uu.seUppsala University Publications
Change search
ReferencesLink to record
Permanent link

Direct link
Synthesis, screening and computational investigation of pentacycloundecane-peptoids as potent CSA-HIV PR inhibitors
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Show others and affiliations
2012 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 57, 459-467 p.Article in journal (Refereed) Published
Abstract [en]

Herein, we present the first pentacycloundecane (PCU) diol peptoid derived HIV protease inhibitors with IC50 values ranging from 6.5 to 0.075 mu M. Five derivatives were synthesized in an attempt to understand the structure activity relationship of this class of compounds for HIV protease inhibition. NMR spectroscopy (new Efficient Adiabatic Symmetrized Rotating Overhauser Effect Spectroscopy, EASY-ROESY) was employed to determine the predominant conformation of the active compound. In this study docking studies and MD simulations provided insight into the binding theme of this class of peptoid inhibitors to the CSA-HIV PR active site. Conserved and stable hydrogen bonding between the hydroxyl groups of the inhibitors and the active site Asp25/Asp25' residues were observed from the docking and along the MD trajectories.

Place, publisher, year, edition, pages
2012. Vol. 57, 459-467 p.
Keyword [en]
Transition state analogs, IC50, Pentacycloundecane diol-peptoid, CSA-HIV-1 wild type C-SA protease, EASY-ROESY, Molecular docking, MD simulations
National Category
Medical and Health Sciences
URN: urn:nbn:se:uu:diva-193042DOI: 10.1016/j.ejmech.2012.06.019ISI: 000312621700047OAI: oai:DiVA.org:uu-193042DiVA: diva2:601158
Available from: 2013-01-28 Created: 2013-01-28 Last updated: 2013-01-28Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Arvidsson, Per I.
By organisation
Organic Pharmaceutical Chemistry
In the same journal
European Journal of Medicinal Chemistry
Medical and Health Sciences

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 174 hits
ReferencesLink to record
Permanent link

Direct link