Metabolic chiral inversion of 2-arylpropionates in different tumor cell lines.
The study presented aimed at investigating whether tumor cell lines in continuous culture could be used as in vitro model for inversion experiments. The effect of culture conditions on the extent of inversion was examined. Under optimized culture conditions human and rat tumor cell lines were incubated with the enantiomers of ibuprofen, ketoprofen and flurbiprofen, respectively. Similarly to the situation in man in vivo, inversion of R-ibuprofen occurred in human hepatoma cells, where no inversion of R-ketoprofen or negligible inversion of R-flurbiprofen could be observed. In contrast to R-flurbiprofen the R-enantiomers of ibuprofen and ketoprofen were substantially inverted in the rat hepatoma cells in accordance with observations in the rat in vivo.
Department of Experimental and Clinical Pharmacology and Toxicology, University of Erlangen, Germany.
S
S
Menzel-Soglowek
G
G
Geisslinger
K
K
Brune
D000818:Animals; D006528:Carcinoma, Hepatocellular / Q000378:metabolism; D002452:Cell Count / Q000187:drug effects; D003470:Culture Media; D005480:Flurbiprofen / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007052:Ibuprofen / Q000737:chemistry / Q000494:pharmacology*; D007660:Ketoprofen / Q000737:chemistry / Q000494:pharmacology*; D008113:Liver Neoplasms / Q000378:metabolism; D008114:Liver Neoplasms, Experimental / Q000378:metabolism; D011422:Propionates / Q000737:chemistry / Q000378:metabolism*; D051381:Rats; D013045:Species Specificity; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D003470:Culture Media; D011422:Propionates; D005480:Flurbiprofen; D007660:Ketoprofen; D007052:Ibuprofen