Identification of the Factors Affecting the Rate of Deactivation of Hypochlorous Acid by Melatonin
It has been found that melatonin reacts rapidly with hypochlorous acid in phosphate-buffered, ethanol–water solutions to produce 2-hydroxymelatonin. The rate law, d[2 − HOMel]/dt − kHOCl[Mel][HOCl] − kOCl−[Mel][OCl−], was obtained. At 37°C and at a water concentration of 23.5 M, kOCl−= 6.0 × 102L ·...
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| Veröffentlicht in: | Biochemical and biophysical research communications 1999-04, Vol.257 (2), p.431-439 |
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| creator | Dellegar, Shawn M. Murphy, Shelly A. Bourne, Andrew E. DiCesare, John C. Purser, Gordon H. |
| description | It has been found that melatonin reacts rapidly with hypochlorous acid in phosphate-buffered, ethanol–water solutions to produce 2-hydroxymelatonin. The rate law, d[2 − HOMel]/dt − kHOCl[Mel][HOCl] − kOCl−[Mel][OCl−], was obtained. At 37°C and at a water concentration of 23.5 M, kOCl−= 6.0 × 102L · mol−1· s−1, and kHOClwas found to be a function of the water concentration, kHOCl= 11 ± 3 L3· mol−3· s−1· [H2O]2, indicating that the availability of water at the site of the reaction plays a significant role. The part that the structural components of melatonin play in determining the reaction pathway was examined by comparing the rate of deactivation of HOCl by melatonin to that of the model compounds indole, 5-methoxyindole, and 3-methylindole. The relative reactivity is explained in terms of steric and electronic effects, and it was found that the presence of the substituent at the 3-position influences the nature of the oxidation product. Melatonin and 3-methylindole yielded hydroxylated products, whereas indole and 5-methoxyindole produce chlorinated products. |
| doi_str_mv | 10.1006/bbrc.1999.0438 |
| format | Article |
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The rate law, d[2 − HOMel]/dt − kHOCl[Mel][HOCl] − kOCl−[Mel][OCl−], was obtained. At 37°C and at a water concentration of 23.5 M, kOCl−= 6.0 × 102L · mol−1· s−1, and kHOClwas found to be a function of the water concentration, kHOCl= 11 ± 3 L3· mol−3· s−1· [H2O]2, indicating that the availability of water at the site of the reaction plays a significant role. The part that the structural components of melatonin play in determining the reaction pathway was examined by comparing the rate of deactivation of HOCl by melatonin to that of the model compounds indole, 5-methoxyindole, and 3-methylindole. The relative reactivity is explained in terms of steric and electronic effects, and it was found that the presence of the substituent at the 3-position influences the nature of the oxidation product. Melatonin and 3-methylindole yielded hydroxylated products, whereas indole and 5-methoxyindole produce chlorinated products.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1006/bbrc.1999.0438</identifier><identifier>PMID: 10198231</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>2-hydroxymelatonin ; 3-methylindole ; 5-methoxyindole ; Antioxidants - chemistry ; Antioxidants - metabolism ; Antioxidants - pharmacology ; Binding Sites ; Chlorine - metabolism ; Chlorine - pharmacology ; Free Radical Scavengers - chemistry ; Free Radical Scavengers - metabolism ; Free Radical Scavengers - pharmacology ; Hydrogen - metabolism ; Hydrogen-Ion Concentration ; Hydroxylation ; hypochlorous acid ; Hypochlorous Acid - metabolism ; indole ; Indoles - chemistry ; Indoles - metabolism ; Indoles - pharmacology ; Kinetics ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; melatonin ; Melatonin - chemistry ; Melatonin - metabolism ; Melatonin - pharmacology ; Models, Chemical ; Oxidants - metabolism ; Reactive Oxygen Species - metabolism ; Skatole - analogs & derivatives ; Skatole - chemistry ; Skatole - metabolism ; Skatole - pharmacology ; Solvents ; Static Electricity ; Water - metabolism</subject><ispartof>Biochemical and biophysical research communications, 1999-04, Vol.257 (2), p.431-439</ispartof><rights>1999 Academic Press</rights><rights>Copyright 1999 Academic Press.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-494dd9a8871b4687775a8d8c52d7a1438adaddeff34b5862be2ad697251401943</citedby><cites>FETCH-LOGICAL-c340t-494dd9a8871b4687775a8d8c52d7a1438adaddeff34b5862be2ad697251401943</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0006291X99904382$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27902,27903,65308</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10198231$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dellegar, Shawn M.</creatorcontrib><creatorcontrib>Murphy, Shelly A.</creatorcontrib><creatorcontrib>Bourne, Andrew E.</creatorcontrib><creatorcontrib>DiCesare, John C.</creatorcontrib><creatorcontrib>Purser, Gordon H.</creatorcontrib><title>Identification of the Factors Affecting the Rate of Deactivation of Hypochlorous Acid by Melatonin</title><title>Biochemical and biophysical research communications</title><addtitle>Biochem Biophys Res Commun</addtitle><description>It has been found that melatonin reacts rapidly with hypochlorous acid in phosphate-buffered, ethanol–water solutions to produce 2-hydroxymelatonin. The rate law, d[2 − HOMel]/dt − kHOCl[Mel][HOCl] − kOCl−[Mel][OCl−], was obtained. At 37°C and at a water concentration of 23.5 M, kOCl−= 6.0 × 102L · mol−1· s−1, and kHOClwas found to be a function of the water concentration, kHOCl= 11 ± 3 L3· mol−3· s−1· [H2O]2, indicating that the availability of water at the site of the reaction plays a significant role. The part that the structural components of melatonin play in determining the reaction pathway was examined by comparing the rate of deactivation of HOCl by melatonin to that of the model compounds indole, 5-methoxyindole, and 3-methylindole. The relative reactivity is explained in terms of steric and electronic effects, and it was found that the presence of the substituent at the 3-position influences the nature of the oxidation product. Melatonin and 3-methylindole yielded hydroxylated products, whereas indole and 5-methoxyindole produce chlorinated products.</description><subject>2-hydroxymelatonin</subject><subject>3-methylindole</subject><subject>5-methoxyindole</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - metabolism</subject><subject>Antioxidants - pharmacology</subject><subject>Binding Sites</subject><subject>Chlorine - metabolism</subject><subject>Chlorine - pharmacology</subject><subject>Free Radical Scavengers - chemistry</subject><subject>Free Radical Scavengers - metabolism</subject><subject>Free Radical Scavengers - pharmacology</subject><subject>Hydrogen - metabolism</subject><subject>Hydrogen-Ion Concentration</subject><subject>Hydroxylation</subject><subject>hypochlorous acid</subject><subject>Hypochlorous Acid - metabolism</subject><subject>indole</subject><subject>Indoles - chemistry</subject><subject>Indoles - metabolism</subject><subject>Indoles - pharmacology</subject><subject>Kinetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>melatonin</subject><subject>Melatonin - chemistry</subject><subject>Melatonin - metabolism</subject><subject>Melatonin - pharmacology</subject><subject>Models, Chemical</subject><subject>Oxidants - metabolism</subject><subject>Reactive Oxygen Species - metabolism</subject><subject>Skatole - analogs & derivatives</subject><subject>Skatole - chemistry</subject><subject>Skatole - metabolism</subject><subject>Skatole - pharmacology</subject><subject>Solvents</subject><subject>Static Electricity</subject><subject>Water - metabolism</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1LAzEQhoMotlavHmX_wK7JbnY3OZZqbUERRMFbyMfERtpNyaaF_nuzVsSLp4GZ5x1mHoSuCS4Ixs2tUkEXhHNeYFqxEzQmmOO8JJieojFORF5y8j5CF33_iTEhtOHnaEQw4aysyBippYEuOuu0jM53mbdZXEE2lzr60GdTa0FH1318d19khIG4gzR2-9_E4rD1erX2we9SRDuTqUP2BGsZfee6S3Rm5bqHq586QW_z-9fZIn98fljOpo-5riiOOeXUGC4Za4miDWvbtpbMMF2XppUkPSeNNAasraiqWVMqKKVpeFvWhKZ3aDVBxXGvDr7vA1ixDW4jw0EQLAZZYpAlBllikJUCN8fAdqc2YP7gRzsJYEcA0tl7B0H02kGnwbiQtAjj3X-7vwDbx3km</recordid><startdate>19990413</startdate><enddate>19990413</enddate><creator>Dellegar, Shawn M.</creator><creator>Murphy, Shelly A.</creator><creator>Bourne, Andrew E.</creator><creator>DiCesare, John C.</creator><creator>Purser, Gordon H.</creator><general>Elsevier Inc</general><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>19990413</creationdate><title>Identification of the Factors Affecting the Rate of Deactivation of Hypochlorous Acid by Melatonin</title><author>Dellegar, Shawn M. ; Murphy, Shelly A. ; Bourne, Andrew E. ; DiCesare, John C. ; Purser, Gordon H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-494dd9a8871b4687775a8d8c52d7a1438adaddeff34b5862be2ad697251401943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>2-hydroxymelatonin</topic><topic>3-methylindole</topic><topic>5-methoxyindole</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - metabolism</topic><topic>Antioxidants - pharmacology</topic><topic>Binding Sites</topic><topic>Chlorine - metabolism</topic><topic>Chlorine - pharmacology</topic><topic>Free Radical Scavengers - chemistry</topic><topic>Free Radical Scavengers - metabolism</topic><topic>Free Radical Scavengers - pharmacology</topic><topic>Hydrogen - metabolism</topic><topic>Hydrogen-Ion Concentration</topic><topic>Hydroxylation</topic><topic>hypochlorous acid</topic><topic>Hypochlorous Acid - metabolism</topic><topic>indole</topic><topic>Indoles - chemistry</topic><topic>Indoles - metabolism</topic><topic>Indoles - pharmacology</topic><topic>Kinetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>melatonin</topic><topic>Melatonin - chemistry</topic><topic>Melatonin - metabolism</topic><topic>Melatonin - pharmacology</topic><topic>Models, Chemical</topic><topic>Oxidants - metabolism</topic><topic>Reactive Oxygen Species - metabolism</topic><topic>Skatole - analogs & derivatives</topic><topic>Skatole - chemistry</topic><topic>Skatole - metabolism</topic><topic>Skatole - pharmacology</topic><topic>Solvents</topic><topic>Static Electricity</topic><topic>Water - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dellegar, Shawn M.</creatorcontrib><creatorcontrib>Murphy, Shelly A.</creatorcontrib><creatorcontrib>Bourne, Andrew E.</creatorcontrib><creatorcontrib>DiCesare, John C.</creatorcontrib><creatorcontrib>Purser, Gordon H.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Biochemical and biophysical research communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dellegar, Shawn M.</au><au>Murphy, Shelly A.</au><au>Bourne, Andrew E.</au><au>DiCesare, John C.</au><au>Purser, Gordon H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of the Factors Affecting the Rate of Deactivation of Hypochlorous Acid by Melatonin</atitle><jtitle>Biochemical and biophysical research communications</jtitle><addtitle>Biochem Biophys Res Commun</addtitle><date>1999-04-13</date><risdate>1999</risdate><volume>257</volume><issue>2</issue><spage>431</spage><epage>439</epage><pages>431-439</pages><issn>0006-291X</issn><eissn>1090-2104</eissn><abstract>It has been found that melatonin reacts rapidly with hypochlorous acid in phosphate-buffered, ethanol–water solutions to produce 2-hydroxymelatonin. The rate law, d[2 − HOMel]/dt − kHOCl[Mel][HOCl] − kOCl−[Mel][OCl−], was obtained. At 37°C and at a water concentration of 23.5 M, kOCl−= 6.0 × 102L · mol−1· s−1, and kHOClwas found to be a function of the water concentration, kHOCl= 11 ± 3 L3· mol−3· s−1· [H2O]2, indicating that the availability of water at the site of the reaction plays a significant role. The part that the structural components of melatonin play in determining the reaction pathway was examined by comparing the rate of deactivation of HOCl by melatonin to that of the model compounds indole, 5-methoxyindole, and 3-methylindole. The relative reactivity is explained in terms of steric and electronic effects, and it was found that the presence of the substituent at the 3-position influences the nature of the oxidation product. Melatonin and 3-methylindole yielded hydroxylated products, whereas indole and 5-methoxyindole produce chlorinated products.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>10198231</pmid><doi>10.1006/bbrc.1999.0438</doi><tpages>9</tpages></addata></record> |
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| subjects | 2-hydroxymelatonin 3-methylindole 5-methoxyindole Antioxidants - chemistry Antioxidants - metabolism Antioxidants - pharmacology Binding Sites Chlorine - metabolism Chlorine - pharmacology Free Radical Scavengers - chemistry Free Radical Scavengers - metabolism Free Radical Scavengers - pharmacology Hydrogen - metabolism Hydrogen-Ion Concentration Hydroxylation hypochlorous acid Hypochlorous Acid - metabolism indole Indoles - chemistry Indoles - metabolism Indoles - pharmacology Kinetics Magnetic Resonance Spectroscopy Mass Spectrometry melatonin Melatonin - chemistry Melatonin - metabolism Melatonin - pharmacology Models, Chemical Oxidants - metabolism Reactive Oxygen Species - metabolism Skatole - analogs & derivatives Skatole - chemistry Skatole - metabolism Skatole - pharmacology Solvents Static Electricity Water - metabolism |
| title | Identification of the Factors Affecting the Rate of Deactivation of Hypochlorous Acid by Melatonin |
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