Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation
Tryptophan oxidation products were determined in pronase E digests of apo B of delipidated, native and Cu 2+ oxidized LDL using a sensitive and specific HPLC method. Oxidized LDL contained N-formylkynurenine, kynurenine and tryptamine but no oxindolylalanine and 5-hydroxytryptophan. N-Formylkynureni...
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| Veröffentlicht in: | FEBS letters 1996-07, Vol.389 (2), p.136-140 |
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| creator | Gieβauf, Andreas van Wickern, Barbara Simat, Thomas Steinhart, Hans Esterbauer, Hermann |
| description | Tryptophan oxidation products were determined in pronase E digests of apo B of delipidated, native and Cu
2+ oxidized LDL using a sensitive and specific HPLC method. Oxidized LDL contained
N-formylkynurenine, kynurenine and tryptamine but no oxindolylalanine and 5-hydroxytryptophan.
N-Formylkynurenine increased from an initial value of 0.21 to 1.67 mollmol apo B within 5 h. Apo B of native LDL also contained kynurenine (0.80 mollmol) and tryptamine (0.13 mol/mol). The results support the assumption that oxidation of Trp residues in apo B is an early event and possibly an elementary reaction involved in initiating LDL oxidation. |
| doi_str_mv | 10.1016/0014-5793(96)00546-7 |
| format | Article |
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2+ oxidized LDL using a sensitive and specific HPLC method. Oxidized LDL contained
N-formylkynurenine, kynurenine and tryptamine but no oxindolylalanine and 5-hydroxytryptophan.
N-Formylkynurenine increased from an initial value of 0.21 to 1.67 mollmol apo B within 5 h. Apo B of native LDL also contained kynurenine (0.80 mollmol) and tryptamine (0.13 mol/mol). The results support the assumption that oxidation of Trp residues in apo B is an early event and possibly an elementary reaction involved in initiating LDL oxidation.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/0014-5793(96)00546-7</identifier><identifier>PMID: 8766816</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>apo B, apolipoprotein B ; Apolipoproteins B - chemistry ; Apolipoproteins B - metabolism ; Chromatography, High Pressure Liquid ; Copper - metabolism ; Free Radicals ; Humans ; Kynurenine ; Kynurenine - analogs & derivatives ; Kynurenine - biosynthesis ; Kynurenine - metabolism ; LDL, low density lipoprotein ; Lipid Peroxidation ; Lipoproteins, LDL - metabolism ; Low density lipoprotein ; McOH, methanol ; MeCN, acetonitrile ; N-Formylkynurenine ; NFK, N-formylkynurenine ; Oxidation-Reduction ; PBS, phosphate buffered saline ; Pronase - metabolism ; TFA, trifluoroacetic acid, 0.1% in water ; Trp, l-tryptophan ; Tryptamine ; Tryptophan ; Tryptophan - chemistry ; Tryptophan - metabolism</subject><ispartof>FEBS letters, 1996-07, Vol.389 (2), p.136-140</ispartof><rights>1996</rights><rights>FEBS Letters 389 (1996) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5327-8120133d7ef7ad8f68124773efd7b4737cd594a57c338488a6d0e749ab95872e3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1016%2F0014-5793%2896%2900546-7$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://dx.doi.org/10.1016/0014-5793(96)00546-7$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1416,3548,27923,27924,45573,45574,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8766816$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gieβauf, Andreas</creatorcontrib><creatorcontrib>van Wickern, Barbara</creatorcontrib><creatorcontrib>Simat, Thomas</creatorcontrib><creatorcontrib>Steinhart, Hans</creatorcontrib><creatorcontrib>Esterbauer, Hermann</creatorcontrib><title>Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>Tryptophan oxidation products were determined in pronase E digests of apo B of delipidated, native and Cu
2+ oxidized LDL using a sensitive and specific HPLC method. Oxidized LDL contained
N-formylkynurenine, kynurenine and tryptamine but no oxindolylalanine and 5-hydroxytryptophan.
N-Formylkynurenine increased from an initial value of 0.21 to 1.67 mollmol apo B within 5 h. Apo B of native LDL also contained kynurenine (0.80 mollmol) and tryptamine (0.13 mol/mol). The results support the assumption that oxidation of Trp residues in apo B is an early event and possibly an elementary reaction involved in initiating LDL oxidation.</description><subject>apo B, apolipoprotein B</subject><subject>Apolipoproteins B - chemistry</subject><subject>Apolipoproteins B - metabolism</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Copper - metabolism</subject><subject>Free Radicals</subject><subject>Humans</subject><subject>Kynurenine</subject><subject>Kynurenine - analogs & derivatives</subject><subject>Kynurenine - biosynthesis</subject><subject>Kynurenine - metabolism</subject><subject>LDL, low density lipoprotein</subject><subject>Lipid Peroxidation</subject><subject>Lipoproteins, LDL - metabolism</subject><subject>Low density lipoprotein</subject><subject>McOH, methanol</subject><subject>MeCN, acetonitrile</subject><subject>N-Formylkynurenine</subject><subject>NFK, N-formylkynurenine</subject><subject>Oxidation-Reduction</subject><subject>PBS, phosphate buffered saline</subject><subject>Pronase - metabolism</subject><subject>TFA, trifluoroacetic acid, 0.1% in water</subject><subject>Trp, l-tryptophan</subject><subject>Tryptamine</subject><subject>Tryptophan</subject><subject>Tryptophan - chemistry</subject><subject>Tryptophan - metabolism</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFu1DAQhi0EKtvCG4DkE4JDwI4d27kgtaULSCu4wNny2pPWkLWDnSzkUfq2ON3VHhEna-b_5xvPDEIvKHlLCRXvCKG8amTLXrfiDSENF5V8hFZUSVYxLtRjtDpZnqLznH-QEivanqEzJYVQVKzQ_TqmnRl9DDh2-EvVlXDuf85hShB8AJyn21vIY8bjHWAf9rHfww7CuNjNEHs_xCHFEXzAVxUlBNsiQgKHxzQPYxzuTMDJOG9NnwvgyPGjP3XdfNjgwvEOD5DiH-8elGfoSVdK4PnxvUDf1zffrj9Vm68fP19fbirbsFpWitaEMuYkdNI41ZWxai4lg87JLZdMWte03DTSMqa4UkY4ApK3Zts2StbALtCrA7eM8Wsqo-qdzxb63gSIU9ZS1YyTWhQjPxhtijkn6PSQ_M6kWVOil4voZd16Wbdul6BcRMtS9vLIn7Y7cKei4wmKvj7ov30P838x9frmql6EJd-Kh-zS6P0BBGVbew9JZ-shWHA-gR21i_7fP_0LgLqwVg</recordid><startdate>19960701</startdate><enddate>19960701</enddate><creator>Gieβauf, Andreas</creator><creator>van Wickern, Barbara</creator><creator>Simat, Thomas</creator><creator>Steinhart, Hans</creator><creator>Esterbauer, Hermann</creator><general>Elsevier B.V</general><scope>6I.</scope><scope>AAFTH</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>19960701</creationdate><title>Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation</title><author>Gieβauf, Andreas ; van Wickern, Barbara ; Simat, Thomas ; Steinhart, Hans ; Esterbauer, Hermann</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5327-8120133d7ef7ad8f68124773efd7b4737cd594a57c338488a6d0e749ab95872e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>apo B, apolipoprotein B</topic><topic>Apolipoproteins B - chemistry</topic><topic>Apolipoproteins B - metabolism</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Copper - metabolism</topic><topic>Free Radicals</topic><topic>Humans</topic><topic>Kynurenine</topic><topic>Kynurenine - analogs & derivatives</topic><topic>Kynurenine - biosynthesis</topic><topic>Kynurenine - metabolism</topic><topic>LDL, low density lipoprotein</topic><topic>Lipid Peroxidation</topic><topic>Lipoproteins, LDL - metabolism</topic><topic>Low density lipoprotein</topic><topic>McOH, methanol</topic><topic>MeCN, acetonitrile</topic><topic>N-Formylkynurenine</topic><topic>NFK, N-formylkynurenine</topic><topic>Oxidation-Reduction</topic><topic>PBS, phosphate buffered saline</topic><topic>Pronase - metabolism</topic><topic>TFA, trifluoroacetic acid, 0.1% in water</topic><topic>Trp, l-tryptophan</topic><topic>Tryptamine</topic><topic>Tryptophan</topic><topic>Tryptophan - chemistry</topic><topic>Tryptophan - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gieβauf, Andreas</creatorcontrib><creatorcontrib>van Wickern, Barbara</creatorcontrib><creatorcontrib>Simat, Thomas</creatorcontrib><creatorcontrib>Steinhart, Hans</creatorcontrib><creatorcontrib>Esterbauer, Hermann</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>Gieβauf, Andreas</au><au>van Wickern, Barbara</au><au>Simat, Thomas</au><au>Steinhart, Hans</au><au>Esterbauer, Hermann</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>1996-07-01</date><risdate>1996</risdate><volume>389</volume><issue>2</issue><spage>136</spage><epage>140</epage><pages>136-140</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><abstract>Tryptophan oxidation products were determined in pronase E digests of apo B of delipidated, native and Cu
2+ oxidized LDL using a sensitive and specific HPLC method. Oxidized LDL contained
N-formylkynurenine, kynurenine and tryptamine but no oxindolylalanine and 5-hydroxytryptophan.
N-Formylkynurenine increased from an initial value of 0.21 to 1.67 mollmol apo B within 5 h. Apo B of native LDL also contained kynurenine (0.80 mollmol) and tryptamine (0.13 mol/mol). The results support the assumption that oxidation of Trp residues in apo B is an early event and possibly an elementary reaction involved in initiating LDL oxidation.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>8766816</pmid><doi>10.1016/0014-5793(96)00546-7</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | FEBS letters, 1996-07, Vol.389 (2), p.136-140 |
| issn | 0014-5793 1873-3468 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; ScienceDirect Journals (5 years ago - present); EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | apo B, apolipoprotein B Apolipoproteins B - chemistry Apolipoproteins B - metabolism Chromatography, High Pressure Liquid Copper - metabolism Free Radicals Humans Kynurenine Kynurenine - analogs & derivatives Kynurenine - biosynthesis Kynurenine - metabolism LDL, low density lipoprotein Lipid Peroxidation Lipoproteins, LDL - metabolism Low density lipoprotein McOH, methanol MeCN, acetonitrile N-Formylkynurenine NFK, N-formylkynurenine Oxidation-Reduction PBS, phosphate buffered saline Pronase - metabolism TFA, trifluoroacetic acid, 0.1% in water Trp, l-tryptophan Tryptamine Tryptophan Tryptophan - chemistry Tryptophan - metabolism |
| title | Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation |
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