Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6)
Flavonoids are conjugated by phase II enzymes in humans to form glucuronidated and sulfated metabolites that are excreted in urine via the kidney. In this study, we examined the interaction between metabolites of quercetin and isoflavonoids found in vivo with human organic anion transporters 1 (OAT1...
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Published in | Biochemical pharmacology Vol. 81; no. 7; pp. 942 - 949 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Amsterdam
Elsevier Inc
01.04.2011
Elsevier |
Subjects | |
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Abstract | Flavonoids are conjugated by phase II enzymes in humans to form glucuronidated and sulfated metabolites that are excreted in urine via the kidney. In this study, we examined the interaction between metabolites of quercetin and isoflavonoids found
in vivo with human organic anion transporters 1 (OAT1) and 3 (OAT3) and their potential in attenuating OAT-induced cytotoxicity of adefovir. Accumulation of flavonoid conjugates was studied in human embryonic kidney 293H cells overexpressing OAT1 or OAT3. OAT1-overexpressing cells exhibited an increased uptake of the sulfated conjugates, genistein-4′-
O-sulfate and quercetin-3′-
O-sulfate. OAT3-overexpressing cells demonstrated enhanced uptake of glucuronide conjugates, such as daidzein-7-
O-glucuronide, genistein-7-
O-glucuronide, glycitein-7-
O-glucuronide and quercetin-3′-
O-glucuronide. Position of conjugation was important since quercetin-3-
O-glucuronide and quercetin-7-
O-glucuronide were poorly transported. Kinetic analysis revealed high affinity uptake of quercetin-3′-
O-sulfate by OAT1 (
K
m
=
1.73
μM;
V
max
=
105
pmol/min/mg). OAT3 transported isoflavone glucuronides with lower affinity (
K
m
=
7.9–19.1
μM) but with higher
V
max (171–420
pmol/min/mg). Quercetin-3′-
O-sulfate strongly inhibited OAT1-mediated
p-aminohippuric acid uptake with an IC
50 of 1.22
μM. Transport of 5-carboxyfluorescein by OAT3 was potently inhibited by quercetin-3-
O-glucuronide, quercetin-3′-
O-glucuronide and quercetin-3′-
O-sulfate (IC
50
=
0.43–1.31
μM). In addition, quercetin-3′-
O-sulfate was shown to effectively reduce OAT1-mediated cytotoxicity of adefovir, an antiviral drug, in a dose-dependent manner. These data suggest that OAT1 and OAT3 are responsible for basolateral uptake of flavonoid conjugates in kidney, and flavonoid conjugates inhibit OAT1 and OAT3 activity at physiologically relevant concentrations. Interaction with OATs limits systemic availability of flavonoids and may be a mechanism of food–drug interaction via inhibition of renal uptake. |
---|---|
AbstractList | Flavonoids are conjugated by phase II enzymes in humans to form glucuronidated and sulfated metabolites that are excreted in urine via the kidney. In this study, we examined the interaction between metabolites of quercetin and isoflavonoids found in vivo with human organic anion transporters 1 (OAT1) and 3 (OAT3) and their potential in attenuating OAT-induced cytotoxicity of adefovir. Accumulation of flavonoid conjugates was studied in human embryonic kidney 293H cells overexpressing OAT1 or OAT3. OAT1-overexpressing cells exhibited an increased uptake of the sulfated conjugates, genistein-4'-O-sulfate and quercetin-3'-O-sulfate. OAT3-overexpressing cells demonstrated enhanced uptake of glucuronide conjugates, such as daidzein-7-O-glucuronide, genistein-7-O-glucuronide, glycitein-7-O-glucuronide and quercetin-3'-O-glucuronide. Position of conjugation was important since quercetin-3-O-glucuronide and quercetin-7-O-glucuronide were poorly transported. Kinetic analysis revealed high affinity uptake of quercetin-3'-O-sulfate by OAT1 (K(m)=1.73μM; V(max)=105 pmol/min/mg). OAT3 transported isoflavone glucuronides with lower affinity (K(m)=7.9-19.1 μM) but with higher V(max) (171-420 pmol/min/mg). Quercetin-3'-O-sulfate strongly inhibited OAT1-mediated p-aminohippuric acid uptake with an IC(50) of 1.22μM. Transport of 5-carboxyfluorescein by OAT3 was potently inhibited by quercetin-3-O-glucuronide, quercetin-3'-O-glucuronide and quercetin-3'-O-sulfate (IC(50)=0.43-1.31μM). In addition, quercetin-3'-O-sulfate was shown to effectively reduce OAT1-mediated cytotoxicity of adefovir, an antiviral drug, in a dose-dependent manner. These data suggest that OAT1 and OAT3 are responsible for basolateral uptake of flavonoid conjugates in kidney, and flavonoid conjugates inhibit OAT1 and OAT3 activity at physiologically relevant concentrations. Interaction with OATs limits systemic availability of flavonoids and may be a mechanism of food-drug interaction via inhibition of renal uptake. Flavonoids are conjugated by phase II enzymes in humans to form glucuronidated and sulfated metabolites that are excreted in urine via the kidney. In this study, we examined the interaction between metabolites of quercetin and isoflavonoids found in vivo with human organic anion transporters 1 (OAT1) and 3 (OAT3) and their potential in attenuating OAT-induced cytotoxicity of adefovir. Accumulation of flavonoid conjugates was studied in human embryonic kidney 293H cells overexpressing OAT1 or OAT3. OAT1-overexpressing cells exhibited an increased uptake of the sulfated conjugates, genistein-4′- O-sulfate and quercetin-3′- O-sulfate. OAT3-overexpressing cells demonstrated enhanced uptake of glucuronide conjugates, such as daidzein-7- O-glucuronide, genistein-7- O-glucuronide, glycitein-7- O-glucuronide and quercetin-3′- O-glucuronide. Position of conjugation was important since quercetin-3- O-glucuronide and quercetin-7- O-glucuronide were poorly transported. Kinetic analysis revealed high affinity uptake of quercetin-3′- O-sulfate by OAT1 ( K m = 1.73 μM; V max = 105 pmol/min/mg). OAT3 transported isoflavone glucuronides with lower affinity ( K m = 7.9–19.1 μM) but with higher V max (171–420 pmol/min/mg). Quercetin-3′- O-sulfate strongly inhibited OAT1-mediated p-aminohippuric acid uptake with an IC 50 of 1.22 μM. Transport of 5-carboxyfluorescein by OAT3 was potently inhibited by quercetin-3- O-glucuronide, quercetin-3′- O-glucuronide and quercetin-3′- O-sulfate (IC 50 = 0.43–1.31 μM). In addition, quercetin-3′- O-sulfate was shown to effectively reduce OAT1-mediated cytotoxicity of adefovir, an antiviral drug, in a dose-dependent manner. These data suggest that OAT1 and OAT3 are responsible for basolateral uptake of flavonoid conjugates in kidney, and flavonoid conjugates inhibit OAT1 and OAT3 activity at physiologically relevant concentrations. Interaction with OATs limits systemic availability of flavonoids and may be a mechanism of food–drug interaction via inhibition of renal uptake. Flavonoids are conjugated by phase II enzymes in humans to form glucuronidated and sulfated metabolites that are excreted in urine via the kidney. In this study, we examined the interaction between metabolites of quercetin and isoflavonoids found with human organic anion transporters 1 (OAT1) and 3 (OAT3) and their potential in attenuating OATs-induced cytotoxicity of adefovir. Accumulation of flavonoid conjugates was studied in human embryonic kidney 293H cells overexpressing OAT1 or OAT3. OAT1-overexpressing cells exhibited an increased uptake of the sulfated conjugates, genistein-4′--sulfate and quercetin-3′--sulfate. OAT3-overexpressing cells demonstrated enhanced uptake of glucuronide conjugates, such as daidzein-7--glucuronide, genistein-7--glucuronide, glycitein-7--glucuronide and quercetin-3′--glucuronide. Position of conjugation was important since quercetin-3--glucuronide and quercetin-7--glucuronide were poorly transported. Kinetic analysis revealed high affinity uptake of quercetin-3′--sulfate by OAT1 (K=1.73μM;V=105 pmol/(min x mg)). OAT3 transported isoflavone glucuronides with lower affinity (K=7.9-19.1μM) but with higher V (171-420 pmol/(min x mg)). Quercetin-3′--sulfate strongly inhibited OAT1-mediated -aminohippuric acid uptake with an IC of 1.22μM. Transport of 5-carboxyfluorescein by OAT3 was potently inhibited by quercetin-3--glucuronide, quercetin-3′--glucuronide and quercetin-3′-sulfate (IC=0.43-1.31μM). In addition, quercetin-3′--sulfate was shown to effectively reduce OAT1-mediated cytotoxicity of adefovir, an antiviral drug, in a dose-dependent manner. These data suggest that OAT1 and OAT3 are responsible for basolateral uptake of flavonoid conjugates in kidney, and flavonoid conjugates inhibit OAT1 and OAT3 activity at physiologically relevant concentrations. Interaction with OATs limits systemic availability of flavonoids and may be a mechanism of food-drug interaction via inhibition of renal uptake. |
Author | Orfila, Caroline Wong, Chi Chun Botting, Nigel P. Al-Maharik, Nawaf Williamson, Gary |
Author_xml | – sequence: 1 givenname: Chi Chun surname: Wong fullname: Wong, Chi Chun email: fsccdw@leeds.ac.uk organization: School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK – sequence: 2 givenname: Nigel P. surname: Botting fullname: Botting, Nigel P. email: npb@st-andrews.ac.uk organization: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST, Scotland, UK – sequence: 3 givenname: Caroline surname: Orfila fullname: Orfila, Caroline email: c.orfila@leeds.ac.uk organization: School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK – sequence: 4 givenname: Nawaf surname: Al-Maharik fullname: Al-Maharik, Nawaf organization: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST, Scotland, UK – sequence: 5 givenname: Gary surname: Williamson fullname: Williamson, Gary email: g.williamson@leeds.ac.uk organization: School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK |
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Copyright | 2011 Elsevier Inc. 2015 INIST-CNRS Copyright © 2011 Elsevier Inc. All rights reserved. Distributed under a Creative Commons Attribution 4.0 International License |
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Keywords | BCRP Organic anion transporters OAT Quercetin MRP Bioavailability Food–drug interaction Isoflavones RNA-directed DNA polymerase Cytotoxicity Nucleotide analog Isoflavone derivatives Flavonoid Food drug interaction Phytoestrogen Polyphenol Reverse transcriptase inhibitor Organic anion transporter Nucleoside analog Antiviral Food-drug interaction Isoflavone Purine nucleotide Acyclic nucleotide Enzyme Transferases Enzyme inhibitor Organic phosphonate Organic anion transporter OAT1 Nucleotidyltransferases Adefovir Phenols Conjugated compound Pharmacokinetics quercetin food-drug interaction isoflavones bioavailability organic anion transporters |
Language | English |
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SubjectTerms | Adenine - analogs & derivatives Adenine - pharmacology Antiviral Agents - pharmacology Bioavailability Biological and medical sciences Cell Line Chromatography, High Pressure Liquid Flavonoids - pharmacology Food–drug interaction Humans Isoflavones Kinetics Life Sciences Medical sciences Organic Anion Transport Protein 1 - metabolism Organic anion transporters Organophosphonates - pharmacology Pharmaceutical sciences Pharmacology Pharmacology. Drug treatments Quercetin |
Title | Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6) |
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