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

Author:

Varvuolytė Gabrielė12ORCID,Řezníčková Eva3ORCID,Bieliauskas Aurimas2ORCID,Kleizienė Neringa2ORCID,Vojáčková Veronika3ORCID,Opichalová Alena3ORCID,Žukauskaitė Asta4ORCID,Kryštof Vladimír35ORCID,Šačkus Algirdas12ORCID

Affiliation:

1. Department of Organic Chemistry Kaunas University of Technology Kaunas Lithuania

2. Institute of Synthetic Chemistry Kaunas University of Technology Kaunas Lithuania

3. Department of Experimental Biology, Faculty of Science Palacký University Olomouc Czech Republic

4. Department of Chemical Biology, Faculty of Science Palacký University Olomouc Czech Republic

5. Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry Palacký University Olomouc Czech Republic

Abstract

AbstractA 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.

Publisher

Wiley

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