Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides
A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data su...
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| Veröffentlicht in: | Journal of medicinal chemistry 1984-03, Vol.27 (3), p.256-261 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 27 |
| creator | Fullerton, Dwight S Kihara, Masaru Deffo, Tamboue Kitatsuji, Eitaro Ahmed, Khalil Simat, Bruce From, Arthur H. L |
| description | A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding. |
| doi_str_mv | 10.1021/jm00369a004 |
| format | Article |
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A systematic study of digitoxigenin D-glycosides</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Fullerton, Dwight S ; Kihara, Masaru ; Deffo, Tamboue ; Kitatsuji, Eitaro ; Ahmed, Khalil ; Simat, Bruce ; From, Arthur H. L</creator><creatorcontrib>Fullerton, Dwight S ; Kihara, Masaru ; Deffo, Tamboue ; Kitatsuji, Eitaro ; Ahmed, Khalil ; Simat, Bruce ; From, Arthur H. L</creatorcontrib><description>A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00369a004</identifier><identifier>PMID: 6321733</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Carbohydrate Conformation ; Cardiac Glycosides - analysis ; Crystallography ; Digitoxigenin - analogs & derivatives ; Digitoxigenin - pharmacology ; Kidney - enzymology ; Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors ; Swine</subject><ispartof>Journal of medicinal chemistry, 1984-03, Vol.27 (3), p.256-261</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-25c77536f85fecf7f19b11e5d18aab5d0040c071902cc2f6d055a073aa8b7c193</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/jm00369a004$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00369a004$$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/6321733$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fullerton, Dwight S</creatorcontrib><creatorcontrib>Kihara, Masaru</creatorcontrib><creatorcontrib>Deffo, Tamboue</creatorcontrib><creatorcontrib>Kitatsuji, Eitaro</creatorcontrib><creatorcontrib>Ahmed, Khalil</creatorcontrib><creatorcontrib>Simat, Bruce</creatorcontrib><creatorcontrib>From, Arthur H. L</creatorcontrib><title>Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.</description><subject>Animals</subject><subject>Carbohydrate Conformation</subject><subject>Cardiac Glycosides - analysis</subject><subject>Crystallography</subject><subject>Digitoxigenin - analogs & derivatives</subject><subject>Digitoxigenin - pharmacology</subject><subject>Kidney - enzymology</subject><subject>Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors</subject><subject>Swine</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1PwzAQhi0EKqUwMSNlggGlnO04TsaqhfJRiYqWhcVyHKdySZpiJ1Lz70mVChiYbnife0_3IHSJYYiB4Lt1AUDDWAIER6iPGQE_iCA4Rn0AQnwSEnqKzpxbQ8thQnuoF1KCOaV9NB1LmxqpvFXeqNKZVLuhh4feyHONq3QhK6M8V9Vp45WZl5qVqcqdWemN2XgT_3fpHJ1kMnf64jAH6P3hfjl-9Gev06fxaOZLyoLKJ0xxzmiYRSzTKuMZjhOMNUtxJGXC0vYFUMBxDEQpkoUpMCaBUymjhCsc0wG67nq3tvyqtatEYZzSeS43uqydiCCOgjDeg7cdqGzpnNWZ2FpTSNsIDGKvTfzR1tJXh9o6KXT6wx48tbnf5aaVsvuJpf0UIaecieV8ISYvy4-353ksFi1_0_FSObEua7tppfx7-Rv2DIKB</recordid><startdate>198403</startdate><enddate>198403</enddate><creator>Fullerton, Dwight S</creator><creator>Kihara, Masaru</creator><creator>Deffo, Tamboue</creator><creator>Kitatsuji, Eitaro</creator><creator>Ahmed, Khalil</creator><creator>Simat, Bruce</creator><creator>From, Arthur H. L</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><scope>7X8</scope></search><sort><creationdate>198403</creationdate><title>Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides</title><author>Fullerton, Dwight S ; Kihara, Masaru ; Deffo, Tamboue ; Kitatsuji, Eitaro ; Ahmed, Khalil ; Simat, Bruce ; From, Arthur H. L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a354t-25c77536f85fecf7f19b11e5d18aab5d0040c071902cc2f6d055a073aa8b7c193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Animals</topic><topic>Carbohydrate Conformation</topic><topic>Cardiac Glycosides - analysis</topic><topic>Crystallography</topic><topic>Digitoxigenin - analogs & derivatives</topic><topic>Digitoxigenin - pharmacology</topic><topic>Kidney - enzymology</topic><topic>Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors</topic><topic>Swine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fullerton, Dwight S</creatorcontrib><creatorcontrib>Kihara, Masaru</creatorcontrib><creatorcontrib>Deffo, Tamboue</creatorcontrib><creatorcontrib>Kitatsuji, Eitaro</creatorcontrib><creatorcontrib>Ahmed, Khalil</creatorcontrib><creatorcontrib>Simat, Bruce</creatorcontrib><creatorcontrib>From, Arthur H. L</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fullerton, Dwight S</au><au>Kihara, Masaru</au><au>Deffo, Tamboue</au><au>Kitatsuji, Eitaro</au><au>Ahmed, Khalil</au><au>Simat, Bruce</au><au>From, Arthur H. L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1984-03</date><risdate>1984</risdate><volume>27</volume><issue>3</issue><spage>256</spage><epage>261</epage><pages>256-261</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>6321733</pmid><doi>10.1021/jm00369a004</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1984-03, Vol.27 (3), p.256-261 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Carbohydrate Conformation Cardiac Glycosides - analysis Crystallography Digitoxigenin - analogs & derivatives Digitoxigenin - pharmacology Kidney - enzymology Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors Swine |
| title | Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides |
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