Structure-Activity Relationship Study of the Ortho and Para Positions of Azide Triggers in Self-Immolative Thiocarbamate Donors

Presenter(s): Rachel Lutz

Faculty Mentor(s): Michael Pluth & Carolyn Levinn

Poster 14

Session: Sciences

Since the discovery of hydrogen sulfide (H2S) as a gasotransmitter in the body, there has been a need for organic donors which can release H2S to mimic its endogenous release in cells. H2S is a key molecule for signaling in the body, is a known vasodilator, and is also involved in promoting cell healing. It is important to learn as much as we can about the relationship between structure and activity of H2S donors so that donor design can be optimized. In this study, we used two self- immolative thiocarbamate donors with azide triggers in the ortho and para positions to observe how the position of the trigger affects the rate of H2S release. When the self-immolative thiocarbamate donors are triggered they produce carbonyl sulfide (COS) as a precursor for H2S. The COS is then converted to hydrogen sulfide via carbonic anhydrase (CA) enzyme. Through a methylene blue assay, we were able to measure the rate of release of H2S of both the ortho and para donors. Structural analysis of these donors will allow for more fine-tuning of H2S donors and a better understanding of how to develop fine-tuned donors.

Leave a Reply

Your email address will not be published. Required fields are marked *