The stereoselective sulfate conjugation of 4'-methoxyfenoterol stereoisomers by sulfotransferase enzymes

Chirality

Volumn 24, Issue 10, 2012, Pages 796-803

  Iyer, Lalitha V ^a   Ramamoorthy, Anuradha ^b   Rutkowska, Ewelina ^c   Furimsky, Anna M ^a   Tang, Liang ^a   Catz, Paul ^a   Green, Carol E ^a   Jozwiak, Krzysztof ^c   Wainer, Irving W ^b  

^a SRI INTERNATIONAL   (United States)

^b NATIONAL INSTITUTE ON AGING   (United States)

^c MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

stereoselective phase II metabolism; sulfotransferases; SULT1A1; SULT1A3; SULT1E1

Indexed keywords

4 METHOXYFENOTEROL; COMPLEMENTARY DNA; DRUG METABOLITE; FENOTEROL; SULFOTRANSFERASE; SULFOTRANSFERASE 1A1; SULFOTRANSFERASE 1A3; SULFOTRANSFERASE 1E1; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CONFORMATION; CONFORMATIONAL TRANSITION; CONJUGATION; DRUG FORMULATION; HYDROGEN BOND; IC 50; MICHAELIS CONSTANT; MOLECULAR DOCKING; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; SULFATION;

BINDING SITES; COMPUTER SIMULATION; FENOTEROL; HUMANS; MODELS, MOLECULAR; PROTEIN ISOFORMS; STEREOISOMERISM; SULFATES; SULFOTRANSFERASES;

EID: 84867074205     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22072     Document Type: Article

References (15)

1. 2 adrenergic receptor agonists. Bioorg Med Chem 2010; 18: 728-736.
2. 2-adrenoceptor. Biochem Pharmacol 2010; 79: 1610-1615.
3. Heel RC, Brogden RN, Speight TM, Avery GS,. Fenoterol: a review of its pharmacological properties and therapeutic efficacy in asthma. Drugs 1978; 15: 3-32.
4. Rominger KL, Herman M,. Neuere Ergrbnisse zur Pharmakokinrtik von Fenoterol. In:, Jung H, Fendel H, Karl C, editors. Neuste Ergrbnisse uber Betamimetika. Darmstadt: Steinkopff; 1995. p 62-65.
5. Hildebrandt R, Wagner B, Preiss-Nowzohour K, Gundert-Remy U,. Fenoterol metabolism in man: sulphation versus glucuronidation. Xenobiotica 1994; 24: 71-77.
6. Wilson AA, Wang J, Koch P, Walle T,. Stereoselective sulphate conjugation of fenoterol by human phenolsulphotransferases. Xenobiotica 1997; 27: 1147-1154.
7. Siluk D, Mager DE, Kim HS, Wang Y, Furimsky AM, Ta A, Iyer LV, Green CE, Wainer, IW,. Pharmacokinetics and metabolism of (R,R)-methoxyfenoterol in rat. Xenobiotica 2010; 40: 195-206.
8. Rominger KL, Pollmann W,. Comparative pharmacokinetic studies on fenoterol-hydrobromide in rat, dog and man. Arzneimittelforschung 1972; 22: 1190-1196.
9. 2 adrenergic receptor. J Med Chem 2007; 50: 2903-2915.
10. Kozocas JA, Bupp JE, Tanga MJ, Pluhar JT, Wainer IW,. Synthesis of tritium-labeled (R,R)-4-methoxyfenoterol. J Label Compd Radiopharm 2010; 53: 68-72.
11. Goodsell DS,. Molecule of the month: sulfotransferases. RCSB PDB Molecule of the Month. 2009. DOI: 10.2210/rcsb-pdb/mom-2009-8.
12. Walle T, Walle UK, Shwed JA, Thornburg KR, Mathis CE, Pesola GR,. Human phenolsulfotransferases: chiral substrates and expression in Hep G2 cells. Chem Biol Interact 1994; 92: 47-55.
13. Falany CN, Xie X, Wang J, Ferrer J, Falany JL,. Molecular cloning and expression of novel sulfotransferase-like cDNAs from human and rat brain. Biochem J 2000; 346: 857-864.
14. Coughtrie MWH,. Sulfation through the looking glass - recent advances in sulfotransferase research for the curious. Pharmacogenomics J 2002; 2: 297-308.
15. Hildebrandt M, Adjei A, Weinshilboum R, Johnson JA, Berlin DS, Klein TE, Altman RB,. Very important pharmacogene summary: sulfotransferase 1A1. Pharmacogenet Genomics 2009; 19: 404-406.