Metabolism of R,S enantiomers of 3-phenylamino-1,2-propanediol, a compound associated with the toxic oil syndrome, in C57BL/6- and A/J-strain mice.
PAP, a very polar substance, is highly metabolized in mice and excreted principally in urine in the form of the 2-hydroxy-3-phenylaminopropanoic acid of each enantiomer. Thus, the major route of PAP elimination in these strains is alkyl chain oxidation. In particular, S-PAP is eliminated principally in the form of that metabolite, whereas R-PAP enantiomer showed further oxidized species at the aromatic ring and alkyl chain, yielding potential decarboxylated compounds and iminoquinones. All these metabolites may have toxicologic implications. On the other hand, OOPAP intestinal hydrolysis in favour of one PAP enantiomer might be expected since lipases show chiral hydrolysis (unpublished data, manuscript in preparation). In this respect, enantiomeric distribution and metabolic differences should be taken into account in the toxicokinetics of these compounds and their potential association with Toxic Oil Syndrome symptoms.
Ladona
M G
MG
Consejo Superior de Investigaciones Cientificas, Barcelona, Spain. mglqob@cid.csic.es
Bujons
J
J
Messeguer
A
A
Ampurdanés
C
C
Morató
A
A
D000814:Aniline Compounds / Q000378:metabolism; D000818:Animals; D002273:Carcinogens / Q000378:metabolism; D004195:Disease Models, Animal; D005229:Fatty Acids, Monounsaturated; D005517:Foodborne Diseases / Q000378:metabolism*; D051379:Mice; D008810:Mice, Inbred C57BL; D010938:Plant Oils / Q000378:metabolism; D011409:Propylene Glycols / Q000737:chemistry / Q000378:metabolism*; D000074262:Rapeseed Oil; D013237:Stereoisomerism
D000814:Aniline Compounds; D002273:Carcinogens; D005229:Fatty Acids, Monounsaturated; D010938:Plant Oils; D011409:Propylene Glycols; D000074262:Rapeseed Oil; C077151:3-phenylamino-1,2-propanediol; C023650:aniline