Synthesis and characterization of hydrazine derivatives of coumarin for bioorthogonal chemistry inside cells
Author ORCID Identifier
Date of Award
Chemistry (BA, BS)
Dr. Susan L. Bane
Science and Mathematics
Oxidative stress; Hydrazones; Fluorescent probes
Protein carbonylation is one manifestation of oxidative stress, which is characteristic of many diseases. Our lab has developed several coumarin-hydrazine based fluorescent probes capable of detecting carbonylation in live cells via the formation of hydrazone conjugates. As an effort to expand and improve on these achievements, this work presents new data regarding the synthesis and characterization of three such probes. Two of the probes—julolidine coumarin hydrazide (JCH) and trifluoromethyl coumarin hydrazine (TFCH)—were previously synthesized by our lab. Here, JCH is studied in terms of its reaction speed and fluorescence enhancement in acylhydrazone formation with aldehydes under various conditions and catalytic schemes. For TFCH, the previously developed synthetic scheme is replicated, and the molecule is subjected to analysis of its reaction with various aldehydes, as well as stability studies. The synthesis of a third probe—coumarin acid hydrazine (CAH)—is developed, adding a novel analog to our library. CAH is substituted with a carboxylic acid at the 4-position, which may confer the benefit of enhanced water solubility and situates it as the precursor to an ester substituted derivative for future work.
Grimaldi, Akiva J., "Synthesis and characterization of hydrazine derivatives of coumarin for bioorthogonal chemistry inside cells" (2022). Undergraduate Honors Theses. 19.