Identification of CYP3A7 for glyburide metabolism in human fetal livers

Biochemical Pharmacology

Volumn 92, Issue 4, 2014, Pages 690-700

  Shuster, Diana L ^a   Risler, Linda J ^a   Prasad, Bhagwat ^a   Calamia, Justina C ^a   Voellinger, Jenna L ^a   Kelly, Edward J ^a   Unadkat, Jashvant D ^a   Hebert, Mary F ^a,b   Shen, Danny D ^a   Thummel, Kenneth E ^a   Mao, Qingcheng ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

CYP3A7; Fetal metabolism; Gestational diabetes mellitus; Glyburide; Human fetal livers

Indexed keywords

CYTOCHROME P450 2A6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; CYTOCHROME P450 3A7; GLIBENCLAMIDE; MIDAZOLAM; PRASTERONE; ANTIDIABETIC AGENT; CYP3A7 PROTEIN, HUMAN; UNSPECIFIC MONOOXYGENASE;

ADULT; ARTICLE; CLINICAL ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; FEMALE; FETUS; FETUS LIVER; GENOTYPE; GESTATIONAL AGE; HUMAN; HUMAN TISSUE; KINETICS; LIVER METABOLISM; LIVER MICROSOME; MALE; METABOLIC CAPACITY; PROTEIN ANALYSIS; PROTEIN CONTENT; AMINO ACID SEQUENCE; CHEMISTRY; EMBRYOLOGY; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER; METABOLISM; MOLECULAR GENETICS; TANDEM MASS SPECTROMETRY;

AMINO ACID SEQUENCE; ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYBURIDE; HUMANS; HYPOGLYCEMIC AGENTS; LIVER; MICROSOMES, LIVER; MOLECULAR SEQUENCE DATA; TANDEM MASS SPECTROMETRY;

EID: 84912141887     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2014.09.025     Document Type: Article

References (43)

1. Paglia MJ, Coustan DR. Gestational diabetes: evolving diagnostic criteria. Curr.Opin. Obstet. Gynecol. 2011;23:72-5.
2. Jovanovic L, Pettitt DJ. Gestational diabetes mellitus. JAMA 2001;286:2516-8.
3. Camelo Castillo W, Boggess K, Sturmer T, Brookhart MA, Benjamin Jr DK, Jonsson Funk M. Trends in glyburide compared with insulin use for gestational diabetes treatment in the United States, 2000-2011. Obstet.Gynecol. 2014;123:1177-84.
4. Coetzee EJ, Jackson WP. The management of non-insulin-dependent diabetes during pregnancy. Diabetes Res Clin.Pract. 1985;1:281-7.
5. Bertini AM, Silva JC, Taborda W, Becker F, Lemos Bebber FR, Zucco Viesi JM, et al. Perinatal outcomes and the use of oral hypoglycemic agents. J.Perinat. Med. 2005;33:519-23.
6. Langer O, Conway DL, Berkus MD, Xenakis EM, Gonzales O. A comparison of glyburide and insulin in women with gestational diabetes mellitus. New Engl. J. Med. 2000;343:1134-8.
7. Anjalakshi C, Balaji V, Balaji MS, Seshiah V. A prospective study comparing insulin and glibenclamide in gestational diabetes mellitus in Asian Indian women. Diabetes Res.Clin. Pract. 2007;76:474-5.
8. Ogunyemi D, Jesse M, Davidson M. Comparison of glyburide versus insulin in management of gestational diabetes mellitus. Endocr.Pract. 2007;13:427-8.
9. Zharikova OL, Fokina VM, Nanovskaya TN, Hill RA, Mattison DR, Hankins GD, et al. Identification of the major human hepatic and placental enzymes responsible for the biotransformation of glyburide. Biochem.Pharmacol. 2009;78: 1483-90.
10. Ravindran S, Zharikova OL, Hill RA, Nanovskaya TN, Hankins GD, Ahmed MS. Identification of glyburide metabolites formed by hepatic and placental microsomes of humans and baboons. Biochem.Pharmacol. 2006;72:1730-7.
11. Hebert MF, Ma X, Naraharisetti SB, Krudys KM, Umans JG, Hankins GD, et al. Are we optimizing gestational diabetes treatment with glyburide? The pharmacologic basis for better clinical practice. Clin.Pharmacol. Ther. 2009;85:607-14.
12. Behravan J, Piquette-Miller M. Drug transport across the placenta, role of the ABC drug efflux transporters. Expert Opin.Drug Metab. Toxicol. 2007;3:819-30.
13. Mao Q. BCRP/ABCG2 in the placenta: expression, function and regulation. Pharm.Res. 2008;25:1244-55.
14. Ceckova-Novotna M, Pavek P, Staud F. P-glycoprotein in the placenta: expression, localization, regulation and function. Reprod.Toxicol. 2006;22:400-10.
15. Ni Z, Mao Q. ATP-binding cassette efflux transporters in human placenta. Curr.Pharm. Biotechnol. 2011;12:674-85.
16. Zhou L, Naraharisetti SB, Wang H, Unadkat JD, Hebert MF, Mao Q. The breast cancer resistance protein (Bcrp1/Abcg2) limits fetal distribution of glyburide in the pregnant mouse: an Obstetric-Fetal Pharmacology Research Unit Network and University of Washington Specialized Center of Research Study. Mol.Pharmacol. 2008;73:949-59.
17. Gedeon C, Behravan J, Koren G, Piquette-Miller M. Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta 2006;27:1096-102.
18. Hemauer SJ, Patrikeeva SL, Nanovskaya TN, Hankins GD, Ahmed MS. Role of human placental apical membrane transporters in the efflux of glyburide, rosiglitazone, and metformin. Am.J. Obstet. Gynecol. 2010;202:383 e1-3837e.
19. Zharikova OL, Ravindran S, Nanovskaya TN, Hill RA, Hankins GD, Ahmed MS. Kinetics of glyburide metabolism by hepatic and placental microsomes of human and baboon. Biochem.Pharmacol. 2007;73:2012-9.
20. Jain S, Zharikova OL, Ravindran S, Nanovskya TN, Mattison DR, Hankins GD, et al. Glyburide metabolism by placentas of healthy and gestational diabetics. Am.J. Perinatol. 2008;25:169-74.
21. Komori M, Nishio K, Kitada M, Shiramatsu K, Muroya K, Soma M, et al. Fetus-specific expression of a form of cytochrome P-450 in human livers. Biochemistry 1990;29:4430-3.
22. Leeder JS, Gaedigk R, Marcucci KA, Gaedigk A, Vyhlidal CA, Schindel BP, et al. Variability of CYP3A7 expression in human fetal liver. J.Pharmacol. Exp. Ther. 2005;314:626-35.
23. Hakkola J, Raunio H, Purkunen R, Saarikoski S, Vahakangas K, Pelkonen O, et al. Cytochrome P450 3A expression in the human fetal liver: evidence that CYP3A5 is expressed in only a limited number of fetal livers. Biol.Neonate 2001;80:193-201.
24. Schuetz JD, Beach DL, Guzelian PS. Selective expression of cytochrome P450 CYP3A mRNAs in embryonic and adult human liver. Pharmacogenetics 1994;4:11-20.
25. Zhou L, Naraharisetti SB, Liu L, Wang H, Lin YS, Isoherranen N, et al. Contributions of human cytochrome P450 enzymes to glyburide metabolism. Biopharm. Drug Dispos. 2010;31:228-42.
26. Chen H, Fantel AG, Juchau MR. Catalysis of the 4-hydroxylation of retinoic acids by cyp3a7 in human fetal hepatic tissues. Drug Metab.Dispos. 2000;28:1051-7.
27. Shimada T, Yamazaki H, Mimura M, Wakamiya N, Ueng YF, Guengerich FP, et al. Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs. Drug Metab.Dispos. 1996;24:515-22.
28. Yang HY, Lee QP, Rettie AE, Juchau MR. Functional cytochrome P4503A isoforms in human embryonic tissues: expression during organogenesis. Mol.- Pharmacol. 1994;46:922-8.
29. Gedeon C, Anger G, Piquette-Miller M, Koren G. Breast cancer resistance protein: mediating the trans-placental transfer of glyburide across the human placenta. Placenta 2008;29:39-43.
30. Rydberg T, Jonsson A, Roder M, Melander A. Hypoglycemic activity of glyburide (glibenclamide) metabolites in humans. Diabetes Care 1994;17:1026-30.
31. Paine MF, Khalighi M, Fisher JM, Shen DD, Kunze KL, Marsh CL, et al. Characterization of interintestinal and intraintestinal variations in human CYP3A-dependent metabolism. J.Pharmacol. Exp. Ther. 1997;283:1552-62.
32. Brzezinski MR, Boutelet-Bochan H, Person RE, Fantel AG, Juchau MR. Catalytic activity and quantitation of cytochrome P-450 2E1 in prenatal human brain. J.Pharmacol. Exp. Ther. 1999;289:1648-53.
33. Thummel KE, Lee CA, Kunze KL, Nelson SD, Slattery JT. Oxidation of acetaminophen to N-acetyl-p-aminobenzoquinone imine by human CYP3A4. Biochem.-Pharmacol. 1993;45:1563-9.
34. Kamiie J, Ohtsuki S, Iwase R, Ohmine K, Katsukura Y, Yanai K, et al. Quantitative atlas of membrane transporter proteins: development and application of a highly sensitive simultaneous LC/MS/MS method combined with novel insilico peptide selection criteria. Pharm.Res. 2008;25:1469-83.
35. Prasad B, Evers R, Gupta A, Hop CE, Salphati L, Shukla S, et al. Interindividual variability in hepatic organic anion-transporting polypeptides and P-glycoprotein (ABCB1) protein expression: quantification by liquid chromatography tandem mass spectroscopy and influence of genotype, age, and sex. Drug Metab.Dispos. 2014;42:78-88.
36. Edson KZ, Prasad B, Unadkat JD, Suhara Y, Okano T, Guengerich FP, et al. Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry 2013;52:8276-85.
37. Shuster DL, Risler LJ, Liang CK, Rice KM, Shen DD, Hebert MF, et al. Maternal-fetal disposition of glyburide in pregnant mice is dependent on gestational age. J.Pharmacol. Exp. Ther. 2014;350:425-34.
38. Nath A, Atkins WM. A theoretical validation of the substrate depletion approach to determining kinetic parameters. Drug Metab.Dispos. 2006;34:1433-5.
39. Ravindran S, Basu S, Gorti SK, Surve P, Sloka N. Metabolic profile of glyburide in human liver microsomes using LC-DAD-Q-TRAP-MS/MS. Biomed.Chromatogr. 2013;27:575-82.
40. Lee SJ, Goldstein JA. Functionally defective or altered CYP3A4 and CYP3A5 single nucleotide polymorphisms and their detection with genotyping tests. Pharmacogenomics 2005;6:357-71.
41. Michaels S, Wang MZ. The revised human liver cytochrome P450 pie: absolute protein quantification of CYP4F and CYP3A enzymes using targeted quantitative proteomics. Drug Metab.Dispos. 2014;42:1241-51.
42. Wang H, Xu D, Peng RX, Yue J. Testosterone-metabolizing capacity and characteristics of adrenal microsomes in human fetus in vitro. J.Pediatr. Endocrinol. Metab. 2010;23:143-52.
43. Wang H, Ping J, Peng RX, Yue J, Xia XY, Li QX, et al. Changes of multiple biotransformation phase I and phase II enzyme activities in human fetal adrenals during fetal development. Acta Pharmacol. Sin. 2008;29:231-8.