Abstract
To find potent chemotherapeutic agents, cytotoxic effects of 42 synthetic chalcone derivatives bearing naphthyl groups on HCT116 human colon cancer cell lines were tested using the clonogenic long-term survival assay. The relationships between their half-maximal cell growth inhibitory concentrations (GI50) and structural properties were obtained using comparative molecular field analysis and comparative molecular similarity indices analysis. The structural conditions that showed maximum cytotoxic effects on the colon cancer cells were determined. In addition, a derivative, (E)-1-(2-hydroxy-4,5-dimethoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one, showing the best GI50 value, was assessed for stimulating reactive oxygen species (ROS) production. While its treatment on non-tumorigenic epithelial MCF-12A cell line did not affect the intracellular ROS levels, its treatment on MDA-MB-231 human breast cancer cell line showed ROS accumulation. These findings demonstrate that naphthalenylchalcones can be developed as potent chemotherapeutic agents.
Highlights
Flavonoids share common features with chalcone, 1,3diphenylprop-2-en-1-one, such as a C6–C3–C6 skeleton (Supplementary Materials Fig. 1A) [1, 2]
Because various substituents can be attached to both phenyl rings, many chalcone derivatives exist, and they show diverse biological activities: anticancer, antimicrobial, antifungal, antiinflammatory, anti-tuberculosis, and anti-malarial effects [3,4,5,6,7,8]
Our previous experiments demonstrated that a compound with Michael acceptor causes reactive oxygen species (ROS) generation [14]
Summary
Flavonoids share common features with chalcone, 1,3diphenylprop-2-en-1-one, such as a C6–C3–C6 skeleton (Supplementary Materials Fig. 1A) [1, 2]. Division of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 05029, Republic of Korea The relationships between the physicochemical properties of naphthalenylchalcone derivatives and their cytotoxic effects on HCT116 human colon cancer cells were elucidated using comparative molecular field analysis and comparative molecular similarity indices analysis.
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