Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β
Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo- l-thyronine ( 2), a novel TRβ-selective indole derivative 6b was prepared and tested in vitro. Its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of 6b com...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-03, Vol.16 (5), p.1240-1244 |
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| creator | Garcia Collazo, Ana-Maria Koehler, Konrad F. Garg, Neeraj Färnegårdh, Mathias Husman, Bolette Ye, Liu Ljunggren, Jan Mellström, Karin Sandberg, Johnny Grynfarb, Marlena Ahola, Harri Malm, Johan |
| description | Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2), a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. Its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.
Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2) a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. This compound was found to be 14 times selective for TRβ over TRα in binding and its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ. |
| doi_str_mv | 10.1016/j.bmcl.2005.11.077 |
| format | Article |
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l-thyronine (
2), a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. Its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.
Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2) a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. This compound was found to be 14 times selective for TRβ over TRα in binding and its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.11.077</identifier><identifier>PMID: 16338239</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Biological and medical sciences ; Crystallography, X-Ray ; Cyclization ; Hormones. Endocrine system ; Humans ; Indane ; Indole ; Indoles - chemistry ; Indoles - metabolism ; Indoles - pharmacology ; Inhibitory Concentration 50 ; Ligands ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Quinoline ; Rats ; Substrate Specificity ; Thyroid hormone receptor agonist ; Thyroid Hormone Receptors beta - agonists ; Thyroid Hormone Receptors beta - chemistry ; Thyroid Hormone Receptors beta - metabolism ; Thyroxine - chemical synthesis ; Thyroxine - chemistry ; TRβ-selectivity ; X-ray</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1240-1244</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-e50ddf9fbd122e3e76d0d310b378eae245a8db3e53fa9c31b22836f069c312c83</citedby><cites>FETCH-LOGICAL-c415t-e50ddf9fbd122e3e76d0d310b378eae245a8db3e53fa9c31b22836f069c312c83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X05015064$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17557265$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16338239$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Garcia Collazo, Ana-Maria</creatorcontrib><creatorcontrib>Koehler, Konrad F.</creatorcontrib><creatorcontrib>Garg, Neeraj</creatorcontrib><creatorcontrib>Färnegårdh, Mathias</creatorcontrib><creatorcontrib>Husman, Bolette</creatorcontrib><creatorcontrib>Ye, Liu</creatorcontrib><creatorcontrib>Ljunggren, Jan</creatorcontrib><creatorcontrib>Mellström, Karin</creatorcontrib><creatorcontrib>Sandberg, Johnny</creatorcontrib><creatorcontrib>Grynfarb, Marlena</creatorcontrib><creatorcontrib>Ahola, Harri</creatorcontrib><creatorcontrib>Malm, Johan</creatorcontrib><title>Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2), a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. Its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.
Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2) a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. This compound was found to be 14 times selective for TRβ over TRα in binding and its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Hormones. Endocrine system</subject><subject>Humans</subject><subject>Indane</subject><subject>Indole</subject><subject>Indoles - chemistry</subject><subject>Indoles - metabolism</subject><subject>Indoles - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>Ligands</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinoline</subject><subject>Rats</subject><subject>Substrate Specificity</subject><subject>Thyroid hormone receptor agonist</subject><subject>Thyroid Hormone Receptors beta - agonists</subject><subject>Thyroid Hormone Receptors beta - chemistry</subject><subject>Thyroid Hormone Receptors beta - metabolism</subject><subject>Thyroxine - chemical synthesis</subject><subject>Thyroxine - chemistry</subject><subject>TRβ-selectivity</subject><subject>X-ray</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM-KFDEQh4Mo7rj6Ah4kF711W0k66W7xsiz-g0U9rOAtpJPqnQzpzpj0DMxr-SA-kxlmZG4eiqLg-_0oPkJeMqgZMPV2Uw-TDTUHkDVjNbTtI7JijWoq0YB8TFbQK6i6vvl5RZ7lvAFgDTTNU3LFlBAdF_2KzPfrQ4re0YQWt0tMNPgHM7tc0-8mLVS-o1_jHgMdvD3Y4C01D3H2efnH0YwB7eL3SMeSXtZY5lS5jmmKM16q__x-Tp6MJmR8cd7X5MfHD_e3n6u7b5--3N7cVbZhcqlQgnNjPw6OcY4CW-XACQaDaDs0yBtpOjcIlGI0vRVs4LwTagR1PLjtxDV5c-rdpvhrh3nRk88WQzAzxl3WrIW2VxwKyE-gTTHnhKPeJj-ZdNAM9NGy3uijZX20rBnTxXIJvTq374YJ3SVy1lqA12fAZGvCmMxsfb5wrZQtV7Jw708cFhd7j0ln63G26HyRtmgX_f_--AvVip0C</recordid><startdate>20060301</startdate><enddate>20060301</enddate><creator>Garcia Collazo, Ana-Maria</creator><creator>Koehler, Konrad F.</creator><creator>Garg, Neeraj</creator><creator>Färnegårdh, Mathias</creator><creator>Husman, Bolette</creator><creator>Ye, Liu</creator><creator>Ljunggren, Jan</creator><creator>Mellström, Karin</creator><creator>Sandberg, Johnny</creator><creator>Grynfarb, Marlena</creator><creator>Ahola, Harri</creator><creator>Malm, Johan</creator><general>Elsevier Ltd</general><general>Elsevier</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20060301</creationdate><title>Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β</title><author>Garcia Collazo, Ana-Maria ; Koehler, Konrad F. ; Garg, Neeraj ; Färnegårdh, Mathias ; Husman, Bolette ; Ye, Liu ; Ljunggren, Jan ; Mellström, Karin ; Sandberg, Johnny ; Grynfarb, Marlena ; Ahola, Harri ; Malm, Johan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-e50ddf9fbd122e3e76d0d310b378eae245a8db3e53fa9c31b22836f069c312c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>Hormones. Endocrine system</topic><topic>Humans</topic><topic>Indane</topic><topic>Indole</topic><topic>Indoles - chemistry</topic><topic>Indoles - metabolism</topic><topic>Indoles - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>Ligands</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinoline</topic><topic>Rats</topic><topic>Substrate Specificity</topic><topic>Thyroid hormone receptor agonist</topic><topic>Thyroid Hormone Receptors beta - agonists</topic><topic>Thyroid Hormone Receptors beta - chemistry</topic><topic>Thyroid Hormone Receptors beta - metabolism</topic><topic>Thyroxine - chemical synthesis</topic><topic>Thyroxine - chemistry</topic><topic>TRβ-selectivity</topic><topic>X-ray</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garcia Collazo, Ana-Maria</creatorcontrib><creatorcontrib>Koehler, Konrad F.</creatorcontrib><creatorcontrib>Garg, Neeraj</creatorcontrib><creatorcontrib>Färnegårdh, Mathias</creatorcontrib><creatorcontrib>Husman, Bolette</creatorcontrib><creatorcontrib>Ye, Liu</creatorcontrib><creatorcontrib>Ljunggren, Jan</creatorcontrib><creatorcontrib>Mellström, Karin</creatorcontrib><creatorcontrib>Sandberg, Johnny</creatorcontrib><creatorcontrib>Grynfarb, Marlena</creatorcontrib><creatorcontrib>Ahola, Harri</creatorcontrib><creatorcontrib>Malm, Johan</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garcia Collazo, Ana-Maria</au><au>Koehler, Konrad F.</au><au>Garg, Neeraj</au><au>Färnegårdh, Mathias</au><au>Husman, Bolette</au><au>Ye, Liu</au><au>Ljunggren, Jan</au><au>Mellström, Karin</au><au>Sandberg, Johnny</au><au>Grynfarb, Marlena</au><au>Ahola, Harri</au><au>Malm, Johan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-03-01</date><risdate>2006</risdate><volume>16</volume><issue>5</issue><spage>1240</spage><epage>1244</epage><pages>1240-1244</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2), a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. Its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.
Based on the examination of the crystal structure of rat TRβ complexed with 3,5,3′-triiodo-
l-thyronine (
2) a novel TRβ-selective indole derivative
6b was prepared and tested in vitro. This compound was found to be 14 times selective for TRβ over TRα in binding and its β-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of
6b complexed with TRα and TRβ.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16338239</pmid><doi>10.1016/j.bmcl.2005.11.077</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1240-1244 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_17079620 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Biological and medical sciences Crystallography, X-Ray Cyclization Hormones. Endocrine system Humans Indane Indole Indoles - chemistry Indoles - metabolism Indoles - pharmacology Inhibitory Concentration 50 Ligands Medical sciences Molecular Structure Pharmacology. Drug treatments Quinoline Rats Substrate Specificity Thyroid hormone receptor agonist Thyroid Hormone Receptors beta - agonists Thyroid Hormone Receptors beta - chemistry Thyroid Hormone Receptors beta - metabolism Thyroxine - chemical synthesis Thyroxine - chemistry TRβ-selectivity X-ray |
| title | Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β |
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