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One-pot preparation of lutein block methoxy polyethylene glycol copolymer-coated lutein nanoemulsion

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Abstract

Lutein-b-methoxy polyethylene glycol (Lutein-b-mPEG) encapsulated lutein nanoemulsion was prepared. First, mercapto-terminated mPEG (mPEG-SH) was prepared. Then, vinyl-terminated lutein was prepared by the esterification reaction of lutein and allyl chloroformate. Finally, Lutein-b-mPEG was synthesized by the thiol-ene reaction of the vinyl-terminated intermediate and mPEG-SH. Lutein-b-mPEG was self-assembled in water to form spherical micelles, and the unreacted lutein was directly loaded in the micelles. The synthesis of the block copolymer and loading of unreacted lutein are completed in one pot. The results of IR, 1H NMR, GPC, and surface tension showed that the Lutein-b-mPEG was prepared. The TEM results showed that Lutein-b-mPEG loaded lutein self-assembled in water to form spherical micelles, and the average size is larger than that of Lutein-b-mPEG micelles. The chemical stability of lutein loaded by Lutein-b-mPEG micelles is greatly enhanced. Moreover, due to the water solubility and micellization of lutein, it is possible to greatly increase its bioavailability.

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References

  1. Cheng X, Zhao X, Huang C et al (2019) Lutein content in petals and leaves of marigold and analysis of lutein synthesis gene expression. Acta Physiol Plant 41(7):128–139. https://doi.org/10.1007/s11738-019-2913-y

    Article  CAS  Google Scholar 

  2. Weerawat C, Pimporn P, Panatpong B et al (2019) Chromatographic modeling of free lutein derived from marigold flowers. Chem Eng Commun 8:1563–5201. https://doi.org/10.1080/00986445.2019.1630390

    Article  CAS  Google Scholar 

  3. Ranganathan A, Hindupur R, Vallikannan B (2016) Biocompatible lutein-polymer-lipid nanocapsules: acute and subacute toxicity and bioavailability in mice. Mater Sci Eng C 69:1318–1327. https://doi.org/10.1016/j.msec.2016.08.029

    Article  CAS  Google Scholar 

  4. Frede K, Ebert F, Kipp A et al (2017) Lutein activates the transcription factor Nrf2 in human retinal pigment epithelial cells. J Agric Food Chem 65(29):1–37. https://doi.org/10.1021/acs.jafc.7b01929

    Article  CAS  Google Scholar 

  5. Chuacharoen T, Sabliov C (2016) Stability and controlled release of lutein loaded in zein nanoparticles with and without lecithin and pluronic F127 surfactants. Colloids Surf A Physicochem Eng Asp 503:11–18. https://doi.org/10.1016/j.colsurfa.2016.04.038

    Article  CAS  Google Scholar 

  6. Xu D, Aihemaiti Z, Cao Y et al (2016) Physicochemical stability, microrheological properties and microstructure of lutein emulsions stabilized by multilayer membranes consisting of whey protein isolate, flaxseed gum and chitosan. Food Chem 202:156–164. https://doi.org/10.1016/j.foodchem.2016.01.052

    Article  CAS  PubMed  Google Scholar 

  7. Davidov-Pardo G, Gumus CE, Mcclements DJ (2016) Lutein-enriched emulsion-based delivery systems: influence of pH and temperature on physical and chemical stability. Food Chem 196:821–827. https://doi.org/10.1016/j.foodchem.2015.10.018

    Article  CAS  PubMed  Google Scholar 

  8. Garrett DA, Failla MF, Sarama RJ (1999) Development of an in vitro digestion method to assess carotenoid bioavailability from meals. J Agric Food Chem 47(10):4301–4309. https://doi.org/10.1021/jf9903298

    Article  CAS  PubMed  Google Scholar 

  9. Matos M, Gutiérrez G, Iglesias O et al (2015) Characterization, stability and rheology of highly concentrated monodisperse emulsions containing lutein. Food Hydrocoll 49:156–163. https://doi.org/10.1016/j.foodhyd.2015.03.021

    Article  CAS  Google Scholar 

  10. Tan TB, Yussof NS, Abas F et al (2016) Stability evaluation of lutein nanodispersions prepared via solvent displacement method: the effect of emulsifiers with different stabilizing mechanisms. Food Chem 205:155–162. https://doi.org/10.1016/j.foodchem.2016.03.008

    Article  CAS  PubMed  Google Scholar 

  11. Brum AAS, Santos PPD, Silva MMD et al (2017) Lutein-loaded lipid-core nanocapsules: physicochemical characterization and stability evaluation. Colloids Surf A Physicochem Eng Asp 522:477–484. https://doi.org/10.1016/j.colsurfa.2017.03.041

    Article  CAS  Google Scholar 

  12. Lacatusu I, Mitrea E, Badea N et al (2013) Lipid nanocarriers for dermal delivery of lutein: preparation, characterization, stability and performance. J Funct Foods 5(3):1260–1269. https://doi.org/10.1016/j.ijpharm.2011.05.008

    Article  CAS  Google Scholar 

  13. Mitri K, Shegokar R, Gohla S et al (2011) Lipid nanocarriers for dermal delivery of lutein: preparation, characterization, stability and performance. Int J Pharm 414(1-2):267–275. https://doi.org/10.1016/j.ijpharm.2011.05.008

    Article  CAS  PubMed  Google Scholar 

  14. Stancanelli R, Lars L, Larsen KL et al (2012) Structural and spectroscopic features of lutein/butanoyl-β-cyclodextrin nanoassemblies. J Pharm Biomed Anal 71:214–218. https://doi.org/10.1016/j.jpba.2012.07.034

    Article  CAS  PubMed  Google Scholar 

  15. Zhao C, Cheng H, Jiang P et al (2014) Preparation of lutein-loaded particles for improving solubility and stability by Polyvinylpyrrolidone (PVP) as an emulsion-stabilizer. Food Chem 156:123–128. https://doi.org/10.1016/j.foodchem.2014.01.086

    Article  CAS  PubMed  Google Scholar 

  16. Qv XY, Zeng ZP, Jiang JG (2011) Preparation of lutein microencapsulation by complex coacervation method and its physicochemical properties and stability. Food Hydrocoll 25(6):1596–1603. https://doi.org/10.1016/j.foodhyd.2011.01.006

    Article  CAS  Google Scholar 

  17. Altamimi M, Haq N, Alshehri S et al (2019) Enhanced skin permeation of hydrocortisone using nanoemulsion as potential vehicle. Chem Select 4(34):10084–10091. https://doi.org/10.1002/slct.201902007

    Article  CAS  Google Scholar 

  18. Guerrero S, Inostroza-Riquelme M, Contreras-Orellana P et al (2018) Curcumin-loaded nanoemulsion: a new safe and effective formulation to prevent tumor reincidence and metastasis. Nanoscale 10:22612–22622. https://doi.org/10.1039/c8nr06173d

    Article  CAS  PubMed  Google Scholar 

  19. Lim C, Kim DW, Sim T et al (2016) Preparation and characterization of a lutein loading nanoemulsion system for ophthalmic eye drops. J Drug Deliv Sci Technol 36:168–174. https://doi.org/10.1016/j.jddst.2016.10.009

    Article  CAS  Google Scholar 

  20. Zong C, Sun Y, Zhang N et al (2019) Synthesis of chitosan-g-poly (ethylene glycol)-g-polyethyleneimine copolymer and its research as drug carrier. Macromol Res 27(8):772–780. https://doi.org/10.1007/s13233-019-7113-5

    Article  CAS  Google Scholar 

  21. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed Eng 40(11):2005–2021. https://doi.org/10.1002/1521-3773(20010601)40:113.0.CO;2-5

    Article  Google Scholar 

  22. Arunkumar R, Prashanth KVH, Baskaran V (2013) Promising interaction between nanoencapsulated lutein with low molecular weight chitosan: characterization and bioavailability of lutein in vitro and in vivo. Food Chem 141(1):327–337. https://doi.org/10.1016/j.foodchem.2013.02.108

    Article  CAS  PubMed  Google Scholar 

  23. Bowen PE, Herbst-Espinosa SM, Hussain EA (2002) Esterification does not impairlutein bioavailability in humans. J Nutr 132(12):3668–3673. https://doi.org/10.1046/j.1365-277X.2002.00398.x

    Article  CAS  PubMed  Google Scholar 

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Funding

This study is funded by the Natural Science Foundation of Shandong Province (ZR2019MEM010).

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Correspondence to Aixiang Li.

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Zijian LYu and Fei Wang do the same contributions to this work.

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LYu, Z., Wang, F., Liu, P. et al. One-pot preparation of lutein block methoxy polyethylene glycol copolymer-coated lutein nanoemulsion. Colloid Polym Sci 299, 1055–1062 (2021). https://doi.org/10.1007/s00396-021-04824-7

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  • DOI: https://doi.org/10.1007/s00396-021-04824-7

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