The general main topic of this work was the use and the development of cleavable linkers in biological systems. This study led to the design of a cleavable enrichment probe in non-denaturing conditions for chemical proteomic applications. In a topoisomerase analysis, this probe allowed the extraction and analysis of a functional DNA gyrase A2B2 complex. For fluorescence imaging, a new concept of chemically deactivatable quencher was introduced. This quencher was used to revealinactivated FRET-based probe in cell experiments. Finally, a methodology based on biolability measurements of acid-sensitive molecules was developed for the evaluation of chemical bond lability in native biological environments. This work was focused on biolability measurements of acidsensitive molecules.