Drug Research Program, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, P.O. Box 56 (Viikinkaari 5 E), 00014, Helsinki, Finland.
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416, Gdańsk, Poland.
Sci Rep. 2022 Sep 5;12(1):15098. doi: 10.1038/s41598-022-19262-w.
Low-molecular synthetic fluorophores are convenient tools in bioimaging applications. Several derivatives of Safirinium dyes as well as their reactive N-hydroxysuccinimide (NHS) esters bearing diverse substituents were synthesized and evaluated experimentally in terms of their lipophilicity by means of reverse-phase and immobilized artificial membrane high-performance liquid chromatography. Subsequently, the selected compounds were employed as novel cellular imaging agents for staining Gram-positive and Gram-negative bacteria, human kidney cell line, as well as human skin tissue. The analyzed dyes allowed for visualization of cellular structures such as mitochondria, endoplasmic reticulum, and cellular nuclei. They proved to be useful in fluorescent staining of stratum corneum, especially in the aspect of xenobiotic exposure and its penetration into the skin. The best results were obtained with the use of moderately lipophilic NHS esters of Safirinium Q. The development of Safirinium dyes is a promising alternative for commercially available dyes since the reported molecules have low molecular masses and exhibit efficient staining and remarkable water solubility. Moreover, they are relatively simple and low-cost in synthesis.
低分子合成荧光团是生物成像应用中的便捷工具。我们合成了几种 Safirinium 染料的衍生物及其带有不同取代基的反应性 N-羟基琥珀酰亚胺（NHS）酯，并通过反相和固定化人工膜高效液相色谱法从亲脂性方面对其进行了实验评估。随后，我们选择了一些化合物作为新型细胞成像试剂，用于对革兰氏阳性和革兰氏阴性细菌、人肾细胞系以及人皮肤组织进行染色。所分析的染料可以可视化细胞结构，如线粒体、内质网和细胞核。它们在角质层的荧光染色方面非常有用，特别是在研究外源性物质暴露及其穿透皮肤方面。使用中等亲脂性的 Safirinium Q NHS 酯可以获得最佳效果。与市售染料相比，Safirinium 染料的开发具有很大的应用前景，因为报道的分子具有低分子量，且表现出高效的染色和显著的水溶性。此外，它们在合成方面相对简单且成本较低。
