Synthesis, characterization and in vitro evaluation of self-assembled poly(ethylene glycol)-glycyrrhetinic acid conjugates

Letters in Organic Chemistry

Volumn 9, Issue 3, 2012, Pages 202-210

  He, Gu ^a   He, Zhiyao ^a   Zheng, Xi ^a   Li, Junmin ^a   Liu, Chi ^a   Song, Xiangrong ^a   Ouyang, Liang ^a   Wu, Fengbo ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Glycyrrhetinic acid; In vitro evaluation; Micelles; Poly(etylene glycol); Self assembly

Indexed keywords

EID: 84860587964     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017812800167448     Document Type: Article

References (22)

1. Asl M.N., Hosseinzadeh H., Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytother. Res. 2008 22(6) 709-724. (Pubitemid 351955567)
2. Luk J.M., Zhang Q.S., Lee N.P., Wo J.Y., Leung P.P., Liu L.X., Hu M.Y., Cheung K.F., Hui C.K., Lau G.K., Fan S.T., Hepatic stellate cell-targeted delivery of M6P-HAS-glycyrrhetinic acid attenuates hepatic fibrogenesis in a bile duct ligation rat model. Liver Int. 2007 27(4) 548-557. (Pubitemid 46534577)
3. Shibata S., A drug over the millennia: Pharmacognosy chemistry and pharmacology of licorice. Yakugaku Zasshi 2000 120(10) 849-862.
4. Rossi T., Castelli M., Zandomeneghi G., Ruberto A., Benassi L., Magnoni C., Santachiara S., Baggio G., Selectivity of action of glycyrrhizin derivatives on the growth of MCF-7 and HEP-2 cells. Anticancer Res. 2003 23(5) 3813-3818. (Pubitemid 37474329)
5. Liu D., Song D.D., Guo G., Wang R., Lu J.L., Jing Y.K., Zhao L.X., The synthesis of 18-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects inleukemia cells. Bioorgan. Med. Chem. 2007 15(16) 5432-5439. (Pubitemid 46962999)
6. He Z.Y., Zheng X., Wu X.H., Song X.R., He G., Wu W.F., Yu S., Mao S.J., Wei Y.Q., Development of Glycyrrhetinic acidmodified stealth cationic liposomes for gene delivery Int. J. Pharm. 2010 397(1-2) 147-154.
7. Lin A.H., Liu Y.M., Huang Y., Sun J.B., Wu Z.F., Zhang X., Ping Q.N., Glycyrrhizin surface-modified chitosan nanoparticles for hepatocyte-targeted delivery. Int. J. Pharm. 2008 359(1-2) 247-253.
8. Mao S.J., Bi Y.Q., Jin H., Wei D.P., He R., Hou S.X., Preparation characterization and uptake by primary cultured rat hepatocytes of liposomes surface-modified with glycyrrhetinic acid. Pharmazie 2007 62(8) 614-619.
9. Tian Q., Zhang C.N., Wang X.H., Wang W., Huang W., Cha R.T., Wang C.H., Yuan Z., Liu M., Wan H.Y., Tang H., Glycyrrhetinic acid-modified chitosan/poly(ethylene glycol) nanoparticles for liver-targeted delivery. Biomaterials 2010 31(17) 4748-4756.
10. Inoue H., Mori T., Shibata S., Koshihara Y., Modulation by glycyrrhetinic acid derivatives of TPA-induced mouse ear edema. Br. J. Pharmacol. 1989 96(1) 204-210. (Pubitemid 19037387)
11. Um S. J., Park M. S., Park S. H., Han H. S., Kwon Y. J., Sin H. S., Synthesis of new glycyrrhetinic acid (GA) derivatives and their effects on tyrosinase activity. Bioorg. Med. Chem. 2003 11(24) 5345-5352.
12. Takahashi H., Onishi H., Machida Y., Glycyrrhetic acid-loaded microparticles: liver-specific delivery and therapeutic potential against carbon tetrachloride-induced hepatitis. J. Pharm. Pharmacol. 2004 56(4) 437-444. (Pubitemid 38455608)
13. Puglia., C., Ostacolo., C., Sacchi., A., Laneri., S., Bonina., F., In-vitro and in-vivo evaluation of oligoethylene esters as dermal prodrugs of 18-glycyrrhetic acid. J. Pharm. Pharmacol. 2006 58(3) 311-319. (Pubitemid 43344573)
14. Marcus Y., Sasson K., Fridkin M., Shechter Y., Turning Low-Molecular-Weight Drugs into Prolonged Acting Prodrugs by Reversible Pegylation: A Study with Gentamicin. J. Med. Chem. 2008 51(14) 4300-4305. (Pubitemid 352032454)
15. Bonina F. P., Puglia C., Barbuzzia T., Caprariisb P., Palagianoc F., Rimolic M. G., Saijad A., In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen naproxen and diclofenac Eur. J. Pharm. Sci. 2001 14(2) 123-134.
16. Richtera A., Olbricha C., Krausea M., Kissel T., Solubilization of Sagopilone a poorly water-soluble anticancer drug using polymeric micelles for parenteral delivery. Int. J. Pharm. 2010 389(1-2) 244-253.
17. Zhang J., Wang L. Q., Wang H. J., Tu K., Micellization phenomena of amphiphilic block copolymers based on methoxy poly (ethylene glycol) and either crystalline or amorphous poly (caprolactone-b-lactide). Biomacromolecules 2006 7(9) 2492-2500 (Pubitemid 44530485)
18. Liu L.H., Guo K., Lu J., Venkatraman S.S., Luo D., Zheng Y., Ng K.C., Ling E., Moochhala S., Yang Y.Y., Biologically active core/shell nanoparticles self-assembled from cholesterolterminated PEG-TAT for drug delivery across the bloodebrain barrier. Biomaterials 2008 29(10) 1509-1517.
19. Torchilin V. P., Micellar Nanocarriers: Pharmaceutical Perspectives. Pharm. Res., 2007 24(1) 1-16. (Pubitemid 44902565)
20. Wang T., Petrenko V. A., Torchilin V. P., Paclitaxel-Loaded Polymeric Micelles Modified with MCF-7 Cell-Specific Phage Protein: Enhanced Binding to Target Cancer Cells and Increased Cytotoxicity. Mol. Pharm. 2010 7(4) 1007-1014.
21. Han X., Liu J., Liu M., Xie C., Zhan C., Gu B., Liu Y., Feng L., Lu W., 9-NC-loaded folate-conjugated polymer micelles as tumor targeted drug delivery system: Preparation and evaluation in vitro. Int. J. Pharm., 2009 372(1-2) 125-131.
22. Ishiwata H., Vertut-doi A., Hirose T., Miyajima K., Physicalchemistry characteristics and biodistribution of poly(ethylene glycol)-coated liposomes using poly(oxyethylene) cholesteryl ether. Chem. Pharm. Bull. 1995 43(6) 1005-1011.