Potentiating Effects of β-Eudesmol-Related Cyclohexylidene Derivatives on Succinylcholine-Induced Neuromuscular Block in Isolated Phrenic Nerve-Diaphragm Muscles of Normal and Alloxan-Diabetic Mice
β-Eudesmol, a sesquiterpenoid alcohol contained in Atractylodes lancea, potentiates succinylcholine (SuCh)-induced neuromuscular blockade. The potentiating effect is greater in diabetic muscles than in normal ones. As a ligand for affinity chromatography to study the potentiating mechanism, we desig...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 1995/03/15, Vol.18(3), pp.407-410 |
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| creator | KIMURA, Masayasu DIWAN, Prakash YANAGI, Seiji KONNO, Yasuo NOJIMA, Hiroshi KIMURA, Ikuko |
| description | β-Eudesmol, a sesquiterpenoid alcohol contained in Atractylodes lancea, potentiates succinylcholine (SuCh)-induced neuromuscular blockade. The potentiating effect is greater in diabetic muscles than in normal ones. As a ligand for affinity chromatography to study the potentiating mechanism, we designed and synthesized newly β-eudesmol-related cyclohexylidene derivatives (2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-13, 2-(3-hydroxy-3-methylbutyl)-4-cyclohexylidene carboxylic acid ; KTE-32 and 4-tert-butoxycarbonyl-2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-33). We examined the potentiating effects of those compounds in phrenic nerve-diaphragm muscle preparations of normal and alloxan-diabetic mice. KTE-33 (100μM) potentiated more greatly SuCh-induced neuromuscular blockade in diabetic muscles than in normal ones (the potentiating ratios in normal and diabetic muscles were 6.7 and 10.6, respectively), while KTE-13 (100 μM) and -32 (200 μM) potentiated weakly. These results suggest that the ester group in KTE-33 rather than a carboxyl group in KTE-32 is important in inducing the potentiation of SuCh-induced neuromuscular blockade in diabetic state. |
| doi_str_mv | 10.1248/bpb.18.407 |
| format | Article |
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The potentiating effect is greater in diabetic muscles than in normal ones. As a ligand for affinity chromatography to study the potentiating mechanism, we designed and synthesized newly β-eudesmol-related cyclohexylidene derivatives (2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-13, 2-(3-hydroxy-3-methylbutyl)-4-cyclohexylidene carboxylic acid ; KTE-32 and 4-tert-butoxycarbonyl-2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-33). We examined the potentiating effects of those compounds in phrenic nerve-diaphragm muscle preparations of normal and alloxan-diabetic mice. KTE-33 (100μM) potentiated more greatly SuCh-induced neuromuscular blockade in diabetic muscles than in normal ones (the potentiating ratios in normal and diabetic muscles were 6.7 and 10.6, respectively), while KTE-13 (100 μM) and -32 (200 μM) potentiated weakly. These results suggest that the ester group in KTE-33 rather than a carboxyl group in KTE-32 is important in inducing the potentiation of SuCh-induced neuromuscular blockade in diabetic state.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.18.407</identifier><identifier>PMID: 7550092</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Biological and medical sciences ; Cyclohexanes - chemical synthesis ; Cyclohexanes - pharmacology ; cyclohexylidene derivative ; Diabetes Mellitus, Experimental - physiopathology ; diabetic mouse ; Diaphragm - drug effects ; Diaphragm - innervation ; Drug Synergism ; Drugs, Chinese Herbal - pharmacology ; Male ; Medical sciences ; Mice ; Mice, Inbred Strains ; Muscle Contraction - drug effects ; neuromuscular blockade ; Neuromuscular Blocking Agents - chemical synthesis ; Neuromuscular Blocking Agents - pharmacology ; Neuromuscular Junction - drug effects ; Pharmacology. Drug treatments ; Phrenic Nerve - drug effects ; potentiation ; Respiratory system ; Sesquiterpenes, Eudesmane ; Stimulation, Chemical ; succinylcholine ; Succinylcholine - pharmacology ; Synaptic Transmission - drug effects ; Terpenes - pharmacology ; β-eudesmol-related compound</subject><ispartof>Biological and Pharmaceutical Bulletin, 1995/03/15, Vol.18(3), pp.407-410</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c574t-6ed128b3e7541f0337dfe84992a5174a35be87464c150f252318e7bd8875dd733</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,4022,27921,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3574837$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7550092$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KIMURA, Masayasu</creatorcontrib><creatorcontrib>DIWAN, Prakash</creatorcontrib><creatorcontrib>YANAGI, Seiji</creatorcontrib><creatorcontrib>KONNO, Yasuo</creatorcontrib><creatorcontrib>NOJIMA, Hiroshi</creatorcontrib><creatorcontrib>KIMURA, Ikuko</creatorcontrib><title>Potentiating Effects of β-Eudesmol-Related Cyclohexylidene Derivatives on Succinylcholine-Induced Neuromuscular Block in Isolated Phrenic Nerve-Diaphragm Muscles of Normal and Alloxan-Diabetic Mice</title><title>Biological & pharmaceutical bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>β-Eudesmol, a sesquiterpenoid alcohol contained in Atractylodes lancea, potentiates succinylcholine (SuCh)-induced neuromuscular blockade. The potentiating effect is greater in diabetic muscles than in normal ones. As a ligand for affinity chromatography to study the potentiating mechanism, we designed and synthesized newly β-eudesmol-related cyclohexylidene derivatives (2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-13, 2-(3-hydroxy-3-methylbutyl)-4-cyclohexylidene carboxylic acid ; KTE-32 and 4-tert-butoxycarbonyl-2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-33). We examined the potentiating effects of those compounds in phrenic nerve-diaphragm muscle preparations of normal and alloxan-diabetic mice. KTE-33 (100μM) potentiated more greatly SuCh-induced neuromuscular blockade in diabetic muscles than in normal ones (the potentiating ratios in normal and diabetic muscles were 6.7 and 10.6, respectively), while KTE-13 (100 μM) and -32 (200 μM) potentiated weakly. These results suggest that the ester group in KTE-33 rather than a carboxyl group in KTE-32 is important in inducing the potentiation of SuCh-induced neuromuscular blockade in diabetic state.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cyclohexanes - chemical synthesis</subject><subject>Cyclohexanes - pharmacology</subject><subject>cyclohexylidene derivative</subject><subject>Diabetes Mellitus, Experimental - physiopathology</subject><subject>diabetic mouse</subject><subject>Diaphragm - drug effects</subject><subject>Diaphragm - innervation</subject><subject>Drug Synergism</subject><subject>Drugs, Chinese Herbal - pharmacology</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred Strains</subject><subject>Muscle Contraction - drug effects</subject><subject>neuromuscular blockade</subject><subject>Neuromuscular Blocking Agents - chemical synthesis</subject><subject>Neuromuscular Blocking Agents - pharmacology</subject><subject>Neuromuscular Junction - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Phrenic Nerve - drug effects</subject><subject>potentiation</subject><subject>Respiratory system</subject><subject>Sesquiterpenes, Eudesmane</subject><subject>Stimulation, Chemical</subject><subject>succinylcholine</subject><subject>Succinylcholine - pharmacology</subject><subject>Synaptic Transmission - drug effects</subject><subject>Terpenes - pharmacology</subject><subject>β-eudesmol-related compound</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kc1uEzEUhS0EKqGwYY_kBatKE-zxOPYsSxogUlsqftYjj30ncfHYkT0TNa_FQ7DkmfCQKBt7cb5z7rUPQm8pmdOykh_aXTuncl4R8QzNKKtEwUvKn6MZqaksFpTLl-hVSo-EEEFKdoEuBOeE1OUM_XkIA_jBqsH6DV51Hegh4dDhv7-L1Wgg9cEV38CpAQxeHrQLW3g6OGvAA76BaPfZuYds8fj7qLX1B6e3wVkPxdqbUWfbPYwx9GPSo1MRf3RB_8LW43UKx9iHbQRvdebiHoobq3bbqDY9vssWB_-3uQ-xVw4rb_C1c-FJ-YlrYci2O6vhNXrRKZfgzem-RD8_rX4svxS3Xz-vl9e3heaiGooFGFrKloHgFe0IY8J0IKu6LhWnolKMtyBFtag05aQrecmoBNEaKQU3RjB2ia6OuTqGlCJ0zS7aXsVDQ0kzddHkLhoqm9xFht8d4d3Y9mDO6Onzs_7-pKukleui8tqmM8byypJNMcsj9pgGtYGzrmJ-vYNpIq1rNk09HXn4WdVbFRvw7B8mFK3w</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>KIMURA, Masayasu</creator><creator>DIWAN, Prakash</creator><creator>YANAGI, Seiji</creator><creator>KONNO, Yasuo</creator><creator>NOJIMA, Hiroshi</creator><creator>KIMURA, Ikuko</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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></search><sort><creationdate>1995</creationdate><title>Potentiating Effects of β-Eudesmol-Related Cyclohexylidene Derivatives on Succinylcholine-Induced Neuromuscular Block in Isolated Phrenic Nerve-Diaphragm Muscles of Normal and Alloxan-Diabetic Mice</title><author>KIMURA, Masayasu ; DIWAN, Prakash ; YANAGI, Seiji ; KONNO, Yasuo ; NOJIMA, Hiroshi ; KIMURA, Ikuko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c574t-6ed128b3e7541f0337dfe84992a5174a35be87464c150f252318e7bd8875dd733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cyclohexanes - chemical synthesis</topic><topic>Cyclohexanes - pharmacology</topic><topic>cyclohexylidene derivative</topic><topic>Diabetes Mellitus, Experimental - physiopathology</topic><topic>diabetic mouse</topic><topic>Diaphragm - drug effects</topic><topic>Diaphragm - innervation</topic><topic>Drug Synergism</topic><topic>Drugs, Chinese Herbal - pharmacology</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred Strains</topic><topic>Muscle Contraction - drug effects</topic><topic>neuromuscular blockade</topic><topic>Neuromuscular Blocking Agents - chemical synthesis</topic><topic>Neuromuscular Blocking Agents - pharmacology</topic><topic>Neuromuscular Junction - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Phrenic Nerve - drug effects</topic><topic>potentiation</topic><topic>Respiratory system</topic><topic>Sesquiterpenes, Eudesmane</topic><topic>Stimulation, Chemical</topic><topic>succinylcholine</topic><topic>Succinylcholine - pharmacology</topic><topic>Synaptic Transmission - drug effects</topic><topic>Terpenes - pharmacology</topic><topic>β-eudesmol-related compound</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KIMURA, Masayasu</creatorcontrib><creatorcontrib>DIWAN, Prakash</creatorcontrib><creatorcontrib>YANAGI, Seiji</creatorcontrib><creatorcontrib>KONNO, Yasuo</creatorcontrib><creatorcontrib>NOJIMA, Hiroshi</creatorcontrib><creatorcontrib>KIMURA, Ikuko</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><jtitle>Biological & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KIMURA, Masayasu</au><au>DIWAN, Prakash</au><au>YANAGI, Seiji</au><au>KONNO, Yasuo</au><au>NOJIMA, Hiroshi</au><au>KIMURA, Ikuko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potentiating Effects of β-Eudesmol-Related Cyclohexylidene Derivatives on Succinylcholine-Induced Neuromuscular Block in Isolated Phrenic Nerve-Diaphragm Muscles of Normal and Alloxan-Diabetic Mice</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>1995</date><risdate>1995</risdate><volume>18</volume><issue>3</issue><spage>407</spage><epage>410</epage><pages>407-410</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>β-Eudesmol, a sesquiterpenoid alcohol contained in Atractylodes lancea, potentiates succinylcholine (SuCh)-induced neuromuscular blockade. The potentiating effect is greater in diabetic muscles than in normal ones. As a ligand for affinity chromatography to study the potentiating mechanism, we designed and synthesized newly β-eudesmol-related cyclohexylidene derivatives (2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-13, 2-(3-hydroxy-3-methylbutyl)-4-cyclohexylidene carboxylic acid ; KTE-32 and 4-tert-butoxycarbonyl-2-(3-hydroxy-3-methylbutyl) cyclohexylidene ; KTE-33). We examined the potentiating effects of those compounds in phrenic nerve-diaphragm muscle preparations of normal and alloxan-diabetic mice. KTE-33 (100μM) potentiated more greatly SuCh-induced neuromuscular blockade in diabetic muscles than in normal ones (the potentiating ratios in normal and diabetic muscles were 6.7 and 10.6, respectively), while KTE-13 (100 μM) and -32 (200 μM) potentiated weakly. These results suggest that the ester group in KTE-33 rather than a carboxyl group in KTE-32 is important in inducing the potentiation of SuCh-induced neuromuscular blockade in diabetic state.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>7550092</pmid><doi>10.1248/bpb.18.407</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Animals Biological and medical sciences Cyclohexanes - chemical synthesis Cyclohexanes - pharmacology cyclohexylidene derivative Diabetes Mellitus, Experimental - physiopathology diabetic mouse Diaphragm - drug effects Diaphragm - innervation Drug Synergism Drugs, Chinese Herbal - pharmacology Male Medical sciences Mice Mice, Inbred Strains Muscle Contraction - drug effects neuromuscular blockade Neuromuscular Blocking Agents - chemical synthesis Neuromuscular Blocking Agents - pharmacology Neuromuscular Junction - drug effects Pharmacology. Drug treatments Phrenic Nerve - drug effects potentiation Respiratory system Sesquiterpenes, Eudesmane Stimulation, Chemical succinylcholine Succinylcholine - pharmacology Synaptic Transmission - drug effects Terpenes - pharmacology β-eudesmol-related compound |
| title | Potentiating Effects of β-Eudesmol-Related Cyclohexylidene Derivatives on Succinylcholine-Induced Neuromuscular Block in Isolated Phrenic Nerve-Diaphragm Muscles of Normal and Alloxan-Diabetic Mice |
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