Photodynamic Action of Synthetic Curcuminoids against Staphylococcus aureus: Experimental and Computational Evaluation

Q3 Chemistry Chemistry Pub Date : 2024-07-25 DOI:10.3390/chemistry6040035
Nícolas J. Melo, Jennifer M. Soares, L. N. Dovigo, Christian Carmona-Vargas, A. S. N. Aguiar, Adriana C. dos Passos, K. D. de Oliveira, V. Bagnato, L. D. Dias, N. Inada
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Abstract

Natural curcumin is composed of three curcuminoids, namely curcumin (CUR), deme-thoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC). These compounds are utilized in various biophotonics applications, including photodynamic therapy (PDT). This work aimed to evaluate the photodynamic action (alternative to antibiotics) of synthetic curcuminoids against Staphylococcus aureus. Herein, we evaluated an optimal proportion of the three curcuminoids mixed in solution to improve photoinactivation effects. Therefore, a set of computational calculations was carried out to understand the photodynamic action (stability and mechanism) of curcuminoids. Regarding computational analysis, the curcuminoid molecules were optimized using DFT with the hybrid exchange–correlation functional M06-2X, which includes long-range correction, and the 6-311++G(d,p) basis set. DMC and BDMC were more effective as photosensitizers than curcumin at a very low concentration of 0.75 µM, inactivating more than five orders of magnitude of S. aureus. Theoretical UV-vis absorption spectra showed that at maximum absorption wavelengths, electronic transitions of the π→π* type originated from H→L excitations. The BDMC was more stable than the other two curcuminoids after photobleaching, and the fluorescence emission was also higher, which could lead to its usage as a fluorescence dye to track bacteria. In fact, the results of electronic structure calculations proved that the stability order of curcuminoids is CUR < DMC < BDMC. The mixture of synthetic curcuminoids was more effective in the inactivation of S. aureus compared to curcumin by itself; for all proposed mixtures, an equal or superior reduction was achieved.
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合成姜黄素对金黄色葡萄球菌的光动力作用:实验和计算评估
天然姜黄素由三种姜黄类化合物组成,即姜黄素(CUR)、去甲氧基姜黄素(DMC)和双去甲氧基姜黄素(BDMC)。这些化合物可用于各种生物光子学应用,包括光动力疗法(PDT)。这项研究旨在评估合成姜黄素对金黄色葡萄球菌的光动力作用(替代抗生素)。在此,我们评估了三种姜黄素在溶液中混合的最佳比例,以提高光活化效果。因此,我们进行了一系列计算,以了解姜黄素的光动力作用(稳定性和机制)。在计算分析方面,利用包含长程校正的混合交换相关函数 M06-2X 和 6-311++G(d,p) 基集进行了姜黄素分子的 DFT 优化。在 0.75 µM 的极低浓度下,DMC 和 BDMC 作为光敏剂比姜黄素更有效,可灭活五个数量级以上的金黄色葡萄球菌。理论紫外-可见吸收光谱显示,在最大吸收波长处,π→π*型电子跃迁源于H→L激发。与其他两种姜黄素相比,BDMC 在光漂白后更加稳定,荧光发射也更高,可用作追踪细菌的荧光染料。事实上,电子结构计算的结果证明,姜黄素的稳定性顺序为 CUR < DMC < BDMC。与姜黄素本身相比,合成姜黄素的混合物在灭活金黄色葡萄球菌方面更为有效;对于所有建议的混合物,都达到了相同或更优的灭活效果。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
2.50
自引率
0.00%
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0
审稿时长
11 weeks
期刊介绍: Chemistry—A European Journal is a truly international journal with top quality contributions (2017 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields.
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