Introduction::
In this contribution, a series of alkoxy substituted chalcone were successfully designed, synthesized, spectroscopically characterized and evaluated for their cytotoxicity potential in inhibiting the growth of MCF-7 cells.
Objective::
In order to investigate the influence between electron density in conjugated π-systems and biological activities, different withdrawing substituent namely nitro (NO2), cyano (C≡N) and trifluoromethyl (CF3) were introduced in chalcone-based molecular system.
Methods::
All the derivatives were then tested on MCF-7 cell line using the fluorescence microscopy-based cytotoxicity analyses.
Results::
The preliminary findings showed that both –NO2 and –CF3 substituents revealed their potential to inhibit the growth of MCF-7 with IC50 values of 14.75 and 13.75 μg/ml, respectively. In addition, the morphological changes of MCF-7 cells were observed in response to alkoxy substituted chalcone treatment through an induction of apoptosis pathway with cell blebbing, phosphatidylserine exposure and autophagic activity with acidification of lysosomal structure. Intermolecular interaction based on in silico investigation on nitro, trifluoromethyl and cyano based chalcones exhibited several types of interactions with tumor necrosis factor receptor (PDB: 1EXT) protein and high hydrogen bond in the molecule-receptor interaction have given significant impact towards their toxicity on MCF-7 cells.
Conclusion::
Significantly, these types of chalcones exhibited ideal and high potential to be further developed as anti-cancer agents.
A new bischalcone consisting hexyloxy (-C6H2n + 1) chain based on ‘Donor (D)-π-Donor (D)’ scheme was successfully designed and synthesized to demonstrate as emitting material for single layer OLEDs. Density functional theory assessment (DFT) at B3LYP/6–31G(d,p) were computed to obtain frontier molecular orbitals (FMO), chemical reactivity and molecular electrostatic potential (MEP). The utilization of alkoxy towards the chalcone moiety has increased the solubility and contributed to HOMO-LUMO gap energy level 3.473 eV by UV–vis spectroscopy and were found to have good agreement with theoretical calculations. The investigation on their optical, electrochemical and thermal behaviour also were conducted via UV-Vis, cyclic voltammetry (CV), thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The entitled alkoxylated bischalcone (CSAB) revealed good thermal stability up to 300˚C and showed high glass transition temperatures. At positive potential, a quasi-reversible oxidation (Eox 1/2) peak at 2.40 V and negative potentials exhibited reduction peak at 0.78 V, respectively. The application of CSAB was tested in the form thin film in respect of their conductivity of electrical current and electroluminescence behaviour. It gave an intense yellow emission has provided the fundamental understanding on its potentiality featuring alkoxylated bischalcone moiety as solution-processed OLEDs material in optoelectronic interest.
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