Chlorin spiro-Tröger's base as a prospective photosensitizer for photodynamic therapy of cancer
Identifikátory výsledku
Kód výsledku v 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>
Nalezeny alternativní kódy
RIV/60461373:22340/24:43928852
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Chlorin spiro-Tröger's base as a prospective photosensitizer for photodynamic therapy of cancer
Popis výsledku v původním jazyce
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).
Název v anglickém jazyce
Chlorin spiro-Tröger's base as a prospective photosensitizer for photodynamic therapy of cancer
Popis výsledku anglicky
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).
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/LTAUSA19065" target="_blank" >LTAUSA19065: Příprava a studium vlastností metaloporfyrinových derivátů Trögerových, spiro-Trögerových a oligo-Trögerových bází</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2024
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
ISSN
1010-6030
e-ISSN
1873-2666
Svazek periodika
453
Číslo periodika v rámci svazku
1 August 2024
Stát vydavatele periodika
CH - Švýcarská konfederace
Počet stran výsledku
8
Strana od-do
—
Kód UT WoS článku
001222591100001
EID výsledku v databázi Scopus
2-s2.0-85188987133