EFFORTS TOWARDS SYNTHESIS OF HYDROGEN SULFIDE ACTIVATED BODIPY BASED PDT AGENT

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2022-5-13

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Canyurt, Merve

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Photodynamic Therapy (PDT) is an effective and minimally invasive method that has recently gained widespread acceptance as a new medical treatment for a variety of conditions. PDT uses photosensitizers in combination with a specific light source and molecular oxygen to form cytotoxic species that can damage organelles and cell membranes directly. The photodynamic reactions start with light absorption by the PS in the target tissue, which sets off a chain of photochemical events. In comparison to existing sensitizers, BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) allows for the creation of next-generation photosensitizers due to their high fluorescence and triplet quantum yields, ease of functionalization, and tunable photophysical properties. The aim of this project is to synthesize two different water-soluble, mitochondria-targeted and activatable photosensitizers. For this purpose, brominated BODIPY core is modified at different positions with pyridinium unit and azido-benzyl masking unit which is activated with H2S, an over-expressed tumor metabolite. In the first sensitizer (S-BODMe), two consecutive Knoevenagel condensation processes were attempted to introduce pyridinium unit to the 5-position and the corresponding protected aldehyde to the 3-position which would have been deprotected and modified with the masking unit for H2S activation. Unfortunately, the target molecule could not be attained. In the second approach (S2-BODMe), the pyridine unit was incorporated to the bromo-BODIPY core and the aldehyde incorporation was introduced with a double Knoevenagel condensation reaction successfully, but insertion of the azido-based masking unit could not be accomplished. Later on, azido-based masking group was successfully attached to the corresponding aldehyde. As a future work, this new aldehyde containing masking unit will be used to modify the bromo-BODIPY core, followed by methylation of the pyridine unit to attain the target molecule.

Subject Keywords

Photodynamic Therapy, BODIPY, Photosensitizer, Singlet Oxygen

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https://hdl.handle.net/11511/97376

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

M. Canyurt, “EFFORTS TOWARDS SYNTHESIS OF HYDROGEN SULFIDE ACTIVATED BODIPY BASED PDT AGENT,” M.S. - Master of Science, Middle East Technical University, 2022.