Study on the metabolic mechanism of chiral inversion of S-Mandelic acid in vitro

Chirality

Volumn 24, Issue 1, 2012, Pages 86-95

  Gao, Ling Bo ^a   Wang, Jin Zhao ^b   Yao, Tong Wei ^a   Zeng, Su ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b Department of Quality Control   (China)

Author keywords

chemical synthesis; chiral inversion; ibuprofen; intestinal bacteria; mandelic acid

Indexed keywords

ARYLPROPIONIC ACID DERIVATIVE; MANDELIC ACID; PHOSPHATE; THIOESTER;

ACIDITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL STRAIN HEPG2; CHIRALITY; CONTROLLED STUDY; CYTOSOL; HYDROLYSIS; INTESTINE FLORA; ISOMER; LIVER HOMOGENATE; MALE; MASS SPECTROMETRY; METABOLISM; MITOCHONDRION; NONHUMAN; PRIORITY JOURNAL; RACEMIZATION; RAT; SYNTHESIS; TOXICOKINETICS;

ANIMALS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; LIVER; MANDELIC ACIDS; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; STEREOISOMERISM; SUBCELLULAR FRACTIONS;

EID: 83955162185     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.21031     Document Type: Article

References (29)

1. Filser JG, Kessler W, Csanády GA,. Estimation of a possible tumorigenic risk of styrene from daily intake via food and ambient air. Toxicol Lett 2002; 126: 1-18. (Pubitemid 34003562)
2. Speita G, Henderson L,. Review of the in vivo genotoxicity tests performed with styrene. Mutat Res 2005; 589: 67-79. (Pubitemid 40094592)
3. Limasset JC, Simon P, Poirot P, Subra I, Grzebyk M,. Estimation of the percutaneous absorption of styrene in an industrial situation. Int Arch Occup Environ Health 1999; 72: 46-51. (Pubitemid 29039109)
4. Manini P, Andreoli R, Poli D, Palma GD, Mutti A, Niessen WMA,. Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. Rapid Commun Mass Spectrom 2002; 16: 2239-2248. (Pubitemid 36018727)
5. Wang JZ, Wang XJ, Tang YH, Shen SJ, Jin YX, Zeng S,. Simultaneous determination of mandelic acid enantiomers and phenylglyoxylic acid in urine by high-performance liquid chromatography with precolumn derivatization. J Chromatogr B Analyt Technol Biomed Life Sci 2006; 840: 50-55. (Pubitemid 44108801)
6. Mingyue M, Tomohiro U, Yuko M, Yingyan G, Yasuaki S, Fumihiro S, Toshio K, Reiko K,. Influence of genetic polymorphisms of styrene-metabolizingenzymes and smoking habits on levels of urinary metabolitesafter occupational exposure to styrene. Toxicol Lett 2005; 160: 84-91.
7. Gagnaire F, Chalansonnet M, Carabin N, Micillino JC,. Effects of subchronic exposure to styrene on the extracellular and tissue levels of dopamine, serotonin and their metabolites in rat brain. Arch Toxico 2006; 80: 703-712. (Pubitemid 44394531)
8. Junichi M, Megumi N, Zhao WY, Kazuo A,. Neurophysiological changes in rats subchronically treated with styrene or its metabolite. J Occup Health 2001; 42: 328-335.
9. Herold BC, Scordi BI, Cheshenko N, Marcellino D, Dzuzelewski M, Francois F,. Mandelic acid condensation polymer: novel candidate microbicide for prevention of human immunodeficiency virus and herpes simplex virus entry. J Virol 2002; 76: 11236-11244. (Pubitemid 35231278)
10. Drummond L, Caldwell J, Wilson HK,. The stereoselectivity of 1, 2-phenylethanediol and mandelic acid metabolism and disposition in the rat. Xenobiotica 1990; 20: 159-168. (Pubitemid 20044710)
11. Kenyon GL, Hegeman GD,. Mandelic acid racemase from Pseudomonas putida. Evidence favoring a carbanion intermediate in the mechanism of action. Biochem 1970; 9: 4036-4043.
12. Maurice SM, Bearne SL,. 2 Kinetics and thermodynamics of mandelate racemase catalysis. Biochemistry 2004; 1: 4048-4058.
13. Hegeman GD, Rosenberg EY, Kenyon GL,. Mandelic acid racemase from Pseudomonas putida. Purification and properties of the enzyme. Biochemistry 1970; 9: 4029-4036.
14. Hall SS, Doweyko LM, Doweyko AM, Zilenovski JS,. Synthesis and evaluation of alpha-hydroxythiol esters as antitumor agents and glyoxalase I inhibitors. J Med Chem 1977; 20: 1239-1242. (Pubitemid 8176884)
15. Zhang K, Tang C, Rashed M, Cui D, Tombret F, Botte H, Lepage F, Levy RH, Baillie TA,. Metabolic chiral inversion of stiripentol in the rat. I. Mechanistic studies. Drug Metab Dispos 1994; 22: 544-553. (Pubitemid 24244863)
16. Reist M, Carrupt PA, Francotte E, Testa B,. Chiral inversion and hydrolysis of thalidomide: mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites. Chem Res Toxico 1998; 11: 1521-1528. (Pubitemid 29013628)
17. Kashiyama E, Yokoi T, Todaka T, Odomi M, Kamataki T,. Chiral inversion of drug: role of intestinal bacteria in the stereoselective sulphoxide reduction of flosequinan. Biochem Pharmaco 1994; 48: 237-243. (Pubitemid 24243964)
18. Ma M, Umemura T, Mori Y, Gong YY, Saijo Y, Sata F, Kawai T, Kishi R,. Influence of genetic polymorphisms of styrene-metabolizing enzymes and smoking habits on levels of urinary metabolites after occupational exposure to styrene. Toxicol Lett 2005; 160: 84-91. (Pubitemid 41501601)
19. Gao LB, Wang JZ, Zeng S,. Cloning, expression and the application of human, rat alcohol dehydrogenase and aldo-keto reductase. Acta Pharma Sin 2009; 44: 778-784.
20. Gao LB, Wang JZ, Yao TW, Zeng S,. Stereoselective metabolism of mandelic acid in rat, mouse and rabbit tissue preparations. Chin J Pharmacol Toxicol 2009; 23: 351-355.
21. Soglowek MS, Geisslinger G, Brune K,. Metabolic chiral inversion of 2-arylpropionates in different tumor cell lines. Agents Actions Suppl 1993; 44: 23-29. (Pubitemid 23211952)
22. Sanins SM, Adams WJ, Kaiser DG, Halstead GW, Hosley J, Barnes H, Baillie TA,. Mechanistic studies on the metabolic chiral inversion of R-ibuprofen in the rat. Drug Metab Dispos 1991; 19: 405-410.
23. Baillie TA, Adams WJ, Kaiser DG, Olanoff LS, Halstead GW, Harpootlian H, Van Giessen GJ,. Mechanistic studies of the metabolic chiral inversion of (R)-ibuprofen in humans. J Pharmacol Exp Ther 1989; 249: 517-523. (Pubitemid 19144843)
24. Wsol V, Skalova L, Szotakova B,. Chiral inversion of drugs, coincidence or principle? Curr Drug Metab 2004; 5: 517-533. (Pubitemid 39539172)
25. Sidenius U, Skonberg C, Olsen J, Hansen SH,. In vitro reactivity of carboxylic acid-CoA thioesters with glutathione. Chem Res Toxicol 2004; 17: 75-81. (Pubitemid 38134062)
26. Carabaza A, Suesa N, Tost D, Pascual J, Gomez M, Gutierrez M, Ortega E, Montserrat X, Garcia AM, Mis R, Cabre F, Mauleon D, Carganico G,. Stereoselective metabolic pathways of ketoprofen in the rat: incorporation into triacylglycerols and enantiomeric inversion. Chirality 1996; 8: 163-172. (Pubitemid 26122090)
27. San Martín MF, Soraci A, Fogel F, Tapia O, Islas S,. Chiral Inversion of (R)-(-)-fenoprofen in guinea-pigs pretreated with clofibrate. Vet Res Commun 2002; 26: 323-332. (Pubitemid 34846749)
28. Nakamura Y, Yamaguchi T, Takahashi S, Hashimoto S, Iwatani K, Nakagawa Y,. Optical isomerization mechanism of R(-)hydratropic acid and derivatives. J Pharmacobiodyn 1981; 4: s-l.
29. Knihinicki RD, Day RO, Williams KM,. Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs-II. Racemization and hydrolysis of (R)- and (S)-ibuprofen-CoA thioesters. Biochem Pharmacol 1991; 42: 1905-1911.