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Azido and diazarinyl analogues of bis-tyrphostin as asymmetrical inhibitors of dynamin GTPase
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
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2009 (Engelska)Ingår i: ChemMedChem, ISSN 1860-7179, Vol. 4, nr 7, 1182-1188 s.Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Probing the dynamin binding site: Bis-tyrphostin (1, Bis-T), is a potent inhibitor of the phospholipid-stimulated GTPase activity of dynamin I. Analogues of Bis-T have significant potential as a biological probes for the dissection of endocytic pathways. Bis-T-derived compounds were synthesised and evaluated for their ability to inhibit the GTPase activity of dynamin I. Two analogues (23 and 24) represent the first asymmetrically substituted Bis-T analogues to retain dynamin inhibition.Two azidobenzyl amide (4 and 23) and one 3-trifluoromethyl-3H-diazirin-3-ylphenyl (24) analogues of bis-tyrphostin (1, Bis-T) were synthesised as potential photoaffinity labels for the elucidation of the binding site of compound 1 in dynamin I. Of the two azidobenzyl amide analogues (4 and 23), the terminally substituted 23 retained dynamin I GTPase inhibition (IC(50)=6.4+/-2.8 microM) whilst 4, which was substituted on the central carbon of the amide linker, displayed no activity. Analogue 24 also retained inhibitory activity (IC(50)=36+/-9 microM). Photoaffinity labelling experiments did not unequivocally elucidate the binding pocket of compound 1. However, compounds 23 and 24 represent the first asymmetrically substituted Bis-T analogues to retain dynamin inhibitory activity, providing a new direction for analogue synthesis.

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2009. Vol. 4, nr 7, 1182-1188 s.
Nationell ämneskategori
Farmaceutiska vetenskaper
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URN: urn:nbn:se:uu:diva-124845DOI: 10.1002/cmdc.200900054ISI: 000267893000018PubMedID: 19437476OAI: oai:DiVA.org:uu-124845DiVA: diva2:318055
Tillgänglig från: 2010-05-06 Skapad: 2010-05-06 Senast uppdaterad: 2018-01-12Bibliografiskt granskad

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