title: Catalytic azide reduction in biological environments.
abstract: In the quest for the identification of catalytic transformations to be used in chemical biology and medicinal chemistry, we identified iron(III) meso-tetraarylporphines as efficient catalysts for the reduction of aromatic azides to their amines. The reaction uses thiols as reducing agents and tolerates water, air, and other biological components. A caged fluorophore was employed to demonstrate that the reduction can be performed even in living mammalian cells. However, in vivo experiments in nematodes (Caenorhabditis elegans) and zebrafish (Danio rerio) revealed a limitation to this method: the metabolic reduction of aromatic azides.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35043 Marburg, Germany.
authors.forename: Pijus K
authors.initials: PK
authors.lastname: Sasmal
authors.forename: Susana
authors.initials: S
authors.lastname: Carregal-Romero
authors.forename: Alice A
authors.initials: AA
authors.lastname: Han
authors.forename: Craig N
authors.initials: CN
authors.lastname: Streu
authors.forename: Zhijie
authors.initials: Z
authors.lastname: Lin
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Namikawa
authors.forename: Samantha L
authors.initials: SL
authors.lastname: Elliott
authors.forename: Reinhard W
authors.initials: RW
authors.lastname: Köster
authors.forename: Wolfgang J
authors.initials: WJ
authors.lastname: Parak
authors.forename: Eric
authors.initials: E
authors.lastname: Meggers
mesh_terms: D000588:Amines / Q000737:chemistry; D000818:Animals; D001386:Azides / Q000737:chemistry*; D017173:Caenorhabditis elegans; D002384:Catalysis; D004777:Environment; D005290:Ferric Compounds / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008665:Metalloporphyrins / Q000737:chemistry*; D010084:Oxidation-Reduction; D015027:Zebrafish
chemical_list: D000588:Amines; D001386:Azides; D005290:Ferric Compounds; D008665:Metalloporphyrins