A new class of bioactivable self-immolative N,O-ligands

作者：Kuznik Nikodem^*; Chrobaczynski Arkadiusz; Mika Malgorzata; Miler Patrycja; Komor Roman; Kubicki Maciej

来源：European Journal of Medicinal Chemistry, 2012, 52: 184-192.

DOI：10.1016/j.ejmech.2012.03.017

• Amino-phenol ligand
• N,O-ligand
• Bioactivation
• beta-Galactosidase
• Self-immolative

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 beta-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.

• 出版日期2012-6