Triazole biotin: a tight-binding biotinidase-resistant conjugate

Abstract

The natural amide bond found in all biotinylated proteins has been replaced with a triazole through CuAAC reaction of an alkynyl biotin derivative. The resultant triazole-linked adducts are shown to be highly resistant to the ubiquitous hydrolytic enzyme biotinidase and to bind avidin with dissociation constants in the low pM range. Application of this strategy to the production of a series of biotinidase-resistant biotin-Gd-DOTA contrast agents is demonstrated.

Click Chemistry in the Development of Contrast Agents for Magnetic Resonance Imaging

“…utilized the advantage of rigid triazole linkers for designing and synthesis of their biotinidase-resistant biotin-Gd-DOTA contrast agents. 19 They have synthesized contrast agents conjugated with biotin via a triazole linkers generated by azide-alkyne cycloaddition. These rigid conjugates are excellent isosteres for similar biotin-amide contrast agents.…”

Chloromethyl-triazole: a new motif for site-selective pseudo-acylation of proteins

“…We have previously demonstrated that a range of non-hydrolysable triazole derivatives of biotin show very strong binding to avidin, with K d values in the pM range. 17 In this instance, functional activity of the H4K12C triazole biotin adduct was demonstrated by Western blot using an anti-biotin antibody ( Fig. 2b ), and the assembly of histone complexes incorporating site-selective biotinylation is currently under investigation.…”

Bis-BODIPY linked-triazole based on catechol core for selective dual detection of Ag+ and Hg2+

“…This stems from a robust and green protocol for the synthesis of triazole derivatives. 33 In addition to metal sensors, triazole is extensively used in the synthesis of catalyst, 34 dendrimers, 35 biomolecule conjugates, 36 and metal organic frameworks. 37 BODIPY-triazole combinations were reported as uorescent chemosensors for the detection of metal ions, e.g.…”