Development of Photo-caged Bioactive Compounds

Hi there! My name is Jaclyn McKenna. I’m from Long Island, New York and I am a senior Chemistry and Kinesiology major at the College.  You might recognize me from the basketball team, but I have also been conducting research now for two years in Dr. Young’s bioorganic chemistry lab.

research

Through organic synthesis and molecular biology techniques, I am working towards developing various photo-caged bioactive compounds.  Essentially, I am taking active molecules and synthesizing them with a photo-protecting group, rendering the molecule inactive.  Then, upon UV-light exposure the photo-protecting group is removed and the molecule regains it’s functionality.  This type of technology has potential in drug therapy because it provides an added degree of special and temporal control, eliminating the unfortunate side effects caused by current chemotherapeutic agents.

For example, theophylline, is a small organic ligand that is capable of binding to an RNA ribozyme and induces self-cleavage to release a microRNA.  MicroRNA are relatively short, single stranded RNA fragments capable of suppressing the translation of a specific protein by complimentary base-pairing to messenger RNA. Therefore, in the presence of free theophylline, the microRNA is produced and the expression of the particular protein is suppressed.  However, if a photo-protecting group is present on the theophylline molecule, this mechanism is inactivated until the system is exposed to UV-light.

theo

Additionally, I have been using this technique to synthesize unnatural amino acids.    Unnatural amino acids serve as a mechanism to expand the genetic code and study the effects of diverse functional groups on proteins.  Site-specific incorporation of these newly synthesized protein building blocks involves significant manipulation of translational machinery. For example, a photo-caged amino acid with an alkynyl group can serve as a handle for “click” reactions. Thus, a therapeutic agent, such as an antibody or miRNA, can be conjugated into the protein and also be readily photo-cleaved with light.

Thank you for following my blog, I’m excited to get working on these projects this summer.  Good luck to everyone with exams!

– Jackie