52923-29-2Relevant articles and documents
The fluorescence properties of 4′-Methoxychalcone derivates modified by substituents and investigation of lysosomal imaging
Cai, Zhengxu,Dong, Yuping,Lin, Na,Shi, Jianbing,Tong, Bin,Wu, Xinghui
, (2022/01/25)
Three types of 4′-methoxychalcone derivatives Cha-1 ～ Cha-9 with different electron-withdrawing or electron-donating substituents at different positions were synthesized and studied. When the A ring has a hydroxyl group at the 2-position, the strong electron-donating groups at the 4-position of the B ring was more conducive to the near-infrared and aggregation-enhanced emission (AEE) features of the compound than the electron withdrawing groups. The single-crystal analysis confirmed that the good planarity of the 4′-methoxychalcone derivatives favors their fluorescence quantum yields. Moreover, chalcone fluorophores with different fluorescence properties could be obtained by modulating substituent at the 2-position of A ring. In addition, Cha-9 was selected as the AEE luminogen to locate the lysosomes in HeLa cells. These results provided fundamental knowledge for the design and application of 4′-methoxychalcone derivatives of aggregation-induced emission (AIE) compounds.
Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
Villena, Joan,Montenegro, Iván,Said, Bastian,Werner, Enrique,Flores, Susana,Madrid, Alejandro
, (2021/01/18)
This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0–94.0%) of eighteen oxyalkylated derivatives of 2′,4′-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive malignancies diagnosed in the world. Cytotoxicity evaluations showed that four of the synthesized compounds exhibited moderate to very high toxic activity against MCF-7 (IC50 = 8.4–34.3 μM) and PC-3 (IC50 = 9.3–29.4 μM) – comparable to 5-fluorouracil (IC50 16.4–22.3 μM). The same compounds only showed moderate activity against HT-29 (IC50 15.3–36.3 μM), closer to daunorubicin (IC50 15.1 μM). Next, although selectivity index (SI) of compounds was weak, compound 18 exhibited a remarkable and selective cytotoxic activity (5.8–10.57) against cancer cells. Outside of these, most compounds significantly reduced cell survival, increased reactive oxygen species (ROS) and caspase activity, and decreased mitochondrial membrane permeability. In this sense, a portion of anti-proliferative activity is due to apoptosis. Notwithstanding, due to its remarkable response, chalcone 18 may be a potential alternative as a chemotherapeutic anti-carcinogen.
Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions
Bu, Ren,Du, Yanqing,Eerdun, Chaolu,Hu, Mixia,Liang, Fengying,Tsuda, Akihiko,Wang, Meiling
, p. 37463 - 37472 (2020/10/28)
A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CH3CN. CLN1provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CH3CN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1caused by the ionization or OH-F?interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.
