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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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Publication details

The article was received on 16 Jul 2019, accepted on 09 Sep 2019 and first published on 26 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO00899C
Org. Chem. Front., 2019,6, 3663-3672

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    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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