Synthesis and plasma pharmacokinetics in CD-1 mice of a 18β-glycyrrhetinic acid derivative displaying anti-cancer activity

Journal of Pharmacy and Pharmacology

Volumn 65, Issue 3, 2013, Pages 402-410

  Lallemand, Benjamin ^a   Ouedraogo, Moustapha ^e   Wauthoz, Nathalie ^b   Lamkami, Touria ^a   Mathieu, Veronique ^c   Jabin, Ivan ^d   Amighi, Karim ^b   Kiss, Robert ^c   Dubois, Jacques ^a   Goole, Jonathan ^b  

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^b Université de Ouagadougou   (Belgium)

^c Laboratory of Toxicology   (Belgium)

^d Université Joseph KI ZERBO   (Belgium)

^e UNIVERSITÉ DE OUAGADOUGOU   (Burkina Faso)

Author keywords

cancer; glycyrrhetinic acid derivatives; mouse; nanoemulsion; plasma pharmacokinetics

Indexed keywords

GLYCYRRHETINIC ACID DERIVATIVE; N [2 [3 [3,5 BIS(TRIFLUOROMETHYL)PHENYL]UREIDO]ETHYL]GLYCYRRHETINAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER CELL; CANCER INHIBITION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG METABOLISM; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; FIBROBLAST; GLIOBLASTOMA; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MAXIMUM PLASMA CONCENTRATION; MAXIMUM TOLERATED DOSE; MOUSE; NONHUMAN; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; EMULSIONS; FEMALE; FIBROBLASTS; GLIOBLASTOMA; GLYCYRRHETINIC ACID; HUMANS; MICE; PARTICLE SIZE; PROTEASOME ENDOPEPTIDASE COMPLEX;

EID: 84873089561     PISSN: 00223573     EISSN: 20427158     Source Type: Journal    
DOI: 10.1111/j.2042-7158.2012.01603.x     Document Type: Article

References (23)

1. Abe H, et al. Effects of glycyrrhizin and glycyrrhetinic acid on growth and melanogenesis in cultured B16 melanoma cells. Eur J Cancer Clin Oncol 1987; 23: 1549-1555.
2. Okamoto H, et al. Inhibition of 12-Otetradecanoylphorbol-13-acetate- induced induction in Epstein-Barr virus early antigen in Raji cells. Cancer Lett 1983; 19: 47-53.
3. Gao Y, et al. The synthesis of glycyrrhetinic acid derivatives containing a nitrogen heterocycle and their antiproliferative effects in human leukemia cells. Molecules 2010; 15: 4439-4449.
4. Lallemand B, et al. Structure-activity relationship analyses of Glycyrrhetinic acid derivatives as anticancer agents. Mini Rev Med Chem 2011; 11: 881-887.
5. Salvi M, et al. Glycyrrhetinic acid-induced permeability transition in rat liver mitochondria. Biochem Pharmacol 2003; 66: 2375-2379.
6. Subba Rao GSR, et al. Chemical modifications of natural triterpenes-glycyrrhetinic and boswellic acids: evaluation of their biological activity. Tetrahedron 2008; 64: 11541-11548.
7. Pang X, et al. Methyl 2-cyano-3,11-dioxo-18-olean-1,12-dien-30-oate, a derivative of glycyrrhetinic acid, functions as a potent angiogenesis inhibitor. J Pharmacol Exp Ther 2010; 335: 172-179.
8. Lee CS, et al. 18beta-Glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity. Life Sci 2008; 83: 481-489.
9. Yu T, et al. Selective cytotoxicity of glycyrrhetinic acid against tumorigenic r/m HM-SFME-1 cells: potential involvement of H-Ras downregulation. Toxicol Lett 2010; 192: 425-430.
10. Yamaguchi H, et al. Novel effects of glycyrrhetinic acid on the central nervous system tumorigenic progenitor cells: induction of actin disruption and tumor cell-selective toxicity. Eur J Med Chem 2010; 45: 2943-2948.
11. Lallemand B, et al. N-(2-{3-[3,5-bis(trifluoromethyl)phenyl]ureido}ethyl) -glycyrrhetinamide (6b): a novel anticancer Glycyrrhetinic acid derivative that targets the proteasome and displays anti-kinase activity. J Med Chem 2011; 54: 6501-6513.
12. Lu Y, et al. In vitro and in vivo evaluation of mPEG-PLA modified liposomes loaded glycyrrhetinic acid. Int J Pharm 2008; 356: 274-281.
13. Hao J, et al. Effect and mechanism of penetration enhancement of organic base and alcohol on Glycyrrhetinic acid in vitro. Int J Pharm 2010; 399: 102-108.
14. Logashenko EB, et al. Synthesis and pro-apoptotic activity of novel glycyrrhetinic acid derivatives. ChemBioChem 2011; 12: 784-794.
15. Gad SC,. Preclinical development handbook: ADME and biopharmaceutical properties. Hoboken, NJ: John Wiley and sons, 2008.
16. Ignatov DV, et al. A simple method for preparation of 18 alpha-glycyrrhetinic acid and its derivatives. Russ J Bioorganic Chem 2003; 29: 390-394.
17. Park JH, Oh CH,. Synthesis of new 6-(-4-fluorophenyl)-5-(2-substituted pyrimidin-4- yl)imidazo[2,1-b] thiazole derivatives and their antiproliferative activity against melanoma cell line. Bull Korean Chem Soc 2010; 31: 2854-2860.
18. Hubert P, et al. Harmonization of strategies for the validation of quantitative analytical procedures. A SFSTP proposal-Part III. J Pharmaceut Biomed 2007; 45: 82-96.
19. Asakawa C, et al. Utilization of [11C]phosphogene for radiosynthesis of N-(2-{3-[3,5-bis(trifluoromethyl)phenyl[11C]ureido}ethyl)-glycyrrhetinamide, an inhibitory agent for proteasome and kinase in tumors. Bioorg Med Chem Lett 2012; 22: 3594-3597.
20. Li P, Zhao L,. Developing early formulations: practice and perspective. Int J Pharm 2007; 341: 1-19.
21. Abikhalil F, et al. A new algorithm for computing the parameters of linear compartment models in pharmacokinetics. Eur J Drug Metab Pharmacokinet 1986; 11: 51-59.
22. Krähenbühl S, et al. Analysis and pharmacokinetics of glycyrrhizic acid and glycyrrhetinic acid in humans and experimental animals. Steroids 1994; 59: 121-126.
23. Tabuchi M, et al. The blood-brain barrier permeability of 18 beta-glycyrrhetinic acid, a major metabolite of glycyrrhizin in Glycyrrhiza root, a constituent of traditional Japanese medicine yokukansan. Cell Mol Neurobiol 2012; 32: 1139-1146.