Glucuronidation and isomerization of all-trans- and 13-CIS-retinoic acid by liver microsomes of phenobarbital- or 3-methylcholanthrene-treated rats
References (41)
- et al.
Retinoyl-β-glucuronide: an endogenous compound of human blood
Am J Clin Nutr
(1986) - et al.
Metabolites of all-trans-retinoic acid in bile: identification of all-transand 13-cis-retinoyl glucuronides
J Biol Chem
(1982) - et al.
Enhancement of biological activity by conjugation reactions
J Nutr
(1992) - et al.
Effects of phenobarbital and 3-methylcholanthrene on ubstrate specificity of rat liver microsomal UDP-glucuronyltransferase
Biochim Biophys Ada
(1973) - et al.
Paracetamol glucuronidation and human phenol UDP-glucuronosyltransferase
Biochem Pharmacol
(1993) - et al.
Protein measurement with the Folin phenol reagent
J Biol Chem
(1951) - et al.
Identification and quantitation of all-trans- and 13-cis-retinoic acid and 13-cis-4-oxoretinoic acid in human plasma
J Lipid Res
(1990) - et al.
Dose-dependent kinetics of all-transretinoic acid in rats: plasma levels and excretion into bile, urine, and faeces
Biochem Pharmacol
(1981) - et al.
Effect of tetrachlorodibenzo-p-dioxin (TCDD) on the glucuronidation of retinoic acid in the rat
Biochim Biophys Acta
(1989) Correlation of transplacental and maternal pharmacokinetics of retinoids during organogenesis with teratogenesis
Teratogenicity and placental transfer of all-trans-, 13-cis-, 4-oxo-all-trans-, and 4-oxo-13-cisretinoic acid after administration of a low oral dose during organogenesis in mice
Toxicol Appl Pharmacol
Prolonged remissions of cystic acne and conglobate acne with 13-cis-retinoic acid
N Engl J Med
Topical tretinoin research: an historical perspective
J Int Med Res
Retinoids in cancer therapy
J Clin Oncol
Retinoic acid: morphogen or more mysteries?
Nutr Rev
Teratogen update: vitamin A congeners
Teratology
Teratogenicity and disposition of various retinoids in vivo and in vitro
Characterization of oxidized and glucuronidated metabolites of retinol in monkey plasma by thermospray liquid chromatography/mass spectrometry
Biomed Mass Spectrom
Isotretinoin (13-cis-retinoic acid) metabolism, cis-trans isomerization, glucuronidation, and transfer to the mouse embryo: consequences for teratogenicity
Teratogen Carcinogen Mutagen
Transplacental pharmacokinetics of all-trans-retinoic acid in the rat: comparison between single and multiple oral application
Teratology
Cited by (36)
Biochemical and physiological importance of the CYP26 retinoic acid hydroxylases
2019, Pharmacology and TherapeuticsCitation Excerpt :The uridine glucuronosyltransferase (UGT) 2B7 as well as UGT1A3 have been shown to catalyze the glucuronidation of atRA, although the catalytic activity of UGT1A3 was considerably lower than that of UGT2B7 towards atRA (Samokyszyn et al., 2000). Glucuronidation of atRA has also been observed in rat liver microsomes from uninduced and induced animals, but the UGT isoforms in the rat liver contributing to atRA clearance have not been identified (Genchi, Wang, Barua, Bidlack, & Olson, 1996; Sass, Forster, Bock, & Nau, 1994). Unfortunately, no systematic studies have tested atRA glucuronidation by a panel of human UGT enzymes and as such the number of UGT enzymes that can glucuronidate atRA remains unknown.
Role of Retinoic Acid-Metabolizing Cytochrome P450s, CYP26, in Inflammation and Cancer
2015, Advances in PharmacologyCitation Excerpt :Yet, 13-cisRA is considered to be devoid of biological activity due to its low affinity to nuclear retinoic acid receptors (RARs) in comparison to atRA (Aström, Pettersson, Krust, Chambon, & Voorhees, 1990). In vivo, 13-cisRA isomerizes to atRA both via glutathione-S-transferase-mediated and thermodynamic processes (Chen & Juchau, 1997; Sass, Forster, Bock, & Nau, 1994). Hence, the activity of 13-cisRA is believed to be a result of isomerization to atRA.
Analysis, occurrence, and function of 9-cis-retinoic acid
2012, Biochimica et Biophysica Acta - Molecular and Cell Biology of LipidsCitation Excerpt :A number of cytochrome P450 (CYP) enzymes catabolize atRA to polar metabolites [86,88]. Glucuronidation has also been described as an important mechanism of atRA metabolism [89,90]. Expression loci of specific retinoid-binding proteins, enzymes, and receptors, which contribute to RA generation, signaling, and catabolism, indicate that RA concentrations in vivo are temporally/spatially controlled to produce the individual actions of vitamin A [86,88,91–94].
Esterase 22 and beta-glucuronidase hydrolyze retinoids in mouse liver
2009, Journal of Lipid ResearchCitation Excerpt :In addition, we found that RAGs represent an additional physiological substrate for Gus. β-Glucuronides of all-trans retinol and of all-trans retinoic acid have been shown to be formed by liver microsomes in vitro (43) and in vivo (25, 42, 45) by the action of microsomal UDP-glucuronosyl transferase (45). Retinoid β-glucuronides have been detected in various mouse tissues (44) and in the circulation (46), suggesting that these compounds could represent a water-soluble transport form of vitamin A channeling retinol through the ER or through the circulation.
Anticancer activity and mechanism of action of retinoids in oral and pharyngeal cancer
2002, Oral OncologyCitation Excerpt :Based on its central role of metabolism all-trans-RA can be considered the most important retinoid (Figs. 1 and 2). Metabolic downstream pathways of all-trans-RA include isomerization, decarboxylation and glucuronidation processes [23–25]. Metabolites of all-trans-RA generated in vivo include 13-cis-RA [26,27], 9-cis-RA [28,29], retinoyl β-glucuronide [26], 5,6-epoxy-RA [30], 4-hydroxy-RA [31], 4-oxo-RA [26,27], and 3,4-didehydro-RA [32].
Cellular metabolism and actions of 13-cis-retinoic acid
2001, Journal of the American Academy of Dermatology