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2,4-Dinitrobenzenesulfonate-functionalized carbon dots as a turn-on fluorescent probe for imaging of biothiols in living cells

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Abstract

The authors describe a carbon dot-based fluorescent probe for biothiols. Green emissive carbon dots (g-CDs; with λex/λem maxima of 407/505 nm) were synthesized by a one-step solvothermal method starting from 3-diethylaminophenol. They were then covalently functionalized with 2,4-dinitrobenzenesulfonyl chloride to afford 2,4-Dinitrobenzenesulfonate-functionalized CDs (g-CD-DNBS) as a nanoprobe for biothiols. The fluorescence of the g-CD-DNBS is quite weak. Upon addition of biothiols, the DNBS group of the probe is removed by thiol groups. This results in gradual restoration of the green fluorescence. The nanoprobe exhibits high selectivity for biothiols over other amino acids and biological molecules. The detection limits for cysteine, homocysteine and glutathione are 69, 74 and 69 nM (S/N = 3), respectively. The probe was applied to image biothiols in SMMC-7721 cells.

Schematic presentation of the mechanism of 2,4-dinitrobenzenesulfonate-functionalized carbon dots (g-CD-DNBS) for the detection of biothiols. g-CDs: green emissive carbon dots.

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Acknowledgments

This research was supported by the Natural Science Foundation of China (Nos. 21475105, 21675123) and the Science & Technology Department (No. 2018JM2001) of Shaanxi Province of China.

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Authors and Affiliations

  1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an, 710069, People’s Republic of China

    Jiangjiang Sun, Jianjian Zhang, Hua Li & Xiao-Feng Yang

  2. Key Laboratory of Catalysis, School of Chemistry and Environment Science, Shaanxi University of Technology, Hanzhong, Shaanxi, 723000, People’s Republic of China

    Qin Wang

  3. College of Life Sciences, Northwest University, Xi’an, 710069, People’s Republic of China

    Jiajun Yang & Zheng Li

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  1. Jiangjiang Sun
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  2. Qin Wang
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Correspondence to Xiao-Feng Yang.

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Sun, J., Wang, Q., Yang, J. et al. 2,4-Dinitrobenzenesulfonate-functionalized carbon dots as a turn-on fluorescent probe for imaging of biothiols in living cells. Microchim Acta 186, 402 (2019). https://doi.org/10.1007/s00604-019-3503-9

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