| pubmed-article:8496936 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C0035647 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C1521970 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C0005456 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C1167622 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C0040399 | lld:lifeskim |
| pubmed-article:8496936 | lifeskim:mentions | umls-concept:C1512628 | lld:lifeskim |
| pubmed-article:8496936 | pubmed:issue | 5 | lld:pubmed |
| pubmed-article:8496936 | pubmed:dateCreated | 1993-6-24 | lld:pubmed |
| pubmed-article:8496936 | pubmed:abstractText | 2-, 3-, and 4-idophenyl derivatives of the high-affinity sigma ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (1) were synthesized in two to four steps starting from N-methyl-2-(1-pyrrolidinyl)ethylamine. These compounds were evaluated for their capacity to label both sigma 1 and sigma 2 subtypes in vitro. sigma-1 binding affinity was determined by measuring competition with [3H]-(+)-pentazocine binding to guinea pig brain membranes while sigma 2 binding was evaluated through competition with [3H]DTG binding to rat liver membranes in the presence of excess dextrallorphan. The binding data revealed that N-[2-(3-iodophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (2) and N-[2-(4-iodophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3) displayed almost identical binding affinity at sigma 1 sites to the parent compound 1. This suggests that the 3- or 4-iodo group can effectively substitute for the 3,4-dichloro substituents of 1. In this series of compounds, Ki's at the sigma 1 site varied from 2.0 nM for N-(4-iodobenzyl)-N-methyl-2-(1-pyrrolidinyl)ethylamine (6) to 26.6 nM for N-(2-iodobenzyl)-N-methyl-2-(1-pyrrolidinyl)ethylamine (4). Ki's for sigma 2 site ranged from 8.1 nM for 1 to 220 nM for N-(3-bromobenzyl)-N-methyl-2-(1-pyrrolidinyl)ethylamine (11) while the sigma 2/sigma 1 ratio varied from 1.8 for 4 to 25 for 11. Comparing halogen substitution, the trend Cl = I > Br > F was observed for binding affinity at sigma 1 sites; no such trend was observed at sigma 2 sites. On the basis of the binding data, compounds 2 and 3 were selected for labeling with 123I. Thus, treatment of the corresponding 3- and 4-(tributylstannyl) intermediates (7 and 8) with Na123I in the presence of excess CH3CO3H furnished [123I]-2 and [123I]-3 in up to 70% radiochemical yield. Preliminary in vitro binding with [123I]-3 indicated up to 97% specific binding with guinea pig brain membranes. | lld:pubmed |
| pubmed-article:8496936 | pubmed:language | eng | lld:pubmed |
| pubmed-article:8496936 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:8496936 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:8496936 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:8496936 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:8496936 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:8496936 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:8496936 | pubmed:month | Mar | lld:pubmed |
| pubmed-article:8496936 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:LeeK SKS | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:WilliamsWW | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:BowerW HWH | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:WeinbergerD... | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:de CostaB RBR | lld:pubmed |
| pubmed-article:8496936 | pubmed:author | pubmed-author:HaX WXW | lld:pubmed |
| pubmed-article:8496936 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:8496936 | pubmed:day | 5 | lld:pubmed |
| pubmed-article:8496936 | pubmed:volume | 36 | lld:pubmed |
| pubmed-article:8496936 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:8496936 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:8496936 | pubmed:pagination | 566-71 | lld:pubmed |
| pubmed-article:8496936 | pubmed:dateRevised | 2006-11-15 | lld:pubmed |
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| pubmed-article:8496936 | pubmed:year | 1993 | lld:pubmed |
| pubmed-article:8496936 | pubmed:articleTitle | Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites. | lld:pubmed |
| pubmed-article:8496936 | pubmed:affiliation | Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892. | lld:pubmed |
| pubmed-article:8496936 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:8496936 | pubmed:publicationType | Comparative Study | lld:pubmed |
| pubmed-article:8496936 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
| pubmed-article:8496936 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:8496936 | lld:chembl |
| http://linkedlifedata.com/r... | pubmed:referesTo | pubmed-article:8496936 | lld:pubmed |
