Dvorak Trevor, Hernandez-Sandoval Haley, Cheku Sunayn, Mora Valencia González Marijose, Borer Linus, Grieser Riley, Carlson Kimberly A, Cao Haishi
Department of Chemistry, University of Nebraska at Kearney, 2504 9th Ave, Kearney, NE 68849, USA.
Department of Biology, University of Nebraska at Kearney, 2504 9th Ave, Kearney, NE 68849, USA.
Biosensors (Basel). 2025 Mar 7;15(3):174. doi: 10.3390/bios15030174.
Hydrogen sulfide (HS) is an important signaling molecule involved in various physiological and pathological processes, making its accurate detection in biological systems highly desirable. In this study, two fluorescent probes ( and ) based on 1,8-naphthalimide were developed for HS detection via a nucleophilic aromatic substitution. demonstrated high sensitivity and selectivity for HS in aqueous media, with a detection limit of 0.64 µM and a strong linear fluorescence response in the range of 0-22 µM of NaHS. The reaction kinetics revealed a rapid response, with a reaction rate constant of 7.56 × 10 M s, and was most effective in the pH range of 6-10. Mechanism studies using H NMR titration confirmed the formation of 4-hydroxyphenyl-1,8-naphthalimide as the product of HS-triggered nucleophilic substitution. was applied in MDA-MB-231 cells for cell imaging, in which provided significant fluorescence enhancement upon NaHS treatment, confirming its applicability for detecting HS in biological environments. In comparison, , designed with extended conjugation for red-shifted emission, exhibited weaker sensitivity due to the reduced stability of its naphtholate product and lower solubility. These results demonstrate that is a highly effective and selective fluorescent probe for detecting HS, providing a valuable resource for investigating the biological roles of HS in health and disease.
硫化氢（HS）是一种重要的信号分子，参与各种生理和病理过程，因此在生物系统中对其进行准确检测非常必要。在本研究中，开发了两种基于1,8-萘二甲酰亚胺的荧光探针（和），用于通过亲核芳香取代检测HS。在水性介质中对HS表现出高灵敏度和选择性，检测限为0.64 μM，在0-22 μM的NaHS范围内有强烈的线性荧光响应。反应动力学显示响应迅速，反应速率常数为7.56×10 M s，并且在pH值6-10的范围内最有效。使用1H NMR滴定的机理研究证实了4-羟基苯基-1,8-萘二甲酰亚胺的形成是HS引发的亲核取代产物。被应用于MDA-MB-231细胞进行细胞成像，其中在NaHS处理后荧光显著增强，证实了其在生物环境中检测HS的适用性。相比之下，设计用于红移发射的扩展共轭的，由于其萘酚盐产物稳定性降低和溶解度较低，灵敏度较弱。这些结果表明是一种用于检测HS的高效且选择性荧光探针，为研究HS在健康和疾病中的生物学作用提供了有价值的资源。
