Inaction of saxitoxin-oximes on the sodium channel of frog skeletal muscle fibers
Three oximes of saxitoxin, saxitoxin oxime, saxitoxin methyloxime, and saxitoxin carboxymethyloxime, were synthesized in which the oxime functions replaced the ketone function on C-12 of saxitoxin. On the voltage-clamped single frog muscle fibers these oximes were very weak or inactive in blocking t...
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| Veröffentlicht in: | Toxicon (Oxford) 1987, Vol.25 (2), p.159-165 |
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| container_end_page | 165 |
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| container_title | Toxicon (Oxford) |
| container_volume | 25 |
| creator | Hu, S.L. Kao, C.Y. Koehn, F.E. Schnoes, H.K. |
| description | Three oximes of saxitoxin, saxitoxin oxime, saxitoxin methyloxime, and saxitoxin carboxymethyloxime, were synthesized in which the oxime functions replaced the ketone function on C-12 of saxitoxin. On the voltage-clamped single frog muscle fibers these oximes were very weak or inactive in blocking the sodium channel. The results indicate that the hydrated ketone function in saxitoxin is essential for blockade of the sodium channel, probably through a hydrogen bonding mechanism with some receptor groups. |
| doi_str_mv | 10.1016/0041-0101(87)90237-6 |
| format | Article |
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On the voltage-clamped single frog muscle fibers these oximes were very weak or inactive in blocking the sodium channel. The results indicate that the hydrated ketone function in saxitoxin is essential for blockade of the sodium channel, probably through a hydrogen bonding mechanism with some receptor groups.</description><identifier>ISSN: 0041-0101</identifier><identifier>EISSN: 1879-3150</identifier><identifier>DOI: 10.1016/0041-0101(87)90237-6</identifier><identifier>PMID: 2437671</identifier><identifier>CODEN: TOXIA6</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Binding Sites ; Biological and medical sciences ; Hydrogen Bonding ; In Vitro Techniques ; Ion Channels - drug effects ; Ion Channels - metabolism ; Medical sciences ; Muscles - drug effects ; Muscles - metabolism ; Oximes - pharmacology ; Plant poisons toxicology ; Rana ; Rana temporaria ; Saxitoxin - analogs & derivatives ; Saxitoxin - pharmacology ; Sodium - metabolism ; Structure-Activity Relationship ; Toxicology</subject><ispartof>Toxicon (Oxford), 1987, Vol.25 (2), p.159-165</ispartof><rights>1987</rights><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c483t-a2df52b832f2ed42f5bfc02c87b28b5d1e65cbaa359b6312c26c782f2c3df9ec3</citedby><cites>FETCH-LOGICAL-c483t-a2df52b832f2ed42f5bfc02c87b28b5d1e65cbaa359b6312c26c782f2c3df9ec3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0041010187902376$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,4010,27900,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8196401$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2437671$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, S.L.</creatorcontrib><creatorcontrib>Kao, C.Y.</creatorcontrib><creatorcontrib>Koehn, F.E.</creatorcontrib><creatorcontrib>Schnoes, H.K.</creatorcontrib><title>Inaction of saxitoxin-oximes on the sodium channel of frog skeletal muscle fibers</title><title>Toxicon (Oxford)</title><addtitle>Toxicon</addtitle><description>Three oximes of saxitoxin, saxitoxin oxime, saxitoxin methyloxime, and saxitoxin carboxymethyloxime, were synthesized in which the oxime functions replaced the ketone function on C-12 of saxitoxin. On the voltage-clamped single frog muscle fibers these oximes were very weak or inactive in blocking the sodium channel. The results indicate that the hydrated ketone function in saxitoxin is essential for blockade of the sodium channel, probably through a hydrogen bonding mechanism with some receptor groups.</description><subject>Animals</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Hydrogen Bonding</subject><subject>In Vitro Techniques</subject><subject>Ion Channels - drug effects</subject><subject>Ion Channels - metabolism</subject><subject>Medical sciences</subject><subject>Muscles - drug effects</subject><subject>Muscles - metabolism</subject><subject>Oximes - pharmacology</subject><subject>Plant poisons toxicology</subject><subject>Rana</subject><subject>Rana temporaria</subject><subject>Saxitoxin - analogs & derivatives</subject><subject>Saxitoxin - pharmacology</subject><subject>Sodium - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Toxicology</subject><issn>0041-0101</issn><issn>1879-3150</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM9r3TAMgE3ZaF-7_gct5DDKdsjmH4ntXAajrGuhMArd2TiKvHpL4s5KRvvfL-l7vGMvkpA-CfExdib4J8GF_sx5JUq-lB-s-dhwqUypD9hGWNOUStT8DdvskSN2TPSbc65sow_ZoayU0UZs2N3N6GGKaSxSKMg_xSk9xbFcwoBULO3pAQtKXZyHAh78OGK_kiGnXwX9wR4n3xfDTNBjEWKLmd6xt8H3hKe7fMJ-Xn27v7wub398v7n8eltCZdVUetmFWrZWySCxq2So2wBcgjWttG3dCdQ1tN6rumm1EhKkBmMXGFQXGgR1wi62dx9z-jsjTW6IBNj3fsQ0kxOV1k1txAJWWxByIsoY3GOOg8_PTnC3mnSrJrdqcta4F5NOL2vnu_tzO2C3X9qpW-bvd3NP4PuQ_QiR9pgVja74in3ZYri4-BcxO4KII2AXM8LkuhRf_-M_n4iPvQ</recordid><startdate>1987</startdate><enddate>1987</enddate><creator>Hu, S.L.</creator><creator>Kao, C.Y.</creator><creator>Koehn, F.E.</creator><creator>Schnoes, H.K.</creator><general>Elsevier Ltd</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>7U7</scope><scope>C1K</scope></search><sort><creationdate>1987</creationdate><title>Inaction of saxitoxin-oximes on the sodium channel of frog skeletal muscle fibers</title><author>Hu, S.L. ; Kao, C.Y. ; Koehn, F.E. ; Schnoes, H.K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-a2df52b832f2ed42f5bfc02c87b28b5d1e65cbaa359b6312c26c782f2c3df9ec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Animals</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Hydrogen Bonding</topic><topic>In Vitro Techniques</topic><topic>Ion Channels - drug effects</topic><topic>Ion Channels - metabolism</topic><topic>Medical sciences</topic><topic>Muscles - drug effects</topic><topic>Muscles - metabolism</topic><topic>Oximes - pharmacology</topic><topic>Plant poisons toxicology</topic><topic>Rana</topic><topic>Rana temporaria</topic><topic>Saxitoxin - analogs & derivatives</topic><topic>Saxitoxin - pharmacology</topic><topic>Sodium - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, S.L.</creatorcontrib><creatorcontrib>Kao, C.Y.</creatorcontrib><creatorcontrib>Koehn, F.E.</creatorcontrib><creatorcontrib>Schnoes, H.K.</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>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Toxicon (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, S.L.</au><au>Kao, C.Y.</au><au>Koehn, F.E.</au><au>Schnoes, H.K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inaction of saxitoxin-oximes on the sodium channel of frog skeletal muscle fibers</atitle><jtitle>Toxicon (Oxford)</jtitle><addtitle>Toxicon</addtitle><date>1987</date><risdate>1987</risdate><volume>25</volume><issue>2</issue><spage>159</spage><epage>165</epage><pages>159-165</pages><issn>0041-0101</issn><eissn>1879-3150</eissn><coden>TOXIA6</coden><abstract>Three oximes of saxitoxin, saxitoxin oxime, saxitoxin methyloxime, and saxitoxin carboxymethyloxime, were synthesized in which the oxime functions replaced the ketone function on C-12 of saxitoxin. On the voltage-clamped single frog muscle fibers these oximes were very weak or inactive in blocking the sodium channel. The results indicate that the hydrated ketone function in saxitoxin is essential for blockade of the sodium channel, probably through a hydrogen bonding mechanism with some receptor groups.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>2437671</pmid><doi>10.1016/0041-0101(87)90237-6</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0041-0101 |
| ispartof | Toxicon (Oxford), 1987, Vol.25 (2), p.159-165 |
| issn | 0041-0101 1879-3150 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_14669571 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Binding Sites Biological and medical sciences Hydrogen Bonding In Vitro Techniques Ion Channels - drug effects Ion Channels - metabolism Medical sciences Muscles - drug effects Muscles - metabolism Oximes - pharmacology Plant poisons toxicology Rana Rana temporaria Saxitoxin - analogs & derivatives Saxitoxin - pharmacology Sodium - metabolism Structure-Activity Relationship Toxicology |
| title | Inaction of saxitoxin-oximes on the sodium channel of frog skeletal muscle fibers |
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