Yang Lu, Jiang Yanglin, Sun Ailin, Chen Mingqing, Li Qiwei, Wang Peng, Zhang Jianping
Key Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, School of Chemistry and Life Resources, Renmin University of China Beijing 100872 China
RSC Adv. 2024 Sep 11;14(39):28957-28964. doi: 10.1039/d4ra03433c. eCollection 2024 Sep 4.
Two styryl BODIPY derivatives, BOH and BOE, with different hydrophilic properties, were investigated for their reaction mechanisms in lipid bilayers against aqueous ClO, by both experimental and theoretical methods. Density functional theory (DFT) calculations confirmed their identical conformations in solution. Fluorescence spectra and high-resolution mass spectra corroborated the central vinyl group as a common antioxidation moiety against ClO oxidation. In giant unilamellar vesicles (GUVs), distinct reaction kinetics with ClO suggested that BOE provided superior protective effects compared to BOH on lipids. Molecular dynamics simulations indicated that the lipophilic octyloxy group in BOE led to its deeper localization within the lipid phase, bringing it closer to the corresponding lipid target group. This study establishes the two styryl BODIPYs as promising fluorescent probes for detecting aqueous ClO in lipid-water polyphasic systems.
通过实验和理论方法，研究了两种具有不同亲水性的苯乙烯基BODIPY衍生物BOH和BOE在脂质双层中与水性次氯酸（ClO）的反应机制。密度泛函理论（DFT）计算证实了它们在溶液中的构象相同。荧光光谱和高分辨率质谱证实了中心乙烯基是对抗ClO氧化的常见抗氧化部分。在巨型单层囊泡（GUVs）中，与ClO不同的反应动力学表明，与BOH相比，BOE对脂质具有更好的保护作用。分子动力学模拟表明，BOE中的亲脂性辛氧基导致其在脂质相中的定位更深，使其更接近相应的脂质靶基团。本研究确定了这两种苯乙烯基BODIPY作为在脂质-水多相系统中检测水性ClO的有前景的荧光探针。
