School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian 271016, PR China.
School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian 271016, PR China.
Spectrochim Acta A Mol Biomol Spectrosc. 2022 Mar 5;268:120644. doi: 10.1016/j.saa.2021.120644. Epub 2021 Nov 19.
Cyanide (CN) is a highly toxic compound that exists in many substances and is harmful to the environment and human health. Therefore, it is of great significance to develop excellent CN ion probes, especially solvent-induced on-off fluorescent probes. Based on the condensation reaction of indolo[2,1-b][1,3]oxazine molecules with aldehydes, probes (E)-13a-(2-(9-ethyl-9H-carbazol-3-yl)vinyl)-14,14-dimethyl-10-nitro-13a,14-dihydro-8H-benzo[e]benzo[5,6][1,3]oxazino[3,2-a]indole (NCO) and (E)-13a-(2-(9-benzyl-9H-carbazol-3-yl)vinyl)-14,14-dimethyl-10-nitro-13a,14-dihydro-8H-benzo[e]benzo[5,6][1,3]oxazino[3,2-a]indole (NBO) were synthesized to detect CN. Compared with other cyanogen ion probes, NCO and NBO have special carbazole ring structures and large conjugate systems. When CN is added to the probe-detection solution, color changes that are visible to the naked eye can occur. The UV-vis spectrum test using differential spectroscopy shows that the probe (i) has excellent solvent-induced switching characteristics and stability (CHOH-HO) and (ii) high selectivity, anti-interference ability, and sensitivity for the detection of CN. The fluorescence limit of detections (LODs) are 1.05 µM for NCO and 1.34 µM for NBO. The UV LODs are 0.83 µM for NCO and 0.87 µM for NBO. Fluorescence spectroscopy shows that the probe has remarkable fluorescence properties. Fluorescence titration experiments, liver cancer cell (Hep G2) imaging, and cytotoxicity experiments all show that the probes have high biocompatibility, low toxicity, high cell permeability, and high sensitivity for the detection of CN in cells. In addition, NCO and NBO have been successfully used for the detection of cyanogenic glycosides in the seeds of ginkgo, crabapple, apple, and cherry. Test strips were fabricated to detect CN. After adding CN, the color of the test strip changed significantly-from brown to light yellow; thus, the test strips have a high application value in the fields of drug quality control, drug safety testing, and pharmacological research.
氰化物（CN）是一种存在于许多物质中的剧毒化合物，对环境和人类健康有害。因此，开发优秀的 CN 离子探针，特别是溶剂诱导的开-关荧光探针，具有重要意义。基于吲哚并[2,1-b][1,3]恶嗪分子与醛的缩合反应，合成了探针（E）-13a-（2-（9-乙基-9H-咔唑-3-基）乙烯基）-14,14-二甲基-10-硝基-13a,14-二氢-8H-苯并[e]苯并[5,6][1,3]恶嗪[3,2-a]吲哚（NCO）和（E）-13a-（2-（9-苄基-9H-咔唑-3-基）乙烯基）-14,14-二甲基-10-硝基-13a,14-二氢-8H-苯并[e]苯并[5,6][1,3]恶嗪[3,2-a]吲哚（NBO），用于检测 CN。与其他氰根离子探针相比，NCO 和 NBO 具有特殊的咔唑环结构和较大的共轭体系。当向探针检测溶液中加入 CN 时，肉眼可见的颜色变化会发生。使用差谱法的 UV-vis 光谱测试表明，探针（i）具有出色的溶剂诱导开关特性和稳定性（CHOH-HO），（ii）对 CN 的检测具有高选择性、抗干扰能力和灵敏度。NCO 的荧光检测限（LOD）为 1.05 μM，NBO 的 LOD 为 1.34 μM。UV 的 LOD 分别为 0.83 μM 和 0.87 μM。荧光光谱表明，探针具有显著的荧光性质。荧光滴定实验、肝癌细胞（Hep G2）成像和细胞毒性实验均表明，探针具有高生物相容性、低毒性、高细胞通透性和对细胞内 CN 检测的高灵敏度。此外，NCO 和 NBO 已成功用于银杏、海棠、苹果和樱桃种子中氰苷的检测。制备了检测 CN 的试纸条。加入 CN 后，试纸条的颜色发生明显变化，从棕色变为浅黄色；因此，试纸条在药物质量控制、药物安全检测和药理学研究等领域具有很高的应用价值。
