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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F24%3A73625374" target="_blank" >RIV/61989592:15310/24:73625374 - isvavai.cz</a>

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/epdf/10.1002/ardp.202400282" target="_blank" >https://onlinelibrary.wiley.com/doi/epdf/10.1002/ardp.202400282</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ardp.202400282" target="_blank" >10.1002/ardp.202400282</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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. Thesecompounds 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 furthe 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 reactiveoxygen species, leading to different types of cell death depending on the compound concentration and the irradiation intensity.

Název v anglickém jazyce

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

Popis výsledku anglicky

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. Thesecompounds 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 furthe 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 reactiveoxygen species, leading to different types of cell death depending on the compound concentration and the irradiation intensity.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30107 - Medicinal chemistry

Projekt

<a href="/cs/project/LX22NPO5102" target="_blank" >LX22NPO5102: Národní ústav pro výzkum rakoviny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ARCHIV DER PHARMAZIE

ISSN

0365-6233

e-ISSN

1521-4184

Svazek periodika

357

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

20

Strana od-do

"e2400282-1"-"e2400282-20"

Kód UT WoS článku

001263254500001

EID výsledku v databázi Scopus

2-s2.0-85197544749