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Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 12
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General Xenobiochemistry

Enzymatic analysis of glucuronidation of synthetic cannabinoid 1-naphthyl 1-(4-fluorobenzyl)-1H-indole-3-carboxylate (FDU-PB-22)

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Pages 1388-1395 | Received 21 Dec 2018, Accepted 05 Feb 2019, Published online: 20 Mar 2019

References

  • Aoshima N, Fujie Y, Itoh T, et al. (2014). Glucose induces intestinal human UDP-glucuronosyltransferase (UGT) 1A1 to prevent neonatal hyperbilirubinemia. Sci Rep 4:6343.
  • Bayewitch M, Rhee MH, Avidor-Reiss T, et al. (1996). Antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase. J Biol Chem 271:9902–5.
  • Chimalakonda KC, Bratton SM, Le VH, et al. (2011). Conjugation of synthetic cannabinoids JWH-018 and JWH-073, metabolites by human UDP-glucuronosyltransferases. Drug Metab Dispos 39:1967–76.
  • Congiu M, Mashford ML, Slavin JL, Desmond PV. (2002). UDP glucuronosyltransferase mRNA levels in human liver disease. Drug Metab Dispos 30:129–34.
  • Currais A, Quehenberger O, Armando AM, et al. (2016). Amyloid proteotoxicity initiates an inflammatory response blocked by cannabinoids. NPJ Aging Mech Dis 2:16012.
  • Dellinger RW, Garcia AM, Meyskens FL. Jr. (2014). Differences in the glucuronidation of resveratrol and pterostilbene: altered enzyme specificity and potential gender differences. Drug Metab Pharmacokinet 29:112–9.
  • Diao X, Scheidweiler KB, Wohlfarth A, et al. (2016). In vitro and in vivo human metabolism of synthetic cannabinoids FDU-PB-22 and FUB-PB-22. AAPS J 18:455–64.
  • D’Souza DC, Perry E, MacDougall L, et al. (2004). The psychotomimetic effects of intravenous delta-9-tetrahydrocannabinol in healthy individuals: implications for psychosis. Neuropsychopharmacology 29:1558–72.
  • Ellis L. (2004). Sex, status, and criminality: a theoretical nexus. Soc Biol 51:144–60.
  • Fujiwara R, Maruo Y, Chen S, Tukey RH. (2015). Role of extrahepatic UDP-glucuronosyltransferase 1A1: advances in understanding breast milk-induced neonatal hyperbilirubinemia. Toxicol Appl Pharmacol 289:124–32.
  • Fujiwara R, Yoda E, Tukey RH. (2018). Species differences in drug glucuronidation: humanized UDP-glucuronosyltransferase 1 mice and their application for predicting drug glucuronidation and drug-induced toxicity in humans. Drug Metab Pharmacokinet 33:9–16.
  • Gall WE, Zawada G, Mojarrabi B, et al. (1999). Differential glucuronidation of bile acids, androgens and estrogens by human UGT1A3 and 2B7. J Steroid Biochem Mol Biol 70:101–8.
  • Ghose R, Omoluabi O, Gandhi A, et al. (2011). Role of high-fat diet in regulation of gene expression of drug metabolizing enzymes and transporters. Life Sci 89:57–64.
  • Guengerich FP. (2006). Cytochrome P450s and other enzymes in drug metabolism and toxicity. AAPS J 8:E101–11.
  • Guillemette C, Lévesque E, Harvey M, et al. (2010). UGT genomic diversity: beyond gene duplication. Drug Metab Rev 42:24–44.
  • Hanioka N, Jinno H, Tanaka-Kagawa T, et al. (2001). Determination of UDP-glucuronosyltransferase UGT1A6 activity in human and rat liver microsomes by HPLC with UV detection. J Pharm Biomed Anal 25:65–75.
  • Hasin DS, Saha TD, Kerridge BT, et al. (2015). Prevalence of marijuana use disorders in the united states between 2001–2002 and 2012–2013. JAMA Psychiatry 72:1235–42.
  • Hutchison RD, Ford BM, Franks LN, et al. (2018). Atypical pharmacodynamic properties and metabolic profile of the abused synthetic cannabinoid AB-PINACA: potential contribution to pronounced adverse effects relative to Δ9-THC. Front Pharmacol 9:1084.
  • Izukawa T, Nakajima M, Fujiwara R, et al. (2009). Quantitative analysis of UDP-glucuronosyltransferase (UGT) 1A and UGT2B expression levels in human livers. Drug Metab Dispos 37:1759–68.
  • Kasper AM, Ridpath AD, Arnold JK, et al. (2015). Severe illness associated with reported use of synthetic cannabinoids-Mississippi, April 2015. MMWR Morb Mortal Wkly Rep 64:1121–2.
  • Kemp DC, Fan PW, Stevens JC. (2002). Characterization of raloxifene glucuronidation in vitro: contribution of intestinal metabolism to presystemic clearance. Drug Metab Dispos 30:694–700.
  • Krishnaswamy S, Duan SX, Von MLL, et al. (2003). Validation of serotonin (5-hydroxtryptamine) as an in vitro substrate probe for human UDP-glucuronosyltransferase (UGT) 1A6. Drug Metab Dispos 31:133–9.
  • Kuehl GE, Lampe JW, Potter JD, Bigler J. (2005). Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027–35.
  • Kumar S, Samuel K, Subramanian R, et al. (2002). Extrapolation of diclofenac clearance from in vitro microsomal metabolism data: role of acyl glucuronidation and sequential oxidative metabolism of the acyl glucuronide. J Pharmacol Exp Ther 303:969–78.
  • Kurkela M, Patana AS, Mackenzie PI, et al. (2007). Interactions with other human UDP-glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6. Pharmacogenet Genomics 17:115–26.
  • Kutsuno Y, Hirashima R, Sakamoto M, et al. (2015). Expression of UDP-glucuronosyltransferase 1 (UGT1) and glucuronidation activity toward endogenous substances in humanized UGT1 mouse brain. Drug Metab Dispos 43:1071–6.
  • Kutsuno Y, Itoh T, Tukey RH, Fujiwara R. (2014). Glucuronidation of drugs and drug-induced toxicity in humanized UDP-glucuronosyltransferase 1 mice. Drug Metab Dispos 42:1146–52.
  • Lapoint J, James LP, Moran CL, et al. (2011). Severe toxicity following synthetic cannabinoid ingestion. Clin Toxicol (Phila) 49:760–4.
  • Law R, Schier J, Martin C, et al. (2015). Centers for disease control (CDC). Notes from the field: increase in reported adverse health effects related to synthetic cannabinoid use-united states, January-May 2015. MMWR Morb Mortal Wkly Rep 64:618–9.
  • Lindigkeit R, Boehme A, Eiserloh I, et al. (2009). Spice: a never ending story? Forensic Sci Int 191:58–63.
  • Mackenzie PI, Bock WK, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–85.
  • Milano W, Tecce MF, Capasso A. (2017). Cannabinoids involvement in neurodegenerative diseases. Curr Neurobiol 8:135–44.
  • Miners JO, McKinnon RA, Mackenzie PI. (2002). Genetic polymorphisms of UDP-glucuronosyltransferases and their functional significance. Toxicology 181–182:453–6.
  • Mitsugi R, Sumida K, Fujie Y, et al. (2016). Acyl-glucuronide as a possible cause of trovafloxacin-induced liver toxicity: induction of chemokine (C-X-C motif) ligand 2 by trovafloxacin acyl-glucuronide. Biol Pharm Bull 39:1604–10.
  • Nakamura A, Nakajima M, Yamanaka H, et al. (2008). Expression of UGT1A and UGT2B mRNA in human normal tissues and various cell lines. Drug Metab Dispos 36:1461–4.
  • Neumann E, Mehboob H, Ramírez J, et al. (2016). Age-dependent hepatic UDP-glucuronosyltransferase gene expression and activity in children. Front Pharmacol 7:437.
  • Ohno S, Nakajin S. (2009). Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction. Drug Metab Dispos 37:32–40.
  • Ohtsuki S, Schaefer O, Kawakami H, et al. (2012). Simultaneous absolute protein quantification of transporters, cytochromes P450, and UDP-glucuronosyltransferases as a novel approach for the characterization of individual human liver: comparison with mRNA levels and activities. Drug Metab Dispos 40:83–92.
  • Patton AL, Seely KA, Yarbrough AL, et al. (2018). Altered metabolism of synthetic cannabinoid JWH-018 by human cytochrome P450 2C9 and variants. Biochem Biophys Res Commun 498:597–602.
  • Romero J, Orgado JM. (2009). Cannabinoids and neurodegenerative diseases. CNS Neurol Disord Drug Targets 8:440–50.
  • Sakamoto M, Itoh T, Tukey RH, Fujiwara R. (2015). Nicotine regulates the expression of UDP-glucuronosyltransferase (UGT) in humanized UGT1 mouse brain. Drug Metab Pharmacokinet 30:269–75.
  • Sten T, Bichlmaier I, Kuuranne T, et al. (2009). UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. Drug Metab Dispos 37:417–23.
  • Strassburg CP, Strassburg A, Kneip S, et al. (2002). Developmental aspects of human hepatic drug glucuronidation in young children and adults. Gut 50:259–65.
  • Takeda S, Kitajima Y, Ishii Y, et al. (2006). Inhibition of UDP-glucuronosyltransferase 2b7-catalyzed morphine glucuronidation by ketoconazole: dual mechanisms involving a novel noncompetitive mode. Drug Metab Dispos 34:1277–82.
  • Troberg J, Järvinen E, Ge GB, et al. (2017). UGT1A10 is a high activity and important extrahepatic enzyme: why has its role in intestinal glucuronidation been frequently underestimated? Mol Pharm 14:2875–83.
  • Tukey RH, Strassburg CP. (2000). Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581–616.
  • Uchaipichat V, Mackenzie PI, Guo XH, et al. (2004). Human UDP-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413–23.
  • Uchiyama N, Shimokawa Y, Kawamura M, et al. (2014). Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–81.
  • Vardakou I, Pistos C, Spiliopoulou C. (2010). Spice drugs as a new trend: mode of action, identification and legislation. Toxicol Lett 197:157–62.
  • Watanabe Y, Nakajima M, Ohashi N, et al. (2003). Glucuronidation of etoposide in human liver microsomes is specifically catalyzed by UDP-glucuronosyltransferase 1A1. Drug Metab Dispos 31:589–95.
  • Williams JA, Hyland R, Jones BC, et al. (2004). Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201–8.
  • Wilson CD, Tai S, Ewing L, et al. (2019). Convulsant effects of abused synthetic cannabinoids JWH-018 and 5F-AB-PINACA are mediated by agonist actions at CB1 receptors in mice. J Pharmacol Exp Ther 368:146–56.
  • Yong WP, Ramirez J, Innocenti F, Ratain MJ. (2005). Effects of ketoconazole on glucuronidation by UDP-glucuronosyltransferase enzymes. Clin Cancer Res 11:6699–704.

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