Synthesis and photo-induced anticancer activity of new 2-phenylethenyl-1H-benzo[e]indole dyes
Language English Country France Media print-electronic
Document type Journal Article
PubMed
39173284
DOI
10.1016/j.ejmech.2024.116777
PII: S0223-5234(24)00658-5
Knihovny.cz E-resources
- Keywords
- DNA damage, Knoevenagel condensation, benzo[e]indole, photo-induced activity, reactive oxygen species,
- MeSH
- Coloring Agents pharmacology chemistry chemical synthesis MeSH
- Photosensitizing Agents pharmacology chemical synthesis chemistry MeSH
- Indoles * chemistry pharmacology chemical synthesis MeSH
- Humans MeSH
- Molecular Structure MeSH
- Cell Line, Tumor MeSH
- DNA Damage drug effects MeSH
- Cell Proliferation drug effects MeSH
- Antineoplastic Agents * pharmacology chemical synthesis chemistry MeSH
- Reactive Oxygen Species metabolism MeSH
- Drug Screening Assays, Antitumor * MeSH
- Light MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Coloring Agents MeSH
- Photosensitizing Agents MeSH
- Indoles * MeSH
- Antineoplastic Agents * MeSH
- Reactive Oxygen Species MeSH
Herein, a series of new 1,1,2-trimethyl-1H-benzo[e]indole dyes was prepared via Knoevenagel condensation reaction between 1,1,2-trimethyl-1H-benzo[e]indole and benzaldehydes, and characterized using various spectroscopic methods. The obtained compounds showed cytotoxic properties in G361 melanoma cell line upon irradiation with 414 nm blue light at submicromolar doses. The mechanism of action of the most potent compound 15 was further investigated. The treatment induced substantial generation of reactive oxygen species, leading to DNA damage followed by cell death depending on the concentration of the photosensitizer compound and the irradiation intensity.
Department of Chemical Biology Faculty of Science Palacký University CZ 77900 Olomouc Czech Republic
Department of Organic Chemistry Kaunas University of Technology LT 50254 Kaunas Lithuania
Institute of Synthetic Chemistry Kaunas University of Technology LT 51423 Kaunas Lithuania
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