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Issue 21, 2019
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Enzymatic triggering of C–ON bond homolysis of alkoxyamines

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Abstract

Alkoxyamine 1 is selectively hydrolyzed by chymotrypsin and substilisin A into alkoxyamine 2H+ for which C–ON bond homolysis occurred with a 4-fold increase in rate constants compared to 1 while non-specific proteases had no effect. This highlights the triggering effect of enzymes. This is a proof of concept for a theranostic approach for treating solid tumors using enzyme-activated alkoxyamines releasing a cytotoxic alkyl radical and a stable nitroxide as a contrast agent for Overhauser-enhanced MRI.

Graphical abstract: Enzymatic triggering of C–ON bond homolysis of alkoxyamines

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Supplementary files

Article information


Submitted
16 Jul 2019
Accepted
09 Sep 2019
First published
26 Sep 2019

Org. Chem. Front., 2019,6, 3663-3672
Article type
Research Article

Enzymatic triggering of C–ON bond homolysis of alkoxyamines

G. Audran, L. Bosco, P. Brémond, N. Jugniot, S. R. A. Marque, P. Massot, P. Mellet, T. Moussounda Moussounda Koumba, E. Parzy, A. Rivot, E. Thiaudière, P. Voisin, C. Wedl and T. Yamasaki, Org. Chem. Front., 2019, 6, 3663 DOI: 10.1039/C9QO00899C

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