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Synthesis, receptor binding affinities and conformational properties of cyclic methylenedithioether analogues of angiotensin II
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för farmaceutisk biovetenskap, Avdelningen för biologisk beroendeforskning. (Drug Dependence)
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2001 (engelsk)Inngår i: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 9, nr 3, s. 763-772Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Cyclic 12-, 13- and 14-membered ring angiotensin II analogues related to disulfides but encompassing methylenedithioether bridges have been prepared. The affinity data from these derivatives were compared to those from the disulfides. The methylenedithioether analogues displayed good binding affinities to rat liver AT1 receptors although in most cases somewhat lower than their disulfide counterparts. One of the methylenedithioethers with a 13-membered ring system demonstrated the highest binding affinity among the thioethers. Theoretical conformational analysis of model compounds of the two series were performed suggesting a similarity between the disulfide and the corresponding methylenedithioether analogues and also between the ring size homologues. This analysis also suggested that some of the model compounds were prone to adopt inverse γ-turn conformations, which was further supported by use of NMR spectroscopy of the 12-membered ring analogue in the series. The easily executed methylenedithioether cyclization should constitute a valuable complement to the common disulfide methodology for fine-tuning and for probing the bioactive conformation of peptides.

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2001. Vol. 9, nr 3, s. 763-772
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URN: urn:nbn:se:uu:diva-51292DOI: 10.1016/S0968-0896(00)00294-7OAI: oai:DiVA.org:uu-51292DiVA, id: diva2:79201
Tilgjengelig fra: 2008-10-17 Laget: 2008-10-17 Sist oppdatert: 2017-12-04bibliografisk kontrollert

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