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
{"title":"Photodynamic Action of Synthetic Curcuminoids against Staphylococcus aureus: Experimental and Computational Evaluation","authors":"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","doi":"10.3390/chemistry6040035","DOIUrl":null,"url":null,"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.","PeriodicalId":9850,"journal":{"name":"Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry","FirstCategoryId":"1089","ListUrlMain":"https://doi.org/10.3390/chemistry6040035","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 0

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.
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
2.50
自引率
0.00%
发文量
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.
期刊最新文献
Photodynamic Action of Synthetic Curcuminoids against Staphylococcus aureus: Experimental and Computational Evaluation Azidoindolines—From Synthesis to Application: A Review Correction: Bagchi et al. Effects of Carboxyl Functionalized CNT on Electrochemical Behaviour of Polyluminol-CNT Composites. Chemistry 2022, 4, 1561–1575 Phytochemistry, Anti-Tyrosinase, and Anti-Diabetes Studies of Extracts and Chemical Constituents of Dicerothamnus rhinocerotis Leaves Recent Advances in Applied Electrochemistry: A Review
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1