Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland.
Chair and Department of Toxicology, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland.
Molecules. 2024 Nov 10;29(22):5304. doi: 10.3390/molecules29225304.
Synthesis, photochemical properties, liposomal encapsulation, and in vitro photodynamic activity studies of novel BODIPY dimer connected at positions and its brominated and iodinated analogs were described. UV-Vis measurements indicated that the dimeric structure of obtained BODIPYs did not significantly influence the positions of the absorption maxima. Emission properties and singlet oxygen generation studies revealed a strong heavy atom effect of brominated and iodinated BODIPY dimers, manifested by fluorescence intensity reduction and increased singlet oxygen generation ability compared to analog without halogen atoms. For the in vitro photodynamic activity studies, dimers were incorporated into two different types of liposomes: positively charged DOTAP:POPC and negatively charged POPG:POPC. The photoinactivation studies revealed high activity of brominated and iodinated dimers incorporated into DOTAP:POPC liposomes on both Gram-positive and Gram-negative . Anticancer studies on human breast adenocarcinoma MDA-MB-231 and human ovarian carcinoma A2780 cells revealed that DOTAP:POPC liposomes containing brominated and iodinated dimers were active even at low nanomolar concentrations. In addition, they were more active against MDA-MB-231 cells than A2780 cells, which is particularly important since the MDA-MB-231 cell line represents triple-negative breast cancer, which has limited therapeutic options.
描述了新型 BODIPY 二聚体在 位连接的，并及其溴代和碘代类似物的合成、光化学性质、脂质体包封和体外光动力活性研究。紫外-可见测量表明，所获得的 BODIPY 的二聚体结构不会显著影响吸收最大值的位置。荧光性质和单线态氧生成研究表明，溴代和碘代 BODIPY 二聚体具有强烈的重原子效应，与不含卤素原子的类似物相比，荧光强度降低，单线态氧生成能力增强。对于体外光动力活性研究，将二聚体掺入两种不同类型的脂质体中：带正电的 DOTAP：POPC 和带负电的 POPG：POPC。光灭活研究表明，在革兰氏阳性菌和革兰氏阴性菌上，掺入 DOTAP：POPC 脂质体的溴代和碘代二聚体具有很高的活性。对人乳腺癌 MDA-MB-231 和人卵巢癌 A2780 细胞的抗癌研究表明，即使在低纳摩尔浓度下，含有溴代和碘代二聚体的 DOTAP：POPC 脂质体也具有活性。此外，它们对 MDA-MB-231 细胞的活性高于 A2780 细胞，这一点尤为重要，因为 MDA-MB-231 细胞系代表三阴性乳腺癌，其治疗选择有限。
