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

doi:10.6023/cjoc202111013

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1463-1473.DOI: 10.6023/cjoc202111013 Previous Articles Next Articles

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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

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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Abstract

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

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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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Fig. & Tab. 15

Scheme 1. Synthetic route of probe DBTMC

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

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

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

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

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)

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)

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.

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

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

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

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)

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

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

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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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