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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
15
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pubmed:dateCreated |
2010-8-5
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pubmed:abstractText |
The enantiomers of cis-(+/-)-methyl (1R,2S/1S,2R)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [1, (+/-)-PPCC], a selective sigma ligand, were synthesized. The (+)- and (-)-enantiomers bind predominantly to sigma(1) receptors and have a reduced sigma(2) affinity. Both individually restore the astroglial oxidative status modified by glutamate, counteracting also transglutaminase-2 overexpression. They exhibited in vivo anti-opioid effects on kappa opioid (KOP) receptor-mediated analgesia. Our findings demonstrate that the enantiomers display mainly sigma(1) agonist activity and that they have neuroprotective effects.
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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 |
http://linkedlifedata.com/resource/pubmed/chemical/3,4-Dichloro-N-methyl-N-(2-(1-pyrrol...,
http://linkedlifedata.com/resource/pubmed/chemical/Analgesics, Non-Narcotic,
http://linkedlifedata.com/resource/pubmed/chemical/Cyclopropanes,
http://linkedlifedata.com/resource/pubmed/chemical/GTP-Binding Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Glutamic Acid,
http://linkedlifedata.com/resource/pubmed/chemical/Glutathione,
http://linkedlifedata.com/resource/pubmed/chemical/Ibogaine,
http://linkedlifedata.com/resource/pubmed/chemical/Ligands,
http://linkedlifedata.com/resource/pubmed/chemical/Neuroprotective Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Pentazocine,
http://linkedlifedata.com/resource/pubmed/chemical/Piperidines,
http://linkedlifedata.com/resource/pubmed/chemical/Reactive Oxygen Species,
http://linkedlifedata.com/resource/pubmed/chemical/Receptors, Opioid, kappa,
http://linkedlifedata.com/resource/pubmed/chemical/Receptors, sigma,
http://linkedlifedata.com/resource/pubmed/chemical/Transglutaminases,
http://linkedlifedata.com/resource/pubmed/chemical/methyl...,
http://linkedlifedata.com/resource/pubmed/chemical/transglutaminase 2
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
1520-4804
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pubmed:author |
pubmed-author:ArenaEmanuelaE,
pubmed-author:AricòGiuseppinaG,
pubmed-author:BertucciCarloC,
pubmed-author:CampisiAgataA,
pubmed-author:ParentiCarmelaC,
pubmed-author:PistolozziMarcoM,
pubmed-author:PrezzaventoOrazioO,
pubmed-author:RonsisvalleGiuseppeG,
pubmed-author:RonsisvalleSimoneS,
pubmed-author:ScotoGiovanna MGM,
pubmed-author:VanellaAngeloA
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pubmed:issnType |
Electronic
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pubmed:day |
12
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pubmed:volume |
53
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
5881-5
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pubmed:meshHeading |
pubmed-meshheading:20684615-3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-ben...,
pubmed-meshheading:20684615-Analgesics, Non-Narcotic,
pubmed-meshheading:20684615-Animals,
pubmed-meshheading:20684615-Astrocytes,
pubmed-meshheading:20684615-Cells, Cultured,
pubmed-meshheading:20684615-Cyclopropanes,
pubmed-meshheading:20684615-Drug Interactions,
pubmed-meshheading:20684615-GTP-Binding Proteins,
pubmed-meshheading:20684615-Glutamic Acid,
pubmed-meshheading:20684615-Glutathione,
pubmed-meshheading:20684615-Ibogaine,
pubmed-meshheading:20684615-Ligands,
pubmed-meshheading:20684615-Neuroprotective Agents,
pubmed-meshheading:20684615-Oxidative Stress,
pubmed-meshheading:20684615-Pentazocine,
pubmed-meshheading:20684615-Piperidines,
pubmed-meshheading:20684615-Rats,
pubmed-meshheading:20684615-Reactive Oxygen Species,
pubmed-meshheading:20684615-Receptors, Opioid, kappa,
pubmed-meshheading:20684615-Receptors, sigma,
pubmed-meshheading:20684615-Stereoisomerism,
pubmed-meshheading:20684615-Structure-Activity Relationship,
pubmed-meshheading:20684615-Transglutaminases
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pubmed:year |
2010
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pubmed:articleTitle |
Synthesis and resolution of cis-(+/-)-methyl (1R,2S/1S,2R)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [(+/-)-PPCC)]: new sigma receptor ligands with neuroprotective effect.
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pubmed:affiliation |
Department of Pharmaceutical Sciences, Medicinal Chemistry Section, University of Catania, Catania, Italy. prezzave@unict.it
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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