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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
6
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pubmed:dateCreated |
2007-3-15
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pubmed:abstractText |
Dicarba analogues of the cyclic opioid peptides H-Tyr-c[d-Cys-Gly-Phe-d(or l)-Cys]NH2 were synthesized on solid phase by substituting allylglycines for the cysteines and cyclization by ring-closing metathesis between the side chains of the allylglycine residues. Mixtures of cis and trans isomers of the resulting olefinic peptides were obtained, and catalytic hydrogenation yielded the saturated -CH2-CH2- bridged peptides. The dicarba analogues retained high mu and delta agonist potencies. Remarkably, the trans isomer of H-Tyr-c[d-Allylgly-Gly-Phe-l-Allylgly]NH2 was a mu agonist/delta agonist with subnanomolar potency at both receptors.
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pubmed:grant |
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pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-10823227,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-11508644,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-12464111,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-12509887,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-15614807,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-16496038,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-2158362,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-217386,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-2822930,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-2832195,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-2845204,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-4202581,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-4655272,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-4854571,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-499333,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-6272756,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-6296388,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-6310598,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17315860-9606018
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0022-2623
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
22
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pubmed:volume |
50
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1414-7
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pubmed:dateRevised |
2011-8-1
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pubmed:meshHeading |
pubmed-meshheading:17315860-Allyl Compounds,
pubmed-meshheading:17315860-Animals,
pubmed-meshheading:17315860-Brain,
pubmed-meshheading:17315860-Enkephalins,
pubmed-meshheading:17315860-Guinea Pigs,
pubmed-meshheading:17315860-Ileum,
pubmed-meshheading:17315860-Male,
pubmed-meshheading:17315860-Models, Molecular,
pubmed-meshheading:17315860-Molecular Conformation,
pubmed-meshheading:17315860-Muscle, Smooth,
pubmed-meshheading:17315860-Muscle Contraction,
pubmed-meshheading:17315860-Peptides, Cyclic,
pubmed-meshheading:17315860-Radioligand Assay,
pubmed-meshheading:17315860-Rats,
pubmed-meshheading:17315860-Receptors, Opioid, delta,
pubmed-meshheading:17315860-Receptors, Opioid, mu,
pubmed-meshheading:17315860-Stereoisomerism,
pubmed-meshheading:17315860-Structure-Activity Relationship,
pubmed-meshheading:17315860-Vas Deferens
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pubmed:year |
2007
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pubmed:articleTitle |
Dicarba analogues of the cyclic enkephalin peptides H-Tyr-c[D-Cys-Gly-Phe-D(or L)-Cys]NH(2) retain high opioid activity.
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pubmed:affiliation |
Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, 110 Pine Avenue West, Montreal, Quebec, Canada H2W 1R7.
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pubmed:publicationType |
Journal Article,
In Vitro,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
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