Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand
LGD1069, 4‐[1‐(3,5,5,8,8‐pentamethyl‐5,6,7,8‐tetrahydro‐2‐naphthyl)ethenyl] benzoic acid, is the first retinoid X receptor (RXR) selective retinoid to enter clinical trials for treatment of dermatological diseases and cancer. In order to examine biological properties such as receptor binding, metabo...
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| Veröffentlicht in: | Journal of labelled compounds & radiopharmaceuticals 1995-07, Vol.36 (7), p.701-712 |
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| creator | Zhang, Lin Badea, Beth Ann Enyeart, Debra Berger, Elaine M. Mais, Dale E. Boehm, Marcus F. |
| description | LGD1069, 4‐[1‐(3,5,5,8,8‐pentamethyl‐5,6,7,8‐tetrahydro‐2‐naphthyl)ethenyl] benzoic acid, is the first retinoid X receptor (RXR) selective retinoid to enter clinical trials for treatment of dermatological diseases and cancer. In order to examine biological properties such as receptor binding, metabolism and bioavailability, [13C]‐, [14C]‐, and [3H]‐labeled LGD1069 is required. Herein, we describe synthetic methods for preparing isotopically labeled homologs of LGD1069 as well as comparative competition binding data for [6,7‐3H]‐LGD1069 and [3H]‐9‐cis retinoic acid with RXR active retinoids. The final radiolabeled products, [6,7‐3H]‐LGD1069 and 3‐[14C]‐LGD1069 have specific activities of 56 Ci/mmol and 49 mCi/mmol, respectively. Radiochemical purities are 99.5% for [6,7‐3H]‐LGD1069 and 99.0% for 3‐[14C]‐LGD1069. The chemical purity is 99.0% for 3‐[13CD3]‐LGD1069. Competition binding studies with known retinoids show similar Kd values when either [6,7‐3H]‐LGD1069 or [3H]‐9‐cis retinoic acid is used as the radioligand. |
| doi_str_mv | 10.1002/jlcr.2580360712 |
| format | Article |
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In order to examine biological properties such as receptor binding, metabolism and bioavailability, [13C]‐, [14C]‐, and [3H]‐labeled LGD1069 is required. Herein, we describe synthetic methods for preparing isotopically labeled homologs of LGD1069 as well as comparative competition binding data for [6,7‐3H]‐LGD1069 and [3H]‐9‐cis retinoic acid with RXR active retinoids. The final radiolabeled products, [6,7‐3H]‐LGD1069 and 3‐[14C]‐LGD1069 have specific activities of 56 Ci/mmol and 49 mCi/mmol, respectively. Radiochemical purities are 99.5% for [6,7‐3H]‐LGD1069 and 99.0% for 3‐[14C]‐LGD1069. The chemical purity is 99.0% for 3‐[13CD3]‐LGD1069. Competition binding studies with known retinoids show similar Kd values when either [6,7‐3H]‐LGD1069 or [3H]‐9‐cis retinoic acid is used as the radioligand.</description><identifier>ISSN: 0362-4803</identifier><identifier>EISSN: 1099-1344</identifier><identifier>DOI: 10.1002/jlcr.2580360712</identifier><language>eng</language><publisher>Chichester: John Wiley & Sons, Ltd</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Isotopes ; Labeled retinoids ; LGD1069 ; Organic chemistry ; Preparations and properties ; RAR ; Retinoid receptors ; RXR ; Tritium</subject><ispartof>Journal of labelled compounds & radiopharmaceuticals, 1995-07, Vol.36 (7), p.701-712</ispartof><rights>Copyright © 1995 John Wiley & Sons, Ltd.</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4242-893737e3a150999f346f06e1c01bbd22628f6152fdc4f0942638f76fabb93a873</citedby><cites>FETCH-LOGICAL-c4242-893737e3a150999f346f06e1c01bbd22628f6152fdc4f0942638f76fabb93a873</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlcr.2580360712$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlcr.2580360712$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3591936$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Lin</creatorcontrib><creatorcontrib>Badea, Beth Ann</creatorcontrib><creatorcontrib>Enyeart, Debra</creatorcontrib><creatorcontrib>Berger, Elaine M.</creatorcontrib><creatorcontrib>Mais, Dale E.</creatorcontrib><creatorcontrib>Boehm, Marcus F.</creatorcontrib><title>Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand</title><title>Journal of labelled compounds & radiopharmaceuticals</title><addtitle>J Label Compd Radiopharm</addtitle><description>LGD1069, 4‐[1‐(3,5,5,8,8‐pentamethyl‐5,6,7,8‐tetrahydro‐2‐naphthyl)ethenyl] benzoic acid, is the first retinoid X receptor (RXR) selective retinoid to enter clinical trials for treatment of dermatological diseases and cancer. In order to examine biological properties such as receptor binding, metabolism and bioavailability, [13C]‐, [14C]‐, and [3H]‐labeled LGD1069 is required. Herein, we describe synthetic methods for preparing isotopically labeled homologs of LGD1069 as well as comparative competition binding data for [6,7‐3H]‐LGD1069 and [3H]‐9‐cis retinoic acid with RXR active retinoids. The final radiolabeled products, [6,7‐3H]‐LGD1069 and 3‐[14C]‐LGD1069 have specific activities of 56 Ci/mmol and 49 mCi/mmol, respectively. Radiochemical purities are 99.5% for [6,7‐3H]‐LGD1069 and 99.0% for 3‐[14C]‐LGD1069. The chemical purity is 99.0% for 3‐[13CD3]‐LGD1069. Competition binding studies with known retinoids show similar Kd values when either [6,7‐3H]‐LGD1069 or [3H]‐9‐cis retinoic acid is used as the radioligand.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Isotopes</subject><subject>Labeled retinoids</subject><subject>LGD1069</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>RAR</subject><subject>Retinoid receptors</subject><subject>RXR</subject><subject>Tritium</subject><issn>0362-4803</issn><issn>1099-1344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><recordid>eNqFUEtrFTEUDqLgtbp2m4WLFiZtXpOZwZVc7a06KPSBgkjIZBJvajoZkqAd_1H_pblcqbiSsziH8z0O5wPgOcHHBGN6cu11PKZ1i5nADaEPwIrgrkOEcf4QrMqWIl7Ax-BJStcYF4zzFbi7WKa8NckkGCx0KeQwO628X6BXg_FmhBx9IeiQVXWptmrRbKasbkzeLh7VlaiasssmR7VdxhgQRZOatzv0qHDMtPivg5l-Baeh0m6Eh_3mNcGiO6qggnPIxQ1Gk90UCnhbRm3mHCJK5bjO7oeB3n1T0_gUPLLKJ_PsTz8AV6dvLtdnqP-4ebt-1SPNKaeo7VjDGsMUqcuLnWVcWCwM0ZgMw0ipoK0VpKZ21NzijlPBWtsIq4ahY6pt2AE42fvqGFKKxso5uhsVF0mw3CUtd0nLv0kXxYu9YlapRGejmrRL9zJWd6RjotBe7mk_nTfL_1zlu359_s8RtFe7lM3tvVrF71KUh2v56cNGnl2-b0971svP7DchFp4e</recordid><startdate>199507</startdate><enddate>199507</enddate><creator>Zhang, Lin</creator><creator>Badea, Beth Ann</creator><creator>Enyeart, Debra</creator><creator>Berger, Elaine M.</creator><creator>Mais, Dale E.</creator><creator>Boehm, Marcus F.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199507</creationdate><title>Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand</title><author>Zhang, Lin ; Badea, Beth Ann ; Enyeart, Debra ; Berger, Elaine M. ; Mais, Dale E. ; Boehm, Marcus F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4242-893737e3a150999f346f06e1c01bbd22628f6152fdc4f0942638f76fabb93a873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Isotopes</topic><topic>Labeled retinoids</topic><topic>LGD1069</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>RAR</topic><topic>Retinoid receptors</topic><topic>RXR</topic><topic>Tritium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Lin</creatorcontrib><creatorcontrib>Badea, Beth Ann</creatorcontrib><creatorcontrib>Enyeart, Debra</creatorcontrib><creatorcontrib>Berger, Elaine M.</creatorcontrib><creatorcontrib>Mais, Dale E.</creatorcontrib><creatorcontrib>Boehm, Marcus F.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Lin</au><au>Badea, Beth Ann</au><au>Enyeart, Debra</au><au>Berger, Elaine M.</au><au>Mais, Dale E.</au><au>Boehm, Marcus F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand</atitle><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle><addtitle>J Label Compd Radiopharm</addtitle><date>1995-07</date><risdate>1995</risdate><volume>36</volume><issue>7</issue><spage>701</spage><epage>712</epage><pages>701-712</pages><issn>0362-4803</issn><eissn>1099-1344</eissn><abstract>LGD1069, 4‐[1‐(3,5,5,8,8‐pentamethyl‐5,6,7,8‐tetrahydro‐2‐naphthyl)ethenyl] benzoic acid, is the first retinoid X receptor (RXR) selective retinoid to enter clinical trials for treatment of dermatological diseases and cancer. In order to examine biological properties such as receptor binding, metabolism and bioavailability, [13C]‐, [14C]‐, and [3H]‐labeled LGD1069 is required. Herein, we describe synthetic methods for preparing isotopically labeled homologs of LGD1069 as well as comparative competition binding data for [6,7‐3H]‐LGD1069 and [3H]‐9‐cis retinoic acid with RXR active retinoids. The final radiolabeled products, [6,7‐3H]‐LGD1069 and 3‐[14C]‐LGD1069 have specific activities of 56 Ci/mmol and 49 mCi/mmol, respectively. Radiochemical purities are 99.5% for [6,7‐3H]‐LGD1069 and 99.0% for 3‐[14C]‐LGD1069. The chemical purity is 99.0% for 3‐[13CD3]‐LGD1069. Competition binding studies with known retinoids show similar Kd values when either [6,7‐3H]‐LGD1069 or [3H]‐9‐cis retinoic acid is used as the radioligand.</abstract><cop>Chichester</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/jlcr.2580360712</doi><tpages>12</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Isotopes Labeled retinoids LGD1069 Organic chemistry Preparations and properties RAR Retinoid receptors RXR Tritium |
| title | Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand |
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