Photodynamic therapy is a minimally invasive and minimally toxic treatment strategy based on photochemistry. A combination of molecular oxygen, specific light, and photosensitizers produce reactive oxygen species, which in turn cause cancer cell death. Apart from being a promising alternative to conventional cancer treatments such as surgery, radio- and chemotherapy, photodynamic therapy has also been successfully employed in treatment of non-malignant diseases, such as psoriasis, acne, etc. Besides the traditional chlorin, porphyrin, and phthalocyanine-based photosensitizers, a number of non-porphyrinoid fluorescent dyes, such as 3H-indole polymethine cyanines have recently been reported as potential photosensitizers that efficiently accumulate in tumours. In this work we describe new 5-[2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3H-indoles, which were prepared via ligand-free Heck reaction of variously substituted 4-ethenyl-1H-pyrazoles with 5-bromo-3H-indoles. Optical properties of the target fluorescent pyrazole-indole compounds were investigated in water, revealing that they possess absorption maxima in the visible light spectrum, namely, in the range of 380-420 nm, and blue-green fluorescence emission. Photodynamic properties of the compounds were subsequently studied in cancer cells under irradiation with blue light (414 nm).

Synthesis and characterization of new fluorescent 5-[2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3H-indoles for photodynamic therapy

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.