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Self‐Immolative Spacers: Kinetic Aspects,Structure–Property Relationships,and Applications
Authors:Dr Ahmed Alouane  Dr Raphaël Labruère  Dr Thomas Le Saux  Dr Frédéric Schmidt  Prof Dr Ludovic Jullien
Institution:1. Ecole Normale Supérieure–PSL Research University, Department of Chemistry, 24, rue Lhomond, 75005 Paris (France);2. Sorbonne Universités, UPMC Univ Paris 06, PASTEUR, 75005 Paris (France);3. CNRS, UMR 8640 PASTEUR, 75005 Paris (France);4. Institut Curie, Centre de Recherche, 26, rue d'Ulm, 75248 Paris (France);5. CNRS, UMR 3666, 75248 Paris (France);6. INSERM, U 1143, 75248 Paris (France);7. Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS 8182, Université Paris Sud, 91405 Orsay Cedex (France)
Abstract:Self‐immolative spacers are covalent assemblies tailored to correlate the cleavage of two chemical bonds after activation of a protective part in a precursor: Upon stimulation, the protective moiety is removed, which generates a cascade of disassembling reactions leading to the temporally sequential release of smaller molecules. Originally introduced to overcome limitations for drug delivery, self‐immolative spacers have gained wide interest in medicinal chemistry, analytical chemistry, and material science. For most applications, the kinetics of the disassembly of the activated self‐immolative spacer governs functional properties. This Review addresses kinetic aspects of self‐immolation. It provides information for selecting a particular self‐immolative motif for a specific demand. Moreover, it should help researchers design kinetic experiments and fully exploit the rich perspectives of self‐immolative spacers.
Keywords:disassembly  kinetics  self‐immolation  self‐immolative spacers
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