title: Water-soluble triazabutadienes that release diazonium species upon protonation under physiologically relevant conditions.
abstract: Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water-soluble. It is shown that these molecules readily release diazonium species in a pH-dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo-release strategies and organelle-specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.
authors: Department of Chemistry and Biochemistry, University of Arizona, 1306 E University Blvd, Tucson, AZ 85721 (USA).
authors: Flora W
authors: FW
authors: Kimani
authors: John C
authors: JC
authors: Jewett
mesh_terms: D002021:Buffers; D002070:Butadienes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D011522:Protons; D012995:Solubility; D014867:Water
chemical_list: D002021:Buffers; D002070:Butadienes; D003979:Diazonium Compounds; D011522:Protons; D014867:Water
keywords: diazonium salts; kinetics; protonation; triazabutadienes