Intracyclization rates of 6-hydroxydopamine and 6-aminodopamine analogs under physiological conditions
It is agreed that the neurotoxic action of 6-hydroxydopamine and 6-aminodopamine is related to their ease of oxidation. The initial oxidation products, the p-quinone and p-quinone imine, readily undergo 1,2-intracyclization. These reactions could represent an important loss of active neurotoxic agen...
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| Veröffentlicht in: | Journal of medicinal chemistry 1976-01, Vol.19 (1), p.178-180 |
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| container_end_page | 180 |
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| container_issue | 1 |
| container_start_page | 178 |
| container_title | Journal of medicinal chemistry |
| container_volume | 19 |
| creator | Blank, C. L McCreery, Richard L Wightman, R. M Chey, W Adams, Ralph N Reid, J. R Smissman, Edward E |
| description | It is agreed that the neurotoxic action of 6-hydroxydopamine and 6-aminodopamine is related to their ease of oxidation. The initial oxidation products, the p-quinone and p-quinone imine, readily undergo 1,2-intracyclization. These reactions could represent an important loss of active neurotoxic agent available uptake. A variety of substituted 6-aminodopamine analogs was prepared and their formal potentials and cyclization rates were measured accurately. The effect of the balance of ease of oxidation vs. rate of cyclization on their neurotoxicity was examined. The results are in general accord with in vivo lifetimes for 6-hydroxydopamine and 6-aminodopamine in rat caudate nucleus. |
| doi_str_mv | 10.1021/jm00223a035 |
| format | Article |
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L ; McCreery, Richard L ; Wightman, R. M ; Chey, W ; Adams, Ralph N ; Reid, J. R ; Smissman, Edward E</creator><creatorcontrib>Blank, C. L ; McCreery, Richard L ; Wightman, R. M ; Chey, W ; Adams, Ralph N ; Reid, J. R ; Smissman, Edward E</creatorcontrib><description>It is agreed that the neurotoxic action of 6-hydroxydopamine and 6-aminodopamine is related to their ease of oxidation. The initial oxidation products, the p-quinone and p-quinone imine, readily undergo 1,2-intracyclization. These reactions could represent an important loss of active neurotoxic agent available uptake. A variety of substituted 6-aminodopamine analogs was prepared and their formal potentials and cyclization rates were measured accurately. The effect of the balance of ease of oxidation vs. rate of cyclization on their neurotoxicity was examined. The results are in general accord with in vivo lifetimes for 6-hydroxydopamine and 6-aminodopamine in rat caudate nucleus.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00223a035</identifier><identifier>PMID: 1246041</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chemical Phenomena ; Chemistry ; Cyclization ; Dopamine - analogs & derivatives ; Dopamine - metabolism ; Half-Life ; Hydroxydopamines - metabolism ; Neurons - metabolism ; Oxidation-Reduction ; Potentiometry</subject><ispartof>Journal of medicinal chemistry, 1976-01, Vol.19 (1), p.178-180</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-f4848a8a8b7934f34dc1a0d52d96c1dd73a738a4e499a1805a10e86ef29b5cf43</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00223a035$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00223a035$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1246041$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Blank, C. 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The effect of the balance of ease of oxidation vs. rate of cyclization on their neurotoxicity was examined. The results are in general accord with in vivo lifetimes for 6-hydroxydopamine and 6-aminodopamine in rat caudate nucleus.</description><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Dopamine - analogs & derivatives</subject><subject>Dopamine - metabolism</subject><subject>Half-Life</subject><subject>Hydroxydopamines - metabolism</subject><subject>Neurons - metabolism</subject><subject>Oxidation-Reduction</subject><subject>Potentiometry</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1976</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLw0AUhQdRaq2uXAvZuZDovPJaarFVqCi06nK4nYdNTTJlJoXGX29CRLuQu7iXcz7OhYPQOcHXBFNysy4xppQBZtEBGpKI4pCnmB-iYaeHNKbsGJ14v8YYM0LZAA0I5THmZIjMY1U7kI0s8i-oc1sFDmrtA2uCOFw1ytldo-wGyrzSAVSqVbvb7mlQ2A8fbCulXbBZNT63rZBLKAJpK5V3of4UHRkovD772SP0OrlfjB_C2fP0cXw7C4FFvA4NT3kK7SyTjHHDuJIEsIqoymJJlEoYJCwFrnmWAUlxBATrNNaGZstIGs5G6KrPlc5677QRG5eX4BpBsOjKEntltfRFT2-2y1KrP7Zvp_XD3s99rXe_NrhPEScsicTiZS4WT-T97W4-FZOWv-x5kF6s7da13fh_P38DQ2yCOg</recordid><startdate>19760101</startdate><enddate>19760101</enddate><creator>Blank, C. L</creator><creator>McCreery, Richard L</creator><creator>Wightman, R. M</creator><creator>Chey, W</creator><creator>Adams, Ralph N</creator><creator>Reid, J. R</creator><creator>Smissman, Edward E</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>19760101</creationdate><title>Intracyclization rates of 6-hydroxydopamine and 6-aminodopamine analogs under physiological conditions</title><author>Blank, C. L ; McCreery, Richard L ; Wightman, R. M ; Chey, W ; Adams, Ralph N ; Reid, J. 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Chem</addtitle><date>1976-01-01</date><risdate>1976</risdate><volume>19</volume><issue>1</issue><spage>178</spage><epage>180</epage><pages>178-180</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>It is agreed that the neurotoxic action of 6-hydroxydopamine and 6-aminodopamine is related to their ease of oxidation. The initial oxidation products, the p-quinone and p-quinone imine, readily undergo 1,2-intracyclization. These reactions could represent an important loss of active neurotoxic agent available uptake. A variety of substituted 6-aminodopamine analogs was prepared and their formal potentials and cyclization rates were measured accurately. The effect of the balance of ease of oxidation vs. rate of cyclization on their neurotoxicity was examined. The results are in general accord with in vivo lifetimes for 6-hydroxydopamine and 6-aminodopamine in rat caudate nucleus.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1246041</pmid><doi>10.1021/jm00223a035</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1976-01, Vol.19 (1), p.178-180 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jm00223a035 |
| source | MEDLINE; ACS Publications |
| subjects | Chemical Phenomena Chemistry Cyclization Dopamine - analogs & derivatives Dopamine - metabolism Half-Life Hydroxydopamines - metabolism Neurons - metabolism Oxidation-Reduction Potentiometry |
| title | Intracyclization rates of 6-hydroxydopamine and 6-aminodopamine analogs under physiological conditions |
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