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Chiral drug fluorometry based on a calix[6]arene/molecularly imprinted polymer double recognition element grafted on nano-C-dots/Ir/Au

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Abstract

A luminescent double recognition nanoprobe is described as a new strategy for the selective determination of chiral molecules. C-dots/Ir/Au fluorescent nanoparticles, synthesised under hydrothermal conditions, are used as a high-performance probe in combination with a molecularly imprinted polymer (MIP) and calix[6]arene as a double recognition element. Thiolated calix[6]arene is grafted on C-dots/Ir/Au as the first recognition element, which then forms a host–guest complex with the target molecule levodopa (L-DOPA). Subsequently, an MIP is prepared on the C-dots/Ir/Au (MIP/C-dots/Ir/Au) by chemical polymerisation. After the removal of L-DOPA, double recognition imprinting cavities are formed. The fluorescence intensity at 478 nm of the nanoprobe is effectively quenched by adsorption of L-DOPA on MIP/C-dots/Ir/Au, which provides a method for L-DOPA determination. Owing to the double recognition strategy, this method has excellent selectivity which can effectively avoid interference from enantiomer D-DOPA, and a imprinting factor of 7.1 is obtained for L-DOPA. This accurate and reliable method, with a wide linear range (5 × 10−10 to 1.2 × 10−7 mol L−1) and a low limit of detection (1.45 × 10−10 mol L−1), was successfully applied to the determination of L-DOPA in real samples, giving standard recoveries of 89.7–110.0%. Thus, the proposed sensing method provides a viable approach for the determination of a single enantiomer.

Schematic presentation of the MIP/C-dots/Ir/Au for L-DOPA detection.

A fluorescence double chiral recognition nanoprobe is prepared of C-dots/Ir/Au nanoparticles as signal probe, and a molecularly imprinted polymer (MIP) and calix[6]arene as a double recognition element. Owing to the double recognition strategy, this method has strong specificity and can effectively avoid interference from enantiomers and racemates.

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Acknowledgements

This work was supported by the Central Public-interest Scientific Institution Basal Research Fund for Chinese Academy of Tropical Agricultural Sciences (Nos. 1630082017002, 1630082020001, and 1630082020009).

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Authors and Affiliations

  1. Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables, Analysis and Test Center of Chinese Academy of Tropical Agricultural Sciences, Haikou, 571101, China

    Shuhuai Li, Chaohai Pang, ** Li

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  1. Shuhuai Li
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  2. Chaohai Pang
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  3. **onghui Ma
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  4. Min Zhao
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  5. Haibo Li
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  6. Mingyue Wang
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  7. Jian** Li
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  8. **hui Luo
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Correspondence to Shuhuai Li, Mingyue Wang or **hui Luo.

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Li, S., Pang, C., Ma, X. et al. Chiral drug fluorometry based on a calix[6]arene/molecularly imprinted polymer double recognition element grafted on nano-C-dots/Ir/Au. Microchim Acta 187, 394 (2020). https://doi.org/10.1007/s00604-020-04356-x

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