The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization
Dimerization of tyrosine phenoxyl radical yields bityrosine (BT) which can easily be monitored by its characteristic fluorescence at 400 nm. The reactivity of tyrosine phenoxyl radical with O 2 was examined by a variety of techniques. BT fluorescence was measured as a function of O 2 concentration....
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| Veröffentlicht in: | Free radical biology & medicine 1989, Vol.6 (6), p.581-585 |
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| creator | Hunter, Edward P.L. Desrosiers, Marc F. Simic, Michael G. |
| description | Dimerization of tyrosine phenoxyl radical yields bityrosine (BT) which can easily be monitored by its characteristic fluorescence at 400 nm. The reactivity of tyrosine phenoxyl radical with O
2 was examined by a variety of techniques. BT fluorescence was measured as a function of O
2 concentration. Over a range of pH values (4–12) there was no effect of oxygen on BT production ([O
2] ≤ 0.72 mM). In addition, oxygen uptake by the phenoxyl radical was measured directly with an oxygen electrode. It was determined by this technique that oxygen does not react with the phenoxyl radical with a rate constant greater than 10
3 M
−1s
−1. Tyrosine phenoxyl radical “repair” by superoxide and physiological antioxidants was examined by BT fluorescence quenching as well as pulse radiolysis. Implications of these results as to the fate of tyrosine phenoxyl radicals produced in biological systems is discussed. |
| doi_str_mv | 10.1016/0891-5849(89)90064-6 |
| format | Article |
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2 was examined by a variety of techniques. BT fluorescence was measured as a function of O
2 concentration. Over a range of pH values (4–12) there was no effect of oxygen on BT production ([O
2] ≤ 0.72 mM). In addition, oxygen uptake by the phenoxyl radical was measured directly with an oxygen electrode. It was determined by this technique that oxygen does not react with the phenoxyl radical with a rate constant greater than 10
3 M
−1s
−1. Tyrosine phenoxyl radical “repair” by superoxide and physiological antioxidants was examined by BT fluorescence quenching as well as pulse radiolysis. Implications of these results as to the fate of tyrosine phenoxyl radicals produced in biological systems is discussed.</description><identifier>ISSN: 0891-5849</identifier><identifier>EISSN: 1873-4596</identifier><identifier>DOI: 10.1016/0891-5849(89)90064-6</identifier><identifier>PMID: 2546863</identifier><identifier>CODEN: FRBMEH</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>560300 - Chemicals Metabolism & Toxicology ; AMINO ACIDS ; Aminoacids, peptides. Hormones. Neuropeptides ; Analytical, structural and metabolic biochemistry ; ANTIOXIDANTS ; ASCORBIC ACID ; Biological and medical sciences ; BIOLOGICAL EFFECTS ; Bityrosine ; CARBOXYLIC ACIDS ; CHEMICAL REACTIONS ; Chromans ; DIMERIZATION ; ELEMENTS ; FLUORESCENCE ; Free Radicals ; Fundamental and applied biological sciences. Psychology ; Gamma radiolysis ; HYDROXY ACIDS ; LUMINESCENCE ; NONMETALS ; ORGANIC ACIDS ; ORGANIC COMPOUNDS ; OXYGEN ; PHENOXY RADICALS ; Phenoxyl ; POLYMERIZATION ; Proteins ; Pulse radiolysis ; RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT ; RADICALS ; Spectrometry, Fluorescence ; SUPEROXIDE RADICALS ; Superoxides ; TYROSINE ; Tyrosine - analogs & derivatives ; Tyrosine - radiation effects ; VITAMINS</subject><ispartof>Free radical biology & medicine, 1989, Vol.6 (6), p.581-585</ispartof><rights>1989</rights><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c480t-dbbb57e171e76280d635744f615575c3bd370650ccb3ac3547eeb22a83e68f113</citedby><cites>FETCH-LOGICAL-c480t-dbbb57e171e76280d635744f615575c3bd370650ccb3ac3547eeb22a83e68f113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0891584989900646$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3537,4010,27900,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19487742$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2546863$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/5542626$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Hunter, Edward P.L.</creatorcontrib><creatorcontrib>Desrosiers, Marc F.</creatorcontrib><creatorcontrib>Simic, Michael G.</creatorcontrib><title>The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization</title><title>Free radical biology & medicine</title><addtitle>Free Radic Biol Med</addtitle><description>Dimerization of tyrosine phenoxyl radical yields bityrosine (BT) which can easily be monitored by its characteristic fluorescence at 400 nm. The reactivity of tyrosine phenoxyl radical with O
2 was examined by a variety of techniques. BT fluorescence was measured as a function of O
2 concentration. Over a range of pH values (4–12) there was no effect of oxygen on BT production ([O
2] ≤ 0.72 mM). In addition, oxygen uptake by the phenoxyl radical was measured directly with an oxygen electrode. It was determined by this technique that oxygen does not react with the phenoxyl radical with a rate constant greater than 10
3 M
−1s
−1. Tyrosine phenoxyl radical “repair” by superoxide and physiological antioxidants was examined by BT fluorescence quenching as well as pulse radiolysis. Implications of these results as to the fate of tyrosine phenoxyl radicals produced in biological systems is discussed.</description><subject>560300 - Chemicals Metabolism & Toxicology</subject><subject>AMINO ACIDS</subject><subject>Aminoacids, peptides. Hormones. Neuropeptides</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>ANTIOXIDANTS</subject><subject>ASCORBIC ACID</subject><subject>Biological and medical sciences</subject><subject>BIOLOGICAL EFFECTS</subject><subject>Bityrosine</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHEMICAL REACTIONS</subject><subject>Chromans</subject><subject>DIMERIZATION</subject><subject>ELEMENTS</subject><subject>FLUORESCENCE</subject><subject>Free Radicals</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gamma radiolysis</subject><subject>HYDROXY ACIDS</subject><subject>LUMINESCENCE</subject><subject>NONMETALS</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>OXYGEN</subject><subject>PHENOXY RADICALS</subject><subject>Phenoxyl</subject><subject>POLYMERIZATION</subject><subject>Proteins</subject><subject>Pulse radiolysis</subject><subject>RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT</subject><subject>RADICALS</subject><subject>Spectrometry, Fluorescence</subject><subject>SUPEROXIDE RADICALS</subject><subject>Superoxides</subject><subject>TYROSINE</subject><subject>Tyrosine - analogs & derivatives</subject><subject>Tyrosine - radiation effects</subject><subject>VITAMINS</subject><issn>0891-5849</issn><issn>1873-4596</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU-LFDEQxYMo67j6DRSCoCjYmnT-9kWQRXcXFrys55BOqp1ITzImPcuOn97EGcbbnoqkfvWo9wqhl5R8pITKT0QPtBOaD-_08H4gRPJOPkIrqhXruBjkY7Q6IU_Rs1J-EUK4YPoMnfWCSy3ZCvnbNWCYJnALThNO9_ufED9gG5eQ7oOvtbSXx2W3hdy-AGfrg7MzThEv-5xKiIC3a4h1eD41fdhADn9s1YnP0ZPJzgVeHOs5-vHt6-3FVXfz_fL64stN57gmS-fHcRQKqKKgZK-Jl0wozidJhVDCsdEzRaQgzo3MOia4Ahj73moGUk-UsnP0-qCbyhJMcWEBt3YpxurOCMF72csKvT1A25x-76AsZhOKg3m2EdKuGDVUJckayA-gqx5Lhslsc9jYvDeUmHYB0-I1LV6jB_PvAqaNvTrq78YN-NPQMfLaf3Ps21KDmrKNLpT_2gPXSvG-cp8PHNTE7gLkZgiiAx9y8-NTeHiRv9Taonk</recordid><startdate>1989</startdate><enddate>1989</enddate><creator>Hunter, Edward P.L.</creator><creator>Desrosiers, Marc F.</creator><creator>Simic, Michael G.</creator><general>Elsevier Inc</general><general>Elsevier Science</general><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><scope>OTOTI</scope></search><sort><creationdate>1989</creationdate><title>The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization</title><author>Hunter, Edward P.L. ; Desrosiers, Marc F. ; Simic, Michael G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c480t-dbbb57e171e76280d635744f615575c3bd370650ccb3ac3547eeb22a83e68f113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>560300 - Chemicals Metabolism & Toxicology</topic><topic>AMINO ACIDS</topic><topic>Aminoacids, peptides. Hormones. Neuropeptides</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>ANTIOXIDANTS</topic><topic>ASCORBIC ACID</topic><topic>Biological and medical sciences</topic><topic>BIOLOGICAL EFFECTS</topic><topic>Bityrosine</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHEMICAL REACTIONS</topic><topic>Chromans</topic><topic>DIMERIZATION</topic><topic>ELEMENTS</topic><topic>FLUORESCENCE</topic><topic>Free Radicals</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gamma radiolysis</topic><topic>HYDROXY ACIDS</topic><topic>LUMINESCENCE</topic><topic>NONMETALS</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>OXYGEN</topic><topic>PHENOXY RADICALS</topic><topic>Phenoxyl</topic><topic>POLYMERIZATION</topic><topic>Proteins</topic><topic>Pulse radiolysis</topic><topic>RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT</topic><topic>RADICALS</topic><topic>Spectrometry, Fluorescence</topic><topic>SUPEROXIDE RADICALS</topic><topic>Superoxides</topic><topic>TYROSINE</topic><topic>Tyrosine - analogs & derivatives</topic><topic>Tyrosine - radiation effects</topic><topic>VITAMINS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hunter, Edward P.L.</creatorcontrib><creatorcontrib>Desrosiers, Marc F.</creatorcontrib><creatorcontrib>Simic, Michael G.</creatorcontrib><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><collection>OSTI.GOV</collection><jtitle>Free radical biology & medicine</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hunter, Edward P.L.</au><au>Desrosiers, Marc F.</au><au>Simic, Michael G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization</atitle><jtitle>Free radical biology & medicine</jtitle><addtitle>Free Radic Biol Med</addtitle><date>1989</date><risdate>1989</risdate><volume>6</volume><issue>6</issue><spage>581</spage><epage>585</epage><pages>581-585</pages><issn>0891-5849</issn><eissn>1873-4596</eissn><coden>FRBMEH</coden><abstract>Dimerization of tyrosine phenoxyl radical yields bityrosine (BT) which can easily be monitored by its characteristic fluorescence at 400 nm. The reactivity of tyrosine phenoxyl radical with O
2 was examined by a variety of techniques. BT fluorescence was measured as a function of O
2 concentration. Over a range of pH values (4–12) there was no effect of oxygen on BT production ([O
2] ≤ 0.72 mM). In addition, oxygen uptake by the phenoxyl radical was measured directly with an oxygen electrode. It was determined by this technique that oxygen does not react with the phenoxyl radical with a rate constant greater than 10
3 M
−1s
−1. Tyrosine phenoxyl radical “repair” by superoxide and physiological antioxidants was examined by BT fluorescence quenching as well as pulse radiolysis. Implications of these results as to the fate of tyrosine phenoxyl radicals produced in biological systems is discussed.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>2546863</pmid><doi>10.1016/0891-5849(89)90064-6</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Free radical biology & medicine, 1989, Vol.6 (6), p.581-585 |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 560300 - Chemicals Metabolism & Toxicology AMINO ACIDS Aminoacids, peptides. Hormones. Neuropeptides Analytical, structural and metabolic biochemistry ANTIOXIDANTS ASCORBIC ACID Biological and medical sciences BIOLOGICAL EFFECTS Bityrosine CARBOXYLIC ACIDS CHEMICAL REACTIONS Chromans DIMERIZATION ELEMENTS FLUORESCENCE Free Radicals Fundamental and applied biological sciences. Psychology Gamma radiolysis HYDROXY ACIDS LUMINESCENCE NONMETALS ORGANIC ACIDS ORGANIC COMPOUNDS OXYGEN PHENOXY RADICALS Phenoxyl POLYMERIZATION Proteins Pulse radiolysis RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT RADICALS Spectrometry, Fluorescence SUPEROXIDE RADICALS Superoxides TYROSINE Tyrosine - analogs & derivatives Tyrosine - radiation effects VITAMINS |
| title | The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization |
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