Chlorin spiro-Tröger's base as a prospective photosensitizer for photodynamic therapy of cancer

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F24%3A43928852" target="_blank" >RIV/60461373:22330/24:43928852 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22340/24:43928852
Result on the web
<a href="https://doi.org/10.1016/j.jphotochem.2024.115618" target="_blank" >https://doi.org/10.1016/j.jphotochem.2024.115618</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jphotochem.2024.115618" target="_blank" >10.1016/j.jphotochem.2024.115618</a>

Result language
angličtina
Original language name
Chlorin spiro-Tröger's base as a prospective photosensitizer for photodynamic therapy of cancer
Original language description
Octahydroxy bis-porphyrin Tröger's base (TB) and octahydroxy porphyrin-chlorin spiro-Tröger's base (spiroTB) derivatives were successfully prepared from their Ni(II) complexes utilizing an optimized demetalation method using H2SO4-TFA followed by demethylation via BBr3. The synthesized TB and spiroTB were then in in vitro experiments for their utility in photodynamic therapy (PDT) of cancer. Compared to temoporfin (mTHPC, Foscan®), the chlorin derivative used in PDT of cancer, TB and spiroTB were localized in lysosomes instead of the endoplasmic reticulum and were found to possess enhanced biocompatibility. Cell culture studies were performed on TRAMP-C2 (prostate cancer), HeLa (cervical cancer), and MRC-5 (non cancerous) cell lines. Both TB and spiroTB displayed negligible dark toxicity but increased production of reactive oxygen species (ROS) when illuminated. In addition, spiroTB displayed significant phototoxicity in TRAMP-C2 cells (IC50, light 0.7 μM after 24 h incubation). Despite the phototoxicity of spiroTB being lower than that of mTHPC (IC50, light 0.02 μM), due to the low dark toxicity (IC50, dark > 100 μM), the therapeutic factor of spiroTB (>150) is six times higher than that of mTHPC (25).
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/LTAUSA19065" target="_blank" >LTAUSA19065: Exploration of properties and preparation of metalloporfyrin derivatives of Tröger’s, spiro-Tröger’s, and oligo-Tröger’s bases</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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