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Synthesis and photodynamic activity of new 5-[(E)-2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-2-phenyl-3H-indoles

G. Varvuolytė, E. Řezníčková, A. Bieliauskas, N. Kleizienė, V. Vojáčková, A. Opichalová, A. Žukauskaitė, V. Kryštof, A. Šačkus

. 2024 ; 357 (10) : e2400282. [pub] 20240705

Language English Country Germany

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc25004059

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

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.

References provided by Crossref.org

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