DBCOs

DBCOs, or dibenzocyclooctynes, are a class of organic compounds that have gained significant attention in chemical biology and materials science due to their unique reactivity. Their structure features a strained cyclooctyne ring fused with two benzene rings. This inherent ring strain makes the alkyne moiety highly reactive towards cycloaddition reactions, particularly with azides.

The most prominent application of DBCOs lies in their use in strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. SPAAC is a bioorthogonal click chemistry technique, meaning it can occur within living systems without interfering with native biochemical processes. Unlike copper-catalyzed azide-alkyne cycloaddition (CuAAC), SPAAC does not require a metal catalyst, which can be toxic to biological environments. The DBCO group readily reacts with azides at room temperature and physiological pH, forming a stable triazole linkage.

This bioorthogonal reactivity makes DBCOs invaluable for various applications. They are frequently employed for the labeling and imaging of biomolecules in living cells and organisms. This includes conjugating fluorescent probes, radiolabels, or other reporter molecules to proteins, nucleic acids, or carbohydrates. Furthermore, DBCOs are utilized in the development of drug delivery systems, the synthesis of complex bioconjugates, and the modification of surfaces. Their stability and efficient reactivity under mild conditions are key advantages that drive their widespread adoption.