title: A new class of bioactivable self-immolative N,O-ligands.
abstract: A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by β-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives.
authors.affiliation: Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland. Nikodem.Kuznik@polsl.pl
authors.forename: Nikodem
authors.initials: N
authors.lastname: Kuźnik
authors.forename: Arkadiusz
authors.initials: A
authors.lastname: Chrobaczyński
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Mika
authors.forename: Patrycja
authors.initials: P
authors.lastname: Miler
authors.forename: Roman
authors.initials: R
authors.lastname: Komor
authors.forename: Maciej
authors.initials: M
authors.lastname: Kubicki
mesh_terms: D000588:Amines / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D010636:Phenols / Q000737:chemistry*; D011522:Protons
chemical_list: D000588:Amines; D006027:Glycosides; D006571:Heterocyclic Compounds; D008024:Ligands; D010636:Phenols; D011522:Protons