dc.contributor.author |
Rendle, PM |
en |
dc.contributor.author |
Kassibawi, F |
en |
dc.contributor.author |
Johnston, KA |
en |
dc.contributor.author |
Hart, JB |
en |
dc.contributor.author |
Cameron, SA |
en |
dc.contributor.author |
Falshaw, A |
en |
dc.contributor.author |
Painter, Gavin |
en |
dc.contributor.author |
Loomes, Kerry |
en |
dc.date.accessioned |
2017-02-07T01:42:25Z |
en |
dc.date.available |
2016-06-25 |
en |
dc.date.issued |
2016-10-21 |
en |
dc.identifier.citation |
European Journal of Medicinal Chemistry, 21 October 2016, 122, 442 - 451 |
en |
dc.identifier.issn |
0223-5234 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/31747 |
en |
dc.description.abstract |
d-chiro-inositol (DCI, 1) evokes therapeutic actions in diabetes and insulin resistance but has sub-optimal pharmacokinetic profiles. To investigate what positions on the DCI cyclohexanol ring may be amenable to modification to improve pharmaceutical formulations, a series of analogues based on DCI were synthesised. These compounds were then evaluated for their ability to stimulate glucose transport using 3T3-L1 adipocytes as a model system. Positional analyses indicate that the hydroxyl group at position 1 is not essential for activity and can be modified without affecting glucose uptake. Removal of the hydroxyl at position 3 also had minimal effect on activity but this group is sensitive to modification. By comparison, the oxygen at position 2 is crucial to the potency of DCI, although this group can withstand modification without fundamentally affecting activity. These data reveal that positions 1 and 2 on the cyclohexanol ring of DCI offer further scope for modification to develop DCI analogues with desirable pharmacokinetic profiles for the potential treatment of metabolic disease. |
en |
dc.description.uri |
https://www.ncbi.nlm.nih.gov/pubmed/27410479 |
en |
dc.format.medium |
Print-Electronic |
en |
dc.language |
English |
en |
dc.publisher |
Elsevier |
en |
dc.relation.ispartofseries |
European 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/0223-5234/
https://www.elsevier.com/about/company-information/policies/sharing |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.title |
Synthesis and biological activities of d-chiro-inositol analogues with insulin-like actions |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1016/j.ejmech.2016.06.047 |
en |
pubs.begin-page |
442 |
en |
pubs.volume |
122 |
en |
dc.description.version |
VoR - Version of Record |
en |
dc.identifier.pmid |
27410479 |
en |
pubs.author-url |
http://www.sciencedirect.com/science/article/pii/S0223523416305372 |
en |
pubs.end-page |
451 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
536246 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Biological Sciences |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
dc.identifier.eissn |
1768-3254 |
en |
pubs.record-created-at-source-date |
2017-02-07 |
en |
pubs.online-publication-date |
2016-06-29 |
en |
pubs.dimensions-id |
27410479 |
en |