Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effects of changes to the chain linking of the C-14-amino group to the aryl ring

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dc.contributor.author Rennison, David en
dc.contributor.author Moynihan, H en
dc.contributor.author Traynor, JR en
dc.contributor.author Lewis, JW en
dc.contributor.author Husbands, SM en
dc.date.accessioned 2012-06-11T20:10:37Z en
dc.date.issued 2006-10-05 en
dc.identifier.citation JOURNAL OF MEDICINAL CHEMISTRY 49(20):6104-6110 05 Oct 2006 en
dc.identifier.issn 0022-2623 en
dc.identifier.uri http://hdl.handle.net/2292/18921 en
dc.description.abstract The 14-aminodihydromorphinone and codeinone series of opioid ligands have produced a number of ligands of substantial interest. To investigate the importance of the 14-substituent, a series of analogues in which the side chain length is varied and the amide and alkene functions are reduced have been prepared. Binding affinity, particularly at the mu-opioid receptor (MOR), was largely determined by the aromatic group of the side chain. In the [S-35] GTP gamma S functional assay, the ligands having a three-carbon side chain were more potent antagonists than their longer chain counterparts, while shorter, two-carbon chain analogues were of higher MOR efficacy, an effect that was confirmed in vivo. Wash-resistant binding was observed within this series and appeared to be unrelated to side-chain length. en
dc.language English en
dc.publisher AMER CHEMICAL SOC en
dc.relation.ispartofseries Journal of Medicinal Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0022-2623/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject Science & Technology en
dc.subject Life Sciences & Biomedicine en
dc.subject Chemistry, Medicinal en
dc.subject Pharmacology & Pharmacy en
dc.subject PHOSPHONATES en
dc.subject CLOCINNAMOX en
dc.subject ANTAGONIST en
dc.subject BINDING en
dc.subject ANALOGS en
dc.title Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effects of changes to the chain linking of the C-14-amino group to the aryl ring en
dc.type Journal Article en
dc.identifier.doi 10.1021/jm060595u en
pubs.issue 20 en
pubs.begin-page 6104 en
pubs.volume 49 en
dc.rights.holder Copyright: 2006 American Chemical Society en
dc.identifier.pmid 17004724 en
pubs.author-url http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=000240826200025&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=6e41486220adb198d0efde5a3b153e7d en
pubs.end-page 6110 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 112469 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.record-created-at-source-date 2012-06-12 en
pubs.dimensions-id 17004724 en


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