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Novel Azole-Modified Porphyrins for Mitochondria-Targeted Photodynamic Therapy
Sabarinathan Rangasamy1,2, Elisa Bandini1, Alessandro Venturini1
1Institute for Organic Synthesis and Photoreactivity (ISOF), National Research Council of Italy (CNR), Via P. Gobetti 101, I-40129 Bologna, Italy.
Abstract:
Photodynamic therapy is a non-invasive treatment strategy for various types of cancer, based on the use of light to activate a photosensitizer which triggers processes leading to cell death. Given the increasing interest in the development of mitochondria-targeted photosensitizers, in this study we synthesized two novel thiadiazol-substituted porphyrins, 5,10,15,20-tetra(2,1,3-benzothiadiazol-5-yl) porphyrin (C1) and 5,10,15,20-tetra(1,2,3-thiadiazol-4-yl) porphyrin (C2), designed to target mitochondria in cancer cells thanks to the azole residues present in their structure. The two porphyrinic compounds were characterized in terms of structural and photophysical properties, revealing high yields of singlet oxygen production. Their interaction with biological structures was analyzed in a triple-negative human breast carcinoma cell line (MDA-MB-231), either as free compounds or delivered via mitochondriotropic liposome formulations. Both newly synthesized porphyrins entered MDA-MB-231 cells, with compound C2 demonstrating more efficient localization in the cytoplasm and in mitochondria. Dark and phototoxicity tests were also performed: both compounds proved to be effective phototoxic agents, with C2 showing the highest activity, making it a promising photosensitizer for mitochondria-targeted photodynamic therapy.
Insights
Researchers developed novel thiadiazol-substituted porphyrins for mitochondria-targeted photodynamic therapy. Compound C2 demonstrated potent phototoxicity and efficient mitochondrial localization in cancer cells, showing promise for cancer treatment.
Area of Science:
- Medicinal Chemistry
- Photochemistry
- Cell Biology
Background:
- Photodynamic therapy (PDT) is a non-invasive cancer treatment using light-activated photosensitizers.
- Mitochondria-targeted photosensitizers are of increasing interest for enhanced therapeutic efficacy.
- Targeting mitochondria can improve cancer cell death induction in PDT.
Purpose of the Study:
- To synthesize and characterize novel thiadiazol-substituted porphyrins for mitochondria-targeted PDT.
- To evaluate the photophysical properties and singlet oxygen production of the synthesized compounds.
- To assess the cellular uptake, localization, and phototoxicity of these porphyrins in cancer cells.
Main Methods:
- Synthesis of two novel thiadiazol-substituted porphyrins (C1 and C2).
- Characterization of structural and photophysical properties, including singlet oxygen yield.
- Evaluation of cellular uptake and mitochondrial localization in MDA-MB-231 cells.
- Assessment of dark and phototoxicity of the compounds.
Main Results:
- Both C1 and C2 exhibited high singlet oxygen production.
- Compound C2 showed more efficient uptake and localization in cancer cell cytoplasm and mitochondria.
- Both compounds demonstrated phototoxic effects, with C2 exhibiting higher activity.
Conclusions:
- The synthesized thiadiazol-substituted porphyrins are effective phototoxic agents.
- Compound C2 is a promising photosensitizer for mitochondria-targeted photodynamic therapy.
- Further development of C2 could lead to improved non-invasive cancer treatments.
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