Synthesis and photodynamic activity of new 5-[(E)-2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-2-phenyl-3H-indoles
Language English Country Germany Media print-electronic
Document type Journal Article
Grant support
S-MIP-23-51
Research Council of Lithuania
LX22NPO5102
The project National Institute for Cancer Research, Programme EXCELES
A-410
Doctoral Fund of Kaunas University of Technology
IGA_PrF_2024_005
Palacký University Olomouc
- Keywords
- cytotoxicity, indole, photodynamic effect, pyrazole, reactive oxygen species,
- MeSH
- Photochemotherapy * MeSH
- Photosensitizing Agents * pharmacology chemical synthesis chemistry MeSH
- Indoles * pharmacology chemistry chemical synthesis MeSH
- Humans MeSH
- MCF-7 Cells MeSH
- Molecular Structure MeSH
- Cell Line, Tumor MeSH
- Breast Neoplasms drug therapy pathology MeSH
- Palladium chemistry pharmacology MeSH
- Antineoplastic Agents * pharmacology chemical synthesis chemistry MeSH
- Pyrazoles * pharmacology chemical synthesis chemistry MeSH
- Reactive Oxygen Species * metabolism MeSH
- Cell Survival drug effects MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Female MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Photosensitizing Agents * MeSH
- Indoles * MeSH
- Palladium MeSH
- Antineoplastic Agents * MeSH
- Pyrazoles * MeSH
- Reactive Oxygen Species * MeSH
A series of new indole-pyrazole hybrids 8a-m were synthesized through the palladium-catalyzed ligandless Heck coupling reaction from easily accessible unsubstituted, methoxy- or fluoro-substituted 4-ethenyl-1H-pyrazoles and 5-bromo-3H-indoles. These compounds exerted cytotoxicity to melanoma G361 cells when irradiated with blue light (414 nm) and no cytotoxicity in the dark at concentrations up to 10 µM, prompting us to explore their photodynamic effects. The photodynamic properties of the example compound 8d were further investigated in breast cancer MCF-7 cells. Evaluation revealed comparable anticancer activities of 8d in both breast and melanoma cancer cell lines within the submicromolar range. The treatment induced a massive generation of reactive oxygen species, leading to different types of cell death depending on the compound concentration and the irradiation intensity.
Department of Chemical Biology Faculty of Science Palacký University Olomouc Czech Republic
Department of Experimental Biology Faculty of Science Palacký University Olomouc Czech Republic
Department of Organic Chemistry Kaunas University of Technology Kaunas Lithuania
Institute of Synthetic Chemistry Kaunas University of Technology Kaunas Lithuania
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