Hop‐derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2)
SCOPE: Hops (Humulus lupulus L.) produce unique prenylflavonoids that exhibit interesting bioactivities. This study investigates the interactions between selected prenylflavonoids and breast cancer resistance protein (BCRP/ABCG2), an efflux transporter important for xenobiotic bioavailability and mu...
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| Veröffentlicht in: | Molecular nutrition & food research 2014-11, Vol.58 (11), p.2099-2110 |
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| creator | Tan, Kee W Cooney, Janine Jensen, Dwayne Li, Yan Paxton, James W Birch, Nigel P Scheepens, Arjan |
| description | SCOPE: Hops (Humulus lupulus L.) produce unique prenylflavonoids that exhibit interesting bioactivities. This study investigates the interactions between selected prenylflavonoids and breast cancer resistance protein (BCRP/ABCG2), an efflux transporter important for xenobiotic bioavailability and multidrug resistance (MDR). METHODS AND RESULTS: ABCG2‐inhibitory activity of xanthohumol (XN), isoxanthohumol (IX), 6‐prenylnaringenin (6‐PN), 8‐prenylnaringenin (8‐PN), and 6,8‐diprenylnarigenin (6,8‐diPN) was evaluated using mitoxantrone accumulation and vesicular transport assays. XN, IX, and 8‐PN were tested for a substrate‐type relationship with ABCG2 using ATPase and bidirectional transport assays. The prenylflavonoids exhibited significant ABCG2‐inhibitory activities in mitoxantrone accumulation and vesicular transport assays. In the ATPase assay, XN, IX, and 8‐PN inhibited baseline and sulfasalazine‐stimulated ATPase activities with IC₅₀of 2.16–27.0 μM. IX and 8‐PNalso displayed bell‐shaped activation curves in Ko143‐suppressed membranes, indicating a substrate‐type relationship. For IX, efflux ratios of 1.25 ± 0.21 and 9.18 ± 0.56 were observed in wild type and ABCG2‐overexpressing MDCKII cell monolayers, respectively. The latter was reduced to 1.25 ± 0.15 in the presence of the ABCG2‐specific inhibitor Ko143, demonstrating an ABCG2‐mediated efflux of IX. Additionally, evidence was shown for the involvement of ABCG2 in the efflux of 8‐PN and/or its sulfate conjugate. CONCLUSION: Prenylflavonoids are potent inhibitors of ABCG2 and therefore implicated in ABCG2‐mediated food/herb‐drug interactions and MDR. ABCG2‐mediated efflux of prenylflavonoids may represent one mechanism that regulates prenylflavonoid bioavailability. |
| doi_str_mv | 10.1002/mnfr.201400288 |
| format | Article |
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This study investigates the interactions between selected prenylflavonoids and breast cancer resistance protein (BCRP/ABCG2), an efflux transporter important for xenobiotic bioavailability and multidrug resistance (MDR). METHODS AND RESULTS: ABCG2‐inhibitory activity of xanthohumol (XN), isoxanthohumol (IX), 6‐prenylnaringenin (6‐PN), 8‐prenylnaringenin (8‐PN), and 6,8‐diprenylnarigenin (6,8‐diPN) was evaluated using mitoxantrone accumulation and vesicular transport assays. XN, IX, and 8‐PN were tested for a substrate‐type relationship with ABCG2 using ATPase and bidirectional transport assays. The prenylflavonoids exhibited significant ABCG2‐inhibitory activities in mitoxantrone accumulation and vesicular transport assays. In the ATPase assay, XN, IX, and 8‐PN inhibited baseline and sulfasalazine‐stimulated ATPase activities with IC₅₀of 2.16–27.0 μM. IX and 8‐PNalso displayed bell‐shaped activation curves in Ko143‐suppressed membranes, indicating a substrate‐type relationship. For IX, efflux ratios of 1.25 ± 0.21 and 9.18 ± 0.56 were observed in wild type and ABCG2‐overexpressing MDCKII cell monolayers, respectively. The latter was reduced to 1.25 ± 0.15 in the presence of the ABCG2‐specific inhibitor Ko143, demonstrating an ABCG2‐mediated efflux of IX. Additionally, evidence was shown for the involvement of ABCG2 in the efflux of 8‐PN and/or its sulfate conjugate. CONCLUSION: Prenylflavonoids are potent inhibitors of ABCG2 and therefore implicated in ABCG2‐mediated food/herb‐drug interactions and MDR. ABCG2‐mediated efflux of prenylflavonoids may represent one mechanism that regulates prenylflavonoid bioavailability.</description><identifier>ISSN: 1613-4125</identifier><identifier>EISSN: 1613-4133</identifier><identifier>DOI: 10.1002/mnfr.201400288</identifier><identifier>PMID: 25044854</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH</publisher><subject>ABC transporter ; ABCG2 ; adenosinetriphosphatase ; Antineoplastic Agents - chemistry ; ATP Binding Cassette Transporter, Sub-Family G, Member 2 ; ATP-Binding Cassette Transporters - antagonists & inhibitors ; ATP-Binding Cassette Transporters - genetics ; bioactive properties ; Bioavailability ; Biological and medical sciences ; Biological Availability ; breast neoplasms ; Breast Neoplasms - metabolism ; Drug Resistance, Neoplasm ; Feeding. Feeding behavior ; Female ; Flavanones - chemistry ; Flavonoids - chemistry ; Fundamental and applied biological sciences. Psychology ; Gene Expression Regulation, Neoplastic ; HEK293 Cells ; Herb-drug interaction ; Herb-Drug Interactions ; Humans ; Humulus - chemistry ; Humulus lupulus ; Medical sciences ; Membrane Transport Proteins - genetics ; Membrane Transport Proteins - metabolism ; Mitoxantrone - chemistry ; Multidrug resistance ; multiple drug resistance ; Multiple tumors. Solid tumors. Tumors in childhood (general aspects) ; Neoplasm Proteins - antagonists & inhibitors ; Neoplasm Proteins - genetics ; Phytoestrogens - chemistry ; Prenylflavonoid ; Propiophenones - chemistry ; sulfates ; Tumors ; Vertebrates: anatomy and physiology, studies on body, several organs or systems ; Xanthones - chemistry ; Xenobiotics - chemistry</subject><ispartof>Molecular nutrition & food research, 2014-11, Vol.58 (11), p.2099-2110</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6080-96a7b8784713c036fc54b4e53884aa88cdd3c85686ee129b0958683bfd8209a93</citedby><cites>FETCH-LOGICAL-c6080-96a7b8784713c036fc54b4e53884aa88cdd3c85686ee129b0958683bfd8209a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmnfr.201400288$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmnfr.201400288$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28911811$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25044854$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tan, Kee W</creatorcontrib><creatorcontrib>Cooney, Janine</creatorcontrib><creatorcontrib>Jensen, Dwayne</creatorcontrib><creatorcontrib>Li, Yan</creatorcontrib><creatorcontrib>Paxton, James W</creatorcontrib><creatorcontrib>Birch, Nigel P</creatorcontrib><creatorcontrib>Scheepens, Arjan</creatorcontrib><title>Hop‐derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2)</title><title>Molecular nutrition & food research</title><addtitle>Mol. Nutr. Food Res</addtitle><description>SCOPE: Hops (Humulus lupulus L.) produce unique prenylflavonoids that exhibit interesting bioactivities. This study investigates the interactions between selected prenylflavonoids and breast cancer resistance protein (BCRP/ABCG2), an efflux transporter important for xenobiotic bioavailability and multidrug resistance (MDR). METHODS AND RESULTS: ABCG2‐inhibitory activity of xanthohumol (XN), isoxanthohumol (IX), 6‐prenylnaringenin (6‐PN), 8‐prenylnaringenin (8‐PN), and 6,8‐diprenylnarigenin (6,8‐diPN) was evaluated using mitoxantrone accumulation and vesicular transport assays. XN, IX, and 8‐PN were tested for a substrate‐type relationship with ABCG2 using ATPase and bidirectional transport assays. The prenylflavonoids exhibited significant ABCG2‐inhibitory activities in mitoxantrone accumulation and vesicular transport assays. In the ATPase assay, XN, IX, and 8‐PN inhibited baseline and sulfasalazine‐stimulated ATPase activities with IC₅₀of 2.16–27.0 μM. IX and 8‐PNalso displayed bell‐shaped activation curves in Ko143‐suppressed membranes, indicating a substrate‐type relationship. For IX, efflux ratios of 1.25 ± 0.21 and 9.18 ± 0.56 were observed in wild type and ABCG2‐overexpressing MDCKII cell monolayers, respectively. The latter was reduced to 1.25 ± 0.15 in the presence of the ABCG2‐specific inhibitor Ko143, demonstrating an ABCG2‐mediated efflux of IX. Additionally, evidence was shown for the involvement of ABCG2 in the efflux of 8‐PN and/or its sulfate conjugate. CONCLUSION: Prenylflavonoids are potent inhibitors of ABCG2 and therefore implicated in ABCG2‐mediated food/herb‐drug interactions and MDR. ABCG2‐mediated efflux of prenylflavonoids may represent one mechanism that regulates prenylflavonoid bioavailability.</description><subject>ABC transporter</subject><subject>ABCG2</subject><subject>adenosinetriphosphatase</subject><subject>Antineoplastic Agents - chemistry</subject><subject>ATP Binding Cassette Transporter, Sub-Family G, Member 2</subject><subject>ATP-Binding Cassette Transporters - antagonists & inhibitors</subject><subject>ATP-Binding Cassette Transporters - genetics</subject><subject>bioactive properties</subject><subject>Bioavailability</subject><subject>Biological and medical sciences</subject><subject>Biological Availability</subject><subject>breast neoplasms</subject><subject>Breast Neoplasms - metabolism</subject><subject>Drug Resistance, Neoplasm</subject><subject>Feeding. Feeding behavior</subject><subject>Female</subject><subject>Flavanones - chemistry</subject><subject>Flavonoids - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gene Expression Regulation, Neoplastic</subject><subject>HEK293 Cells</subject><subject>Herb-drug interaction</subject><subject>Herb-Drug Interactions</subject><subject>Humans</subject><subject>Humulus - chemistry</subject><subject>Humulus lupulus</subject><subject>Medical sciences</subject><subject>Membrane Transport Proteins - genetics</subject><subject>Membrane Transport Proteins - metabolism</subject><subject>Mitoxantrone - chemistry</subject><subject>Multidrug resistance</subject><subject>multiple drug resistance</subject><subject>Multiple tumors. Solid tumors. Tumors in childhood (general aspects)</subject><subject>Neoplasm Proteins - antagonists & inhibitors</subject><subject>Neoplasm Proteins - genetics</subject><subject>Phytoestrogens - chemistry</subject><subject>Prenylflavonoid</subject><subject>Propiophenones - chemistry</subject><subject>sulfates</subject><subject>Tumors</subject><subject>Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><subject>Xanthones - chemistry</subject><subject>Xenobiotics - chemistry</subject><issn>1613-4125</issn><issn>1613-4133</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9u00AQhy0EoiVw5Qh7QSoHp_vf62MTkRRRCipUIC6r9XqWLjh22LVLc-PQB-gz8iRs5BCOnGZG-mbmpy_LnhI8JRjT41XrwpRiwtOg1L3skEjCck4Yu7_vqTjIHsX4DWNGKGcPswMqMOdK8MPs9rRb__51V0Pw11CjdYB207jGXHdt5-uITAAUhyr2wfSQxrZGvr3yle-7EFHnUH8FCJxrhhuUmDauu9BDQFUAE3tkTWvTFCD62G_79KHrwbfoaDa_eH98Mpsv6cvH2QNnmghPdnWSXS5efZyf5mfvlq_nJ2e5lVjhvJSmqFSheEGYxUw6K3jFQTCluDFK2bpmVgmpJAChZYVLoaRilasVxaUp2SQ7Gu-mED8GiL1e-WihaUwL3RA1kVQwzmgSNcmmI2pDF2MAp9fBr0zYaIL11rzemtd782nh2e72UK2g3uN_VSfgxQ4w0ZrGJVnWx3-cKglRhCSOj9xP38DmP2_12_PFBaV8Gzgf15JouNmvmfBdy4IVQn86X2r-mcnFl3Km3yT--cg702nzNaQolx_SXYkxVlKQkv0BME210Q</recordid><startdate>201411</startdate><enddate>201411</enddate><creator>Tan, Kee W</creator><creator>Cooney, Janine</creator><creator>Jensen, Dwayne</creator><creator>Li, Yan</creator><creator>Paxton, James W</creator><creator>Birch, Nigel P</creator><creator>Scheepens, Arjan</creator><general>Wiley-VCH</general><general>Blackwell Publishing Ltd</general><general>Wiley</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201411</creationdate><title>Hop‐derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2)</title><author>Tan, Kee W ; Cooney, Janine ; Jensen, Dwayne ; Li, Yan ; Paxton, James W ; Birch, Nigel P ; Scheepens, Arjan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6080-96a7b8784713c036fc54b4e53884aa88cdd3c85686ee129b0958683bfd8209a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>ABC transporter</topic><topic>ABCG2</topic><topic>adenosinetriphosphatase</topic><topic>Antineoplastic Agents - chemistry</topic><topic>ATP Binding Cassette Transporter, Sub-Family G, Member 2</topic><topic>ATP-Binding Cassette Transporters - antagonists & inhibitors</topic><topic>ATP-Binding Cassette Transporters - genetics</topic><topic>bioactive properties</topic><topic>Bioavailability</topic><topic>Biological and medical sciences</topic><topic>Biological Availability</topic><topic>breast neoplasms</topic><topic>Breast Neoplasms - metabolism</topic><topic>Drug Resistance, Neoplasm</topic><topic>Feeding. Feeding behavior</topic><topic>Female</topic><topic>Flavanones - chemistry</topic><topic>Flavonoids - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gene Expression Regulation, Neoplastic</topic><topic>HEK293 Cells</topic><topic>Herb-drug interaction</topic><topic>Herb-Drug Interactions</topic><topic>Humans</topic><topic>Humulus - chemistry</topic><topic>Humulus lupulus</topic><topic>Medical sciences</topic><topic>Membrane Transport Proteins - genetics</topic><topic>Membrane Transport Proteins - metabolism</topic><topic>Mitoxantrone - chemistry</topic><topic>Multidrug resistance</topic><topic>multiple drug resistance</topic><topic>Multiple tumors. Solid tumors. Tumors in childhood (general aspects)</topic><topic>Neoplasm Proteins - antagonists & inhibitors</topic><topic>Neoplasm Proteins - genetics</topic><topic>Phytoestrogens - chemistry</topic><topic>Prenylflavonoid</topic><topic>Propiophenones - chemistry</topic><topic>sulfates</topic><topic>Tumors</topic><topic>Vertebrates: anatomy and physiology, studies on body, several organs or systems</topic><topic>Xanthones - chemistry</topic><topic>Xenobiotics - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Kee W</creatorcontrib><creatorcontrib>Cooney, Janine</creatorcontrib><creatorcontrib>Jensen, Dwayne</creatorcontrib><creatorcontrib>Li, Yan</creatorcontrib><creatorcontrib>Paxton, James W</creatorcontrib><creatorcontrib>Birch, Nigel P</creatorcontrib><creatorcontrib>Scheepens, Arjan</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Molecular nutrition & food research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Kee W</au><au>Cooney, Janine</au><au>Jensen, Dwayne</au><au>Li, Yan</au><au>Paxton, James W</au><au>Birch, Nigel P</au><au>Scheepens, Arjan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hop‐derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2)</atitle><jtitle>Molecular nutrition & food research</jtitle><addtitle>Mol. Nutr. Food Res</addtitle><date>2014-11</date><risdate>2014</risdate><volume>58</volume><issue>11</issue><spage>2099</spage><epage>2110</epage><pages>2099-2110</pages><issn>1613-4125</issn><eissn>1613-4133</eissn><abstract>SCOPE: Hops (Humulus lupulus L.) produce unique prenylflavonoids that exhibit interesting bioactivities. This study investigates the interactions between selected prenylflavonoids and breast cancer resistance protein (BCRP/ABCG2), an efflux transporter important for xenobiotic bioavailability and multidrug resistance (MDR). METHODS AND RESULTS: ABCG2‐inhibitory activity of xanthohumol (XN), isoxanthohumol (IX), 6‐prenylnaringenin (6‐PN), 8‐prenylnaringenin (8‐PN), and 6,8‐diprenylnarigenin (6,8‐diPN) was evaluated using mitoxantrone accumulation and vesicular transport assays. XN, IX, and 8‐PN were tested for a substrate‐type relationship with ABCG2 using ATPase and bidirectional transport assays. The prenylflavonoids exhibited significant ABCG2‐inhibitory activities in mitoxantrone accumulation and vesicular transport assays. In the ATPase assay, XN, IX, and 8‐PN inhibited baseline and sulfasalazine‐stimulated ATPase activities with IC₅₀of 2.16–27.0 μM. IX and 8‐PNalso displayed bell‐shaped activation curves in Ko143‐suppressed membranes, indicating a substrate‐type relationship. For IX, efflux ratios of 1.25 ± 0.21 and 9.18 ± 0.56 were observed in wild type and ABCG2‐overexpressing MDCKII cell monolayers, respectively. The latter was reduced to 1.25 ± 0.15 in the presence of the ABCG2‐specific inhibitor Ko143, demonstrating an ABCG2‐mediated efflux of IX. Additionally, evidence was shown for the involvement of ABCG2 in the efflux of 8‐PN and/or its sulfate conjugate. CONCLUSION: Prenylflavonoids are potent inhibitors of ABCG2 and therefore implicated in ABCG2‐mediated food/herb‐drug interactions and MDR. ABCG2‐mediated efflux of prenylflavonoids may represent one mechanism that regulates prenylflavonoid bioavailability.</abstract><cop>Weinheim</cop><pub>Wiley-VCH</pub><pmid>25044854</pmid><doi>10.1002/mnfr.201400288</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | ABC transporter ABCG2 adenosinetriphosphatase Antineoplastic Agents - chemistry ATP Binding Cassette Transporter, Sub-Family G, Member 2 ATP-Binding Cassette Transporters - antagonists & inhibitors ATP-Binding Cassette Transporters - genetics bioactive properties Bioavailability Biological and medical sciences Biological Availability breast neoplasms Breast Neoplasms - metabolism Drug Resistance, Neoplasm Feeding. Feeding behavior Female Flavanones - chemistry Flavonoids - chemistry Fundamental and applied biological sciences. Psychology Gene Expression Regulation, Neoplastic HEK293 Cells Herb-drug interaction Herb-Drug Interactions Humans Humulus - chemistry Humulus lupulus Medical sciences Membrane Transport Proteins - genetics Membrane Transport Proteins - metabolism Mitoxantrone - chemistry Multidrug resistance multiple drug resistance Multiple tumors. Solid tumors. Tumors in childhood (general aspects) Neoplasm Proteins - antagonists & inhibitors Neoplasm Proteins - genetics Phytoestrogens - chemistry Prenylflavonoid Propiophenones - chemistry sulfates Tumors Vertebrates: anatomy and physiology, studies on body, several organs or systems Xanthones - chemistry Xenobiotics - chemistry |
| title | Hop‐derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2) |
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