| pubmed-article:17933541 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C0597357 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C0028621 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C2917322 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C1705920 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C2917194 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C1510827 | lld:lifeskim |
| pubmed-article:17933541 | lifeskim:mentions | umls-concept:C0243072 | lld:lifeskim |
| pubmed-article:17933541 | pubmed:issue | 1 | lld:pubmed |
| pubmed-article:17933541 | pubmed:dateCreated | 2008-1-14 | lld:pubmed |
| pubmed-article:17933541 | pubmed:abstractText | A series of 5'-carbamoyl and 5'-thionocarbamoyl derivatives of 2'-C-methyl analogues of the A(1) adenosine receptor (A(1)AR) full agonists N(6)-cyclopentyladenosine (CPA), 2-chloro-N(6)-cyclopentyladenosine (CCPA), N(6)-[3-(R)-tetrahydrofuranyl]adenosine (tecadenoson), and 2-chloro analogue (2-Cl-tecadenoson) was synthesized and evaluated for their affinity for adenosine receptor subtypes from bovine, porcine, and human species. In the N(6)-cyclopentylamino series, the 5'-substituted derivatives showed a reduced affinity at the bovine A(1)AR compared to the parent compounds; however, the selectivity for A(1) versus A(2A) receptor was retained or increased. The corresponding N(6)-3-(R)-tetrahydrofuranylamino analogues displayed a very low affinity toward the bovine A(1)AR. The 5'-methylthionocarbamoyl derivative of 2'-Me-CCPA showed the best affinity at porcine A(1)AR with a K(i) value of 13 nM. At human AR subtypes tecadenoson derivatives showed 2.3- to 5-fold lower affinity at A(1)AR and very low affinity at the other subtypes (A(2A), A(2B), and A(3)) compared to the corresponding N(6)-cyclopentyl analogues. The 5'-carbamoyl and 5'-thionocarbamoyl derivatives of 2'-Me-CCPA 3, 4, 7 and tecadenoson derivative 12 were found to be partial A(1) agonists at the porcine receptor. Docking studies explained the lower affinity of N(6)-3-(R)-tetrahydrofuranyl-substituted compounds at bovine A(1)AR compared to that of N(6)-cyclopentyl analogues, showing that the oxygen of the tetrahydrofuranyl ring establishes unfavorable electrostatic interactions with the CO oxygen of Asn254. The low binding affinity of the 2'-C-methyl-N(6)-3-(R)-tetrahydrofuranyl adenosine analogues at human A(1)AR may be ascribed to the presence of unfavorable interactions between the hydrophilic tetrahydrofuranyl ring and the surrounding hydrophobic residues Leu250 (TM6) and Ile274 (TM7). | lld:pubmed |
| pubmed-article:17933541 | pubmed:language | eng | lld:pubmed |
| pubmed-article:17933541 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:17933541 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:17933541 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:17933541 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:17933541 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:17933541 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:17933541 | pubmed:month | Jan | lld:pubmed |
| pubmed-article:17933541 | pubmed:issn | 1464-3391 | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:CostaBarbaraB | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:MartiniClaudi... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:KlotzKarl-Nor... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:CappellacciLo... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:GrifantiniMar... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:FranchettiPal... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:LavecchiaAnto... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:PetrelliRicca... | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:VitaPatriziaP | lld:pubmed |
| pubmed-article:17933541 | pubmed:author | pubmed-author:SpinettiFranc... | lld:pubmed |
| pubmed-article:17933541 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:17933541 | pubmed:day | 1 | lld:pubmed |
| pubmed-article:17933541 | pubmed:volume | 16 | lld:pubmed |
| pubmed-article:17933541 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:17933541 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:17933541 | pubmed:pagination | 336-53 | lld:pubmed |
| pubmed-article:17933541 | pubmed:dateRevised | 2010-11-18 | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:meshHeading | pubmed-meshheading:17933541... | lld:pubmed |
| pubmed-article:17933541 | pubmed:year | 2008 | lld:pubmed |
| pubmed-article:17933541 | pubmed:articleTitle | 5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species. | lld:pubmed |
| pubmed-article:17933541 | pubmed:affiliation | Dipartimento di Scienze Chimiche, Università di Camerino, 62032 Camerino, Italy. | lld:pubmed |
| pubmed-article:17933541 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:17933541 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:17933541 | lld:chembl |
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