From Spanish fly to room-temperature ionic liquids (RTILs): synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs (original) (raw)
* Corresponding authors
a Chemistry, School of Environmental & Life Sciences, The University of Newcastle, Callaghan, Australia
E-mail: Adam.McCluskey@newcastle.edu.au
Fax: 612 49215472
Tel: 612 9216486
b Cell Signalling Unit, Children’s Medical Research Institute, 214 Hawkesbury Road, Westmead, Australia
Abstract
In a series of simple synthetic manipulations the active component of the aphrodisiac Spanish fly has resulted in the generation of a new family of room-temperature ionic liquids (RTILs). These RTILs are synthesized in high yield from readily attainable starting materials and can be generated in either meso or chiral forms dependant on the starting furan analogue. Substituted furans (2-methyl and 2-ethyl) afford chiral RTILs, furan affords a family of meso RTILs. In all cases the counterion was crucial, with CH3SO3– consistently displaying the lowest melting points. Of the RTILs synthesized, TGA plots showed most to be stable up to at least 250 °C. We had sought to use these RTILs in a series of dynamic combinatorial chemistry (DCC) assembly reactions via solubulisation of dynamin GTPases pleckstrin homology (PH) domain, as such all analogues were screened as potential inhibitors. Screening reveals that these RTILs display varying levels of dynamin GTPase inhibition with a number amongst the most potent inhibitors of dynamin GTPase yet discovered, e.g.13 IC50 = 2.3 ± 0.3 µM (4-(N,_N_-dimethyl-_N_-octadecyl-_N_-ethyl)-4-aza-10-oxatricyclo[5.2.1]decane-3,5-dione bromide. Accordingly these RTILs have limited utility for DCC assembly with dynamin GTPase, but may be of use with other proteins or in other fields of study.
You have access to this article
Please wait while we load your content... Something went wrong. Try again?
Supplementary files
Article information
DOI
https://doi.org/10.1039/B707092F
Article type
Paper
Submitted
10 May 2007
Accepted
21 Aug 2007
First published
10 Sep 2007
Download Citation
New J. Chem., 2008,32, 28-36
Permissions
From Spanish fly to room-temperature ionic liquids (RTILs): synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs
J. Zhang, G. A. Lawrance, N. Chau, P. J. Robinson and A. McCluskey,New J. Chem., 2008, 32, 28DOI: 10.1039/B707092F
To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.
If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.
If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.
Read more about how to correctly acknowledge RSC content.