Sulfation of opioid drugs by human cytosolic sulfotransferases: metabolic labeling study and enzymatic analysis.

PubWeight™: 0.78‹?›

🔗 View Article (PMC 4459640)

Published in Eur J Pharm Sci on May 14, 2014

Authors

Katsuhisa Kurogi1, Andriy Chepak1, Michael T Hanrahan1, Ming-Yih Liu2, Yoichi Sakakibara3, Masahito Suiko3, Ming-Cheh Liu4

Author Affiliations

1: Department of Pharmacology, College of Pharmacy and Pharmaceutical Sciences, The University of Toledo, Toledo, OH 43614, USA.
2: National Synchrotron Radiation Research Center, Hsinchu, Taiwan, ROC.
3: Biochemistry and Applied Biosciences, University of Miyazaki, Miyazaki 889-2192, Japan.
4: Department of Pharmacology, College of Pharmacy and Pharmaceutical Sciences, The University of Toledo, Toledo, OH 43614, USA. Electronic address: ming.liu@utoledo.edu.

Articles cited by this

Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (1970) 1528.65

A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem (1976) 903.81

Naltrexone in the treatment of alcohol dependence. N Engl J Med (2001) 4.68

Biological sulfate activation and transfer. Science (1958) 2.95

Enzymology of human cytosolic sulfotransferases. FASEB J (1997) 2.56

Efficacy of opioids for chronic pain: a review of the evidence. Clin J Pain (2008) 2.38

Human sulfotransferases and their role in chemical metabolism. Toxicol Sci (2005) 2.27

Pharmacological mechanisms of opioid analgesics. Clin Neuropharmacol (1993) 2.04

UDP-glucuronosyltransferases. Curr Drug Metab (2000) 1.94

Clinical pharmacology of opioids for pain. Clin J Pain (2002) 1.85

Opioid metabolism. Mayo Clin Proc (2009) 1.76

Opioid antagonists. Pharmacol Rev (1967) 1.67

The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab Dispos (1998) 1.58

Naltrexone. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in the management of opioid dependence. Drugs (1988) 1.41

Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT "pie". Drug Metab Dispos (2009) 1.38

A comprehensive review of naloxone for the emergency physician. Am J Emerg Med (1994) 1.33

Sulfation through the looking glass--recent advances in sulfotransferase research for the curious. Pharmacogenomics J (2002) 1.29

Phase II enzyme levels in HepG2 cells and cryopreserved primary human hepatocytes and their induction in HepG2 cells. Toxicol In Vitro (2007) 1.24

Buprenorphine/naloxone: a review of its use in the treatment of opioid dependence. Drugs (2009) 1.22

Human cytosolic sulphotransferases: genetics, characteristics, toxicological aspects. Mutat Res (2001) 1.14

Sulfotransferases: genetics and role in toxicology. Toxicol Lett (2000) 1.13

Butorphanol: a review of its pharmacological properties and therapeutic efficacy. Drugs (1978) 1.13

Morphine blood-brain barrier transport is influenced by probenecid co-administration. Pharm Res (2003) 1.11

Identification and localization of soluble sulfotransferases in the human gastrointestinal tract. Biochem J (2007) 1.11

cDNA cloning, expression, and characterization of the human bifunctional ATP sulfurylase/adenosine 5'-phosphosulfate kinase enzyme. Biosci Biotechnol Biochem (1998) 1.10

Expression profiling of human sulfotransferase and sulfatase gene superfamilies in epithelial tissues and cultured cells. Biochem Biophys Res Commun (2000) 1.09

Localization and functional analysis of the substrate specificity/catalytic domains of human M-form and P-form phenol sulfotransferases. J Biol Chem (1998) 1.07

Cortisol, dehydroepiandrosterone (DHEA), and DHEA sulfate in the cerebrospinal fluid of man: relation to blood levels and the effects of age. J Clin Endocrinol Metab (1996) 1.06

Hydromorphone: pharmacology and clinical applications in cancer patients. Support Care Cancer (2001) 1.04

Molecular enzymology of human liver cytosolic sulfotransferases. Trends Pharmacol Sci (1991) 1.04

Pharmacology of opioids in the treatment of chronic pain syndromes. Pain Physician (2011) 1.01

In vivo blood-brain barrier transport of oxycodone in the rat: indications for active influx and implications for pharmacokinetics/pharmacodynamics. Drug Metab Dispos (2006) 0.99

Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases. Biochem Biophys Res Commun (2000) 0.97

Differential xenoestrogen-sulfating activities of the human cytosolic sulfotransferases: molecular cloning, expression, and purification of human SULT2B1a and SULT2B1b sulfotransferases. Biochim Biophys Acta (2002) 0.92

Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician (2008) 0.92

Blood-brain barrier equilibration of codeine in rats studied with microdialysis. Pharm Res (1998) 0.92

Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient. Xenobiotica (2002) 0.90

Sulfation of budesonide by human cytosolic sulfotransferase, dehydroepiandrosterone-sulfotransferase (DHEA-ST). Drug Metab Dispos (2002) 0.89

Development of opioid formulations with limited diversion and abuse potential. Drug Alcohol Depend (2006) 0.88

Methotrexate induction of human sulfotransferases in Hep G2 and Caco-2 cells. J Appl Toxicol (2005) 0.87

Sulfation of tibolone and tibolone metabolites by expressed human cytosolic sulfotransferases. J Steroid Biochem Mol Biol (2004) 0.87

Hep G2 cell line as a human model for sulphate conjugation of drugs. Xenobiotica (1992) 0.87

Distinct pharmacological properties of morphine metabolites at G(i)-protein and β-arrestin signaling pathways activated by the human μ-opioid receptor. Biochem Pharmacol (2011) 0.86

Sulfation of drugs and hormones in mid-gestation human fetus. Early Hum Dev (2004) 0.86

Isolation and identification of morphine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal sulfate, normorphine, and normorphine 6-glucuronide as morphine metabolites in humans. J Pharm Sci (1977) 0.84

Sulfation of buprenorphine, pentazocine, and naloxone by human cytosolic sulfotransferases. Drug Metab Lett (2012) 0.83

Involvement of SULT1A3 in elevated sulfation of 4-hydroxypropranolol in Hep G2 cells pretreated with beta-naphthoflavone. Biochem Pharmacol (2005) 0.81

De novo sulfation of L-tyrosine in HepG2 human hepatoma cells and its possible functional implication. Eur J Biochem (1994) 0.81

Regulation of sulfotransferase and UDP-glucuronosyltransferase gene expression by the PPARs. PPAR Res (2009) 0.81

Analgesic potencies of morphine 3- and 6-sulfates after intracerebroventricular administration in mice: relationship to structural characteristics defined by mass spectrometry and nuclear magnetic resonance. J Pharm Sci (1985) 0.80

Sulfation of nitrotyrosine: biochemistry and functional implications. IUBMB Life (2007) 0.80

Effectiveness and safety of oral extended-release oxymorphone for the treatment of cancer pain: a pilot study. Support Care Cancer (2004) 0.80

The isolation of morphine ethereal sulfate from urine of the chicken and cat. J Pharmacol Exp Ther (1969) 0.79

Glucuronidation of opioids, carboxylic acid-containing drugs, and hydroxylated xenobiotics catalyzed by expressed monkey UDP-glucuronosyltransferase 2B9 protein. Drug Metab Dispos (1997) 0.79

Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone. Xenobiotica (2004) 0.78

Differential roles of human monoamine (M)-form and simple phenol (P)-form phenol sulfotransferases in drug metabolism. J Biochem (2003) 0.77

Dehydroepiandrosterone sulphate in rat brain: incorporation from blood and metabolism in vivo. J Neurochem (1972) 0.77

Pharmacological characterization of morphine-6-sulfate and codeine-6-sulfate. Brain Res (1999) 0.77

Morphine sulfate and naltrexone hydrochloride extended release capsules for the management of chronic, moderate-to-severe pain, while reducing morphine-induced subjective effects upon tampering by crushing. Expert Opin Pharmacother (2011) 0.77

Species differences in the biliary excretion of morphine, morphine-3-glucuronide and morphine-3-ethereal sulfate in the cat and rat. Biochem Pharmacol (1973) 0.76

Pharmacotherapy for acute pain: implications for practice. J Perianesth Nurs (2008) 0.76

The metabolism of (-)-3-phenoxy-N-methylmorphinan in dogs. Drug Metab Dispos (1981) 0.76

Isolation and characterization of urinary metabolites of nalorphine in dogs and cats. J Pharm Sci (1971) 0.76