Synthesis, stability and pharmacological evaluation of a novel codrug consisting of lamivudine and ursolic acid

European Journal of Pharmaceutical Sciences

Volumn 45, Issue 1-2, 2012, Pages 110-115

  Zhong, Yan ^a   Dai, Zhaohui ^b   Xu, Yi ^b   Teng, Yanbo ^b   Wu, Bin ^b  

^a SOUTHEAST UNIVERSITY   (China)

^b NANJING MEDICAL UNIVERSITY   (China)

Author keywords

Anti HBV activity; Codrug; Hepatoprotective activity; Lamivudine; Stability; Ursolic acid

Indexed keywords

ALANINE AMINOTRANSFERASE; ASPARTATE AMINOTRANSFERASE; CHLOROACETIC ACID; LAMIVUDINE; PLACEBO; TRIACYLGLYCEROL LIPASE; URSOLIC ACID;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIVIRAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG DECOMPOSITION; DRUG DESIGN; DRUG EFFICACY; DRUG HALF LIFE; DRUG INHIBITION; DRUG STABILITY; DRUG SYNTHESIS; HEPATITIS B; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; LIVER INJURY; LIVER PROTECTION; MALE; NONHUMAN; PLASMA; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TREATMENT OUTCOME;

ANIMALS; ANTIVIRAL AGENTS; DRUG COMBINATIONS; DRUG STABILITY; DRUG-INDUCED LIVER INJURY; DUCKS; HALF-LIFE; HEPADNAVIRIDAE INFECTIONS; HEPATITIS B VIRUS, DUCK; HEPATITIS, VIRAL, ANIMAL; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; LAMIVUDINE; LIPASE; MICE; MICE, INBRED ICR; PLASMA; PRODRUGS; PROTECTIVE AGENTS; RANDOM ALLOCATION; TRITERPENES;

EID: 83655167043     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.10.028     Document Type: Article

References (35)

1. M.Q. Amjad, M.R. Meriem, and M.T. Bassam Synthesis, characterization and in vitro hydrolysis of a gemfibrozil-nicotinic acid codrug for improvement of lipid profile Eur. J. Pharm. Sci. 43 3 2011 99 108
2. B. Anders, and B. Hans Prodrugs of 5-fluorouracil. III. Hydrolysis kinetics in aqueous solution and biological media, lipophilicity and solubility of various 1-carbamoyl derivatives of 5-fluorouracil Int. J. Pharm. 23 2 1985 209 222
3. E. Bjornesson, and R. Olsson Suspected drug-induced liver fatalities reported to the WHO database Dig. Liver Dis. 38 1 2006 33 38 (Pubitemid 44356129)
4. L. Chen, Q. Zhang, D.M. Yu, M.B. Wan, and X.X. Zhang Early changes of hepatitis B virus quasi species during lamivudine treatment and the correlation with antiviral efficacy J. Hepatology 50 5 2009 895 905
5. P. Chen, Y. Luo, L. Hai, S. Qian, and Y. Wu Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity Eur. J. Med. Chem. 45 7 2010 3005 3010
6. N. Das, M. Dhanawat, B. Dash, R.C. Nagarwal, and S.K. Shrivastava Codrug: an efficient approach for drug optimization Eur. J. Pharm. Sci. 41 5 2010 571 588
7. N.W. Fadnavis, R.L. Babu, S.K. Vadivel, A.A. Deshpande, and U.T. Bhalerao Lipase catalyzed regio- and stereospecific hydrolysis: chemoenzymatic synthesis of both (R)- and (S)-enantiomers of α-lipoic acid Tetrahedron: Asymmetry 23 9 1998 4109 4112 (Pubitemid 29009754)
8. R. Gish Clinical trial results of new therapies for HBV: implications for treatment guidelines Semin. Liver Dis. 25 S1 2005 29 39 (Pubitemid 41254591)
9. Q.L. Guo, L. Zhao, Q.D. You, Y. Yang, H.Y. Gu, G.L. Song, N. Lu, and J. Xin Anti-hepatitis B virus activity of wogonin in vitro and in vivo Antiviral Res. 74 1 2007 16 24 (Pubitemid 46366014)
10. Y.Q. Han, Z.M. Huang, X.B. Yang, H.Z. Liu, and G.X. Wu In vivo and in vitro anti-hepatitis B virus activity of total phenolics from Oenanthe javanica J. Ethnopharmacol. 118 1 2008 148 153
11. F. Hideaki, W. Akio, N. Toru, N. Minoru, M. Kan, N. Atsushi, S. Tsutomu, and N. Hiroshi Synthesis of novel twin drug consisting 8- oxaendoethanotetrahydromorphides with a 1, 4-dioxane spacer and its pharmacological activities: μ, κ, and putative opioid receptor antagonists Bioorg. Med. Chem. Lett. 19 2 2009 438 441
12. P. Honkoop, H.G. Niesters, R.A. de Man, A.D. Osterhaus, and S.W. Schalm Lamivudine resistance in immunocompetent chronic hepatitis B. Incidence and patterns J. Hepatol. 26 6 1997 1393 1395 (Pubitemid 27346654)
13. F. Jing, X.Q. An, and W.G. Shen The characteristics of hydrolysis of triolein catalyzed by wheat germ lipase in water-in-oil microemulsions J. Mol. Catal. B: Enzym. 24-25 1 2003 3 60
14. I.P. Julie, C. Dawn, R. Rezvan, Y. Nancy, D.B. Susan, S.W. John, and M.H. Christine Drug-induced liver injury following positive drug rechallenge Regul. Toxicol. Pharmacol. 54 1 2009 84 90
15. R.G. Knodell, K.G. Ishak, W.C. Black, T.S. Chen, R. Craig, N. Kaplowitz, T.W. Kiernan, and J. Wollman Formulation and application of a numerical scoring system for assessing histological activity in asymptomatic chronic active hepatitis Hepatology 1 5 1981 431 435 (Pubitemid 12218164)
16. A.P. Kozikowski, D. Ma, J. Brewer, S. Sun, E. Coasta, E. Romeo, and A. Guidotti Chemistry, binding affinities, and behavioral properties of a new class of "antineophobic" mitochondrial DBI receptor complex (mDRC) ligands J. Med. Chem. 36 20 1993 2908 2920 (Pubitemid 23315394)
17. C.C. Krishna, K.A. Hitesh, K. Anil, P. Keykavous, and M. Reza Synthesis, analysis, in vitro characterization, and in vivo disposition of a lamivudine-dextran conjugate for selective antiviral delivery to the liver Bioconjug. Chem. 18 6 2007 2097 2108
18. W.M. Lau, A.W. White, S.J. Gallagher, M. Donaldson, G. McNaughton, and C.M. Heard Scope and limitations of the co-drug approach to topical drug delivery Curr. Pharm. Des. 14 8 2008 794 802 (Pubitemid 351736437)
19. J. Liu Pharmacology of oleanolic acid and ursolic acid J. Ethnopharmacol. 49 1 1995 57 68 (Pubitemid 26010740)
20. J. Liu, Y.P. Liu, Q. Mao, and D.K. Curtis The effects of 10 triterpenoid compounds on experimental liver injury in mice Fundam. Appl. Toxicol. 22 1 1994 34 40 (Pubitemid 24073654)
21. A.S.F. Lok Chronic hepatitis B N. Engl. J. Med. 346 22 2002 1682 1683
22. S. Mahmoud, K. Alaa, and E. Hosny Biological and metabolic study of naproxen-propyphenazone mutual prodrug Eur. J. Pharm. Sci. 17 3 2002 121 130
23. F.M. Menger, and M.J. Rourk Synthesis and reactivity of 5-fluorouracil/cytarabine mutual prodrugs J. Org. Chem. 62 26 1997 9083 9088 (Pubitemid 28053099)
24. A. Nurmuhammat, U. Halmurat, and B. Biljana In vivo hepatoprotective activity of the aqueous extract of Artemisia absinthium L. against chemically and immunologically induced liver injuries in mice J. Ethnopharmacol. 131 2 2010 478 484
25. V. Pierre, K.K.L. George, L.R. Geert, H. Yves, G. Edward, T. Tawesak, I. Mohd, M. Bin, M.W. Khin, T. Christian, C. Graham, W. Martine, and F. Carlo Therapeutic vaccination of chronic hepatitis B patients with virus suppression by antiviral therapy: A randomized, controlled study of co-administration of HBsAg/AS02 candidate vaccine and lamivudine Vaccine 25 51 2007 8585 8597
26. S. Rajendnasozhan, V. Periyaswamy, and V.P. Kodukkur Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats Life Sci. 78 7 2006 713 718
27. C. Shyamala, M. Abee, M.R. Al-Ghananeem Robert, and A.C. Peter Synthesis and stability of two indomethacin prodrugs Bioorg. Med. Chem. Lett. 16 7 2006 1874 1879
28. D. Sriram, P. Yogeeswari, and G. Gopal Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs Eur. J. Med. Chem. 40 12 2005 1373 1376 (Pubitemid 41618280)
29. W.L. Susan, S. Martin, A. Michael, and L. Claus Kinetics of degradation of 4-imidazolidinone prodrug types obtained from reacting prilocaine with formaldehyde and acetaldehyde Eur. J. Pharm. Sci. 20 2 2003 233 240
30. W.L. Susan, A. Michael, and L. Claus Kinetics of degradation and oil solubility of ester prodrugs of a model dipeptide (Gly-Phe) Eur. J. Pharm. Sci. 22 5 2004 399 408
31. G.F. Wang, L.P. Shi, Y.D. Ren, Q.F. Liu, H.F. Liu, R.J. Zhang, Z. Li, F.H. Zhu, P.L. He, W. Tang, P.Z. Tao, C. Li, W.M. Zhao, and J.P. Zuo Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro Antiviral Res. 83 2 2009 186 190
32. X.A. Wen, P. Zhang, J. Liu, L.Y. Zhang, X.M. Wu, P.Z. Ni, and H.B. Sun Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatiaes as glycogen phosphorylase inhibitors Bioorg. Med. Chem. Lett. 16 3 2006 722 726 (Pubitemid 43014868)
33. C.G. Wermuth The Practice of Medicinal Chemistry C.G. Wermuth, Homo and Heterodimer Ligands: The Twin Drug Approach 2008 Academic Press California 380 383
34. Z.Q. Wu, P. Ashish, D. Rutesh, and X.D. Yuan Development of acetaminophen proline prodrug Bioorg. Med. Chem. Lett. 20 13 2010 3851 3854
35. Zhong, Y., Zhou, J.P., Huo, M.R. Preparation and application of a novel lamivudine codrug. CN Patent 10/101766632.