1. A new class of bioactivable self-immolative N,O-ligands.
- Author
-
Kuźnik N, Chrobaczyński A, Mika M, Miler P, Komor R, and Kubicki M
- Subjects
- Chemistry Techniques, Synthetic, Crystallography, X-Ray, Glycosides chemistry, Ligands, Protons, Amines chemistry, Heterocyclic Compounds chemical synthesis, Heterocyclic Compounds chemistry, Phenols chemistry
- 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., (Copyright © 2012 Elsevier Masson SAS. All rights reserved.)
- Published
- 2012
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