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Alkoxyamines: a new family of pro-drugs against cancer. Concept for theranostics

Gérard Audran 1 Paul Brémond 1 Jean-Michel Franconi 2 Sylvain R.A. Marque 1 Philippe Massot 2 Philippe Mellet 2 Elodie Parzy 2 Eric Thiaudière 2
1 ICR - Institut de Chimie Radicalaire
2 RMSB - Résonance magnétique des systèmes biologiques
Abstract : Development of anti-cancerous theranostic agents is a vivid field. This article describes a theranostic approach that relies on the triggering of cancer cell death by generation of alkyl radicals at the right place and at the right time using the presence of active proteases in the tumour environment. Alkoxyamines ((RRNOR3)-R-1-N-2) are labile molecules that homolyze into nitroxides ((RRNO center dot)-R-1-N-2) and reactive alkyl radicals (R-3 center dot). They are used as a source of active alkyl radicals for curing and nitroxides for monitoring by Overhauser-enhanced magnetic resonance imaging (OMRI). Herein, the requirements needed for applying alkoxyamines are described: (i) highly selective activation of the alkoxyamine by specific proteases; (ii) fast homolysis of the alkoxyamine C-ON bond at physiological temperature; (iii) activation of cell death processes through an increase of the local oxidative stress or potential re-activation of the immune system due to short-lived alkyl radicals; and (iv) imaging of the tumor and the drug release by sensing the nitroxide by OMRI.
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Submitted on : Tuesday, February 7, 2017 - 4:54:13 PM
Last modification on : Tuesday, October 19, 2021 - 10:49:47 PM

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Gérard Audran, Paul Brémond, Jean-Michel Franconi, Sylvain R.A. Marque, Philippe Massot, et al.. Alkoxyamines: a new family of pro-drugs against cancer. Concept for theranostics. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2014, 12 (5), pp.719--723. ⟨10.1039/c3ob42076k⟩. ⟨hal-01460497⟩

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