Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Tuning and predicting biological affinity: arylnitriles as cysteine protease inhibitors†‡§

Veronika Ehmke,a   Jose Enrico Q. Quinsaat,a   Pablo Rivera-Fuentes,a   Cornelia Heindl,b   Céline Freymond,cd   Matthias Rottmann,cd   Reto Brun,cd   Tanja Schirmeisterbe  and  François Diederich*a  

* Corresponding authors

a Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland
E-mail: diederich@org.chem.ethz.ch
Fax: (+41)44-632-1109

b Institute of Pharmacy and Food Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany

c Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland

d University of Basel, Petersplatz 1, 4003 Basel, Switzerland

e Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University Mainz, Staudinger Weg 5, 55128 Mainz, Germany

Abstract

A series of aryl nitrile-based ligands were prepared to investigate the effect of their electrophilicity on the affinity against the cysteine proteases rhodesain and human cathepsin L. Density functional theory calculations provided relative reactivities of the nitriles, enabling prediction of their biological affinity and cytotoxicity and a clear structure–activity relationship.

Graphical abstract: Tuning and predicting biological affinity: aryl nitriles as cysteine protease inhibitors

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Article information

DOI
https://doi.org/10.1039/C2OB00034B
Article type
Communication
Submitted
05 Phe 2012
Accepted
23 Phe 2012
First published
16 Kol 2012

Org. Biomol. Chem., 2012,10, 5764-5768

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Tuning and predicting biological affinity: aryl nitriles as cysteine protease inhibitors

V. Ehmke, J. E. Q. Quinsaat, P. Rivera-Fuentes, C. Heindl, C. Freymond, M. Rottmann, R. Brun, T. Schirmeister and F. Diederich, Org. Biomol. Chem., 2012, 10, 5764 DOI: 10.1039/C2OB00034B

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