三唑基团功能化的三苯胺类Cu2+荧光探针的合成及在检测和HeLa细胞中的应用

doi:10.6023/cjoc202111013

有机化学 ›› 2022, Vol. 42 ›› Issue (5): 1463-1473.DOI: 10.6023/cjoc202111013 上一篇下一篇

研究论文

三唑基团功能化的三苯胺类Cu²⁺荧光探针的合成及在检测和HeLa细胞中的应用

文乙评^a^,^b, 解正峰^a^,^b^,^*(), 史天柱^a^,^c, 褚义成^a, 周荣贵^a, 陶奕杉^a, 梁焕敏^a, 邱海燕^a, 赵云辉^d^,^*()

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
c 茅台学院酿酒工程系贵州仁怀 564500
d 湖南科技大学化学化工学院湖南湘潭 411201

收稿日期:2021-11-15 修回日期:2022-01-12 发布日期:2022-01-27
通讯作者: 解正峰, 赵云辉
基金资助:
四川省青年科技创新研究团队(2020JDTD0018); 贵州省遵义市科学技术局及茅台学院市校联合科技合作资金(遵市科合HZ字[2021]333号资助项目)

Synthesis of Triazole Functionalized Triphenylamine Cu²⁺ Fluorescent Probe and Its Application in Detection and HeLa Cells

Yiping Wen^a^,^b, Zhengfeng Xie^a^,^b(), Tianzhu Shi^a^,^c, Yicheng Chu^a, Ronggui Zhou^a, Yishan Tao^a, Huanmin Liang^a, Haiyan Qiu^a, Yunhui Zhao^d()

a Oil & Gas Field Applied Chemistry Key Laboratory 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
c Department of Brewing Engineering, Moutai Institute, Renhuai, Guizhou 564500
d School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201

Received:2021-11-15 Revised:2022-01-12 Published:2022-01-27
Contact: Zhengfeng Xie, Yunhui Zhao
Supported by:
Sichuan Youth Science and Technology Innovation Research Team Project(2020JDTD0018); Zunyi Science and Technology Bureau of Guizhou Province and the Maotai Institute Joint Science and Technology Cooperation Fund Project(Zunyi Kehe HZ [2021]333)

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摘要/Abstract

以2-(4-溴苯基)-2H-1,2,3-三唑-4-甲醛、(4-(二苯基氨基)苯基)硼酸和氨基硫脲为原料, 设计合成了一种新型的可高选择性快速识别Cu²⁺的荧光探针分子N'-((2-(4'-(二苯胺基)-[1,1'-联苯]-4-基)-2H-1,2,3-三唑-4-基)亚甲基)肼-1-硫代酰胺(DBTMC). DBTMC展示出优异的溶剂效应和聚集态效应, 对Cu²⁺展现出高选择、高灵敏和快速响应性, 检测限为4.48×10^–8 mol/L. 通过job’s曲线、¹H NMR滴定、HRMS及密度泛函理论(DFT)计算对其可能的响应机理进行了探究. 用探针DBTMC制备的测试条, 可用于快速检测Cu²⁺. 将DBTMC应用于检测HeLa细胞中的Cu²⁺, 也取得了良好的效果, 具有潜在的应用价值.

关键词: 荧光探针, 铜离子, 溶剂效应, 聚集态效应, HeLa细胞

A novel fluorescence probe N'-((2-(4'-(diphenyl)-[1,1'-biphenyl]-4-yl)-2H-1,2,3-triazole-4-yl)methylene) hydrazine- 1-thioamide (DBTMC) was designed and synthesized from (4-(diphenylamino)-phenyl)boronic acid, (4-bromophenyl)- 2H-[1,2,3]-triazole-4-carbaldehyde and thiosemicarbazide. DBTMC possessed excellent solvent effect and aggregation effect, and exhibited high selectivity, high sensitivity and rapid response to Cu²⁺ with detection limit of 4.48×10^–8 mol/L. The possible response mechanism was explored through job’s curve, ¹H NMR titration, HRMS and density functional theory (DFT) calculations. The test strip prepared with the probe DBTMC solution could be used for quick recognition of Cu²⁺. DBTMC was applied to HeLa cells to detect Cu²⁺ and excellent results were achieved, possessing potential application.

Key words: fluorescent probe, copper ion, solvent effect, aggregation effect, HeLa cells

引用此文

文乙评, 解正峰, 史天柱, 褚义成, 周荣贵, 陶奕杉, 梁焕敏, 邱海燕, 赵云辉. 三唑基团功能化的三苯胺类Cu²⁺荧光探针的合成及在检测和HeLa细胞中的应用[J]. 有机化学, 2022, 42(5): 1463-1473.

Yiping Wen, Zhengfeng Xie, Tianzhu Shi, Yicheng Chu, Ronggui Zhou, Yishan Tao, Huanmin Liang, Haiyan Qiu, Yunhui Zhao. Synthesis of Triazole Functionalized Triphenylamine Cu²⁺ Fluorescent Probe and Its Application in Detection and HeLa Cells[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1463-1473.

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图/表 15

图式1. 探针分子DBTMC的合成路线

Scheme 1. Synthetic route of probe DBTMC

图1. DBTMC在乙酸乙酯、THF、丙酮、DMF和DMSO中的(a)紫外吸收光谱和(b)荧光发射光谱, 以及(c)在365 nm紫外灯照射下拍摄的照片

Figure 1. (a) UV absorption spectrum and (b) fluorescence emission spectrum of DBTMC in ethylacetate, THF, acetone, DMF, DMSO, and (c) photos taken under the irradiation of a 365 nm UV lamp DBTMC: 1.0×10–5 mol/L; excitation wavelength: 365 nm; slit: 5 nm×5 nm

DBTMC	λ_abs/nm	λ_em/nm	Strength	Stokes shift/cm^–1
Ethyl acetate	355	456	7268	6239.2
THF	358	460	6201	6193.8
Acetone	357	502	2795	8090.9
DMF	359	506	2529	8092.3
DMSO	362	513	1869	8131.1

表1. 探针DBTMC在不同溶剂中的光学性质(λabs, 最大吸收量; λem, 最大发射量)

Table 1. Optical characteristics of DBTMC in different solvents (λabs, absorption maximum; λem, emission maximum)

图2. DBTMC在不同比例THF/H2O的混合液中的紫外光谱(a)和荧光光谱(b)及(c)在紫外灯365 nm下的照片

Figure 2. (a) Ultraviolet spectra and (b) fluorescence spectra of DBTMC in mixture of THF and water and (c) photos taken under UV lamp (365 nm) DBTMC: 1.0×10–5 mol/L; excitation wavelength 365 nm; slit: 5 nm×5 nm; blank indicates the fluorescence intensity of DBTMC in pure THF

图3. (a) DBTMC在不同THF/H2O体积比下的[DBTMC]、[DBTMC+Ag+]和[DBTMC+Hg2+]的荧光强度柱状图、(b)在DBTMC的THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4)混合溶剂中加入Cys后对阳离子Cu2+、Hg2+和Ag+响应的荧光光谱图、(c) DBTMC与Cu2+的反应时间以及(d)在不同pH条件下DBTMC和[DBTMC+Cu2+]的荧光折线图

Figure 3. (a) Histogram of fluorescence intensity of [DBTMC], [DBTMC+Ag+], [DBTMC+Hg2+] of DBTMC at different THF/H2O ratios, (b) fluorescence spectrum of the response of DMTH to Cu2+, Hg2+ and Ag+ after adding Cys to a mixed THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4) solvent of DBTMC, (c) reaction time of DBTMC and Cu2+, and (d) fluorescence intensities of DBTMC, [DBTMC+Cu2+] under different pH conditions Blank indicates the fluorescence intensity of DBTMC in different ratios of THF/H2O

图4. DBTMC (1×10–5 mol/L)在THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L)溶液中对不同离子 (1×10–4 mol/L)的(a)紫外-可见吸收光谱和(b)荧光光谱

Figure 4. (a) UV absorption and (b) fluorescence spectrum of DBTMC response to different ions (1×10–4 mol/L) in a mixed solvent of THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L)

图5. 在混合溶剂THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L)中存在各种离子时探针DBTMC对Cu2+响应的荧光强度柱状图

Figure 5. Fluorescent bar graph of probe DBTMC responding to Cu2+ in the presence of various ions in THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L)

图6. (a) 在502 nm处DBTMC (10 μmol/L)在含有不同浓度的Cu2+ (0.05, 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.2, 1.4, 1.6, 1.8, 2.0 μmol/L)的THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L)中的荧光光谱图和(b) DBTMC (10 μmol/L)对502 nm处不同浓度的Cu2+的荧光响应的点状图

Figure 6. (a) Fluorescence spectra of DBTMC (10 μmol/L) in THF/H2O (V∶V=2∶8, 5 mmol/L, PBS, pH=7.4, Cys: 3 mmol/L) toward varying concentrations of Cu2+ (0.05, 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.2, 1.4, 1.6, 1.8, 2.0 μmol/L) at 502 nm, and (b) dot diagram of the fluorescence responses of DBTMC (10 μmol/L) toward varying concentrations of Cu2+ at 502 nm Inset: linear fitting curve between DBTMC fluorescence intensity and Cu2+ concentration between 0.1~0.3 μmol/L.

图7. 探针DBTMC加入Cu2+的核磁滴定图

Figure 7. 1H NMR titration of DBTMC after adding Cu2+ in DMSO-d6

图式2. DBTMC检测Cu2+的可能的机理

Scheme 2. Proposed plausible mechanisms for detection of Cu2+ by DBTMC

图8. DBTMC和DBTMC+Cu2+的优化结构及前沿分子轨道结构和能带能的电子密度图

Figure 8. Optimized structures of DBTMC and DBTMC+Cu2+ and electron density maps of frontier molecular orbital structures and band gap energies of probe

图9. (a)日光和(b)紫外灯(365 nm)下添加不同金属离子后测试条的荧光变化

Figure 9. Change of the fluorescent of the test strip after adding different metal ions under (a) the sunlight and (b) UV lamp (365 nm)

图10. 探针DBTMC对HeLa细胞在不同浓度下的细胞毒性测定

Figure 10. Cytotoxicity assay of probe DBTMC for HeLa cells at different concentrations

图11. HeLa细胞与DBTMC (10 μmol/L)在37 ℃培养30 min, 随后与Cu2+ (0, 50, 100, 250 μmol/L)培养30 min后的荧光图像(最上)、明场图像(中间)和叠加图像(最下) (激发波长365 nm)

Figure 11. Fluorescence image (top), brightfield image (middle), and overlay image (bottom) of (excitation wavelength 365 nm) of HeLa cells after cultured with DBTMC (10 μmol/L) for 30 min, and then with Cu2+ (0, 50, 100, 250 μmol/L) for 30 min under 37 ℃

Solvent (V∶V)	LOD/(mol•L^–1)	ICT	AIE	pH	Time	Cell	Ref.
C₂H₅OH/H₂O (2∶3)	9.80×10^–8	ICT	—	7	10 s	—	[38]
CH₃CN/H₂O (1∶1)	5.80×10^–8	—	—	7.2	1 h	MCF-7 cells	[41]
ACN/PBS (4∶6)	1.57×10^–7	—	—	7.4	—	Hela cells	[42]
CH₃CN/HEPES (4∶1)	3.20×10^–7	—	—	7.4	20 min	293 T cells	[3]
CH₃CN/HEPES (1∶9)	2.19×10^–7	—	—	7.0	11 min	HepG2 cells	[43]
CH₃CN/HEPES (4∶1)	3.30×10^–5	—	—	7.3	—	HepG2 cells	[44]
CH₃CN	1.80×10^–7	—	—	—	—	—	[45]
THF/H₂O (1∶4)	4.48×10^–8	ICT	AIE	7.4	5 s	Hela cells	This work

表2. 探针DBTMC与其它已报道的Cu2+探针的比较

Table 2. Comparison of probe DBTMC with other Cu2+ probes reported

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三唑基团功能化的三苯胺类Cu²⁺荧光探针的合成及在检测和HeLa细胞中的应用

Synthesis of Triazole Functionalized Triphenylamine Cu²⁺ Fluorescent Probe and Its Application in Detection and HeLa Cells

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