiol. 297 2009 G371 G377
11. J.A. Esté, and T. Cihlar Current status and challenges of antiretroviral research and therapy Antiviral Res. 85 2010 25 33
12. D. Gagey, S. Ravetti, E.F. Castro, M.S. Gualdesi, M.C. Briñon, R.H. Campos, and L.V. Cavallaro Antiviral activity of 5′-O-carbonate-2′, 3′-dideoxy-3′-thiacytidine prodrugs against hepatitis B virus in HepG2 2.2.15 cells Int. J. Antimicrob. Agents 36 2010 566 569
13. H.Q. Gao, P.L. Boyer, S.G. Sarafianos, E. Arnold, and S.H. Hughes The role of steric hindrance in 3TC resistance of human immunodeficiency virus type-1 reverse transcriptase J. Mol. Biol. 300 2000 403 418
14. P.C.D. Hawkins, A.G. Skillman, G.L. Warren, B.A. Ellingson, and M.T. Stahl Conformer generation with OMEGA: algorithm and validation using high quality structures from the protein databank and cambridge structural database J. Chem. Inf. Model. 50 2010 572 584
15. B. Kuhn, P. Gerber, T. Schulz-Gasch, and M. Stahl Validation and use of the MM-PBSA approach for drug discovery J. Med. Chem. 48 2005 4040 4048 (Pubitemid 40800612)
16. T.T. Mariappan, and S. Singh Gastrointestinal permeability studies using combinations of rifampicin and nucleoside analogue reverse transcriptase inhibitors in rats Indian J. Med. Res. 39 2007 284 290 (Pubitemid 351300753)
17. M. McGann FRED pose prediction and virtual screening accuracy J. Chem. Inf. Model. 51 2011 578 596
18. a prediction method using grid molecular interaction fields J. Chem. Inf. Model. 47 2007 2172 2181 (Pubitemid 350275083)
19. G.N. Moroni, M.A. Quevedo, S. Ravetti, and M.C. Briñón Lipophilic character of novel amino acid derivatives of zidovudine with anti HIV activity J. Liq. Chrom. Rel. Technol. 25 2002 1345 1365 (Pubitemid 34686368)
20. M.A. Quevedo, and M.C. Briñón In vitro and in vivo pharmacokinetic characterization of two novel prodrugs of zidovudine Antiviral Res. 83 2009 103 111
21. M.A. Quevedo, L.E. Nieto, and M.C. Briñón P-glycoprotein limits the absorption of the anti-HIV drug zidovudine through rat intestinal segments Eur. J. Pharm. Sci. 43 2011 151 159
22. S. Ravetti, M.S. Gualdesi, and M.C. Briñón Lipophilicity of 5′-carbonates of lamivudine with antiretroviral activity. Correlation between different methods J. Liq. Chrom. Rel. Technol. 31 2008 1014 1032 (Pubitemid 351302260)
23. S. Ravetti, M.S. Gualdesi, J.S. Trinchero-Hernández, G. Turk, and M.C. Briñón Synthesis and anti-HIV activity of novel 2′,3′-dideoxy-3′-thiacytidine prodrugs Bioorg. Med. Chem. 17 2009 6407 6413
24. R.W. Robey, K.K.K. To, O. Polgar, M. Dohse, P. Fetsch, M. Dean, and S.E. Bates ABCG2: a perspective Adv. Drug Deliv. Rev. 61 2009 3 13
25. B. Samuel The development of antiretroviral therapy and its impact on the HIV-1/AIDS pandemic Antiviral Res. 85 2010 1 18
26. V.P. Shah, K.K. Midha, J.W.A. Findlay, H.M. Hill, J.D. Hulse, I.J. McGilveray, G. McKay, K.J. Miller, R.N. Patnaik, M.L. Powell, A. Tonelli, C.T. Viswanathan, and A. Yacobi Bioanalytical method validation - a revisit with a decade of progress Pharm. Res. 17 2000 1551 1557 (Pubitemid 32217566)
27. N. Shaik, N. Giri, G. Pan, and W.F. Elmquist P-glycoprotein-mediated active efflux of the anti-HIV1 nucleoside abacavir limits cellular accumulation and brain distribution Drug Metab. Dispos. 35 2007 2076 2085 (Pubitemid 350005198)
28. P. Sharma, H.P.S. Chawla, and R. Panchagnula LC determination of cephalosporins in in vitro rat intestinal sac absorption model J. Pharm. Biomed. Anal. 27 2002 39 50 (Pubitemid 33001380)
29. S. Strauch, E. Jantratid, J.B. Dressman, H.E. Junginger, S. Kopp, K.K. Midha, V.P. Shah, S. Stavchansky, and D.M. Barends Biowaiver monographs for immediate release solid oral dosage forms: lamivudine J. Pharm. Sci. 100 2011 2054 2063
30. G. Szakacs, A. Varadi, C. Ozvegy-Laczka, and B. Sarkadi The role of ABC transporters in drug absorption, distribution, metabolism, excretion and toxicity (ADME-Tox) Drug Discov. Today 13 2008 379 393
31. H. Trevor Understanding and managing the adverse effects of antiretroviral therapy Antiviral Res. 85 2010 201 209
32. A.C. Wallace, R.A. Laskowski, and J.M. Thornton LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions Protein Eng. 8 1995 127 134
33. Y. Zhong, Z. Dai, Y. Xu, Y. Teng, and B. Wu Synthesis, stability and pharmacological evaluation of a novel codrug consisting of lamivudine and ursolic acid Eur. J. Pharm. Sci. 45 2012 110 115
34. S.F. Zhou Structure, function and regulation of P-glycoprotein and its clinical relevance in drug disposition Xenobiotica 38 2008 802 832