Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent: A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products
Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radica...
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| Veröffentlicht in: | Organic letters 2003-07, Vol.5 (15), p.2659-2662 |
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| creator | Culbertson, Sean M Enright, Gary D Ingold, K. U |
| description | Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM). |
| doi_str_mv | 10.1021/ol0348147 |
| format | Article |
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Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0348147</identifier><identifier>PMID: 12868883</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antioxidants - chemical synthesis ; Antioxidants - pharmacology ; Cross-Linking Reagents - chemistry ; Free Radicals - chemistry ; Glycation End Products, Advanced - antagonists & inhibitors ; Lipid Peroxidation - drug effects ; Proteins - chemistry ; Pyridoxamine - analogs & derivatives ; Pyridoxamine - chemical synthesis ; Pyridoxamine - pharmacology ; Ribose - chemistry ; Spectrometry, Fluorescence - methods</subject><ispartof>Organic letters, 2003-07, Vol.5 (15), p.2659-2662</ispartof><rights>Copyright © 2003 by the American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-52da6fc4855a133e7c845e7be4223ac6d67c656cd1ce329a9c90327ccdf9691b3</citedby><cites>FETCH-LOGICAL-a311t-52da6fc4855a133e7c845e7be4223ac6d67c656cd1ce329a9c90327ccdf9691b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol0348147$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0348147$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12868883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Culbertson, Sean M</creatorcontrib><creatorcontrib>Enright, Gary D</creatorcontrib><creatorcontrib>Ingold, K. U</creatorcontrib><title>Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent: A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).</description><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - pharmacology</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>Free Radicals - chemistry</subject><subject>Glycation End Products, Advanced - antagonists & inhibitors</subject><subject>Lipid Peroxidation - drug effects</subject><subject>Proteins - chemistry</subject><subject>Pyridoxamine - analogs & derivatives</subject><subject>Pyridoxamine - chemical synthesis</subject><subject>Pyridoxamine - pharmacology</subject><subject>Ribose - chemistry</subject><subject>Spectrometry, Fluorescence - methods</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9u1DAQxi0EoqVw4AWQLyB6SPGfxEm4RatlqbSiFZRzNLGdrSuvndpJ1dy48kY8T5-kpru0F04z-uY330jzIfSWkhNKGP3kLeF5RfPyGTqkBeNZSQr2_LEX5AC9ivGKEJqU-iU6oKwSVVXxQ_Tnx-zGSx1NxL7HgL_5G23xd1BGgsUXAYbBuA0Gp_ACQufdbPEq-Gl4mjVuNFmzWuJmo934-e7Xb9zg8zkY5W9ha5xOBFi_mTTufcCn7tJ0ZnzYVDfgpFZ4ZWcJo_EOf0xGxw_n1mbwt0b9k9dJXib5PHg1yTG-Ri96sFG_2dcj9PPL8mLxNVufrU4XzToDTumYFUyB6GVeFQVQznUpq7zQZadzxjhIoUQpRSGkolJzVkMta8JZKaXqa1HTjh-hDzvfIfjrScex3ZootbXgtJ9iW_K8FIIXCTzegTL4GIPu2yGYLYS5paT9G1P7GFNi3-1Np26r1RO5zyUB73cAyNhe-SmkD8b_GN0DK5OaRA</recordid><startdate>20030724</startdate><enddate>20030724</enddate><creator>Culbertson, Sean M</creator><creator>Enright, Gary D</creator><creator>Ingold, K. 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Lett</addtitle><date>2003-07-24</date><risdate>2003</risdate><volume>5</volume><issue>15</issue><spage>2659</spage><epage>2662</epage><pages>2659-2662</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12868883</pmid><doi>10.1021/ol0348147</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2003-07, Vol.5 (15), p.2659-2662 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Antioxidants - chemical synthesis Antioxidants - pharmacology Cross-Linking Reagents - chemistry Free Radicals - chemistry Glycation End Products, Advanced - antagonists & inhibitors Lipid Peroxidation - drug effects Proteins - chemistry Pyridoxamine - analogs & derivatives Pyridoxamine - chemical synthesis Pyridoxamine - pharmacology Ribose - chemistry Spectrometry, Fluorescence - methods |
| title | Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent: A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products |
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