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Porphyrinogenic activity and ferrochelatase-inhibitory activity of sydnones in chick embryo liver cells
3-[2-(2,4,6-Trimethylphenyl)thioethyl]-4-methylsydnone was shown to be a potent porphyrinogenic agent in chick embryo liver cells. The accumulation of protoporphyrin IX was consistent with the finding that ferrochelatase activity was inhibited. 3-Benzyl-4-phenylsydnone did not inhibit ferrochelatase...
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| Published in: | FEBS letters 1986-03, Vol.197 (1), p.17-20 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c5157-f6715dd9e88c3246b8fae66eec0d189e9cacbcad6876e2b9dd828a4470cc1a393 |
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| cites | cdi_FETCH-LOGICAL-c5157-f6715dd9e88c3246b8fae66eec0d189e9cacbcad6876e2b9dd828a4470cc1a393 |
| container_end_page | 20 |
| container_issue | 1 |
| container_start_page | 17 |
| container_title | FEBS letters |
| container_volume | 197 |
| creator | Sutherland, E.P. Marks, G.S. Grab, L.A. de Montellano, P.R.Ortiz |
| description | 3-[2-(2,4,6-Trimethylphenyl)thioethyl]-4-methylsydnone was shown to be a potent porphyrinogenic agent in chick embryo liver cells. The accumulation of protoporphyrin IX was consistent with the finding that ferrochelatase activity was inhibited. 3-Benzyl-4-phenylsydnone did not inhibit ferrochelatase activity and protoporphyrin IX was found to constitute only a minor fraction of the porphyrins. These results support the idea that the porphyrinogenicity of 3-[2-(2,4,6-trimethylphenyl)thioethyl]-4-methylsydnone is due to its catalytic activation by cytochrome P-450 leading to heme alkylation and formation of
N-vinylprotoporphyrin IX which inhibits ferrochelatase. |
| doi_str_mv | 10.1016/0014-5793(86)80289-7 |
| format | article |
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N-vinylprotoporphyrin IX which inhibits ferrochelatase.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cells, Cultured</subject><subject>Chick Embryo</subject><subject>Cytochrome P-450 Enzyme System - physiology</subject><subject>Dicarbethoxydihydrocollidine - pharmacology</subject><subject>Ferrochelatase - antagonists & inhibitors</subject><subject>General pharmacology</subject><subject>Liver - drug effects</subject><subject>Liver - metabolism</subject><subject>Lyases - antagonists & inhibitors</subject><subject>Medical sciences</subject><subject>Oxadiazoles - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Physicochemical properties. Structure-activity relationships</subject><subject>Porphyria Ferrochelatase N-Alkylprotophyrm Sydnone Cytochrome P-450 (Chick embryo liver)</subject><subject>Porphyrins - biosynthesis</subject><subject>Protoporphyrins - biosynthesis</subject><subject>Sydnones - pharmacology</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><recordid>eNqNkU2P0zAQhi0EWsrCPwApB4TgELDz4Y_LSrDaAtJKcICz5Ywn24HULnZalH9Psq3KDXGyPO8z74xfM_Zc8LeCC_mOc9GUrTL1ay3faF5pU6oHbCW0qsu6kfohW52Rx-xJzj_4fNfCXLCL2jSGi3rF7r7GtNtMiUK8w0BQOBjpQONUuOCLHlOKsMHBjS5jSWFDHY0xTX-x2Bd58iEGzAWFAjYEPwvcdmmKxUAHTAXgMOSn7FHvhozPTucl-76--Xb9qbz98vHz9fvbElrRqrKXSrTeG9Qa6qqRne4dSokI3Att0ICDDpyXWkmsOuO9rrRrGsUBhKtNfcleHX13Kf7aYx7tlvKygQsY99mqeYBUvJ3B5ghCijkn7O0u0dalyQpul3ztEp5dwrNa2vt8rZrbXpz8990W_bnpFOisvzzpLoMb-uQCUD5jev6ASooZWx-x3zTg9F-j7frmQ7UIS13L--qyz9XRCOdQD4TJZiAMgJ4Swmh9pH8_6A_STqzO</recordid><startdate>19860303</startdate><enddate>19860303</enddate><creator>Sutherland, E.P.</creator><creator>Marks, G.S.</creator><creator>Grab, L.A.</creator><creator>de Montellano, P.R.Ortiz</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>6I.</scope><scope>AAFTH</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>19860303</creationdate><title>Porphyrinogenic activity and ferrochelatase-inhibitory activity of sydnones in chick embryo liver cells</title><author>Sutherland, E.P. ; Marks, G.S. ; Grab, L.A. ; de Montellano, P.R.Ortiz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5157-f6715dd9e88c3246b8fae66eec0d189e9cacbcad6876e2b9dd828a4470cc1a393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>Chick Embryo</topic><topic>Cytochrome P-450 Enzyme System - physiology</topic><topic>Dicarbethoxydihydrocollidine - pharmacology</topic><topic>Ferrochelatase - antagonists & inhibitors</topic><topic>General pharmacology</topic><topic>Liver - drug effects</topic><topic>Liver - metabolism</topic><topic>Lyases - antagonists & inhibitors</topic><topic>Medical sciences</topic><topic>Oxadiazoles - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Physicochemical properties. Structure-activity relationships</topic><topic>Porphyria Ferrochelatase N-Alkylprotophyrm Sydnone Cytochrome P-450 (Chick embryo liver)</topic><topic>Porphyrins - biosynthesis</topic><topic>Protoporphyrins - biosynthesis</topic><topic>Sydnones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sutherland, E.P.</creatorcontrib><creatorcontrib>Marks, G.S.</creatorcontrib><creatorcontrib>Grab, L.A.</creatorcontrib><creatorcontrib>de Montellano, P.R.Ortiz</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sutherland, E.P.</au><au>Marks, G.S.</au><au>Grab, L.A.</au><au>de Montellano, P.R.Ortiz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Porphyrinogenic activity and ferrochelatase-inhibitory activity of sydnones in chick embryo liver cells</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>1986-03-03</date><risdate>1986</risdate><volume>197</volume><issue>1</issue><spage>17</spage><epage>20</epage><pages>17-20</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><coden>FEBLAL</coden><abstract>3-[2-(2,4,6-Trimethylphenyl)thioethyl]-4-methylsydnone was shown to be a potent porphyrinogenic agent in chick embryo liver cells. The accumulation of protoporphyrin IX was consistent with the finding that ferrochelatase activity was inhibited. 3-Benzyl-4-phenylsydnone did not inhibit ferrochelatase activity and protoporphyrin IX was found to constitute only a minor fraction of the porphyrins. These results support the idea that the porphyrinogenicity of 3-[2-(2,4,6-trimethylphenyl)thioethyl]-4-methylsydnone is due to its catalytic activation by cytochrome P-450 leading to heme alkylation and formation of
N-vinylprotoporphyrin IX which inhibits ferrochelatase.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>3949013</pmid><doi>10.1016/0014-5793(86)80289-7</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0014-5793 |
| ispartof | FEBS letters, 1986-03, Vol.197 (1), p.17-20 |
| issn | 0014-5793 1873-3468 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76716705 |
| source | SCIENCE DIRECT |
| subjects | Animals Biological and medical sciences Cells, Cultured Chick Embryo Cytochrome P-450 Enzyme System - physiology Dicarbethoxydihydrocollidine - pharmacology Ferrochelatase - antagonists & inhibitors General pharmacology Liver - drug effects Liver - metabolism Lyases - antagonists & inhibitors Medical sciences Oxadiazoles - pharmacology Pharmacology. Drug treatments Physicochemical properties. Structure-activity relationships Porphyria Ferrochelatase N-Alkylprotophyrm Sydnone Cytochrome P-450 (Chick embryo liver) Porphyrins - biosynthesis Protoporphyrins - biosynthesis Sydnones - pharmacology |
| title | Porphyrinogenic activity and ferrochelatase-inhibitory activity of sydnones in chick embryo liver cells |
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