The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells
[Display omitted] As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activitie...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2019-06, Vol.29 (11), p.1403-1406 |
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| container_issue | 11 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 29 |
| creator | Ruparelia, Ketan C. Lodhi, Sabahat Ankrett, Dyan N. Wilsher, Nicola E. Arroo, Randolph R.J. Potter, Gerard A. Beresford, Kenneth J.M. |
| description | [Display omitted]
As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds. |
| doi_str_mv | 10.1016/j.bmcl.2019.03.030 |
| format | Article |
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As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2019.03.030</identifier><identifier>PMID: 30935796</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>4,6-Diaryl-2-pyridones ; Antiproliferative ; Chalcones ; CYP1B1 ; Prodrug</subject><ispartof>Bioorganic & medicinal chemistry letters, 2019-06, Vol.29 (11), p.1403-1406</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c400t-8675c9ee06c111b57f941415eb1fb27dbdfcce0af90bd4261723c2147df938153</citedby><cites>FETCH-LOGICAL-c400t-8675c9ee06c111b57f941415eb1fb27dbdfcce0af90bd4261723c2147df938153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2019.03.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27926,27927,45997</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30935796$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ruparelia, Ketan C.</creatorcontrib><creatorcontrib>Lodhi, Sabahat</creatorcontrib><creatorcontrib>Ankrett, Dyan N.</creatorcontrib><creatorcontrib>Wilsher, Nicola E.</creatorcontrib><creatorcontrib>Arroo, Randolph R.J.</creatorcontrib><creatorcontrib>Potter, Gerard A.</creatorcontrib><creatorcontrib>Beresford, Kenneth J.M.</creatorcontrib><title>The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.</description><subject>4,6-Diaryl-2-pyridones</subject><subject>Antiproliferative</subject><subject>Chalcones</subject><subject>CYP1B1</subject><subject>Prodrug</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE2LFDEQhoMo7rj6BzxIjh7ssSqdTk_AiwyrKyzoYQU9hXxU3Aw93WPSszj_3jSz7lF4oS5PvVQ9jL1GWCOger9bu70f1gJQr6GtgSdshVLJppXQPWUr0AqajZY_LtiLUnYAKEHK5-yiBd12vVYrFm_viJfTON9RSYVPkct3qgnJ5tPQiOZwyilMIxVux8ArlDJ3abJ-Tvd2TtPI08i3P78hpz-HTKWk8Rd3mWyZubejp8w9DUN5yZ5FOxR69TAv2fdPV7fb6-bm6-cv2483jZcAc7NRfec1ESiPiK7ro5YosSOH0Yk-uBC9J7BRgwtSKOxF6wXKPkTdbrBrL9nbc-8hT7-PVGazT2W5wI40HYsRApZopSsqzqjPUymZojnktK9_GwSz-DU7s_g1i18DbQ3UpTcP_Ue3p_C48k9oBT6cAapf3ifKpvhEVURImfxswpT-1_8Xzs2Lxg</recordid><startdate>20190601</startdate><enddate>20190601</enddate><creator>Ruparelia, Ketan C.</creator><creator>Lodhi, Sabahat</creator><creator>Ankrett, Dyan N.</creator><creator>Wilsher, Nicola E.</creator><creator>Arroo, Randolph R.J.</creator><creator>Potter, Gerard A.</creator><creator>Beresford, Kenneth J.M.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20190601</creationdate><title>The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells</title><author>Ruparelia, Ketan C. ; Lodhi, Sabahat ; Ankrett, Dyan N. ; Wilsher, Nicola E. ; Arroo, Randolph R.J. ; Potter, Gerard A. ; Beresford, Kenneth J.M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c400t-8675c9ee06c111b57f941415eb1fb27dbdfcce0af90bd4261723c2147df938153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>4,6-Diaryl-2-pyridones</topic><topic>Antiproliferative</topic><topic>Chalcones</topic><topic>CYP1B1</topic><topic>Prodrug</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ruparelia, Ketan C.</creatorcontrib><creatorcontrib>Lodhi, Sabahat</creatorcontrib><creatorcontrib>Ankrett, Dyan N.</creatorcontrib><creatorcontrib>Wilsher, Nicola E.</creatorcontrib><creatorcontrib>Arroo, Randolph R.J.</creatorcontrib><creatorcontrib>Potter, Gerard A.</creatorcontrib><creatorcontrib>Beresford, Kenneth J.M.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ruparelia, Ketan C.</au><au>Lodhi, Sabahat</au><au>Ankrett, Dyan N.</au><au>Wilsher, Nicola E.</au><au>Arroo, Randolph R.J.</au><au>Potter, Gerard A.</au><au>Beresford, Kenneth J.M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2019-06-01</date><risdate>2019</risdate><volume>29</volume><issue>11</issue><spage>1403</spage><epage>1406</epage><pages>1403-1406</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP)1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6–60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30935796</pmid><doi>10.1016/j.bmcl.2019.03.030</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| source | Access via ScienceDirect (Elsevier) |
| subjects | 4,6-Diaryl-2-pyridones Antiproliferative Chalcones CYP1B1 Prodrug |
| title | The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells |
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