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基于亚甲基蓝的 7-硝基-1,2,3-苯并恶二唑近红外荧光探针被 HS 触发。

Methylene blue-based 7-nitro-1,2,3-benzoxadiazole NIR fluorescent probe triggered by HS.

机构信息

Affiliated Hospital of Shandong Academy of Medical Sciences, Shandong First Medical University, Jinan 250031, Shandong, China.

Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250062, Shandong, China.

出版信息

Bioorg Med Chem Lett. 2020 Jul 1;30(13):127221. doi: 10.1016/j.bmcl.2020.127221. Epub 2020 Apr 27.

DOI:10.1016/j.bmcl.2020.127221
PMID:32386977
Abstract

A new Methylene blue-based 7-nitro-1,2,3-benzoxadiazole NIR fluorescent probe 3, 7-bis-dimethylamino-10-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)-10H-phenothiazine (leuco-MB-NBD) was designed and synthesized. Leuco-MB-NBD showed high sensitivity and selectivity for HS as a fluorescent probe in CHOH-PBS (9:1, v/v, pH = 7.4) solution, this fluorescent assay showed a linear range of 0-50.0 μM and a LOD (limit of detection) of 0.43 μM. Moreover, the probe leuco-MB-NBD has lower toxicity at low concentrations to HCT-116 cells and can be used for cell imaging. Additionally, Leuco-MB-NBD is triggered by hydrogen sulfide to generate methylene blue, methylene blue which has potential rescuing effects on the mitochondrial activity can act as an antidote against sulfide intoxication.

摘要

一种新型的亚甲蓝基 7-硝基-1,2,3-苯并恶二唑近红外荧光探针 3,7-双二甲氨基-10-(7-硝基苯并[c][1,2,5]恶二唑-4-基)-10H-吩噻嗪(亮甲亚蓝-NBD)被设计和合成。亮甲亚蓝-NBD 作为一种荧光探针,在 CHOH-PBS(9:1,v/v,pH=7.4)溶液中对 HS 表现出高灵敏度和选择性,这种荧光测定法显示出 0-50.0 μM 的线性范围和 0.43 μM 的检测限(LOD)。此外,探针亮甲亚蓝-NBD 在低浓度时对 HCT-116 细胞的毒性较低,可用于细胞成像。此外,亮甲亚蓝-NBD 被硫化氢触发生成亚甲蓝,亚甲蓝对线粒体活性具有潜在的挽救作用,可以作为对抗硫化物中毒的解毒剂。

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