Interaction of hesperetin glucuronide conjugates with human BCRP, MRP2 and MRP3 as detected in membrane vesicles of overexpressing baculovirus-infected Sf9 cells

Biopharmaceutics and Drug Disposition

Volumn 32, Issue 9, 2011, Pages 530-535

  Brand, Walter ^a,b   Oosterhuis, Berend ^c   Krajcsi, Peter ^c   Barron, Denis ^a   Dionisi, Fabiola ^a   Van Bladeren, Peter J ^a,b   Rietjens, Ivonne M C M ^b   Williamson, Gary ^a,d  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c SOLVO BIOTECHNOLOGY   (Hungary)

^d UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

ABC transporters; ATPase activity; flavonoid; glucuronide conjugate; MRP3

Indexed keywords

ADENOSINE TRIPHOSPHATASE; BREAST CANCER RESISTANCE PROTEIN; GLUCURONIDE; HESPERETIN; HESPERETIN 3' O GLUCURONIDE; HESPERETIN 7 O GLUCURONIDE; MULTIDRUG RESISTANCE PROTEIN 2; MULTIDRUG RESISTANCE PROTEIN 3; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL LINE; DRUG EFFECT; DRUG PROTEIN BINDING; ENZYME INHIBITION; GLUCURONIDATION; MEMBRANE VESICLE; NONHUMAN;

ADENOSINE TRIPHOSPHATASES; ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; BACULOVIRIDAE; CELL LINE; CELL MEMBRANE; GLUCURONIDES; HESPERIDIN; HUMANS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NEOPLASM PROTEINS; SPODOPTERA; TRANSPORT VESICLES;

EID: 82155162339     PISSN: 01422782     EISSN: 1099081X     Source Type: Journal    
DOI: 10.1002/bdd.780     Document Type: Article

References (20)

1. Yanez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM,. Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices. Biopharm Drug Dispos 2008; 29: 63-82. doi: 10.1002/bdd.588. (Pubitemid 351516388)
2. Garg A, Garg S, Zaneveld LJ, Singla AK,. Chemistry and pharmacology of the citrus bioflavonoid hesperidin. Phytother Res 2001; 15: 655-669. doi: 10.1002/ptr.1074. (Pubitemid 34016792)
3. Horcajada MN, Habauzit V, Trzeciakiewicz A, et al,. Hesperidin inhibits ovariectomized-induced osteopenia and shows differential effects on bone mass and strength in young and adult intact rats. J Appl Physiol 2008; 104: 648-654. doi: 10.1152/japplphysiol.00441.2007. (Pubitemid 351468792)
4. Brand W, Boersma MG, Bik H, et al,. Phase II metabolism of hesperetin by individual UDP-glucuronosyltransferases and sulfotransferases and rat and human tissue samples. Drug Metab Dispos 2010; 38: 617-625. doi: 10.1124/dmd.109. 031047.
5. Brand W, Shao J, Hoek-van den Hil EF, et al,. Stereoselective conjugation, transport and bioactivity of S- and R-hesperetin enantiomers in vitro. J Agric Food Chem 2010; 58: 6119-6125. doi: 10.1021/jf1008617.
6. Liu Z, Hu M,. Natural polyphenol disposition via coupled metabolic pathways. Expert Opin Drug Metab Toxicol 2007; 3: 389-406. doi: 10.1517/17425255.3.3.389. (Pubitemid 47316031)
7. Brand W, van der Wel PAI, Rein MJ, et al,. Metabolism and transport of the citrus flavonoid hesperetin in Caco-2 cell monolayers. Drug Metab Dispos 2008; 36: 1794-1802. doi: 10.1124/dmd.107.019943.
8. Brett GM, Hollands W, Needs PW, et al,. Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion. Br J Nutr 2009; 101: 664-675. doi: 10.1017/S000711450803081X.
9. Matsumoto H, Ikoma Y, Sugiura M, Yano M, Hasegawa Y,. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. J Agric Food Chem 2004; 52: 6653-6659. doi: 10.1021/jf0491411.
10. Mullen W, Archeveque MA, Edwards CA, Matsumoto H, Crozier A,. Bioavailability and metabolism of orange juice flavanones in humans: impact of a full-fat yogurt. J Agric Food Chem 2008; 56: 11157-11164. doi: 10.1021/jf801974v.
11. Taipalensuu J, Tornblom H, Lindberg G, et al,. Correlation of gene expression of ten drug efflux proteins of the ATP-binding cassette transporter family in normal human jejunum and in human intestinal epithelial Caco-2 cell monolayers. J Pharmacol Exp Ther 2001; 299: 164-170. (Pubitemid 32905131)
12. Glavinas H, Kis E, Pal A, et al,. ABCG2 (breast cancer resistance protein/mitoxantrone resistance-associated protein) ATPase assay: a useful tool to detect drug-transporter interactions. Drug Metab Dispos 2007; 35: 1533-1542. doi: 10.1124/dmd.106.014605. (Pubitemid 47296046)
13. Boumendjel A, Blanc M, Williamson G, Barron D,. Efficient synthesis of flavanone glucuronides. J Agric Food Chem 2009; 57: 7264-7267. doi: 10.1021/jf9011467.
14. Zhang L, Lin G, Kovacs B, Jani M, Krajcsi P, Zuo Z,. Mechanistic study on the intestinal absorption and disposition of baicalein. Eur J Pharm Sci 2007; 31: 221-231. doi: 10.1016/j.ejps.2007.04.001. (Pubitemid 46818982)
15. Bodo A, Bakos E, Szeri F, Varadi A, Sarkadi B,. Differential modulation of the human liver conjugate transporters MRP2 and MRP3 by bile acids and organic anions. J Biol Chem 2003; 278: 23529-23537. doi: 10.1074/jbc.M303515200. (Pubitemid 36830172)
16. van Zanden JJ, van der Woude H, Vaessen J, et al,. The effect of quercetin phase rential. Biochem Pharmacol 2007; 74: 345-351. doi: 10.1016/j.bcp.2007.04.002.
17. Williamson G, Aeberli I, Miguet L, et al,. Interaction of positional isomers of quercetin glucuronides with the transporter ABCC2 (cMOAT, MRP2). Drug Metab Dispos 2007; 35: 1262-1268. doi: 10.1124/dmd.106.014241. (Pubitemid 47121765)
18. Buxbaum E,. Co-operative binding sites for transported substrates in the multiple drug resistance transporter Mdr1. Eur J Biochem 1999; 265: 64-70. doi: 10.1046/j.1432-1327.1999.00644.x. (Pubitemid 29466012)
19. Brand W, Padilla B, van Bladeren PJ, Williamson G, Rietjens IMCM,. The effect of co-administered flavonoids on the metabolism of hesperetin and the disposition of its metabolites in Caco-2 cell monolayers. Mol Nutr Food Res 2010; 54: 851-860. doi: 10.1002/mnfr.200900183.
20. Brand W, Schutte ME, Williamson G, et al,. Flavonoid-mediated inhibition of intestinal ABC transporters may affect the oral bioavailability of drugs, food-borne toxic compounds and bioactive ingredients. Biomed Pharmacother 2006; 60: 508-519. doi: 10.1016/j.biopha.2006.07.081. (Pubitemid 44635082)