Linked Life Data

2824775

Source:http://linkedlifedata.com/resource/pubmed/id/2824775

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
1988-1-21
pubmed:abstractText
The synthesis of different diazonium salts derived from homo- and heterocyclic aromatic amines bearing anionic residues is described. The chemical stabilities of these compounds were established at different pH's, and the compounds were tested accordingly in binding experiments for the rat brain gamma-aminobutyric acid (GABA) receptor, for which they could ultimately be used as irreversible affinity or photoaffinity probes. The aromatic heterocyclic series studied were 2-aminoimidazole, 2-aminothiazole, and 4-aminopyridine N-oxide. The derived diazonium salts are unstable compounds at neutral pH unless they are able to be deprotonated to the corresponding diazo form. As such, the 2-diazoimidazole-4(5)-acetic acid (3b) is stable in neutral medium and recognizes the GABA receptor (IC50 = 70 microM). The homocyclic aromatic diazonium salts showed sufficient stability to be tested in binding experiments. The diazonium salts derived from m-sulfanilic acid and 8-sulfonaphthylamine were the most interesting (10b, IC50 = 10 microM; 15b, IC50 less than 100 microM). In this series, the compounds that deprotonate at neutral pH (hydroxybenzenediazonium derivatives 12b-14b) showed increased chemical stability but decreased affinity for the GABA receptor. This difference between the diazoimidazole and the diazohydroxybenzene series is attributed to a different charge distribution between the two series. The ligands 3b, 10b, and 15b can be used as potential irreversible probes for the GABA receptor.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
30
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2222-7
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1987
pubmed:articleTitle
Aryl diazo compounds and diazonium salts as potential irreversible probes of the gamma-aminobutyric acid receptor.
pubmed:affiliation
Laboratoire de Chimie Bio-Organique (UA31 CNRS), Faculté de Pharmacie, Université Louis Pasteur, Strasbourg, France.
pubmed:publicationType
Journal Article, In Vitro, Research Support, Non-U.S. Gov't