Enzymatic triggering of C–ON bond homolysis of alkoxyamines
Literature Information
Publication Date
2019-09-26
DOI
10.1039/C9QO00899C
Impact Factor
5.281
Authors
Gérard Audran, Lionel Bosco, Paul Brémond, Natacha Jugniot, Sylvain R. A. Marque, Philippe Massot, Tataye Moussounda Moussounda Koumba, Elodie Parzy, Angélique Rivot, Eric Thiaudière, Pierre Voisin, Carina Wedl, Toshihide Yamasaki
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
![2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione structure](https://static.chemtradehub.com/structs/308/3089-17-6-750b.webp "2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione structure")
2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
CAS Number:
3089-17-6
Molecular Formula:
C20H10Cl2N2O2
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