A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd2+ Detection and Bioimaging

doi:10.6023/cjoc202112004

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1786-1791.DOI: 10.6023/cjoc202112004 Previous Articles Next Articles

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一种以2-羟基-N,N-二甲基苄胺为新识别基团的钯离子近红外荧光探针及其细胞成像

张向阳^*(), 吴庆林, 王菲菲, 申有名, 唐裕才^*()

湖南文理学院水处理功能材料湖南省重点实验室湖南常德 415000

收稿日期:2021-12-02 修回日期:2022-01-08 发布日期:2022-02-25
通讯作者: 张向阳, 唐裕才
基金资助:
湖南省教育厅优秀青年基金(19B390); 湖南省教育厅优秀青年基金(19C1254); 湖南省自然科学基金(2020JJ4445); 湖南省自然科学基金(2020JJ5390)

A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd²⁺ Detection and Bioimaging

Xiangyang Zhang(), Qinglin Wu, Feifei Wang, Youming Shen, Yucai Tang()

Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan University of Arts and Science,Changde, Hunan 415000

Received:2021-12-02 Revised:2022-01-08 Published:2022-02-25
Contact: Xiangyang Zhang, Yucai Tang
Supported by:
Scientific Research Foundation of Hunan Provincial Education Department(19B390); Scientific Research Foundation of Hunan Provincial Education Department(19C1254); Hunan Provincial Natural Science Foundation of China(2020JJ4445); Hunan Provincial Natural Science Foundation of China(2020JJ5390)

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Abstract

A near-infrared fluorescent probe DHDM bearing isophorone skeleton and 2-hydroxy-N,N-dimethylbenzylamine has been rationally designed and synthesized. DHDM showed excellent Pd²⁺ specificity with a low detection limit of 53 nmol/L and a large Stokes shift (220 nm). The fluorescence intensity at 660 nm was linear to Pd²⁺ concentrations in a wide range (0~70 μmol/L). Additionally, a possible sensing mechanism was proposed based on the results of the mass spectroscopy, infrared spectrum, a comparative experiment and density functional theory (DFT) calculations. Finally, DHDM was further successfully used to image Pd²⁺ in live cells, suggesting its potential applications in biological systems. The design strategy based on 2-hydroxy-N,N-dimethylbenzylamine or one of its analogues as a new recognition fragment will inspire researchers to construct privileged fluorescence probes in the future.

Key words: new identify group, divalent palladium ion, detection, near-infrared fluorescent probe, facile synthesis

Cite this article

Xiangyang Zhang, Qinglin Wu, Feifei Wang, Youming Shen, Yucai Tang. A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd²⁺ Detection and Bioimaging[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1786-1791.

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Fig. & Tab. 11

Scheme 1. Synthesis route of DHDM

Figure 1. Absorption spectral changes of DHDM (10 μmol/L) upon addition 20 μmol/L Pd2+ in dimethyl sulfoxide (DMSO)/ phosphate buffered saline (PBS) (V∶V=20∶80, pH=7.4, 50 mmol/L)

Figure 2. (a) Fluorescence response of DHDM (10 μmol/L) after the addition of Pd2+ (0~70 μmol/L) in DMSO/PBS buffer solution (V∶V=20∶80, pH=7.4, 50 mmol/L) and (b) fluorescence intensity of DHDM at 660 nm vs. the concentration of Pd2+ (λex=440 nm)

Figure 3. Flurorescence response of DHDM (10 μmol/L) in DMSO/PBS buffer solution (V∶V=20∶80, pH=7.4, 50 mmol/ L) with various metal ions (70 μmol/L)

Figure 4. Time-dependent fluorescence intensity changes of DHDM (10 μmol/L) in the absence of Pd2+ and in the presence of 70 μmol/L Pd2+ in DMSO/PBS buffer solution (V∶V=20∶80, pH=7.4, 50 mmol/L)

Figure 5. Fluorescence intensities of DHDM (10 μmol/L) without Pd2+ (B) and with 70 μmol/L of Pd2+ (D) in various pH values (ranging from 2 to 12), respectively. These experiments were all performed in DMSO/PBS (V∶V=20∶80, 50 mmol/L) buffer solution

Scheme 2. Structure changes of DHDM at different pH values

Figure 6. (a) FT-IR spectra and (b) ESI-MS spectra of DHDM and complex DHDM-Pd2+

Scheme 3. Proposed sensing mechanism of DHDM toward Pd2+

Figure 7. Frontier molecular orbital profiles of DHDM and DHDM-Pd2+ complex based on the DFT (B3LYP-d3bj/def2SVP) calculations

Figure 8. Fluorescence images of Hela cells incubated with DHDM (10 μmol/L) for 30 min (a1~a3), and (b) those first incubated with DHDM (10 μmol/L) for 30 min, and then incubated with Pd2+ (50 μmol/L) for 15 min (b1~b3) (λex=458 nm)

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一种以2-羟基-N,N-二甲基苄胺为新识别基团的钯离子近红外荧光探针及其细胞成像

A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd²⁺ Detection and Bioimaging

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