Quantification of conjugated metabolites of drugs in biological matrices after the hydrolysis with β-glucuronidase and sufatase: A review of bio-analytical methods

Biomedical Chromatography

Volumn 27, Issue 10, 2013, Pages 1280-1295

  Ding, Yue ^a   Peng, Ming ^a,b   Zhang, Tong ^a   Tao, Jian Sheng ^a   Cai, Zhen Zhen ^a   Zhang, Yong ^a  

^a SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b SHANGHAI INSTITUTE FOR FOOD AND DRUG CONTROL   (China)

Author keywords

Conjugated metabolites; Hydrolysis; Pharmacokinetics; Review; Sulfatase; glucuronidase

Indexed keywords

BIOACTIVITY; ENZYMATIC HYDROLYSIS; KETONES; MAMMALS; METABOLISM; PHARMACOKINETICS; PHYSIOLOGY; SULFUR COMPOUNDS;

ANALYTICAL METHOD; BIOLOGICAL MATRIXES; CONJUGATED METABOLITES; DRUG METABOLISMS; DRUG-CONJUGATES; FREEFORMS; GLUCURONIDASE; GLUCURONIDATION; SULFATASES; Β-GLUCURONIDASE;

METABOLITES;

(10) GINGEROL; (6) GINGEROL; 4,4' ISOPROPYLIDENEDIPHENOL; 7 ETHOXYCOUMARIN; ALOE EMODIN; BAICALEIN; BETA GLUCURONIDASE; BIOCHANIN A; CARBAMIC ACID; CATECHIN; CHRYSOPHANIC ACID; DAIDZEIN; DIOSMETIN; EMODIN; EPICATECHIN; GENISTEIN; GINGER EXTRACT; HESPERETIN; MORIN; NARINGENIN; PARACETAMOL; PUERARIN; QUERCETIN; RESVERATROL; RETIGABINE; RHEIN; SULFATASE; TAXIFOLIN; UNINDEXED DRUG; WOGONIN;

ANALYTIC METHOD; ARTICLE; DRUG GLUCURONIDATION; DRUG HYDROLYSIS; DRUG ISOLATION; DRUG METABOLISM; DRUG PURIFICATION; DRUG SULFATION; HUMAN; INCUBATION TIME; LIQUID LIQUID EXTRACTION; NONHUMAN; PH; PRECIPITATION; QUANTITATIVE ASSAY; SOLID PHASE EXTRACTION; TEMPERATURE;

MAMMALIA;

EID: 84883559560     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.2912     Document Type: Article

References (55)

1. Aarbakke J. Clinical pharmacokinetics of phenylbutazone. Clinical Pharmacokinetics 1978; 3: 369-380.
2. Alvarez-Sánchez B, Priego-Capote F and Luque de Castro MD. Ultrasound-enhanced enzymatic hydrolysis of conjugated female steroids as pretreatment for their analysis by LC-MS/MS in urine. Analyst 2009; 134: 1416-1422.
3. Azuma K, Ippoushi K, Ito H, Horie H and Terao J. Enhancing effect of lipids and emulsifiers on the accumulation of quercetin metabolites in blood plasma after the short-term ingestion of onion by rats. Bioscience, Biotechnology, and Biochemistry 2003; 67: 2548-2555.
4. Baranowska I and Magiera S. Analysis of isoflavones and flavonoids in human urine by UHPLC. Analytical and Bioanalytical Chemistry 2011; 399: 3211-3219.
5. Campanero MA, Escolar M, Perez G, Garcia-Quetglas E, Sadaba B and Azanza JR. Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study. Journal of Pharmaceutical and Biomedical Analysis 2010; 51: 875-881.
6. César IC, Byrro RM, Santana E, Silva Cardoso FF, Mundim IM, Souza Teixeira L, Gomes SA, Bonfim RR and Pianetti GA. Development and validation of a high-performance liquid chromatography-electrospray ionization-MS/MS method for the simultaneous quantitation of levodopa and carbidopa in human plasma. Journal of Mass Spectrometry 2011; 46: 943-948.
7. Chetiyanukornkul T, Toriba A, Kameda T, Tang N and Hayakawa K. Simultaneous determination of urinary hydroxylated metabolites of naphthalene, fluorene, phenanthrene, fluoranthene and pyrene as multiple biomarkers of exposure to polycyclic aromatic hydrocarbons. Analytical and Bioanalytical Chemistry 2006; 386: 712-718.
8. Ding Y, Zhang T, Tao JS, Tan B, Guo CR and Yang L. HPLC-MS/MS method to determine genipin in rat plasma after hydrolysis with sulfatase and its application to a pharmacokinetic study. Biomedical Chromatography 2012; 26: 816-825.
9. Edwards DR, Lohman DC and Wolfenden R. Catalytic proficiency: the extreme case of S-O cleaving sulfatases. Journal of the American Chemical Society 2012; 134: 525-531.
10. Elsohly MA, Gul W, Feng S and Murphy TP. Hydrolysis of conjugated metabolites of buprenorphine II. The quantitative enzymatic hydrolysis of norbuprenorphine- 3-β-d-glucuronide in human urine. Journal of Analytical Toxicology 2005; 29: 570-573.
11. Fang SH, Hou YC, Chang WC, Hsiu SL, Chao PD and Chiang BL. Morin sulfates/glucuronides exert anti-inflammatory activity on activated macrophages and decreased the incidence of septic shock. Life Sciences 2003; 74: 743-756.
12. Feng S, ElSohly MA and Duckworth DT. Hydrolysis of conjugated metabolites of buprenorphine. I. The quantitative enzymatic hydrolysis of buprenorphine- 3-β-d-glucuronide in human urine. Journal of Analytical Toxicology 2001; 25: 589-593.
13. Gao S, Yang Z, Yin T, You M and Hu M. Validated LC-MS/MS method for the determination of maackiain and its sulfate and glucuronide in blood: application to pharmacokinetic and disposition studies. Journal of Pharmaceutical and Biomedical Analysis 2011; 55: 288-293.
14. Gunduz M, Argikar UA, Baeschlin D, Ferreira S, Hosagrahara V and Harriman S. Identification of a novel N-carbamoyl glucuronide: in vitro, in vivo, and mechanistic studies. Drug Metabolism and Disposition 2010; 38: 361-367.
15. Hiller A, Nguyen N, Strassburg CP, Li Q, Jainta H, Pechstein B, Ruus P, Engel J, Tukey RH and Kronbach T. Retigabine N-glucuronidation and its potential role in enteroheapatic circulation. Drug Metabolism and Disposition 1999; 27: 605-612.
16. Hoffmann P, Hartmann MF, Remer T, Zimmer KP and Wudy SA. Profiling oestrogens and testosterone in human urine by stable isotope dilution/benchtop gas chromatography-mass spectrometry. Steroids 2010; 75: 1067-1074.
17. Hou YC, Lin SP, Tsai SY, Ko MH, Chang YC and Chao PD. Flavonoid pharmacokinetics and tissue distribution after repeated dosing of the roots of Scutellaria baicalensis in rats. Planta Medica 2011; 77: 455-460.
18. Jin D, Hakamata H, Takahashi K, Kotani A and Kusu F. Determination of quercetin in human plasma after ingestion of commercial canned green tea by semi-micro HPLC with electrochemical detection. Biomedical Chromatography 2004; 18: 662-666.
19. Jing X, Bing S, Xiaoyan W, Xiaojie S and Yongning W. A study on bisphenol A, nonylphenol, and octylphenol in human urine amples detected by SPE-UPLC-MS. Biomedical and Environmental Sciences 2011; 24: 40-46.
20. Kanaze FI, Kokkalou E, Georgarakis M and Niopas I. A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. Journal of Pharmaceutical and Biomedical Analysis 2004; 36: 175-181.
21. Kerdpin O, Elliot DJ, Mackenzie PI and Miners JO. Sulfinpyrazone C-glucuronidation is catalyzed selectively by human UDP-glucuronosyltransferase 1A9. Drug Metabolism and Disposition 2006; 34: 1950-1953.
22. Lai MY, Hsiu SL, Chen CC, Hou YC and Chao PD. Urinary pharmacokinetics of baicalein, wogonin and their glycosides after oral administration of scutellariae radix in humans. Biological and Pharmaceutical Bulletin 2003; 26: 79-83.
23. Lévèques A, Actis-Goretta L, Rein MJ, Williamson G, Dionisi F and Giuffrida F. UPLC-MS/MS quantification of total hesperetin and hesperetin enantiomers in biological matrices. Journal of Pharmaceutical and Biomedical Analysis 2012; 57: 1-6.
24. Lewis AJ, Otake Y and Walle UK, Walle T. Sulphonation of N-hydroxy-2-acetylaminofluorene by human dehydroepiandrosterone sulphotransferase. Xenobiotica 2000; 30: 253-261.
25. Lin SP, Chu PM, Tsai SY, Wu MH and Hou YC. Pharmacokinetics and tissue distribution of resveratrol, emodin and their metabolites after intake of Polygonum cuspidatum in rats. Journal of Ethnopharmacology 2012; 144: 671-676.
26. Liu Y, Huang J, Liu J, Ma L, Lv Y and Shi S. A simple and sensitive liquid chromatographic technique for the determination of cefotetan disodium in human plasma and its application in a pharmacokinetic study. Journal of Huazhong University of Science and Technology. Medical Sciences 2012; 32: 779-784.
27. Magiera S, Uhlschmied C, Rainer M, Huck ChW, Baranowska I and Bonn GK. GC-MS method for the simultaneous determination of β-blockers, flavonoids, isoflavones and their metabolites in human urine. Journal of Pharmaceutical and Biomedical Analysis 2011; 56: 93-102.
28. Menozzi-Smarrito C, Wong CC, Meinl W, Glatt H, Fumeaux R, Munari C, Robert F, Williamson G and Barron D. First chemical synthesis and in vitro characterization of the potential human metabolites 5-O-feruloylquinic acid 4′-sulfate and 4′-O-glucuronide. Journal of Agricultural and Food Chemistry 2011; 59: 5671-5676.
29. Nakamura T, Tanaka R and Ashida H. Possible evidence of contamination by catechins in deconjugation enzymes from Helix pomatia and Abalone entrails. Bioscience, Biotechnology, and Biochemistry 2011; 75: 1506-1510.
30. Neirinckx E, Vervaet C, De Boever S, Remon JP, Gommeren K, Daminet S, De Backer P and Croubels S. Species comparison of oral bioavailability, first-pass metabolism and pharmacokinetics of acetaminophen. Research in Veterinary Science 2010; 89: 113-119.
31. Plomley JB, Jackson RL, Schwen RJ and Greiwe JS. Development of chiral liquid chromatography-tandem mass spectrometry isotope dilution methods for the determination of unconjugated and total S-equol in human plasma and urine. Journal of Pharmaceutical and Biomedical Analysis 2011; 55: 125-134.
32. Pozharitskaya ON, Karlina MV, Shikov AN, Kosman VM, Makarova MN and Makarov VG. Determination and pharmacokinetic study of taxifolin in rabbit plasma by high-performance liquid chromatography. Phytomedicine 2009; 16: 244-251.
33. Pritchett JJ, Kuester RK and Sipes IG. Metabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans. Drug Metabolism and Disposition 2002; 30: 1180-1185.
34. Saha S, Hollands W, Needs PW, Ostertag LM, de Roos B, Duthie GG and Kroon PA. Human O-sulfated metabolites of (-)-epicatechin and methyl-(-)-epicatechin are poor substrates for commercial aryl-sulfatases: Implications for studies concerned with quantifying epicatechin bioavailability. Pharmacological Research 2012; 65: 592-602.
35. Shelnutt SR, Cimino CO, Wiggins PA and Badger TM. Urinary pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein. Cancer Epidemiology, Biomarkers & Prevention 2000; 9: 413-419.
36. Shelnutt SR, Cimino CO, Wiggins PA, Ronis MJ and Badger TM. Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage. American Society for Clinical Nutrition 2002; 76: 588-594.
37. Shia CS, Juang SH, Tsai SY, Chang PH, Kuo SC, Hou YC and Chao PD. Metabolism and pharmacokinetics of anthraquinones in Rheum palmatum in rats and ex vivo antioxidant activity. Planta Medica 2009; 75: 1386-1392.
38. Shia CS, Hou YC, Tsai SY, Huieh PH, Leu YL and Chao PD. Differences in pharmacokinetics and ex vivo antioxidant activity following intravenous and oral administrations of emodin to rats. Journal of Pharmaceutical Sciences 2010; 99: 2185-2195.
39. Shia CS, Tsai SY, Lin JC, Li ML, Ko MH, Chao PD, Huang YC and Hou YC. Steady-state pharmacokinetics and tissue distribution of anthraquinones of Rhei Rhizoma in rats. Journal of Ethnopharmacology 2011a; 137: 1388-1394.
40. Shia CS, Hou YC, Juang SH, Tsai SY, Hsieh PH, Ho LC and Chao PD. Metabolism and pharmacokinetics of San-Huang-Xie-Xin-Tang, a polyphenol-rich Chinese medicine formula, in rats and ex-vivo antioxidant activity. Evidence-Based Complementary and Alternative Medicine 2011b; 2011: article ID 721293; doi: 10.1093/ecam/nep124
41. Shirai M, Kawai Y, Yamanishi R, Kinoshita T, Chuman H and Terao J. Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells. Free Radical Research 2006; 40: 1047-1053.
42. Taylor JI, Grace PB and Bingham SA. Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. Analytical Biochemistry 2005; 341: 220-229.
43. Teekachunhatean S, Pongnad P, Rojanasthein N, Manorot M and Sangdee C. Effects of vitamin D plus calcium supplements on pharmacokinetics of isoflavones in Thai postmenopausal women. Evidence-Based Complementary and Alternative Medicine 2011; 2011: article ID 895471; doi: 10.1155/2011/895471
44. Toennes SW and Maurer HH. Efficient cleavage of conjugates of drugs or poisons by immobilized β-glucuronidase and arylsulfatase in columns. Clinical Chemistry 1999; 45: 2173-2182.
45. Uetrecht JP and Trager W. Drug Metabolism: Chemical and Enzymatic Aspects. New York: Informa Healthcare, 2007; 130.
46. US Department of Health and Human Services, Food and Drug Administration Centre for Drug Evaluation and Research and Centre for Veterinary Medicine. Guidance for Industry, Bioanalytical Method Validation, May 2001.
47. Vaidyanathan JB and Walle T. Glucuronidation and sulfation of the tea flavonoid (-)-epicatechin by the human and rat enzymes. Drug Metabolism and Disposition 2002; 30: 897-903.
48. Walle T. Bioavailability of resveratrol. Annals of the New York Academy of Sciences 2011; 1215: 9-15.
49. Wang L and Morris ME. Liquid chromatography-tandem mass spectroscopy assay for quercetin and conjugated quercetin metabolites in human plasma and urine. Journal of Chromatography B: Biomedical Sciences and Applications 2005; 821: 194-201.
50. Wong CK and Keung WM. Daidzein sulfoconjugates are potent inhibitors of sterol sulfatase (EC 3.1.6.2). Biochemical and Biophysical Research Communications 1997; 233: 579-583.
51. Yang JH, Hsia TC, Kuo HM, Chao PD, Chou CC, Wei YH and Chung JG. Inhibition of lung cancer cell growth by quercetin glucuronides via G2/M arrest and induction of apoptosis. Drug Metabolism and Disposition 2006; 34: 296-304.
52. Yoshino S, Hara A, Sakakibara H, Kawabata K, Tokumura A, Ishisaka A, Kawai Y and Terao J. Effect of quercetin and glucuronide metabolites on the monoamine oxidase - a reaction in mouse brain mitochondria. Nutrition 2011; 27: 847-852.
53. Yu Y, Zick S, Li X, Zou P, Wright B and Sun D. Examination of the pharmacokinetics of active ingredients of ginger in humans. The AAPS Journal 2011; 13: 417-426.
54. Zhang Y, Song TT, Cunnick JE, Murphy PA and Hendrich S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and actiate human natural killer cells at nutritionally relevant concentrations. The Journal of Nutrition 1999; 129: 399-405.
55. Zhang Y, Hendrich S and Murphy PA. Glucuronides are the main isoflavone metabolites in women. The Journal of Nutrition 2003; 133: 399-404.