A Study on the Structure, Optical Properties and Cellular Localization of Novel 1,3-Benzothiazole-Substituted BODIPYs

Colorants Pub Date : 2023-12-31 DOI:10.3390/colorants3010002

Olga Kirkilessi, C. Arapatzi, Heribert Reis, V. Kostourou, Kyriakos C. Prousis, T. Calogeropoulou

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Abstract

A library of seven novel 1,3-benzothiazole-substituted BODIPY derivatives with tunable optical properties was synthesized. The new fluorescent dyes exhibited bathochromically shifted absorptions (up to 670 nm) and emissions centered in the red and near-infrared spectral region (up to 677 nm) in comparison to the parent compound 8-phenyl BODIPY (λabs: 499 nm, λemi: 508 nm). (TD)DFT calculations were performed to rationalize the spectroscopic properties of the new dyes. The cellular biodistribution of the new BODIPY dyes, their fluorescence stability and toxicity were investigated in both living and fixed fibroblasts using time-lapse fluorescent imaging and confocal microscopy. Six of the seven new dyes were photostable and non-toxic in vitro at 10 μM concentration. In addition, they efficiently stained the cell membrane, showing diffuse and dotty localization within the cell at low concentrations (1.0 and 0.1 μM). Specifically, dye TC498 was localized in vesicular structures in both live and fixed cells and could be used as a suitable marker in co-staining studies with other commonly used fluorescent probes.

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新型 1,3-苯并噻唑取代 BODIPYs 的结构、光学特性和细胞定位研究

我们合成了七个具有可调光学特性的新型 1,3-苯并噻唑取代 BODIPY 衍生物库。与母体化合物 8-苯基 BODIPY（λabs：499 nm，λemi：508 nm）相比，这些新型荧光染料表现出浴色偏移吸收（高达 670 nm），以及以红色和近红外光谱区（高达 677 nm）为中心的发射。进行的 (TD)DFT 计算使新染料的光谱特性更加合理。利用延时荧光成像和共聚焦显微镜研究了新型 BODIPY 染料在活体和固定成纤维细胞中的细胞生物分布、荧光稳定性和毒性。在 10 μM 浓度下，七种新型染料中有六种在体外具有光稳定性和无毒性。此外，它们还能有效染色细胞膜，在低浓度（1.0 和 0.1 μM）时，在细胞内呈弥漫和点状定位。具体来说，染料 TC498 定位于活细胞和固定细胞的液泡结构中，可用作与其他常用荧光探针共同染色研究的合适标记。

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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Colorants

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