Antagonistic activity of 24-oxa-analogs of vitamin D
24-Oxa-vitamin D 3 (24-oxa-D 3) and 24-oxa-1α-hydroxyvitamin D 3 were designed as possible inhibitors of the vitamin D metabolic activation pathway. Their affinity for the vitamin D receptor (from pig intestine) and human vitamin binding protein were reduced, and their potency to induce cell differe...
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| Veröffentlicht in: | Steroids 1995-06, Vol.60 (6), p.484-490 |
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| creator | Allewaert, Katrien Sarandeses, Luis A. Mourino, Antonio Convents, Renilde Tan, Biauw-Keng Zhao, Jie Bouillon, Roger |
| description | 24-Oxa-vitamin D
3 (24-oxa-D
3) and 24-oxa-1α-hydroxyvitamin D
3 were designed as possible inhibitors of the vitamin D metabolic activation pathway. Their affinity for the vitamin D receptor (from pig intestine) and human vitamin binding protein were reduced, and their potency to induce cell differentiation of human leukemia cells (HL 60) or osteosarcoma cells (MG 63) was markedly reduced (19% and 3%, respectively), in comparison with calcitriol. A single or chronic injection of 24-oxa-D
3 had no biological activity, whereas chronic administration of 24-oxa-1α-hydroxy-D
3 showed weak agonist activity in rachitic chicks. When the 24-oxa-D
3 was given prior to a single injection of vitamin D
3, lower values of serum calcium (64% of the value obtained in vitamin D—treated animals), osteocalcin (52%), 25-(OH)D
3 (45%) and duodenal calbindin-D 28K (9.4%) were found. When given chronically in a 100-fold more excess no clear antagonistic effects were observed. 24-Oxa-D
3 is thus a new metabolic weak antagonist of vitamin D
3, but adding a hydroxyl group at C-1 creates a weak agonist. |
| doi_str_mv | 10.1016/0039-128X(95)00036-P |
| format | Article |
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3 (24-oxa-D
3) and 24-oxa-1α-hydroxyvitamin D
3 were designed as possible inhibitors of the vitamin D metabolic activation pathway. Their affinity for the vitamin D receptor (from pig intestine) and human vitamin binding protein were reduced, and their potency to induce cell differentiation of human leukemia cells (HL 60) or osteosarcoma cells (MG 63) was markedly reduced (19% and 3%, respectively), in comparison with calcitriol. A single or chronic injection of 24-oxa-D
3 had no biological activity, whereas chronic administration of 24-oxa-1α-hydroxy-D
3 showed weak agonist activity in rachitic chicks. When the 24-oxa-D
3 was given prior to a single injection of vitamin D
3, lower values of serum calcium (64% of the value obtained in vitamin D—treated animals), osteocalcin (52%), 25-(OH)D
3 (45%) and duodenal calbindin-D 28K (9.4%) were found. When given chronically in a 100-fold more excess no clear antagonistic effects were observed. 24-Oxa-D
3 is thus a new metabolic weak antagonist of vitamin D
3, but adding a hydroxyl group at C-1 creates a weak agonist.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/0039-128X(95)00036-P</identifier><identifier>PMID: 7676483</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>agonist ; Animals ; antagonist ; Biological and medical sciences ; calcemic effect ; Calcitriol - pharmacology ; Calcium - blood ; Cell Differentiation - drug effects ; Chickens ; cholecalciferol ; Cholecalciferol - analogs & derivatives ; Cholecalciferol - metabolism ; Cholecalciferol - pharmacology ; differentiation ; Hormones. Endocrine system ; Humans ; Leukemia, Promyelocytic, Acute ; Medical sciences ; Osteosarcoma ; Pharmacology. Drug treatments ; receptor ; Receptors, Calcitriol - metabolism ; Swine ; Tumor Cells, Cultured ; Vitamin D - antagonists & inhibitors ; Vitamin D-Binding Protein - metabolism</subject><ispartof>Steroids, 1995-06, Vol.60 (6), p.484-490</ispartof><rights>1995</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c335t-347dd2b9d03de312f99457feb31738cc0135ba5cbecebd797668b881298843a03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0039-128X(95)00036-P$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3616239$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7676483$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Allewaert, Katrien</creatorcontrib><creatorcontrib>Sarandeses, Luis A.</creatorcontrib><creatorcontrib>Mourino, Antonio</creatorcontrib><creatorcontrib>Convents, Renilde</creatorcontrib><creatorcontrib>Tan, Biauw-Keng</creatorcontrib><creatorcontrib>Zhao, Jie</creatorcontrib><creatorcontrib>Bouillon, Roger</creatorcontrib><title>Antagonistic activity of 24-oxa-analogs of vitamin D</title><title>Steroids</title><addtitle>Steroids</addtitle><description>24-Oxa-vitamin D
3 (24-oxa-D
3) and 24-oxa-1α-hydroxyvitamin D
3 were designed as possible inhibitors of the vitamin D metabolic activation pathway. Their affinity for the vitamin D receptor (from pig intestine) and human vitamin binding protein were reduced, and their potency to induce cell differentiation of human leukemia cells (HL 60) or osteosarcoma cells (MG 63) was markedly reduced (19% and 3%, respectively), in comparison with calcitriol. A single or chronic injection of 24-oxa-D
3 had no biological activity, whereas chronic administration of 24-oxa-1α-hydroxy-D
3 showed weak agonist activity in rachitic chicks. When the 24-oxa-D
3 was given prior to a single injection of vitamin D
3, lower values of serum calcium (64% of the value obtained in vitamin D—treated animals), osteocalcin (52%), 25-(OH)D
3 (45%) and duodenal calbindin-D 28K (9.4%) were found. When given chronically in a 100-fold more excess no clear antagonistic effects were observed. 24-Oxa-D
3 is thus a new metabolic weak antagonist of vitamin D
3, but adding a hydroxyl group at C-1 creates a weak agonist.</description><subject>agonist</subject><subject>Animals</subject><subject>antagonist</subject><subject>Biological and medical sciences</subject><subject>calcemic effect</subject><subject>Calcitriol - pharmacology</subject><subject>Calcium - blood</subject><subject>Cell Differentiation - drug effects</subject><subject>Chickens</subject><subject>cholecalciferol</subject><subject>Cholecalciferol - analogs & derivatives</subject><subject>Cholecalciferol - metabolism</subject><subject>Cholecalciferol - pharmacology</subject><subject>differentiation</subject><subject>Hormones. Endocrine system</subject><subject>Humans</subject><subject>Leukemia, Promyelocytic, Acute</subject><subject>Medical sciences</subject><subject>Osteosarcoma</subject><subject>Pharmacology. Drug treatments</subject><subject>receptor</subject><subject>Receptors, Calcitriol - metabolism</subject><subject>Swine</subject><subject>Tumor Cells, Cultured</subject><subject>Vitamin D - antagonists & inhibitors</subject><subject>Vitamin D-Binding Protein - metabolism</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtLAzEQx4MotVa_gcIeRPSwmsfmdRFKfULBHhS8hWySLZF91M222G9v1i49ehpm_r8Zhh8A5wjeIojYHYREpgiLz2tJb2DsWLo4AGMkuEipYPwQjPfIMTgJ4StCjEg8AiPOOMsEGYNsWnd62dQ-dN4k2nR-47tt0hQJztLmR6e61mWzDP0kJrrydfJwCo4KXQZ3NtQJ-Hh6fJ-9pPO359fZdJ4aQmiXkoxbi3NpIbGOIFxImVFeuJwgToQxEBGaa2pyZ1xuueSMiVwIhKUQGdGQTMDV7u6qbb7XLnSq8sG4stS1a9ZBcU4xpoxHMNuBpm1CaF2hVq2vdLtVCKpelupNqN6EklT9yVKLuHYx3F_nlbP7pcFOzC-HXAejy6LVtfFhjxGGGCYyYvc7zEUXG-9aFYx3tXHWt850yjb-_z9-Ae3WhC0</recordid><startdate>19950601</startdate><enddate>19950601</enddate><creator>Allewaert, Katrien</creator><creator>Sarandeses, Luis A.</creator><creator>Mourino, Antonio</creator><creator>Convents, Renilde</creator><creator>Tan, Biauw-Keng</creator><creator>Zhao, Jie</creator><creator>Bouillon, Roger</creator><general>Elsevier Inc</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>7X8</scope></search><sort><creationdate>19950601</creationdate><title>Antagonistic activity of 24-oxa-analogs of vitamin D</title><author>Allewaert, Katrien ; Sarandeses, Luis A. ; Mourino, Antonio ; Convents, Renilde ; Tan, Biauw-Keng ; Zhao, Jie ; Bouillon, Roger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c335t-347dd2b9d03de312f99457feb31738cc0135ba5cbecebd797668b881298843a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>agonist</topic><topic>Animals</topic><topic>antagonist</topic><topic>Biological and medical sciences</topic><topic>calcemic effect</topic><topic>Calcitriol - pharmacology</topic><topic>Calcium - blood</topic><topic>Cell Differentiation - drug effects</topic><topic>Chickens</topic><topic>cholecalciferol</topic><topic>Cholecalciferol - analogs & derivatives</topic><topic>Cholecalciferol - metabolism</topic><topic>Cholecalciferol - pharmacology</topic><topic>differentiation</topic><topic>Hormones. Endocrine system</topic><topic>Humans</topic><topic>Leukemia, Promyelocytic, Acute</topic><topic>Medical sciences</topic><topic>Osteosarcoma</topic><topic>Pharmacology. Drug treatments</topic><topic>receptor</topic><topic>Receptors, Calcitriol - metabolism</topic><topic>Swine</topic><topic>Tumor Cells, Cultured</topic><topic>Vitamin D - antagonists & inhibitors</topic><topic>Vitamin D-Binding Protein - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Allewaert, Katrien</creatorcontrib><creatorcontrib>Sarandeses, Luis A.</creatorcontrib><creatorcontrib>Mourino, Antonio</creatorcontrib><creatorcontrib>Convents, Renilde</creatorcontrib><creatorcontrib>Tan, Biauw-Keng</creatorcontrib><creatorcontrib>Zhao, Jie</creatorcontrib><creatorcontrib>Bouillon, Roger</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>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Allewaert, Katrien</au><au>Sarandeses, Luis A.</au><au>Mourino, Antonio</au><au>Convents, Renilde</au><au>Tan, Biauw-Keng</au><au>Zhao, Jie</au><au>Bouillon, Roger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antagonistic activity of 24-oxa-analogs of vitamin D</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1995-06-01</date><risdate>1995</risdate><volume>60</volume><issue>6</issue><spage>484</spage><epage>490</epage><pages>484-490</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>24-Oxa-vitamin D
3 (24-oxa-D
3) and 24-oxa-1α-hydroxyvitamin D
3 were designed as possible inhibitors of the vitamin D metabolic activation pathway. Their affinity for the vitamin D receptor (from pig intestine) and human vitamin binding protein were reduced, and their potency to induce cell differentiation of human leukemia cells (HL 60) or osteosarcoma cells (MG 63) was markedly reduced (19% and 3%, respectively), in comparison with calcitriol. A single or chronic injection of 24-oxa-D
3 had no biological activity, whereas chronic administration of 24-oxa-1α-hydroxy-D
3 showed weak agonist activity in rachitic chicks. When the 24-oxa-D
3 was given prior to a single injection of vitamin D
3, lower values of serum calcium (64% of the value obtained in vitamin D—treated animals), osteocalcin (52%), 25-(OH)D
3 (45%) and duodenal calbindin-D 28K (9.4%) were found. When given chronically in a 100-fold more excess no clear antagonistic effects were observed. 24-Oxa-D
3 is thus a new metabolic weak antagonist of vitamin D
3, but adding a hydroxyl group at C-1 creates a weak agonist.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>7676483</pmid><doi>10.1016/0039-128X(95)00036-P</doi><tpages>7</tpages></addata></record> |
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| ispartof | Steroids, 1995-06, Vol.60 (6), p.484-490 |
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| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | agonist Animals antagonist Biological and medical sciences calcemic effect Calcitriol - pharmacology Calcium - blood Cell Differentiation - drug effects Chickens cholecalciferol Cholecalciferol - analogs & derivatives Cholecalciferol - metabolism Cholecalciferol - pharmacology differentiation Hormones. Endocrine system Humans Leukemia, Promyelocytic, Acute Medical sciences Osteosarcoma Pharmacology. Drug treatments receptor Receptors, Calcitriol - metabolism Swine Tumor Cells, Cultured Vitamin D - antagonists & inhibitors Vitamin D-Binding Protein - metabolism |
| title | Antagonistic activity of 24-oxa-analogs of vitamin D |
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