Scope and Limitations of Boron Fluorescent Complexes from Stable Nitrile Oxides in ABPP Assays

Mattia Moiola; Stefano Crespi; Misal Memeo; Simona Collina; Herman Overkleeft; Bogdan Florea; Paolo Quadrelli

doi:10.1021/acsomega.9b00672

Scope and Limitations of Boron Fluorescent Complexes from Stable Nitrile Oxides in ABPP Assays

ACS Omega. 2019 Apr 29;4(4):7766-7774. doi: 10.1021/acsomega.9b00672. eCollection 2019 Apr 30.

Authors

Mattia Moiola¹, Stefano Crespi¹, Misal Memeo¹, Simona Collina², Herman Overkleeft³, Bogdan Florea³, Paolo Quadrelli¹

Affiliations

¹ Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
² Department of Drug Sciences, University of Pavia, Viale Taramelli 14, 27100 Pavia, Italy.
³ Leiden Institute of Chemistry, Leiden University, Einsteingweg 55, 2333CC Leiden, The Netherlands.

Abstract

Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reactions with 1-substituted-4-(prop-2-yn-1-yloxy)benzene affording the expected isoxazoles in good yields and as single regioisomers. N-O Bond cleavage and boron complexation afforded the corresponding boron complexes, derivatized with either a triple bond for click-chemistry applications or an oxime group for nitrile oxide 1,3-dipolar cycloaddition. The optical properties of these compounds show potential for employment as fluorescent tags in imaging techniques. The activity-based protein profiling assays showed good reactivity for the synthesized probes even with short peptide chains (epoxomicin). Scope and limitations are discussed in the light of the obtained results.