Weight loss effects of quaternary salts of 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles; structure-activity relationships

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dc.contributor.author Tercel, Moana en
dc.contributor.author Stevenson, Ralph en
dc.contributor.author Lu, Guo-Liang en
dc.contributor.author Stribbling, SM en
dc.contributor.author Wilson, William en
dc.contributor.author Tatnell, MA en
dc.contributor.author Marnane, RN en
dc.contributor.author Mountjoy, Kathleen en
dc.contributor.author Denny, William en
dc.coverage.spatial England en
dc.date.accessioned 2012-03-27T20:45:14Z en
dc.date.issued 2012-01 en
dc.identifier.citation Bioorg Med Chem 20(2):734-749 15 Jan 2012 en
dc.identifier.issn 0968-0896 en
dc.identifier.uri http://hdl.handle.net/2292/15694 en
dc.description.abstract Quaternary salt analogues based on the DNA minor groove binder and adenine N3 alkylating agent 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (aminoCBI) show remarkable effects on the body weight of mice (a long-term failure to gain weight relative to matched controls with no loss of appetite or perceptible deterioration in health) following administration of a single (non-toxic) dose between about 0.5-5μmol/kg. The nature of the quaternizing group was not important, but a related hydroxyCBI analogue was much less effective. Compounds where the chloro group was replaced by a hydrogen or hydroxy group (thus abrogating DNA alkylating capability) showed no weight control activity. It is speculated, based on other studies, that the marked long-term weight control effect is due to inhibition of bile flow into the intestine and reduced absorption of triglycerides, together with accelerated cell death in spleen and white adipose tissues due to drug accumulation there. This class of compound may serve as interesting tools for further study of these phenomena. en
dc.language eng en
dc.publisher Elsevier en
dc.relation.ispartofseries Bioorganic & 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/0968-0896/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Weight loss effects of quaternary salts of 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles; structure-activity relationships en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.bmc.2011.12.007 en
pubs.issue 2 en
pubs.begin-page 734 en
pubs.volume 20 en
dc.rights.holder Copyright: Elsevier en
dc.identifier.pmid 22200344 en
pubs.author-url http://www.sciencedirect.com/science/article/pii/S0968089611010133 en
pubs.end-page 749 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 267508 en
pubs.org-id Medical and Health Sciences en
pubs.org-id Medical Sciences en
pubs.org-id Auckland Cancer Research en
pubs.org-id Physiology Division en
pubs.org-id Science en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
dc.identifier.eissn 1464-3391 en
dc.identifier.pii S0968-0896(11)01013-3 en
pubs.record-created-at-source-date 2012-02-22 en
pubs.online-publication-date 2011-12-09 en
pubs.dimensions-id 22200344 en

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