Synthesis and photodynamic properties of pyrazole-indole hybrids in the human skin melanoma cell line G361
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F20%3A00532929" target="_blank" >RIV/61389030:_____/20:00532929 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15110/20:73602382 RIV/61989592:15310/20:73602382
Result on the web
<a href="http://doi.org/10.1016/j.dyepig.2020.108666" target="_blank" >http://doi.org/10.1016/j.dyepig.2020.108666</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2020.108666" target="_blank" >10.1016/j.dyepig.2020.108666</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and photodynamic properties of pyrazole-indole hybrids in the human skin melanoma cell line G361
Original language description
Three conjugated pyrazole-indole hybrids, 5, 7 and 10, were synthesized from easily accessible 3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde 1 and 5-iodo-3,3-dimethyl-2-phenyl-3H-indole 4 employing olefination reactions (Wittig, Ramirez), Vilsmeier-Haack formylation and palladium-catalysed cross coupling reactions (ligand-free Heck, Sonogashira). The compounds displayed no cytotoxicity in the melanoma cell line G361 unless irradiated with visible blue light (414 nm), and the potency of the compounds increased with light intensity. Lead compound 7 displayed EC50 values of 3.08, 0.26 and 0.05 μM in cells irradiated with 1, 10 and 50 J/cm2, respectively. The following experiments revealed increased levels of reactive oxygen species in treated cells and a decrease in JC-1 polymer aggregation within the mitochondria, suggesting mitochondrial membrane depolarization. In addition, extensive DNA fragmentation was detected using the comet assay and by detection of phosphorylated histone H2A.X, the level of which increased with both increased compound concentration and irradiation energy. In control experiments, cells kept either in the dark or without compound 7 did not show any DNA damage. Overall, the results demonstrated that fluorescent pyrazole-indole hybrids may serve as an interesting source of photosensitizing compounds with anticancer activity.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10601 - Cell biology
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dyes and Pigments
ISSN
0143-7208
e-ISSN
1873-3743
Volume of the periodical
183
Issue of the periodical within the volume
DEC
Country of publishing house
GB - UNITED KINGDOM
Number of pages
12
Pages from-to
108666
UT code for WoS article
000569771600010
EID of the result in the Scopus database
2-s2.0-85089688038