| pubmed-article:1322988 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0035647 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0034801 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C1882365 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0023688 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0220825 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0040399 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0034559 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0182400 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0127400 | lld:lifeskim |
| pubmed-article:1322988 | lifeskim:mentions | umls-concept:C0086684 | lld:lifeskim |
| pubmed-article:1322988 | pubmed:issue | 15 | lld:pubmed |
| pubmed-article:1322988 | pubmed:dateCreated | 1992-9-4 | lld:pubmed |
| pubmed-article:1322988 | pubmed:abstractText | The epimeric 6 beta- and 6 alpha-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinans (1, ioxy) and (2, epioxy), respectively, were each synthesized in five steps starting with naltrexone. The configuration of the 6-iodo group of 1 was unequivocally determined to be beta-based on single crystal X-ray analysis of its precursor 3-acetoxy-6 beta-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinan (10). Both 1 and 2 as well as their corresponding 3-O-acetates 10 and 11 were found to readily cross the blood-brain barrier and completely reverse the analgesic effects of a 10 mg/kg intraperitoneal dose of morphine sulfate as determined by the paw withdrawal latency test. Compounds 1 and 2 were found to bind with high affinity to mu, delta, and kappa receptors in vitro. In general, 1 and 2 exhibited higher affinity for mu and kappa receptors than naltrexone while the 6 beta-iodo epimer 1 (ioxy) was more potent than its epimer 2. In a comparison of the 6 beta-halogen substituent on binding affinity across opioid receptor subtypes, it was generally found that I greater than Br greater than F. On the basis of the results of in vitro and in vivo testing, 1 was selected as a target for radioiodination and evaluation as a potential single photon emission computed tomography imaging agent for opioid receptors. Carrier-free [125I]-1 was synthesized in near quantitative yield by the sequence of reaction of excess 3-acetoxy-6 alpha-[[(trifluoromethyl)sulfonyl]oxy]-14-hydroxy-17- (cyclopropylmethyl)-4,5 alpha-epoxymorphinan (8) with anhydrous Na125I in dry acetonitrile for 90 min at 76 degrees C followed by deacetylation of the product with 1:1 aqueous ammonia/acetonitrile at 25 degrees C. The potential of [125I]-1 as an in vivo imaging agent for opioid receptors is evaluated and discussed. | lld:pubmed |
| pubmed-article:1322988 | pubmed:language | eng | lld:pubmed |
| pubmed-article:1322988 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:1322988 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:1322988 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:1322988 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:1322988 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:1322988 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:1322988 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:1322988 | pubmed:month | Jul | lld:pubmed |
| pubmed-article:1322988 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:JacobsonA EAE | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:RiceK CKC | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:GeorgeCC | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:IadarolaM JMJ | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:RothmanR BRB | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:de CostaB RBR | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:NewmanA HAH | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:BermanK FKF | lld:pubmed |
| pubmed-article:1322988 | pubmed:author | pubmed-author:MahboubiAA | lld:pubmed |
| pubmed-article:1322988 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:1322988 | pubmed:day | 24 | lld:pubmed |
| pubmed-article:1322988 | pubmed:volume | 35 | lld:pubmed |
| pubmed-article:1322988 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:1322988 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:1322988 | pubmed:pagination | 2826-35 | lld:pubmed |
| pubmed-article:1322988 | pubmed:dateRevised | 2003-11-14 | lld:pubmed |
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| pubmed-article:1322988 | pubmed:meshHeading | pubmed-meshheading:1322988-... | lld:pubmed |
| pubmed-article:1322988 | pubmed:year | 1992 | lld:pubmed |
| pubmed-article:1322988 | pubmed:articleTitle | Probes for narcotic receptor mediated phenomena. 18. Epimeric 6 alpha- and 6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography: synthesis, evaluation, and radiochemistry of [125I]-6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinan. | lld:pubmed |
| pubmed-article:1322988 | pubmed:affiliation | Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892. | lld:pubmed |
| pubmed-article:1322988 | pubmed:publicationType | Journal Article | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:1322988 | lld:chembl |
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