Peroxynitrite reactivity with amino acids and proteins
Peroxynitrite, the product of the fast reaction between nitric oxide (•NO) and superoxide O₂•⁻radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts...
Gespeichert in:
| Veröffentlicht in: | Amino acids 2003-12, Vol.25 (3-4), p.295-311 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 311 |
|---|---|
| container_issue | 3-4 |
| container_start_page | 295 |
| container_title | Amino acids |
| container_volume | 25 |
| creator | Alvarez, B Radi, R |
| description | Peroxynitrite, the product of the fast reaction between nitric oxide (•NO) and superoxide O₂•⁻radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts directly with cysteine, methionine and tryptophan residues. Second, peroxynitrite reacts fast with transition metal centers and selenium-containing amino acids. Third, secondary free radicals arising from peroxynitrite homolysis such as hydroxyl and nitrogen dioxide, and the carbonate radical formed in the presence of carbon dioxide, react with protein moieties too. Nitration of tyrosine residues is being recognized as a marker of the contribution of nitric oxide to oxidative damage. Peroxynitrite-dependent tyrosine nitration is likely to occur through the initial reaction of peroxynitrite with carbon dioxide or metal centers leading to secondary nitrating species. The preferential protein targets of peroxynitrite and the role of proteins in peroxynitrite detoxifying pathways are discussed. |
| doi_str_mv | 10.1007/s00726-003-0018-8 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71430031</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2785555651</sourcerecordid><originalsourceid>FETCH-LOGICAL-c407t-bdc184cf17b2b1f0b9e54b7adcef08ed3134bfc295a53c994affccc065ee58803</originalsourceid><addsrcrecordid>eNp90E1LAzEQBuAgiq0fP8CLLgjiZXUmyWaToxS_QFDQnkM2m2ik3dVkq_bfG2lB8OAhk8szM8xLyAHCGQLU5ykXKkoAlh_KUm6QMXImS4pKbZIxKKZKzisckZ2UXrOhEsU2GSEXAkHRMREPLvZfyy4MMQyuiM7YIXyEYVl8huGlMPPQ9YWxoU2F6driLfaDC13aI1vezJLbX_-7ZHp1-TS5Ke_ur28nF3el5VAPZdNalNx6rBvaoIdGuYo3tWmt8yBdy5DxxluqKlMxqxQ33ltrQVTOVVIC2yUnq7l58fvCpUHPQ7JuNjOd6xdJ1_ncfD5mePovREAlahBAMz3-Q1_7RezyGVmpSgiFNc8KV8rGPqXovH6LYW7iMiP9k75epa_zev2Tvpa553A9edHMXfvbsY47g6MV8KbX5jmGpKePFFAAAOWsVuwbm7-IUw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1095669174</pqid></control><display><type>article</type><title>Peroxynitrite reactivity with amino acids and proteins</title><source>MEDLINE</source><source>SpringerLink Journals - AutoHoldings</source><creator>Alvarez, B ; Radi, R</creator><creatorcontrib>Alvarez, B ; Radi, R</creatorcontrib><description>Peroxynitrite, the product of the fast reaction between nitric oxide (•NO) and superoxide O₂•⁻radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts directly with cysteine, methionine and tryptophan residues. Second, peroxynitrite reacts fast with transition metal centers and selenium-containing amino acids. Third, secondary free radicals arising from peroxynitrite homolysis such as hydroxyl and nitrogen dioxide, and the carbonate radical formed in the presence of carbon dioxide, react with protein moieties too. Nitration of tyrosine residues is being recognized as a marker of the contribution of nitric oxide to oxidative damage. Peroxynitrite-dependent tyrosine nitration is likely to occur through the initial reaction of peroxynitrite with carbon dioxide or metal centers leading to secondary nitrating species. The preferential protein targets of peroxynitrite and the role of proteins in peroxynitrite detoxifying pathways are discussed.</description><identifier>ISSN: 0939-4451</identifier><identifier>EISSN: 1438-2199</identifier><identifier>DOI: 10.1007/s00726-003-0018-8</identifier><identifier>PMID: 14661092</identifier><language>eng</language><publisher>Austria: Springer-Verlag</publisher><subject>Amino acids ; Amino Acids - chemistry ; Amino Acids - metabolism ; Animals ; Antioxidants - chemistry ; Antioxidants - metabolism ; Carbon dioxide ; cysteine ; Cytosol - metabolism ; Free Radicals - metabolism ; Humans ; methionine ; Models, Chemical ; Molecular Structure ; Nitration ; Nitric oxide ; Nitric Oxide - metabolism ; Nitrogen dioxide ; Oxidation-Reduction ; Pathways ; Peroxynitrous Acid - chemistry ; Peroxynitrous Acid - metabolism ; Proteins ; Proteins - chemistry ; Proteins - metabolism ; Radicals ; Residues ; superoxide anion ; Superoxides - metabolism ; tryptophan ; Tyrosine</subject><ispartof>Amino acids, 2003-12, Vol.25 (3-4), p.295-311</ispartof><rights>Springer-Verlag/Wien 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c407t-bdc184cf17b2b1f0b9e54b7adcef08ed3134bfc295a53c994affccc065ee58803</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14661092$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alvarez, B</creatorcontrib><creatorcontrib>Radi, R</creatorcontrib><title>Peroxynitrite reactivity with amino acids and proteins</title><title>Amino acids</title><addtitle>Amino Acids</addtitle><description>Peroxynitrite, the product of the fast reaction between nitric oxide (•NO) and superoxide O₂•⁻radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts directly with cysteine, methionine and tryptophan residues. Second, peroxynitrite reacts fast with transition metal centers and selenium-containing amino acids. Third, secondary free radicals arising from peroxynitrite homolysis such as hydroxyl and nitrogen dioxide, and the carbonate radical formed in the presence of carbon dioxide, react with protein moieties too. Nitration of tyrosine residues is being recognized as a marker of the contribution of nitric oxide to oxidative damage. Peroxynitrite-dependent tyrosine nitration is likely to occur through the initial reaction of peroxynitrite with carbon dioxide or metal centers leading to secondary nitrating species. The preferential protein targets of peroxynitrite and the role of proteins in peroxynitrite detoxifying pathways are discussed.</description><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Amino Acids - metabolism</subject><subject>Animals</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - metabolism</subject><subject>Carbon dioxide</subject><subject>cysteine</subject><subject>Cytosol - metabolism</subject><subject>Free Radicals - metabolism</subject><subject>Humans</subject><subject>methionine</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Nitration</subject><subject>Nitric oxide</subject><subject>Nitric Oxide - metabolism</subject><subject>Nitrogen dioxide</subject><subject>Oxidation-Reduction</subject><subject>Pathways</subject><subject>Peroxynitrous Acid - chemistry</subject><subject>Peroxynitrous Acid - metabolism</subject><subject>Proteins</subject><subject>Proteins - chemistry</subject><subject>Proteins - metabolism</subject><subject>Radicals</subject><subject>Residues</subject><subject>superoxide anion</subject><subject>Superoxides - metabolism</subject><subject>tryptophan</subject><subject>Tyrosine</subject><issn>0939-4451</issn><issn>1438-2199</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp90E1LAzEQBuAgiq0fP8CLLgjiZXUmyWaToxS_QFDQnkM2m2ik3dVkq_bfG2lB8OAhk8szM8xLyAHCGQLU5ykXKkoAlh_KUm6QMXImS4pKbZIxKKZKzisckZ2UXrOhEsU2GSEXAkHRMREPLvZfyy4MMQyuiM7YIXyEYVl8huGlMPPQ9YWxoU2F6driLfaDC13aI1vezJLbX_-7ZHp1-TS5Ke_ur28nF3el5VAPZdNalNx6rBvaoIdGuYo3tWmt8yBdy5DxxluqKlMxqxQ33ltrQVTOVVIC2yUnq7l58fvCpUHPQ7JuNjOd6xdJ1_ncfD5mePovREAlahBAMz3-Q1_7RezyGVmpSgiFNc8KV8rGPqXovH6LYW7iMiP9k75epa_zev2Tvpa553A9edHMXfvbsY47g6MV8KbX5jmGpKePFFAAAOWsVuwbm7-IUw</recordid><startdate>20031201</startdate><enddate>20031201</enddate><creator>Alvarez, B</creator><creator>Radi, R</creator><general>Springer-Verlag</general><general>Springer Nature B.V</general><scope>FBQ</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>3V.</scope><scope>7TK</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20031201</creationdate><title>Peroxynitrite reactivity with amino acids and proteins</title><author>Alvarez, B ; Radi, R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c407t-bdc184cf17b2b1f0b9e54b7adcef08ed3134bfc295a53c994affccc065ee58803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Amino Acids - metabolism</topic><topic>Animals</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - metabolism</topic><topic>Carbon dioxide</topic><topic>cysteine</topic><topic>Cytosol - metabolism</topic><topic>Free Radicals - metabolism</topic><topic>Humans</topic><topic>methionine</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Nitration</topic><topic>Nitric oxide</topic><topic>Nitric Oxide - metabolism</topic><topic>Nitrogen dioxide</topic><topic>Oxidation-Reduction</topic><topic>Pathways</topic><topic>Peroxynitrous Acid - chemistry</topic><topic>Peroxynitrous Acid - metabolism</topic><topic>Proteins</topic><topic>Proteins - chemistry</topic><topic>Proteins - metabolism</topic><topic>Radicals</topic><topic>Residues</topic><topic>superoxide anion</topic><topic>Superoxides - metabolism</topic><topic>tryptophan</topic><topic>Tyrosine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alvarez, B</creatorcontrib><creatorcontrib>Radi, R</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Neurosciences Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Amino acids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alvarez, B</au><au>Radi, R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peroxynitrite reactivity with amino acids and proteins</atitle><jtitle>Amino acids</jtitle><addtitle>Amino Acids</addtitle><date>2003-12-01</date><risdate>2003</risdate><volume>25</volume><issue>3-4</issue><spage>295</spage><epage>311</epage><pages>295-311</pages><issn>0939-4451</issn><eissn>1438-2199</eissn><abstract>Peroxynitrite, the product of the fast reaction between nitric oxide (•NO) and superoxide O₂•⁻radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts directly with cysteine, methionine and tryptophan residues. Second, peroxynitrite reacts fast with transition metal centers and selenium-containing amino acids. Third, secondary free radicals arising from peroxynitrite homolysis such as hydroxyl and nitrogen dioxide, and the carbonate radical formed in the presence of carbon dioxide, react with protein moieties too. Nitration of tyrosine residues is being recognized as a marker of the contribution of nitric oxide to oxidative damage. Peroxynitrite-dependent tyrosine nitration is likely to occur through the initial reaction of peroxynitrite with carbon dioxide or metal centers leading to secondary nitrating species. The preferential protein targets of peroxynitrite and the role of proteins in peroxynitrite detoxifying pathways are discussed.</abstract><cop>Austria</cop><pub>Springer-Verlag</pub><pmid>14661092</pmid><doi>10.1007/s00726-003-0018-8</doi><tpages>17</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0939-4451 |
| ispartof | Amino acids, 2003-12, Vol.25 (3-4), p.295-311 |
| issn | 0939-4451 1438-2199 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71430031 |
| source | MEDLINE; SpringerLink Journals - AutoHoldings |
| subjects | Amino acids Amino Acids - chemistry Amino Acids - metabolism Animals Antioxidants - chemistry Antioxidants - metabolism Carbon dioxide cysteine Cytosol - metabolism Free Radicals - metabolism Humans methionine Models, Chemical Molecular Structure Nitration Nitric oxide Nitric Oxide - metabolism Nitrogen dioxide Oxidation-Reduction Pathways Peroxynitrous Acid - chemistry Peroxynitrous Acid - metabolism Proteins Proteins - chemistry Proteins - metabolism Radicals Residues superoxide anion Superoxides - metabolism tryptophan Tyrosine |
| title | Peroxynitrite reactivity with amino acids and proteins |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T16%3A07%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Peroxynitrite%20reactivity%20with%20amino%20acids%20and%20proteins&rft.jtitle=Amino%20acids&rft.au=Alvarez,%20B&rft.date=2003-12-01&rft.volume=25&rft.issue=3-4&rft.spage=295&rft.epage=311&rft.pages=295-311&rft.issn=0939-4451&rft.eissn=1438-2199&rft_id=info:doi/10.1007/s00726-003-0018-8&rft_dat=%3Cproquest_cross%3E2785555651%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1095669174&rft_id=info:pmid/14661092&rfr_iscdi=true |