| pubmed-article:18210999 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C0439849 | lld:lifeskim |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C0037659 | lld:lifeskim |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C0679622 | lld:lifeskim |
| pubmed-article:18210999 | lifeskim:mentions | umls-concept:C0205314 | lld:lifeskim |
| pubmed-article:18210999 | pubmed:issue | 3 | lld:pubmed |
| pubmed-article:18210999 | pubmed:dateCreated | 2008-2-8 | lld:pubmed |
| pubmed-article:18210999 | pubmed:abstractText | We describe synthesis, conformational studies, and binding to the five somatostatin receptors (sst 1-5) of a few analogues of the cyclic octapeptide octreotide (1), where the disulfide bridge was replaced by a dicarba group. These analogues were prepared by on-resin RCM of linear hepta-peptides containing two allylglycine residues; first- and second-generation Grubbs catalyst efficiencies were compared. The C=C bridge was hydrogenated via two different methods. Binding experiments showed that two analogues had good affinity and high selectivity for the sst5 receptor. Three-dimensional structures of the active analogues were determined by (1)H NMR spectroscopy. Conformation-affinity relationships confirmed the importance of D-Phe(2) orientation for sst2 affinity. Moreover, helical propensities well correlates with the peptide sst5 affinity. The presence of the bulky aromatic side chain of Tyr(Bzl)(10) favored the formation of a 3(10)-helix and enhanced the sst5 selectivity suppressing the sst2 affinity. Finally, a new pharmacophore model for the sst5 was developed. | lld:pubmed |
| pubmed-article:18210999 | pubmed:language | eng | lld:pubmed |
| pubmed-article:18210999 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:18210999 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18210999 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:18210999 | pubmed:month | Feb | lld:pubmed |
| pubmed-article:18210999 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:ReubiJean... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:CarotenutoAlf... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:NovellinoEtto... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:PapiniAnna... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:GinanneschiMa... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:GoriFrancesca... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:PiccandVéroni... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:D'AddonaDebor... | lld:pubmed |
| pubmed-article:18210999 | pubmed:author | pubmed-author:Di... | lld:pubmed |
| pubmed-article:18210999 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:18210999 | pubmed:day | 14 | lld:pubmed |
| pubmed-article:18210999 | pubmed:volume | 51 | lld:pubmed |
| pubmed-article:18210999 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:18210999 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:18210999 | pubmed:pagination | 512-20 | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:meshHeading | pubmed-meshheading:18210999... | lld:pubmed |
| pubmed-article:18210999 | pubmed:year | 2008 | lld:pubmed |
| pubmed-article:18210999 | pubmed:articleTitle | Novel sst5-selective somatostatin dicarba-analogues: synthesis and conformation-affinity relationships. | lld:pubmed |
| pubmed-article:18210999 | pubmed:affiliation | Laboratory of Peptides and Proteins, Chemistry and Biology, Department of Organic Chemistry, University of Firenze, Via Lastruccia 13 I-50019, Sesto Fiorentino, Italy. | lld:pubmed |
| pubmed-article:18210999 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:18210999 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:18210999 | lld:chembl |
