Linked Life Data

15324897

Source:http://linkedlifedata.com/resource/pubmed/id/15324897

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
18
pubmed:dateCreated
2004-8-24
pubmed:abstractText
2',6'-Dimethyl substitution of the Tyr(1) residue in opioid agonist peptides and deletion of the N-terminal amino group, as achieved by replacement of Tyr(1) with 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acid (Dhp), have been shown to produce opioid antagonists. To examine the effect of beta-methylation of Dhp(1) in opioid peptides on the activity profile, stereoselective syntheses of (3S)- and (3R)-3-methyl-3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acid [(3S)- and (3R)-Mdp] were carried out. In comparison with the cyclic parent antagonist peptide Dhp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys]NH(2), the methylated analogue (3S)-Mdp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys]NH(2) showed higher micro, delta and kappa antagonist potencies in functional assays and higher binding affinities for micro, delta and kappa opioid receptors (K(i)(micro)=2.03 nM; K(i)(delta)=2.34 nM; K(i)(kappa)=49.5 nM), whereas the corresponding (3R)-Mdp(1)-analogue was less potent by 1-2 orders of magnitude.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
0960-894X
pubmed:author
pubmed:issnType
Print
pubmed:day
20
pubmed:volume
14
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4731-3
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
2004
pubmed:articleTitle
A novel cyclic enkephalin analogue with potent opioid antagonist activity.
pubmed:affiliation
Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, 110 Pine Avenue West, Montreal, Quebec, Canada H2W 1R7.
pubmed:publicationType
Journal Article, Comparative Study, In Vitro, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't