Synthesis and photodynamic activity of new 5-[(E)-2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-2-phenyl-3H-indoles
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
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
PubMed
38969965
DOI
10.1002/ardp.202400282
Knihovny.cz E-zdroje
- Klíčová slova
- cytotoxicity, indole, photodynamic effect, pyrazole, reactive oxygen species,
- MeSH
- fotochemoterapie * MeSH
- fotosenzibilizující látky * farmakologie chemická syntéza chemie MeSH
- indoly * farmakologie chemie chemická syntéza MeSH
- lidé MeSH
- MFC-7 buňky MeSH
- molekulární struktura MeSH
- nádorové buněčné linie MeSH
- nádory prsu farmakoterapie patologie MeSH
- palladium chemie farmakologie MeSH
- protinádorové látky * farmakologie chemická syntéza chemie MeSH
- pyrazoly * farmakologie chemická syntéza chemie MeSH
- reaktivní formy kyslíku * metabolismus MeSH
- viabilita buněk účinky léků MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- fotosenzibilizující látky * MeSH
- indoly * MeSH
- palladium MeSH
- protinádorové látky * MeSH
- pyrazoly * MeSH
- reaktivní formy kyslíku * 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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