Linked Life Data

2415705

Source:http://linkedlifedata.com/resource/pubmed/id/2415705

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
11
pubmed:dateCreated
1985-12-27
pubmed:abstractText
The affinities of the oxymorphamine epimers for mu and delta opioid receptors were determined in vitro. The 6 alpha and 6 beta epimers are potent mu-selective ligands with similar receptor-binding profiles. The relatively undramatic effect of C-6 chirality on receptor interactions is intriguing in view of the recently demonstrated profound influence of C-6 chirality on ring-C solution conformations (ring C is a chair conformer in the beta epimer but adopts a twist-boat conformation in the alpha epimer) and prompted the determination of the crystal structure of alpha-oxymorphamine. The crystal structure showed that ring C in this epimer also adopts a twist-boat conformation in the solid state. Molecular modeling of the oxymorphamines in the preferred ring-C conformations (alpha = boat, beta = chair) demonstrated that the 6-amino groups project to spatial loci significantly more proximal (0.35 A) than would be the case (2.2 A) if both epimers adopted chair conformations for ring C. Consequently, although the epimeric oxymorphamines differ in ring-C conformation, the principle potential heteroatomic binding sites in each epimer are oriented similarly, which may be partly responsible for the lack of dramatic differences in receptor binding profiles.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
28
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1652-6
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1985
pubmed:articleTitle
Opioid receptor interactions and conformations of the 6 alpha and 6 beta epimers of oxymorphamine. Solid-state conformation of 6 alpha-oxymorphamine.
pubmed:publicationType
Journal Article, Comparative Study