Synthesis, nonlinear optical activity, solvents effect, β-cyclodextrin effect, and cytotoxic activity on skin fibroblast and breast cancer cell lines of a new chalcone derivative of nabumetone.

Autor: Meenatchi V; School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongsangbuk-do 38541, Republic of Korea; Department of Physiology, Saveetha Dental College and Hospitals, Saveetha Institute of Medical and Technical Science (SIMATS), Saveetha University, Chennai 600077, India. Electronic address: meena.gaya1986@gmail.com., Kim S; School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongsangbuk-do 38541, Republic of Korea., Won SY; School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongsangbuk-do 38541, Republic of Korea., Buvaneswari K; KCG College of Technology, KCG Nagar, Rajiv Gandhi Salai, Karapakkam, Chennai 600 097, Tamil Nadu, India., Han SS; School of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongsangbuk-do 38541, Republic of Korea. Electronic address: sshan@yu.ac.kr.
Jazyk: angličtina
Zdroj: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2025 Jan 15; Vol. 325, pp. 125148. Date of Electronic Publication: 2024 Sep 15.
DOI: 10.1016/j.saa.2024.125148
Abstrakt: The use of small organic molecules, such as chalcones, for efficient applications as organic luminescent materials has attracted increasing attention owing to their interesting optical, photophysical, and biological properties. In this study, a new chalcone, 1-(4-isopropylphenyl)-5-(6-methoxynaphthalen-2-yl)pent-1-en-3-one (INM), was synthesized via base condensation between nabumetone and cuminaldehyde. INM was subsequently identified and characterized by FT-IR, NMR spectroscopy ( 1 H and 13 C), mass spectrometry, elemental analysis, X-ray diffraction, thermogravimetric analysis, and FESEM studies. Investigation of the solvent effect revealed that the π → π* transition involved a bathochromic shift from hexane to water and a large Stokes-shifted, twisted intramolecular charge-transfer emission in water. Diffuse reflectance spectral studies confirmed the formation of transparent INM chalcones with excellent crystallinity, and photoluminescence studies substantiated the low recombination rate of electrons and holes. Tauc plot analysis with the Kubelka-Munk algorithm revealed higher direct (3.57 eV) and indirect (3.41 eV) bandgap energies of INM. Density functional theory calculations at B3LYP/6-31G(d,p) revealed that INM had promising nonlinear optical activity (β ≈ 30.504 × 10 -30 compared to a reference material, urea. Cell biocompatibility was evaluated after culturing skin fibroblasts and breast cancer cells with INM using the MTT assay and fluorescence microscopy of the live/dead cell assay. It was observed that INM exhibited good NIH/3T3 cell adhesion and proliferation and the weak inhibiting ability of MDA-MB231.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024. Published by Elsevier B.V.)
Databáze: MEDLINE
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