Dyes and Pigments ( IF 4.1 ) Pub Date : 2021-06-10 , DOI: 10.1016/j.dyepig.2021.109554 Jie Zhang , Haishuang Jia , Wenfang Liu , Jun Wang , Dawei Fang
Cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen sulfide (H2S) are essential active substance in human body. The identification and detection of biothiols and H2S are of great significance for the early diagnosis of certain diseases. In this paper, a new dual excitation and dual emission fluorescent probe, carbon quantum dot-O-7-nitrobenzo-2-oxa-1,3-diazole (CQDs-O-NBD), for the detection of biothiols and H2S was synthesized. The carbon quantum dots (CQDs-OH) (λex/em maxima = 377 nm/467 nm) were synthesized by a microwave-assisted method using hydroquinone as the carbon source. Through the reaction of the phenolic hydroxyl group of the carbon quantum dots and 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl), the CQDs-O-NBD was synthesized. Due to the static quenching (SQ) and the photo-induced electron transfer (PET) from CQDs to NBD, the fluorescence of the CQDs-O-NBD is very weak. After adding biothiols and H2S, the ether bond of the CQDs-O-NBD was broken through nucleophilic substitution reaction, which led to the release of the CQDs-OH (channel 1 is turned on) and generation of a new compound NBD-thiols (channel 2). The CQDs-O-NBD as a probe shows the high selectivity and sensitivity for Cys/Hcy/GSH/NaHS (LOD of 0.24 μM/0.21 μM/0.19 μM/0.18 μM) over other aminos and ions by channel 1. The new formed compounds from NBD and Cys/Hcy have strong fluorescence under 470 nm wavelength light excitation (channel 2 is turned on), while the formed compounds from NBD and GSH/NaHS have no fluorescence (no channel 2), so the CQDs-O-NBD can discriminate Cys/Hcy (LOD: 0.07 μM/0.06 μM) from GSH/NaHS. In addition, the CQDs-O-NBD shows low toxicity and can be applied to the detection of Cys in fetal bovine serum and imaging in living cells.
中文翻译:
基于碳量子点的新型双激发双发射荧光探针 (CQDs-O-NBD) 用于检测和区分活细胞中的 Cys/Hcy 和 GSH/H 2 S
半胱氨酸(Cys)、高半胱氨酸(Hcy)、谷胱甘肽(GSH)和硫化氢(H 2 S)是人体必需的活性物质。生物硫醇和H 2 S的鉴定和检测对于某些疾病的早期诊断具有重要意义。在本文中,一种新的双激发和双发射荧光探针,碳量子点-O-7-硝基苯并-2-氧杂-1,3-二唑(CQDs-O-NBD),用于检测生物硫醇和 H 2 S被合成。碳量子点 (CQDs-OH) (λ ex/emmaxima = 377 nm/467 nm)是通过微波辅助方法合成的,使用氢醌作为碳源。通过碳量子点的酚羟基与4-氯-7-硝基苯并-2-氧杂-1,3-二唑(NBD-Cl)反应,合成了CQDs-O-NBD。由于静态猝灭 (SQ) 和从 CQDs 到 NBD 的光诱导电子转移 (PET),CQDs-O-NBD 的荧光非常弱。加入生物硫醇和 H 2 后S,CQDs-O-NBD 的醚键通过亲核取代反应断裂,导致 CQDs-OH 释放(通道 1 打开)并生成新化合物 NBD-硫醇(通道 2)。CQDs-O-NBD 作为探针显示出对 Cys/Hcy/GSH/NaHS(0.24 μM/0.21 μM/0.19 μM/0.18 μM)的高选择性和灵敏度,超过通道 1 的其他氨基和离子。新形成的NBD 和 Cys/Hcy 的化合物在 470 nm 波长光激发下有很强的荧光(通道 2 打开),而 NBD 和 GSH/NaHS 形成的化合物没有荧光(无通道 2),因此 CQDs-O-NBD可以区分 Cys/Hcy (LOD: 0.07 μM/0.06 μM) 和 GSH/NaHS。此外,CQDs-O-NBD具有低毒性,可应用于胎牛血清中Cys的检测和活细胞成像。