高选择性快速检测Hg2+的磺酰腙型探针的合成及其在吸附和HeLa细胞中的应用

doi:10.6023/cjoc202010017

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 1138-1145.DOI: 10.6023/cjoc202010017 上一篇下一篇

研究论文

高选择性快速检测Hg²⁺的磺酰腙型探针的合成及其在吸附和HeLa细胞中的应用

薛松松^a, 解正峰^a^,^b^,^*(), 褚义成^a, 岳永双^a, 石伟^a, 周家斌^a

a 西南石油大学化学化工学院油气田应用化学四川省重点实验室成都 610500
b 西南石油大学工业危废处置与资源化利用研究院成都 610500

收稿日期:2020-10-12 修回日期:2020-11-03 发布日期:2020-11-19
通讯作者: 解正峰
基金资助:
西南石油大学精细化学品青年科技创新团队(2017CXTD05)

Synthesis of Sulfonylhydrazone Type Probe with High Selectivity for Rapid Detection of Mercury and Its Application in Adsorption and HeLa Cell

Songsong Xue^a, Zhengfeng Xie^a^,^b^,^*(), Yicheng Chu^a, Yongshuang Yue^a, Wei Shi^a, Jiabin Zhou^a

a Key Laboratory of Oil & Gas Field Applied Chemistry of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500
b Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization, Southwest Petroleum University, Chengdu 610500

Received:2020-10-12 Revised:2020-11-03 Published:2020-11-19
Contact: Zhengfeng Xie
About author:
* Corresponding author. E-mail: xiezhf@swpu.edu.cn
Supported by:
Youth Science and Technology Innovation Team of Southwest Petroleum University(2017CXTD05)

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摘要/Abstract

以苯磺酰肼和4-二苯胺基苯甲醛为原料, 通过缩合反应设计和合成了一种新型磺酰腙汞离子(Hg²⁺)探针N'-(4-(二苯氨基)亚苄基)苯磺酰腙(S1). 在二甲基亚砜(DMSO)/H₂O (V∶V=7∶3, pH=7)溶液体系中,S1对Hg²⁺展示出快速响应、高选择和高荧光灵敏性. 通过¹H NMR和HRMS探究了可能的机理. 聚丙烯酰胺(PAM)掺杂S1 (PAMS)对Hg²⁺有高的吸附性能, 其去除率达到99.99%, 并且在紫外灯下通过肉眼很容易区分. 通过扫描电子显微镜(SEM)观察了PAMS吸附前后的微观形貌. 此外, S1具有优异的生物相容性, 可以极好地检测HeLa细胞中的Hg²⁺.

关键词: 磺酰腙, 汞离子, 聚丙烯酰胺掺杂, 吸附, HeLa细胞

A novel sulfonylhydrazone Hg²⁺ probe (4-(diphenylamino)benzylidene)benzenesulfonyl hydrazone (S1) was designed and synthesized by condensation reaction between benzenesulfonyl hydrazide and 4-(diphenylamino)benzaldehyde. Probe S1 exhibited a rapid response time, high selectivity and sensitivity fluorescent response to Hg²⁺ in dimethyl sulfoxide (DMSO)/H₂O (V∶V=7∶3, pH=7) solution. The possible mechanism was studied by¹H NMR and HRMS. Polyacrylamide (PAM) doped S1 (PAMS) had high adsorption for Hg²⁺ with removal rate of 99.99% and could easily be distinguished by the naked-eye in UV lamp. And, the micro-morphology of PAMS before and after adsorption was observed by scanning electron microscope (SEM). In addition, probe S1 had excellent biocompatibility and could primely detected Hg²⁺ in HeLa cells.

Key words: sulfonylhydrazone, mercury, polyacrylamide doping, adsorption, HeLa cell

引用此文

薛松松, 解正峰, 褚义成, 岳永双, 石伟, 周家斌. 高选择性快速检测Hg²⁺的磺酰腙型探针的合成及其在吸附和HeLa细胞中的应用[J]. 有机化学, 2021, 41(3): 1138-1145.

Songsong Xue, Zhengfeng Xie, Yicheng Chu, Yongshuang Yue, Wei Shi, Jiabin Zhou. Synthesis of Sulfonylhydrazone Type Probe with High Selectivity for Rapid Detection of Mercury and Its Application in Adsorption and HeLa Cell[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1138-1145.

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图/表 10

Scheme 1. Synthetic procedure of fluorescence probe S1

Figure 1. (a) UV spectra of S1 (1.0×10–5 mol/L) in DMSO/H2O (V∶V=7∶3, pH=7) upon addition of various cations (1.0×10–4 mol/L), (b) fluorescence spectra of S1 (1.0×10–5 mol/L) upon the addition of cations (1.0×10–4mol/L) in DMSO/H2O (V∶V=7∶3, pH=7) (λex=357 nm, slit width: 5 nm×5 nm) and (c) photograph of the fluorescence of S1 (1.0×10–5 mol/L) in the presence of various other cations (1.0×10–4 mol/L) under UV lamp at 365 nm

Figure 2. Interference experiments with Hg2+ (1.0×10–4 mol/L) and ions coexisting in DMSO/H2O (V∶V=7∶3, pH=7) (λex=357 nm, slit width: 5 nm×5 nm)

Figure 3. Response time of fluorescence probe S1 to Hg2+ (λex=357 nm, slit width: 5 nm×5 nm)

Figure 4. (a) Fluorescence of S1 (1.0×10–5 mol/L) in DMSO/ H2O (V∶V=7∶3, pH=7) upon the addition of Hg2+ (5.0×10–7~1.0×10–4 mol/L) and (b) fluorescence value at 495 nm versus the concentration of Hg2+ (λex=357 nm, slit width: 5 nm×5 nm; inset is the relationship between the concentration of Hg2+ and the fluorescence intensity of S1)

Figure 5. 1H NMR spectra of S1 with Hg2+ in DMSO-d6

Figure 6. Possible binding mechanisms of S1 and Hg2+

Figure 7. (a, b) Diagrams of PAM (left) and PAMS (right) without absorb Hg2+ solution in natural light and (c, d) diagrams of PAM (left) and PAMS (right) with absorb Hg2+ solution in UV lamp (365 nm)

Figure 8. (a) SEM and (b) EDS micrographs before PAMS adsorption of Hg2+, and (c) SEM and (d) EDS micrographs after PAMS adsorption of Hg2+

Figure 9. Fluorescence micro-graphs of HeLa cells under different conditions (temperature: 37 ℃, λ ex=357 nm) HeLa cells were soaked with 10 μmol?L –1 S1 for 30 min. Blue channel for probe S1

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高选择性快速检测Hg²⁺的磺酰腙型探针的合成及其在吸附和HeLa细胞中的应用

Synthesis of Sulfonylhydrazone Type Probe with High Selectivity for Rapid Detection of Mercury and Its Application in Adsorption and HeLa Cell

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