Preparation, isolation, analysis, and characterization of 3-benzo[a]pyrenyl-beta-D-glucopyranosiduronic acid: a metabolite of 3-hydroxybenzo[a]pyrene with potentially high carcinogenic activity.
The aglycone, 3-hydroxybenzo[a]pyrene, was metabolized to 3-benzo[a]pyrenyl-beta-D-glucopyranosiduronic acid in the presence of uridine 5'-diphosphoglucuronic acid and rabbit liver microsomes. The course of the biosynthetic reaction was followed by fluorimetry and reverse-phase, paired-ion high pressure liquid chromatography (HPLC). Also, the HPLC system was used to analyze for glucuronide and 3-hydroxybenzo[a]pyrene during the isolation procedure. The existence of a glucuronide of 3-hydroxybenzo[a]pyrene was determined by radiotracer and enzymic techniques, utilizing the HPLC system. Field desorption and direct inlet mass spectral techniques were used to characterize the 3-hydroxybenzo[a]pyrene glucuronide.
Midwest Research Institute, Kansas City, Missouri 64110, USA.
D B
DB
Johnson
J F
JF
Engel
E E
EE
Murrill
P E
PE
Guire
C W
CW
Barker
C M
CM
Bardwell
A Y
AY
Shan
M J
MJ
Swanson
J G
JG
Stone-Heurner
D000818:Animals; D001580:Benzopyrenes / Q000032:analysis / Q000302:isolation & purification* / Q000378:metabolism; D002273:Carcinogens / Q000032:analysis / Q000302:isolation & purification* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D066298:In Vitro Techniques; D013058:Mass Spectrometry; D008862:Microsomes, Liver / Q000378:metabolism; D011817:Rabbits; D013050:Spectrometry, Fluorescence
D001580:Benzopyrenes; D002273:Carcinogens; C039301:benzo(a)pyrene-3-O-glucuronide; C021338:3-hydroxybenzo(a)pyrene