Abstract
Magnetic nanoparticles (MNPs) are highly attractive due to their ease of recovery and recycling uses, nontoxicity, and convenient availability. MNPs also show other advantages in that they can be easily functionalized and immobilized with various species of interest. On the other hand, chiral science, chiral technologies, and chiral materials are currently drawing rapidly growing attention because of their far-reaching implications. When chiral substances are judiciously combined with MNPs, a new class of chiral magnetic materials with unique properties is anticipated thereof. The emerging chiral composite MNPs have demonstrated important and promising application prospects in a diversity of significant fields. This review summarizes the state-of-the-art achievements in preparation, functionalization, and applications of Fe3O4-based chiral magnetic nanoparticles (CMNPs). Chiral small organic molecules, biomacromolecules, chiral metal complexes, and chiral synthetic polymers have been employed to construct CMNPs, and their potential uses have been substantially explored in multiple research fields associated with chirality, including asymmetric catalysis, chiral resolution, chiral recognition, and biomedical materials. We hope this review can promote further advancements in design and fabrication of chiral magnetic hybrid materials and practical uses thereof.
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References
Ahmadabad FK, Pourayoubi M, Bakhshi H (2019) Decorated single-enantiomer phosphoramide-based silica/magnetic nanocomposites for direct enantioseparation. RSC Adv 9(47):27147–27156. https://doi.org/10.1039/c9ra03260f
Ahmadi M, Madrakian T, Afkhami A (2015) Chiral magnetic nanospheres resonance light scattering properties studies for selective determination of naproxen and phenylglycine enantiomers. Sensors Actuators B Chem 210:439–445. https://doi.org/10.1016/j.snb.2015.01.005
Andrade LH, Rebelo LP, Netto CGCM et al (2010) Kinetic resolution of a drug precursor by Burkholderia cepacia lipase immobilized by different methodologies on superparamagnetic nanoparticles. J Mol Catal B Enzym 66(1–2):55–62. https://doi.org/10.1016/j.molcatb.2010.03.002
Antal I, Strbak O, Khmara I et al (2020) MRI relaxivity changes of the magnetic nanoparticles induced by different amino acid coatings. Nano 10(2):394. https://doi.org/10.3390/nano10020394
Bealer EJ, Kavetsky K, Dutko S et al (2020) Protein and polysaccharide-based magnetic composite materials for medical applications. Int J Mol Sci 21(1):186. https://doi.org/10.3390/ijms21010186
Çakmak R, Topal G, Çınar E (2020) Covalent immobilization of candida rugosa lipase on epichlorohydrin-coated magnetite nanoparticles: enantioselective hydrolysis studies of some racemic esters and HPLC analysis. Appl Biochem Biotechnol 191:1411–1431. https://doi.org/10.1007/s12010-020-03274-1
Chen X, Rao J, Wang J et al (2011) A facile enantioseparation for amino acids enantiomers using beta-cyclodextrins functionalized Fe3O4 nanospheres. Chem Commun 47(37):10317–10319. https://doi.org/10.1039/c1cc13734d
Chen H, Li L, Liu D et al (2014) Optically active helical polyacetylene/Fe3O4 composite microspheres: prepared by precipitation polymerization and used for enantioselective crystallization. RSC Adv 4(109):63611–63619. https://doi.org/10.1039/c4ra12267d
Chen H, Zhou J, Deng J (2016) Helical polymer/Fe3O4 NPs constructing optically active, magnetic core/shell microspheres: preparation by emulsion polymerization and recycling application in enantioselective crystallization. Polym Chem 7(1):125–134. https://doi.org/10.1039/c5py01549a
Deepthi SS, Prasad E, Venkata Subba Reddy B et al (2014) A green approach towards the synthesis of enantio pure diols using horse radish peroxidase enzyme immobilized on magnetic nanoparticles. Green Sustain Chem 4(1):15–19. https://doi.org/10.4236/gsc.2014.41003
Fu Y, Huang T, Chen B et al (2013) Enantioselective resolution of chiral drugs using BSA functionalized magnetic nanoparticles. Sep Purif Technol 107:11–18. https://doi.org/10.1016/j.seppur.2013.01.007
Gao X, Liu R, Zhang D et al (2014) Phenylene-coated magnetic nanoparticles that boost aqueous asymmetric transfer hydrogenation reactions. Chemistry 20(6):1515–1519. https://doi.org/10.1002/chem.201302797
Goyal G, Bhakta S, Mishra P (2019) Surface molecularly imprinted biomimetic magnetic nanoparticles for enantioseparation. ACS Appl Nano Mater 2(10):6747–6756. https://doi.org/10.1021/acsanm.9b01649
Guo L-D, Song Y-Y, Yu H-R et al (2017) Novel smart chiral magnetic microspheres for enantioselective adsorption of tryptophan enantiomers. Appl Surf Sci 407:82–92. https://doi.org/10.1016/j.apsusc.2017.02.121
Hadian-Dehkordi L, Hosseini-Monfared H, Aleshkevych P (2017) A novel chiral manganese-tetraamide macrocycle complex covalently attached to magnetite as recyclable catalyst for aerobic asymmetric epoxidation of olefins. Inorg Chim Acta 462:142–151. https://doi.org/10.1016/j.ica.2017.03.019
Hu A, Liu S, Lin W (2012) Immobilization of chiral catalysts on magnetite nanoparticles for highly enantioselective asymmetric hydrogenation of aromatic ketones. RSC Adv 2(6):2576–2580. https://doi.org/10.1039/c2ra01073a
Huang J, Su P, Zhao B et al (2015) Facile one-pot synthesis of β-cyclodextrin-polymer-modified Fe3O4 microspheres for stereoselective absorption of amino acid compounds. Anal Methods 7(6):2754–2761. https://doi.org/10.1039/c5ay00013k
Jiang Y, Guo C, Xia H et al (2008) Asymmetric aldol addition by oligopeptide immobilized on magnetic particles through an ionic liquids spacer. Ind Eng Chem Res 47(23):9628–9635. https://doi.org/10.1021/ie0712131
Karkhah MK, Kefayati H, Shariati S (2019) Enantioselective synthesis of 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives by Fe3O4@PS-arginine as an efficient chiral magnetic nanocatalyst. Appl Organomet Chem 33(10):e5139. https://doi.org/10.1002/aoc.5139
Kong Y, Tan R, Zhao L et al (2013) L-Proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusable organocatalyst for direct asymmetric aldol reaction in water. Green Chem 15(9):2422–2433. https://doi.org/10.1039/C3GC40772A
Lee SY, Ahn CY, Lee J et al (2012) Amino acid side chain-like surface modification on magnetic nanoparticles for highly efficient separation of mixed proteins. Talanta 93:160–165. https://doi.org/10.1016/j.talanta.2012.02.003
Lee YK, Tay KS, Lee VS et al (2015) A magnetically recyclable heterogeneous BINOL organocatalyst for the asymmetric aldol reaction. Appl Catal A Gen 502:246–253. https://doi.org/10.1016/j.apcata.2015.06.004
Li W, Deng J (2016) Optically active particles with tunable morphology: prepared by embedding graphene oxide/Fe3O4 in helical polyacetylene. ACS Appl Mater Interfaces 8(25):16273–16279. https://doi.org/10.1021/acsami.6b02654
Li K, Wang J, He Y et al (2018) Enhancing enzyme activity and enantioselectivity of Burkholderia cepacia lipase via immobilization on melamine-glutaraldehyde dendrimer modified magnetic nanoparticles. Chem Eng J 351:258–268. https://doi.org/10.1016/j.cej.2018.06.086
Li X, Meng C, Chen Q et al (2019) Combining enzymatic hydrolysis with magnetic nanoparticles for resolution of chiral substances. Colloids Surf A Physicochem Eng Asp 564:101–107. https://doi.org/10.1016/j.colsurfa.2018.12.042
Liu D, Chen H, Deng J et al (2013) Optically active, magnetic gels consisting of helical substituted polyacetylene and Fe3O4 nanoparticles: preparation and chiral recognition ability. J Mater Chem C 1(48):8066–8074. https://doi.org/10.1039/c3tc31802h
Liu Y, Li Z, Jia L (2020) Synthesis of molecularly imprinted polymer modified magnetic particles for chiral separation of tryptophan enantiomers in aqueous medium. J Chromatogr A 1622:461147. https://doi.org/10.1016/j.chroma.2020.461147
Panella B, Vargas A, Baiker A (2009) Magnetically separable Pt catalyst for asymmetric hydrogenation. J Catal 261(1):88–93. https://doi.org/10.1016/j.jcat.2008.11.002
Riente P, Yadav J, Pericàs MA (2012) A click strategy for the immobilization of MacMillan organocatalysts onto polymers and magnetic nanoparticles. Org Lett 14(14):3668–3671. https://doi.org/10.1021/ol301515d
Safaei-Ghomi J, Zahedi S (2015) L-Proline-functionalized Fe3O4 nanoparticles as a novel magnetic chiral catalyst for the direct asymmetric Mannich reaction. Appl Organomet Chem 29(8):566–571. https://doi.org/10.1002/aoc.3333
Shi X, Wang Y, Peng C et al (2017) Enantiorecognition of tyrosine based on a novel magnetic electrochemical chiral sensor. Electrochim Acta 241:386–394. https://doi.org/10.1016/j.electacta.2017.04.155
Song Y-Y, Song X-D, Yuan H et al (2016) Thermo-responsive adsorption and separation of amino acid enantiomers using smart polymer-brush-modified magnetic nanoparticles. New J Chem 40(4):3194–3207. https://doi.org/10.1039/c5nj03516c
Spelmezan CG, Bencze LC, Katona G et al (2020) Efficient and stable magnetic chitosan-lipase B from candida Antarctica bioconjugates in the enzymatic kinetic resolution of racemic heteroarylethanols. Molecules 25(2):350. https://doi.org/10.3390/molecules25020350
Tarhan T, Tural B, Tural S et al (2015) Enantioseparation of mandelic acid enantiomers with magnetic nano-sorbent modified by a chiral selector. Chirality 27(11):835–842. https://doi.org/10.1002/chir.22524
Tural B, Tural S, Demir AS (2013) Carboligation reactions mediated by benzoylformate decarboxylase immobilized on a magnetic solid support. Chirality 25(7):415–421. https://doi.org/10.1002/chir.22181
Wang H, Zhou Y, Guo Y et al (2012) β-Cyclodextrin/Fe3O4 hybrid magnetic nano-composite modified glassy carbon electrode for tryptophan sensing. Sensors Actuators B Chem 163(1):171–178. https://doi.org/10.1016/j.snb.2012.01.031
Wang Y, Su P, Wang S et al (2013) Dendrimer modified magnetic nanoparticles for immobilized BSA: a novel chiral magnetic nano-selector for direct separation of racemates. J Mater Chem B 1(38):5028–5035. https://doi.org/10.1039/c3tb20889c
Wang Z, Zhang X, Jiang S et al (2018) Magnetic solid-phase extraction based on magnetic multiwalled carbon nanotubes for the simultaneous enantiomeric analysis of five beta-blockers in the environmental samples by chiral liquid chromatography coupled with tandem mass spectrometry. Talanta 180:98–107. https://doi.org/10.1016/j.talanta.2017.12.034
Wang Q, Tang Y, Wu L et al (2020) Thermal and magnetic dual-responsive L-proline nanohybrids for aqueous asymmetric aldol reaction. React Funct Polym 149:104508. https://doi.org/10.1016/j.reactfunctpolym.2020.104508
Weldemhret TG, Nisola GM, Ramos KRM et al (2020) Tyrosinase-catalyzed phenol-mediated immobilization of β-agarase on L-lysine-coated magnetic particles for the production of neoagarooligosaccharides from Gelidium amansii. ACS Sustain Chem Eng 8(9):3573–3582. https://doi.org/10.1021/acssuschemeng.9b05796
Wu J, Su P, Huang J et al (2013) Synthesis of teicoplanin-modified hybrid magnetic mesoporous silica nanoparticles and their application in chiral separation of racemic compounds. J Colloid Interface Sci 399:107–114. https://doi.org/10.1016/j.jcis.2013.02.045
Wu J, Su P, Guo D et al (2014) Cationic β-cyclodextrin-modified hybrid magnetic microspheres as chiral selectors for selective chiral absorption of dansyl amino acids. New J Chem 38(8):3630–3636. https://doi.org/10.1039/c4nj00030g
Wu L-L, Liang R-P, Chen J et al (2018) Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography. Electrophoresis 39(2):356–362. https://doi.org/10.1002/elps.201700334
Wu J, Li Z, Jia L (2019) Solid phase extraction and capillary electrophoretic separation of racemic catecholamines by using magnetic particles coated with a copolymer prepared from poly(3,4-dihydroxyphenylalanine) and polyethyleneimine. Mikrochim Acta 186(9):627. https://doi.org/10.1007/s00604-019-3731-z
Xiao X, Wu J, Li Z et al (2019) Enantioseparation and sensitive analysis of ofloxacin by poly(3,4-dihydroxyphenylalanine) functionalized magnetic nanoparticles-based solid phase extraction in combination with on-line concentration capillary electrophoresis. J Chromatogr A 1587:14–23. https://doi.org/10.1016/j.chroma.2018.11.026
Yang H, Li S, Wang X et al (2012) Core–shell silica magnetic microspheres supported proline as a recyclable organocatalyst for the asymmetric aldol reaction. J Mol Catal A Chem 363–364:404–410. https://doi.org/10.1016/j.molcata.2012.07.017
Yang X, Sun X, Feng Z et al (2019) Open-tubular capillary electrochromatography with beta-cyclodextrin-functionalized magnetic nanoparticles as stationary phase for enantioseparation of dansylated amino acids. Mikrochim Acta 186(4):244. https://doi.org/10.1007/s00604-019-3318-8
Ye X, Cui J, Li B et al (2019) Enantiomer-selective magnetization of conglomerates for quantitative chiral separation. Nat Commun 10(1):1964. https://doi.org/10.1038/s41467-019-09997-y
Yuan X, Tan Y, Wei X et al (2017) Chiral determination of cinchonine using an electrochemiluminescent sensor with molecularly imprinted membrane on the surfaces of magnetic particles. Luminescence 32(7):1116–1122. https://doi.org/10.1002/bio.3297
Zhang H, Qian G, Song J et al (2014) Optically active, magnetic microparticles: constructed by chiral helical substituted polyacetylene/Fe3O4 nanoparticles and recycled for uses in enantioselective crystallization. Ind Eng Chem Res 53(44):17394–17402. https://doi.org/10.1021/ie503114z
Zhang L, Song P, Long H et al (2017) Magnetism based electrochemical immunosensor for chiral separation of amlodipine. Sensors Actuators B Chem 248:682–689. https://doi.org/10.1016/j.snb.2017.04.010
Zhao Z, Chang F, Wang T et al (2019) Facile assembly of bifunctional, magnetically retrievable mesoporous silica for enantioselective cascade reactions. Chem Commun 55(90):13578–13581. https://doi.org/10.1039/c9cc07123g
Zheng X, Zhang L, Li J et al (2011) Magnetic nanoparticle supported polyoxometalates (POMs) via non-covalent interaction: reusable acid catalysts and catalyst supports for chiral amines. Chem Commun 47(45):12325–12327. https://doi.org/10.1039/c1cc14178c
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Li, P., Deng, J. (2022). Chiral Magnetic Nanocomposite Particles: Preparation and Chiral Applications. In: Handbook of Magnetic Hybrid Nanoalloys and their Nanocomposites. Springer, Cham. https://doi.org/10.1007/978-3-030-34007-0_47-1
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DOI: https://doi.org/10.1007/978-3-030-34007-0_47-1
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