Synthesis and in vitro Activity of Heterocyclic Inhibitors of CYP2A6 and CYP2A13, Two Cytochrome P450 Enzymes Present in the Respiratory Tract
To be sniffed at: Several 1- and 2-substituted 1H-imidazoles and 2-substituted oxazoles, oxazolines and pyrazines have been synthesized and tested as inhibitors of the cytochrome P450 enzymes CYP2A6 and CYP2A13. 1-Substituted 1H-imidazoles bearing short chains (pentyl, hexyl or hexenyl) were found t...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2009-06, Vol.10 (9), p.1562-1567 |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Chougnet, Antoinette Woggon, Wolf-D Locher, Esther Schilling, Boris |
| description | To be sniffed at: Several 1- and 2-substituted 1H-imidazoles and 2-substituted oxazoles, oxazolines and pyrazines have been synthesized and tested as inhibitors of the cytochrome P450 enzymes CYP2A6 and CYP2A13. 1-Substituted 1H-imidazoles bearing short chains (pentyl, hexyl or hexenyl) were found to be potent inhibitors of both enzymes, and showed IC₅₀ values of about 2 μM.The synthesis of several heterocyclic compounds (1- or 2-substituted 1H-imidazoles and 2-substituted oxazoles, oxazolines and pyrazines) has been achieved. These compounds were tested as inhibitors of CYP2A6 and CYP2A13--two cytochrome P450 enzymes present in the respiratory tract--with a view to preventing the formation of carcinogenic metabolites of nicotine and inhibiting the metabolism of fragrances. 1-Substituted imidazoles bearing short alkyl chains displayed IC₅₀ values of around 2 μM for both enzymes, together with high vapour pressures. |
| doi_str_mv | 10.1002/cbic.200800712 |
| format | Article |
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These compounds were tested as inhibitors of CYP2A6 and CYP2A13--two cytochrome P450 enzymes present in the respiratory tract--with a view to preventing the formation of carcinogenic metabolites of nicotine and inhibiting the metabolism of fragrances. 1-Substituted imidazoles bearing short alkyl chains displayed IC₅₀ values of around 2 μM for both enzymes, together with high vapour pressures.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.200800712</identifier><identifier>PMID: 19434638</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors ; Aryl Hydrocarbon Hydroxylases - metabolism ; CYP2A13 ; CYP2A6 ; Cytochrome P-450 CYP2A6 ; cytochromes ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacology ; Humans ; Imidazoles - chemical synthesis ; Imidazoles - chemistry ; Imidazoles - pharmacology ; inhibitors ; Respiratory System - enzymology ; Respiratory System - metabolism ; respiratory tract</subject><ispartof>Chembiochem : a European journal of chemical biology, 2009-06, Vol.10 (9), p.1562-1567</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. 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These compounds were tested as inhibitors of CYP2A6 and CYP2A13--two cytochrome P450 enzymes present in the respiratory tract--with a view to preventing the formation of carcinogenic metabolites of nicotine and inhibiting the metabolism of fragrances. 1-Substituted imidazoles bearing short alkyl chains displayed IC₅₀ values of around 2 μM for both enzymes, together with high vapour pressures.</description><subject>Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors</subject><subject>Aryl Hydrocarbon Hydroxylases - metabolism</subject><subject>CYP2A13</subject><subject>CYP2A6</subject><subject>Cytochrome P-450 CYP2A6</subject><subject>cytochromes</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacology</subject><subject>Humans</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - chemistry</subject><subject>Imidazoles - pharmacology</subject><subject>inhibitors</subject><subject>Respiratory System - enzymology</subject><subject>Respiratory System - metabolism</subject><subject>respiratory tract</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkF9v0zAUxS0EYmPwyiP4A5By_Sdx8thFY6tUbdXaMcGL5Tg2NbRxZRtG-BB85qVLNfbG0z3S_Z1zdQ9CbwlMCAD9qBunJxSgBBCEPkPHhLMqEwVjzw-aUyqO0KsYvwNAVTDyEh2RijNesPIY_V32XVqb6CJWXYtdh3-5FDye6uQG1WNv8YVJJnjd643TeNatXeOSD3G_qr8s6LR4sD5Iwj7g1Z3HdZ-8Xge_NXjBc8Bn3Z9-ayJeBBNNl_Z3hqv42sSdC2pI6_EqKJ1eoxdWbaJ5c5gn6ObT2aq-yOZX57N6Os80H97MiBItB0uBct2UJRFCQKMFI1VJWtIoWoqyVSJXprTKKtBMU22tUKZVqlGanaDJmKuDjzEYK3fBbVXoJQG5L1bui5WPxQ6Gd6Nh97PZmvYffmhyAKoRuHMb0_8nTtans_ppeDZ6XUzm96NXhR-yEEzk8vbyXN7Ol_Tr5_xUXg_8-5G3ykv1Lbgob5YUCANS8LzMGbsHgDWeKw</recordid><startdate>20090615</startdate><enddate>20090615</enddate><creator>Chougnet, Antoinette</creator><creator>Woggon, Wolf-D</creator><creator>Locher, Esther</creator><creator>Schilling, Boris</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</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></search><sort><creationdate>20090615</creationdate><title>Synthesis and in vitro Activity of Heterocyclic Inhibitors of CYP2A6 and CYP2A13, Two Cytochrome P450 Enzymes Present in the Respiratory Tract</title><author>Chougnet, Antoinette ; Woggon, Wolf-D ; Locher, Esther ; Schilling, Boris</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4712-1a7d40f2024cb8817770bc731981d1ba2878da75ae8fafa0c3c2cff7aedaabac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors</topic><topic>Aryl Hydrocarbon Hydroxylases - metabolism</topic><topic>CYP2A13</topic><topic>CYP2A6</topic><topic>Cytochrome P-450 CYP2A6</topic><topic>cytochromes</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - pharmacology</topic><topic>Humans</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - chemistry</topic><topic>Imidazoles - pharmacology</topic><topic>inhibitors</topic><topic>Respiratory System - enzymology</topic><topic>Respiratory System - metabolism</topic><topic>respiratory tract</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chougnet, Antoinette</creatorcontrib><creatorcontrib>Woggon, Wolf-D</creatorcontrib><creatorcontrib>Locher, Esther</creatorcontrib><creatorcontrib>Schilling, Boris</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chougnet, Antoinette</au><au>Woggon, Wolf-D</au><au>Locher, Esther</au><au>Schilling, Boris</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and in vitro Activity of Heterocyclic Inhibitors of CYP2A6 and CYP2A13, Two Cytochrome P450 Enzymes Present in the Respiratory Tract</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>ChemBioChem</addtitle><date>2009-06-15</date><risdate>2009</risdate><volume>10</volume><issue>9</issue><spage>1562</spage><epage>1567</epage><pages>1562-1567</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>To be sniffed at: Several 1- and 2-substituted 1H-imidazoles and 2-substituted oxazoles, oxazolines and pyrazines have been synthesized and tested as inhibitors of the cytochrome P450 enzymes CYP2A6 and CYP2A13. 1-Substituted 1H-imidazoles bearing short chains (pentyl, hexyl or hexenyl) were found to be potent inhibitors of both enzymes, and showed IC₅₀ values of about 2 μM.The synthesis of several heterocyclic compounds (1- or 2-substituted 1H-imidazoles and 2-substituted oxazoles, oxazolines and pyrazines) has been achieved. These compounds were tested as inhibitors of CYP2A6 and CYP2A13--two cytochrome P450 enzymes present in the respiratory tract--with a view to preventing the formation of carcinogenic metabolites of nicotine and inhibiting the metabolism of fragrances. 1-Substituted imidazoles bearing short alkyl chains displayed IC₅₀ values of around 2 μM for both enzymes, together with high vapour pressures.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>19434638</pmid><doi>10.1002/cbic.200800712</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; Wiley Journals |
| subjects | Aryl Hydrocarbon Hydroxylases - antagonists & inhibitors Aryl Hydrocarbon Hydroxylases - metabolism CYP2A13 CYP2A6 Cytochrome P-450 CYP2A6 cytochromes Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Humans Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - pharmacology inhibitors Respiratory System - enzymology Respiratory System - metabolism respiratory tract |
| title | Synthesis and in vitro Activity of Heterocyclic Inhibitors of CYP2A6 and CYP2A13, Two Cytochrome P450 Enzymes Present in the Respiratory Tract |
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