Perhaps one of the most powerful tools available to cell biologists today are molecular imaging probes; small organic molecules and metal complexes with the potential to become fluorescent or exhibit an increase in fluorescence when specific functional groups on the probe react with target analytes in their chemical environment. Understanding how cells process reactive oxygen species (ROS) such as hydrogen peroxide (H2O2) and superoxide anion (O2-) is of particular interest because of the role they are believed to play in the manifestation of disease states such as cancer, Alzheimer's, and other neurodegenerative diseases. Reactive sulfur species (RSS) such as (H2S) and (HS-) reduce ROS and thereby help to maintain cell homeostasis. It is difficult however to understand this process precisely without first understanding the relative distribution of these molecules within the cell. To address this issue we sought to combine proven methods for the selective detection of ROS with dioxaborolans and RSS with azides into one cohesive bi-functional probe built on a fluorescent coumarin scaffold. To test this hypothesis control compounds were synthesized, their reactivity tested with fluorescence spectroscopy, and improvements to the preliminary design were made accordingly. Presented here are the steps, tests, and considerations that have taken place thus far in the design process. Synthesis of an improved design which relies on a maleimide based detection mechanism for RSS is currently underway and nearing completion. Once in hand this compound has the potential to elucidate the valuable spatiotemporal information necessary for understanding the dynamic relationship between ROS and RSS in the redox processes that take place within living organisms.

Design and synthesis of potential bi-functional fluorescent probes for monitoring reactive oxygen and sulfur species in biological systems

248th National Meeting (2014)

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