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Molecularly imprinted thermosensitive probe based on fluorescent advanced glycation end products to detect α-dicarbonyl compounds and inhibit pyrraline formation

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Abstract

A thermal-sensitive molecularly imprinted optosensing probe based on fluorescent advanced glycation end products (AGEs) was prepared by one-pot hydrothermal synthesis. Carbon dots (CDs) derived from fluorescent AGEs were used as the luminous centers, while molecularly imprinted polymers (MIPs) were wrapped outside of the CDs to form specific target recognition sites to highly selectively adsorb the intermediate product of AGEs of 3-deoxyglucosone (3-DG). Thermosensitive N-isopropylacrylamide (NIPAM) was combined with acrylamide (AM) as co-functional monomers, and ethylene glycol dimethacrylate (EGDMA) was chosen as a cross-linker for targeting identification and detection of 3-DG. Under optimal conditions, the fluorescence of MIPs could be gradually quenched with the adsorption of 3-DG on the surface of MIPs in the linear range of 1–160 μg/L, and the detection limit was 0.31 μg/L. The spiked recoveries of MIPs ranged from 82.97 to 109.94% in two milk samples, and the relative standard deviations were all less than 1.8%. In addition, the inhibition rate for non-fluorescent AGEs of pyrraline (PRL) was 23% by adsorbing 3-DG in the simulated milk system of casein and d-glucose, indicating that temperature-responsive MIPs not only could detect the dicarbonyl compound 3-DG quickly and sensitively, but also had an excellent inhibitory effect on AGEs.

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References

  1. Zhao W, Cai P, Zhang N, Wu T, Sun A, Jia G. Inhibitory effects of polyphenols from black chokeberry on advanced glycation end-products (AGEs) formation. Food Chem. 2022;392: 133295.

    Article  CAS  PubMed  Google Scholar 

  2. Chen Y, Tang S, Chen Y, Zhang R, Zhou M, Wang C, Feng N, Wu Q. Structure-activity relationship of procyanidins on advanced glycation end products formation and corresponding mechanisms. Food Chem. 2019;272:679–87.

    Article  CAS  PubMed  Google Scholar 

  3. van Dongen KCW, Kappetein L, Miro Estruch I, Belzer C, Beekmann K, Rietjens IMCM. Differences in kinetics and dynamics of endogenous versus exogenous advanced glycation end products (AGEs) and their precursors. Food Chem Toxicol. 2022;164: 112987.

    Article  PubMed  Google Scholar 

  4. Chen JH, Lin X, Bu C, Zhang X. Role of advanced glycation end products in mobility and considerations in possible dietary and nutritional intervention strategies. Nutr Metab (Lond). 2018;15:72.

    Article  PubMed  Google Scholar 

  5. Yuan X, He J, Su H, Liu H, Sun B. Magnetically controlled nanorobots based on red emissive peptide dots and artificial antibodies for specific recognition and smart scavenging of Nε-(carboxymethyl)lysine in dairy products. J Agr Food Chem. 2023;71(12):4970–81.

    Article  CAS  Google Scholar 

  6. Uribarri J, Woodruff S, Goodman S, Cai W, Chen X, Pyzik R, Yong A, Striker GE, Vlassara H. Advanced glycation end products in foods and a practical guide to their reduction in the diet. J Am Diet Assoc. 2010;110(6):911-16.e12.

    Article  PubMed  PubMed Central  Google Scholar 

  7. Yuan X, Meng C, Liu H, Sun B. Magnetically driven nanorobots based on peptides nanodots with tunable photoluminescence for rapid scavenging reactive α-dicarbonyl species and effective blocking of advanced glycation end products. Food Chem. 2023;422: 136252.

    Article  CAS  PubMed  Google Scholar 

  8. Liu H, Mu L, Chen X, Wang J, Wang S, Sun B. Core-shell metal-organic frameworks/molecularly imprinted nanoparticles as absorbents for the detection of pyrraline in milk and milk powder. J Agric Food Chem. 2017;65(4):986–92.

    Article  CAS  PubMed  Google Scholar 

  9. Liu H, Ni T, Mu L, Zhang D, Wang J, Wang S, Sun B. Sensitive detection of pyrraline with a molecularly imprinted sensor based on metal-organic frameworks and quantum dots. Sens Actuators B Chem. 2018;256:1038–44.

    Article  CAS  Google Scholar 

  10. Singh R, Barden A, Mori T, Beilin L. Advanced glycation end-products: a review. Diabetologia. 2001;44(2):129–46.

    Article  CAS  PubMed  Google Scholar 

  11. Ayerdurai V, Garcia-Cruz A, Piechowska J, Cieplak M, Borowicz P, Noworyta KR, Spolnik G, Danikiewicz W, Lisowski W, Pietrzyk-Le A, D’Souza F, Kutner W, Sharma PS. Selective impedimetric chemosensing of carcinogenic heterocyclic aromatic amine in pork by dsdna-mimicking molecularly imprinted polymer film-coated electrodes. J Agric Food Chem. 2021;69(48):14689–98.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Ma H, Yang M, Wang X, Yang B, Zhang F, Zhang F, Li Y, Liu T, He M, Wang Q. Sulfonamide-selective ambient mass spectrometry ion source obtained by modification of an iron sheet with a hydrophilic molecularly imprinted polymer. J Agric Food Chem. 2021;69(50):15425–33.

    Article  CAS  PubMed  Google Scholar 

  13. Wang S, Shao R, Li W, Li X, Sun J, Jiao S, Dai S, Dou M, Xu R, Li Q, Li J. Three-dimensional ordered macroporous magnetic inverse photonic crystal microsphere-based molecularly imprinted polymer for selective capture of aflatoxin b(1). ACS Appl Mater Interfaces. 2022;14(16):18845–53.

    Article  CAS  PubMed  Google Scholar 

  14. Fang L, Jia M, Zhao H, Kang L, Shi L, Zhou L, Kong W. Molecularly imprinted polymer-based optical sensors for pesticides in foods: recent advances and future trends. Trends Food Sci Tech. 2021;116:387–404.

    Article  CAS  Google Scholar 

  15. Wu H, Lin G, Liu C, Chu S, Mo C, Liu X. Progress and challenges in molecularly imprinted polymers for adsorption of heavy metal ions from wastewater. Trends Environ Anal. 2022;36: e00178.

    Article  CAS  Google Scholar 

  16. Li Z, Liu J, Liu J, Wang Z, Wang J. Determination of sulfonamides in meat with dummy-template molecularly imprinted polymer-based chemiluminescence sensor. Anal Bioanal Chem. 2019;411(14):3179–89.

    Article  CAS  PubMed  Google Scholar 

  17. Bai X, Zhang B, Liu M, Hu X, Fang G, Wang S. Molecularly imprinted electrochemical sensor based on polypyrrole/dopamine@graphene incorporated with surface molecularly imprinted polymers thin film for recognition of olaquindox. Bioelectrochemistry. 2020;132: 107398.

    Article  CAS  PubMed  Google Scholar 

  18. Biyana Regasa M, Nyokong T. Synergistic recognition and electrochemical sensing of 17β-estradiol using ordered molecularly imprinted polymer-graphene oxide-silver nanoparticles composite films. J Electroanal Chem. 2022;922: 116713.

    Article  CAS  Google Scholar 

  19. Wang F, Ling B, Li Q, Abouhany R. Dual roles of 3-aminopropyltriethoxysilane in preparing molecularly imprinted silica particles for specific recognition of target molecules. RSC Adv. 2020;10(34):20368–73.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Sullivan MV, Henderson A, Hand RA, Turner NW. A molecularly imprinted polymer nanoparticle-based surface plasmon resonance sensor platform for antibiotic detection in river water and milk. Anal Bioanal Chem. 2022;414(12):3687–96.

    Article  CAS  PubMed  Google Scholar 

  21. Li L, Lu Y, Bie Z, Chen HY, Liu Z. Photolithographic boronate affinity molecular imprinting: a general and facile approach for glycoprotein imprinting. Angew Chem Int Ed Engl. 2013;52(29):7451–4.

    Article  CAS  PubMed  Google Scholar 

  22. Li S, Yang K, Deng N, Min Y, Liu L, Zhang L, Zhang Y. Thermoresponsive epitope surface-imprinted nanoparticles for specific capture and release of target protein from human plasma. ACS Appl Mater Interfaces. 2016;8(9):5747–51.

    Article  CAS  PubMed  Google Scholar 

  23. Yoshimatsu K, Lesel BK, Yonamine Y, Beierle JM, Hoshino Y, Shea KJ. Temperature-responsive “catch and release” of proteins by using multifunctional polymer-based nanoparticles. Angew Chem Int Ed Engl. 2012;51(10):2405–8.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Zhang W, Liu W, Li P, Xiao H, Wang H, Tang B. A fluorescence nanosensor for glycoproteins with activity based on the molecularly imprinted spatial structure of the target and boronate affinity. Angew Chem Int Ed Engl. 2014;53(46):12489–93.

    CAS  PubMed  Google Scholar 

  25. Cui Y, He Z, Xu Y, Su Y, Ding L, Li Y. Fabrication of molecularly imprinted polymers with tunable adsorption capability based on solvent-responsive cross-linker. Chem Eng J. 2021;405: 126608.

    Article  CAS  Google Scholar 

  26. Xiong H, Fan Y, Mao X, Guo L, Yan A, Guo X, WanY, Wan H. Thermosensitive and magnetic molecularly imprinted polymers for selective recognition and extraction of aristolochic acid i. Food Chem. 2022;372:131250.

  27. Xiong H, Guo L, Mao X, Tan T, Wan H, Wan Y. A magnetic hydrophilic molecularly imprinted material with multiple stimuli-response properties for efficient recognition of bisphenol a in beverages. Food Chem. 2020;331: 127311.

    Article  CAS  PubMed  Google Scholar 

  28. Jiang C, Wang Q, Wang T. Thermoresponsive pnipaam-modified cotton fabric surfaces that switch between superhydrophilicity and superhydrophobicity. Appl Surf Sci. 2012;258(11):4888–92.

    Article  CAS  Google Scholar 

  29. Lu F, Lin X, Wu Q, Zhou B, Lan R, Zhou S, Wu W. Observation of unusual thermoresponsive volume phase transition behavior of cubic poly(N-isopropylacrylamide) microgels. Acs Macro Lett. 2020;9(2):266–71.

    Article  CAS  PubMed  Google Scholar 

  30. Nakamura C, Yamamoto T, Manabe K, Nakamura T, Einaga Y, Shiratori S. Thermoresponsive, freezing-resistant smart windows with adjustable transition temperature made from hydroxypropyl cellulose and glycerol. Ind Eng Chem Res. 2019;58(16):6424–8.

    Article  CAS  Google Scholar 

  31. Thara CR, Korah BK, Mathew S, John BK, Mathew B. Dual mode detection and sunlight-driven photocatalytic degradation of tetracycline with tailor-made n-doped carbon dots. Environ Res. 2023;216:114450.

  32. Zhu X, Han L, Liu H, Sun B. A smartphone-based ratiometric fluorescent sensing system for on-site detection of pyrethroids by using blue-green dual-emission carbon dots. Food Chem. 2022;379: 132154.

    Article  CAS  PubMed  Google Scholar 

  33. Sk MP, Jaiswal A, Paul A, Ghosh SS, Chattopadhyay A. Presence of amorphous carbon nanoparticles in food caramels. Sci Rep. 2012;2:383.

    Article  PubMed  PubMed Central  Google Scholar 

  34. Li D, Na X, Wang H, Xie Y, Cong S, Song Y, Xu X, Zhu BW, Tan M. Fluorescent carbon dots derived from maillard reaction products: their properties, biodistribution, cytotoxicity, and antioxidant activity. J Agric Food Chem. 2018;66(6):1569–75.

    Article  CAS  PubMed  Google Scholar 

  35. Wang T, Chen C, Wang C, Tan YZ, Liao W. Multicolor functional carbon dots via one-step refluxing synthesis. ACS Sensors. 2017;2(3):354–63.

    Article  CAS  PubMed  Google Scholar 

  36. Bohlooli M, Ghaffari-Moghaddam M, Khajeh M, Aghashiri Z, Sheibani N, Moosavi-Movahedi AA. Acetoacetate promotes the formation of fluorescent advanced glycation end products (AGEs). J Biomol Struct Dyn. 2016;34(12):2658–66.

    CAS  PubMed  PubMed Central  Google Scholar 

  37. Zhang Y, Zhu X, Li M, Liu H, Sun B. Temperature-responsive covalent organic framework-encapsulated carbon dot-based sensing platform for pyrethroid detection via fluorescence response and smartphone readout. J Agr Food Chem. 2022;70(20):6059–71.

    Article  CAS  Google Scholar 

  38. Zhu X, Zhang Y, Han L, Liu H, Sun B. Quantum confined peptide assemblies in a visual photoluminescent hydrogel platform and smartphone-assisted sample-to-answer analyzer for detecting trace pyrethroids. Biosens Bioelectron. 2022;210: 114265.

    Article  CAS  PubMed  Google Scholar 

  39. Guo T, Deng Q, Fang G, Yun Y, Hu Y, Wang S. A double responsive smart upconversion fluorescence sensing material for glycoprotein. Biosens Bioelectron. 2016;85:596–602.

    Article  CAS  PubMed  Google Scholar 

  40. Li X, Zhang B, Li W, Lei X, Fan X, Tian L, Zhang H, Zhang Q. Preparation and characterization of bovine serum albumin surface-imprinted thermosensitive magnetic polymer microsphere and its application for protein recognition. Biosens Bioelectron. 2014;51:261–7.

    Article  CAS  PubMed  Google Scholar 

  41. Zhang Y, Xu Y, Liu H, Sun B. Ultrahigh sensitivity nitrogen-doping carbon nanotubes-based metamaterial-free flexible terahertz sensing platform for insecticides detection. Food Chem. 2022;394: 133467.

    Article  CAS  PubMed  Google Scholar 

  42. Zhao Y, Zhang Y, Liu H, Sun B. A visual chiroptical system with chiral assembly graphene quantum dots for d-phenylalanine detection. Anal Bioanal Chem. 2022;414(17):4885–96.

    Article  CAS  PubMed  Google Scholar 

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Funding

This research was funded by the National Natural Science Foundation of China (No.32072335), and the Cultivation Project of Double First-Class Disciplines of Food Science and Engineering, Beijing Technology & Business University (BTBU).

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Authors and Affiliations

  1. Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University), Ministry of Education, Beijing Technology and Business University, 11 Fucheng Road, Beijing, 100048, China

    Jingbo He, Chenchen Xie, Chen Meng, Xiaolin Chen, Huilin Liu & Baoguo Sun

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  1. Jingbo He
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  2. Chenchen Xie
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  4. Xiaolin Chen
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  5. Huilin Liu
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Correspondence to Huilin Liu.

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He, J., Xie, C., Meng, C. et al. Molecularly imprinted thermosensitive probe based on fluorescent advanced glycation end products to detect α-dicarbonyl compounds and inhibit pyrraline formation. Anal Bioanal Chem 415, 5011–5021 (2023). https://doi.org/10.1007/s00216-023-04787-4

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