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Tuning the Polarity of Fullerene C60 Derivatives for Enhanced Photodynamic Inactivation†
Photochemistry and Photobiology ( IF 3.3 ) Pub Date : 2021-06-11 , DOI: 10.1111/php.13465
Yohana B Palacios 1 , Javier E Durantini 2 , Daniel A Heredia 1 , Sol R Martínez 2 , Laura González de la Torre 1 , Andrés M Durantini 1
Affiliation  

In this article, four novel fulleropyrrolidines derivatives were synthesized to study how the effect of polarity and positive charge distribution can influence the efficacy of photodynamic inactivation treatments to kill bacteria. The design of the photosensitizers was based on DFT calculations that allowed us to estimate the dipolar moment of the molecules. Neutral compounds bearing N-methyl bis-acetoxy-ethyl (1) and bis-hydroxyethyl (2) amine were the starting material to obtain the dicationic analogs N,N-dimethyl bis-methoxyethyl (3), and bis-acetoxy-ethyl) (4) methylammonio. As expected from fullerene C60 derivatives, compounds 1-4 absorb in the UV region, with a peak at 430 nm, a broader range of absorption up to 710 nm, and exhibit weak fluorescence emission in toluene and reverse micelles. In the biomimetic AOT micellar system, the highest singlet oxygen photosensitization was found for compounds 1, followed by 3, 2, and 4. Whereas 4 was the most effective reducing nitro blue tetrazolium in the presence of β-NADH. The influence of type I and type II mechanism on the photodynamic activity of compounds 3 and 4 was further examined in the presence of L-tryptophan and two reactive oxygen species scavengers. In vitro experiments indicated that the compounds with the highest dipolar moments, 3 (37.19 D) and 4 (38.46 D), inactivated methicillin-resistant Staphylococcus aureus and Escherichia coli bacteria using an energy dose <2.4 J cm−2. No inactivation was observed for the neutral analogs with the lowest dipolar moments. These findings help to optimize sensitizer structures to improve photodynamic inactivation.

中文翻译:

调整富勒烯 C60 衍生物的极性以增强光动力灭活†

在本文中,合成了四种新型富勒吡咯烷衍生物,以研究极性和正电荷分布的影响如何影响光动力灭活处理杀死细菌的功效。光敏剂的设计基于 DFT 计算,使我们能够估计分子的偶极矩。带有N-甲基双-乙酰氧基-乙基 (1) 和双-羟乙基 (2) 胺的中性化合物是获得双阳离子类似物N,N-二甲基双-甲氧基乙基 (3) 和双-乙酰氧基-乙基)的起始材料(4) 甲基铵。正如富勒烯 C 60所预期的那样衍生物,化合物 1-4 在紫外区有吸收,在 430 nm 处有一个峰,吸收范围较宽,可达 710 nm,在甲苯和反胶束中表现出微弱的荧光发射。在仿生 AOT 胶束系统中,化合物 1 的单线态氧光敏性最高,其次是 3、2 和 4。而 4 是在 β-NADH 存在下最有效的还原硝基蓝四唑。在存在 L-色氨酸和两种活性氧清除剂的情况下,进一步研究了 I 型和 II 型机理对化合物 3 和 4 的光动力活性的影响。体外实验表明,具有最高偶极矩的化合物 3(37.19 D)和 4(38.46 D)灭活了耐甲氧西林金黄色葡萄球菌使用能量剂量<2.4 J cm -2的大肠杆菌。对于具有最低偶极矩的中性类似物,没有观察到失活。这些发现有助于优化敏化剂结构以改善光动力失活。
更新日期:2021-06-11
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