Synthesis of Lamivudine stearate and antiviral activity of stearic acid-g-chitosan oligosaccharide polymeric micelles delivery system

European Journal of Pharmaceutical Sciences

Volumn 41, Issue 3-4, 2010, Pages 498-507

  Li, Qian ^a,b   Du, Yong Zhong ^b   Yuan, Hong ^b   Zhang, Xing Guo ^c   Miao, Jing ^c   Cui, Fu De ^a   Hu, Fu Qiang ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

Anti HBV activity; Chitosan oligosaccharide; Esterification; Lamivudine; Polymeric micelles; Stearic acid

Indexed keywords

ANTIVIRUS AGENT; CHITOSAN; LAMIVUDINE; LAMIVUDINE STEARATE; OCTANOL; OLIGOSACCHARIDE; POLYMER; STEARIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AMINO ACID SUBSTITUTION; ANTIGEN EXPRESSION; ANTIVIRAL ACTIVITY; ARTICLE; CELL STRAIN HEPG2; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DNA REPLICATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ESTERIFICATION; HEPATITIS B VIRUS; HEPATOBLASTOMA; HUMAN; HUMAN CELL; LIPOPHILICITY; MICELLE; PARTICLE SIZE; PARTITION COEFFICIENT; PH; PRIORITY JOURNAL; TUMOR CELL; ZETA POTENTIAL;

ANTIVIRAL AGENTS; CHITOSAN; DRUG DELIVERY SYSTEMS; HEPATITIS B VIRUS; LAMIVUDINE; MICELLES; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; STEARIC ACIDS;

EID: 77957279491     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.08.004     Document Type: Article

References (37)

1. Asselah T., Ripault M.P., Castelnau C. The current status of antiviral therapy of chronic hepatitis B. J. Clin. Virol. 2005, 34:S115-S124.
2. Bernkop-Schnurch A., Krajicek M.E. Mucoadhesive polymers as platforms for peroral peptide delivery and absorption: synthesis and evaluation of different chitosan-EDTA conjugates. J. Control. Release 1998, 50:215-223.
3. Cavalli R., Donalisio M., Civra A., Ferruti P., Ranucci E., Trotta F., Lembo D. Enhanced antiviral activity of Acyclovir loaded into β-cyclodextrin-poly (4-acryloylmorpholine) conjugate nanoparticles. J. Control. Release 2009, 137:116-122.
4. Chawla J.S., Amiji M.M. Biodegradable poly (epsilon-caprolactone) nanoparticles for tumor-targeted delivery of tamoxifen. Int. J. Pharm. 2002, 249:127-138.
5. Craxi A., Antonucci G., Camma C. Treatment options in HBV. J. Hepatol. 2006, 44:S77-S83.
6. Cunningham D., Littleford R.E., Smith W.E., Lundahl P.J., Khan I., McComb D.W. Practical control of SERRS enhancement. Faraday Discuss. 2006, 132:135-145.
7. Desai M.P., Labhasetawar V., Walter E., Levy R.J., Amidon G.L. The mechanism of uptake of biodegradable microparticles in Caco-2 cells is size dependent. Pharm. Res. 1997, 14:1568-1573.
8. Hoofnagle J.H. Alpha-interferon therapy of chronic hepatitis B. Current status and recommendations. J. Hepatol. 1990, 11:S100-S107.
9. Hu F.Q., Li Y.H., Yuan H., Zeng S. Novel self-aggregates of chitosan oligosaccharide grafted steric acid: preparation, characterization and protein association. Pharmazie 2006, 61:194-198.
10. Hu F.Q., Ren G.F., Yuan H., Du Y.Z., Zeng S. Shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel. Colloids Surf. B 2006, 50:97-103.
11. Hu F.Q., Zhao M.D., Yuan H., You J., Du Y.Z., Zeng S. A novel chitosan oligosaccharide-stearic acid micelles for gene delivery: properties and in vitro transfection studies. Int. J. Pharm. 2006, 315:158-166.
12. Hu F.Q., Wu X.L., Du Y.Z., You J., Yuan H. Cellular uptake and cytotoxicity of shell crosslinked stearic acid grafted chitosan oligosaccharide micelles encapsulating doxorubicin. Eur. J. Pharm. Biopharm. 2008, 69:117-125.
13. Kabanov A.V., Bronich T.K., Kabanov V.A. Soluble stoichiometric complexes from poly (N-ethyl-4-vinylpyridinium) cations and poly (ethylene oxide) block-polymethacrylate anions. Macromolecules 1996, 29:67-97.
14. Kerr S.G., Kalman T.I., Med J. Highly water-soluble lipophilic prodrugs of the anti-HIV nudeoside analog 2',3'-dideoxycytidine and its 3'-fluoro derivative. J. Med. Chem. 1992, 35:1996-2001.
15. Lai S.K., Hida K., Man S.T., Chen C., Machamer C., Schroer T.A., Hanes J. Privileged delivery of polymer nanoparticles to the perinuclear region of live cells via a nonclathrin, non-degradative pathway. Biomaterials 2007, 28:2876-2884.
16. Langer R. Drug delivery and targeting. Nature 1998, 392:5-10.
17. Lee K.Y., Kwon I.C., Kim Y.H., Jo W.H., Jeong S.Y. Preparation of chitosan self-aggregates as a gene delivery system. J. Control. Release 1998, 51:213-220.
18. Leinweber F.J. Possible physiological roles of carboxylic ester hydrolases. Drug Metab. Rev. 1987, 18:379-439.
19. Lien E.J., Ren S.J. Partition coefficients. Encyclopedia Pharm. Technol. 2002, 2012-2019.
20. Liu S.Q., Wiradharma N., Gao S.J., Tong Y.W., Yang Y.Y. Biofunctional micelles self-assembled from a folate-conjugated block copolymer for targeted intracellular delivery of anticancer drugs. Biomaterials 2007, 28:1423-1433.
21. Maeda Y., Kim J., Koseki I., Mekada E., Shiokawa Y., Okada Y. Modification of cell membranes with viral envelopes during fusion of cells with HVJ (sendai virus). III. Effects of mono- and di-saccharides on cell fusion and membrane movement of fused cells. Exp. Cell Res. 1977, 108:95-106.
22. Nishiyama N., Kato Y., Sugiyama Y., Kataoka K. Cisplatin-loaded polymer-metal complex micelle with time-modulated decaying property as a novel drug delivery system. Pharm. Res. 2001, 18:1035-1041.
23. Prabaharan M., Grailer J.J., Pilla S., Steeber D.A., Gong S. Folate-conjugated amphiphilic hyperbranched block copolymers based on Boltorn-H40, poly-(l-lactide) and poly(ethylene glycol) for tumor-targeted drug delivery. Biomaterials 2009, 30:3009-3019.
24. Raney A.K., Hamatake R.K., Hong Z. Agents in clinical development for the treatment of chronic hepatitis B. Expert Opin. Investig. Drugs 2003, 12:1281-1295.
25. Shaw T., Bartholomeusz A., Locarnini S. HBV drug resistance: mechanisms, detection and interpretation. J. Hepatol. 2006, 44:593-606.
26. Stempel A., Landgraf F.W. Quinazolines and 1,4-benzodiazopines-9,2-carbobenzoxyglycylamidobenzophenones and their conversion to 1,4-benzodiazopines. J. Org. Chem. 1962, 27:4675-4677.
27. Vladimir P., Torchilin Tat peptide-mediated intracellular delivery of pharmaceutical nanocarriers. Adv. Drug Deliv. Rev. 2008, 60:548-558.
28. Wang Q.Z., Chen X.G., Liu N., Wang S.X., Liu C.S., Meng X.H., Liu C.G. Protonation constants of chitosan with different molecular weight and degree of deacetylation. Carbohydr. Polym. 2006, 65:194-201.
29. Xue K.C., Gu Y., Zhang S.Q., Jiang Y.P., Wu D.C. Preparation of lamivudyl palmitate solid lipid nanoparticles. J. Fourth Mil. Med. Univ. 2003, 10:890-892.
30. Ye Y.Q., Yang F.L., Hu F.Q., Du Y.Z., Yuan H., Yu H.Y. Core-modified chitosan based polymeric micelles for controlled release of doxorubicin. Int. J. Pharm. 2008, 352:294-301.
31. Yokoyama M., Okano T., Sakurai Y., Suwa S., Kataoka K. Introduction of cisplatin into polymeric micelle. J. Control. Release 1996, 39:351-356.
32. You J., Hu F.Q., Du Y.Z., Yuan H. Polymeric micelles with glycolipid-like structure and multiple hydrophobic domains for mediating-target delivery of paclitaxel. Biomacromolecules 2007, 8:2450-2456.
33. You J., Hu F.Q., Du Y.Z., Yuan H., Ye B.F. High cytotoxicity and resistant-cell reversal of novel paclitaxel loaded micelles by enhancing molecular-target delivery of the drug. Nanotechnology 2007, 18:495101.
34. You J., Hu F.Q., Du Y.Z., Yuan H. Improved cytotoxicity of doxorubicin by enhancing its nuclear delivery mediated via nanosized micelles. Nanotechnology 2008, 19:255103.
35. You J., Li X., Cui F.D., Du Y.Z., Yuan H., Hu F.Q. Folate conjugated polymer micelles for active-targeting to cancer cells: preparation, in vitro evaluation of targeting ability and cell cytotoxicity. Nanotechnology 2008, 19:045102.
36. Zhang Y.D., Hu Z.Y., Ye M.Y., Pan Y.F., Chen J.J., Luo Y.L., Zhang Y.Q., He L.X., Wang J.W. Effect of poly (ethylene glycol)-blockpolylactide micelles on hepatic cells of mouse: low cytotoxicity, but efflux of the micelles by ATP-binding cassette transporters. Eur. J. Pharm. Biopharm. 2007, 66:268-280.
37. Zoulim F., Perrillo R. Hepatitis B: reflections on the current approach to antiviral therapy. J. Hepatol. 2008, 48:2-19.