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Organic Chemistry



Synthetic Chemistry

The Theodorakis group is engaged in the synthesis and study of small molecules that can be used as biological tools to control cellular function and as lead structures for the discovery of new therapeutic agents. Building upon the foundations of organic chemistry, the research activities invoke interdisciplinary interactions with other scientific fields such as bioengineering, biochemistry, biology, pharmacology and drug design. The ultimate goal of this program is the application of organic synthesis for the investigation of interesting questions or problems in biology and medicine. Our current research activities are focused on two topics: (a) the natural products-driven synthesis and drug discovery and (b) the development of fluorescent probes for imaging and sensing.

Natural Products Synthesis and Drug Discovery

Natural products represent unique targets of opportunity for discovery across various scientific fields. Arguably, natural products synthesis is the best way to test the scope and limitations of known or new reactions thereby enhancing our knowledge of chemical reactivity. In turn, this knowledge can be used for the construction of privileged structures and can facilitate pharmacologically relevant modifications of the parent structure. The Theodorakis group strives to design innovative methods and divergent strategies that generate structural complexity and allow chemical functionalization. Moreover, efforts to translate chemical reactivity of the target molecules to biological properties yield important insights regarding natural products-based biology, mode of action and drug discovery.

Fluorescent Probes for Imaging and Sensing

The Theodorakis group is engaged in the design of fluorescent probes whose emission profile changes as a function of their environment. Thus, these probes can sense and measure variations of properties such as viscosity and polarity at a nanoscale level. Since these variations are linked to cellular function and disease, the designed probes can be used as diagnostic tools for several biomedical applications. For example, acting as fluorescent nanoviscometers, these probes can measure viscosity of cellular compartments, liposomes, biofluids as well as microfluidic chambers. Moreover, when bound to a protein or protein aggregate, these probes can report changes in the electronic environment of their binding site. Along these lines, the Theodorakis group designs probes that target, monitor and colorimetrically discriminate between amyloids of various diseases. The biomedical and bioengineering applications of these fluorescent nanotopographers are explored.



The Theodorakis group benefits from collaborations with other scientists. UCSD-based collaborators include: Christina Sigurdson (School of Medicine), Victor Nizet (Skaggs School of Pharmacy and Pharmaceutical Sciences), Gurol Suel (Biological Sciences), Jerry Yang and Patricia Jennings (Chemistry & Biochemistry). Collaborators outside UCSD include: Len Neckers (NCI, NIH), Jose Onuchic (Rice U.), Mary Alpaugh (Rowan University), Maria Theodoraki (Arcadia University) and D. Vourloumis (Demokritos Res. Institute, Greece).




We welcome inquiry from individuals who share our passion and dedication to science. Prospective students or those seeking post-doctoral work are encouraged to contact Professor Theodorakis directly. For more information on our Ph.D. and M.Sc. programs,
please visit UCSD Graduate Admissions.