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Facile and scalable fabrication engineering of fullerenol nanoparticles by improved alkaline-oxidation approach and its antioxidant potential in maize

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Abstract

A feasible in operation, labor-saving and low-cost one-step technology to fabricate fullerenol nanoparticles (FNPs) up to 10 g in laboratory was developed by improved alkaline-oxidation approach using moderately concentrated sodium hydroxide solution as the hydroxylation agent and o-dichlorobenzene as the solvent. This strategy paves the avenue for industrial-scale bulk production of FNPs. The resulted product, [C60(OH)22·8H2O]n, were characterized by various measurements including matrix-assisted laser desorption ionization time-of-flight mass spectrometry, high-resolution 1H nuclear magnetic resonance spectrometry, Fourier transform infrared spectroscopy, UV-Visible spectrophotometer, thermogravimetric analysis, differential scanning calorimetry, dynamic light scattering analysis, scanning electron microscopy, and electron spin resonance spectrometer. Radical scavenging assay in vitro confirmed the high efficiency of water-soluble [C60(OH)22·8H2O]n as a novel radical scavenger. Furthermore, [C60(OH)22·8H2O]n as an excellent candidate has the potential to serve as the plant defense stimulation agent in maize.

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References

  • Alves GC, Ladeira LO, Righi A, Krambrock K, Calado HD, Gil RPDF, Pinheiro MVB (2006) Synthesis of C60(OH)18-20 in aqueous alkaline solution under O2-atmosphere. J Brazil Chem Soc 17:1186–1190

    Article  Google Scholar 

  • Arrais A, Diana E (2003) Highly water soluble C60 derivatives: a new synthesis. Fuller Nanotub Car N 11:35–46

    Article  Google Scholar 

  • Beeby A, Eastoe J, Heenan RK (1994) Solubilization of C60 in aqueous micellar solution. J Chem Soc Chem Comm :173–175

  • Cataldo F, Ursini O, Angelini G (2008a) Radiation-cured polyisoprene/C60 fullerene nanocomposite. Part 2: synthesis in decalin. Radiat Phys Chem 77:742–750

    Article  Google Scholar 

  • Cataldo F, Ursini O, Angelini G (2008b) Radiation-cured polyisoprene/C60 fullerene nanocomposite. Part 1: synthesis in hexane and in toluene. Radiat Phys Chem 77:734–741

    Article  Google Scholar 

  • Chen ZY, Ma LJ, Liu Y, Chen CY (2012) Applications of functionalized fullerenes in tumor theranostics. Theranostics 2:238–250

    Article  Google Scholar 

  • Chiang LY, Bhonsle JB, Wang LY, Shu SF, Chang TM, Hwu JR (1996) Efficient one-flask synthesis of water-soluble [60]fullerenols. Tetrahedron 52:4963–4972

    Article  Google Scholar 

  • Chiang LY, Swirczewski JW, Hsu CS, Chowdhury SK, Cameron S, Creegan K (1992a) Multihydroxy Additions onto C60 Fullerene Molecules. J Chem Soc Chem Comm :1791–1793

  • Chiang LY, Upasani RB, Swirczewski JW (1992b) Versatile nitronium chemistry for C60 fullerene functionalization. J Am Chem Soc 114:10154–10157

    Article  Google Scholar 

  • Chiang LY, Upasani RB, Swirczewski JW, Soled S (1993) Evidence of Hemiketals incorporated in the structure of fullerols derived from aqueous acid chemistry. J Am Chem Soc 115:5453–5457

    Article  Google Scholar 

  • Chiang LY, Wang LY, Swirczewski JW, Soled S, Cameron S (1994) Efficient synthesis of polyhydroxylated fullerene derivatives via hydrolysis of Polycyclosulfated precursors. J Org Chem 59:3960–3968

    Article  Google Scholar 

  • Djordjevic A, Srdjenovic B, Seke M, Petrovic D, Injac R, Mrdjanovic J (2015) Review of synthesis and antioxidant potential of fullerenol nanoparticles. J Nanomater 2015:567073

    Article  Google Scholar 

  • Gao J et al (2011) Polyhydroxy fullerenes (fullerols or fullerenols): beneficial effects on growth and lifespan in diverse biological models. PLoS One 6:e19976

    Article  Google Scholar 

  • Goswami TH, Singh R, Alam S, Mathur GN (2004) Thermal analysis: a unique method to estimate the number of substituents in fullerene derivatives. Thermochim Acta 419:97–104

    Article  Google Scholar 

  • Grebowski J, Kazmierska P, Krokosz A (2013) Fullerenols as a new therapeutic approach in nanomedicine. Biomed Res Int. doi:10.1155/2013/751913

    Google Scholar 

  • Husebo LO, Sitharaman B, Furukawa K, Kato T, Wilson LJ (2004) Fullerenols revisited as stable radical anions. J Am Chem Soc 126:12055–12064

    Article  Google Scholar 

  • Jagerovic N, Elguero J, Aubagnac JL (1996) Reaction of 2-azidobenzothiazole and 1-azido-4-(3′, 5′-dimethyl-1′-pyrazolyl) tetrafluorobenzene with [60] fullerene and characterization of the adducts by fast-atom bombardment mass spectrometry. Tetrahedron 52:6733–6738

    Article  Google Scholar 

  • Janaki J, Premila M, Gopalan P, Sastry VS, Sundar CS (2000) Thermal stability of a fullerene-amine adduct. Thermochim Acta 356:109–116

    Article  Google Scholar 

  • Khot LR, Sankaran S, Maja JM, Ehsani R, Schuster EW (2012) Applications of nanomaterials in agricultural production and crop protection: a review. Crop Prot 35:64–70

    Article  Google Scholar 

  • Kokubo K, Matsubayashi K, Tategaki H, Takada H, Oshima T (2008) Facile synthesis of highly water-soluble fullerenes more than half-covered by hydroxyl groups. ACS Nano 2:327–333

    Article  Google Scholar 

  • Kokubo K, Shirakawa S, Kobayashi N, Aoshima H, Oshima T (2011) Facile and scalable synthesis of a highly hydroxylated water-soluble fullerenol as a single nanoparticle. Nano Res 4:204–215

    Article  Google Scholar 

  • Kole C et al (2013) Nanobiotechnology can boost crop production and quality: first evidence from increased plant biomass, fruit yield and phytomedicine content in bitter melon (Momordica charantia). BMC Biotechnol 13:37

    Article  Google Scholar 

  • Lahiani MH, Chen JH, Irin F, Puretzky AA, Green MJ, Khodakovskaya MV (2015) Interaction of carbon nanohorns with plants: uptake and biological effects. Carbon 81:607–619

    Article  Google Scholar 

  • Li J, Takeuchi A, Ozawa M, Li XH, Saigo K, Kitazawa K (1993) C60 fullerol formation catalyzed by quaternary ammonium hydroxides. J Chem Soc Chem Comm 23:1784–1785

  • Li J et al (2012a) Separation and purification of fullerenols for improved biocompatibility. Carbon 50:460–469

    Article  Google Scholar 

  • Li XC, Lin J, Gao YX, Han WJ, Chen DF (2012b) Antioxidant activity and mechanism of Rhizoma Cimicifugae. Chem Cent J 6:140

    Article  Google Scholar 

  • Markovic Z, Trajkovic V (2008) Biomedical potential of the reactive oxygen species generation and quenching by fullerenes (C60). Biomaterials 29:3561–3573

    Article  Google Scholar 

  • Mirkov SM et al (2004) Nitric oxide-scavenging activity of polyhydroxylated fullerenol, C60(OH)24. Nitric Oxide 11:201–207

    Article  Google Scholar 

  • Mittler R (2002) Oxidative stress, antioxidants and stress tolerance. Trends Plant Sci 7:405–410

    Article  Google Scholar 

  • Mukherjee A, Majumdar S, Servin AD, Pagano L, Dhankher OP, White JC (2016) Carbon nanomaterials in agriculture: a critical review. Front Plant Sci 7:172

    Article  Google Scholar 

  • Nielsen GD, Roursgaard M, Jensen KA, Poulsen SS, Larsen ST (2008) In vivo biology and toxicology of fullerenes and their derivatives. Basic Clin Pharmacol Toxicol 103:197–208

    Article  Google Scholar 

  • Prior RL, Cao GH (1999) In vivo total antioxidant capacity: comparison of different analytical methods. Free Radic Biol Med 27:1173–1181

    Article  Google Scholar 

  • Ratnikova OV et al (2004) The new method for the synthesis of fullerols based on radical reaction. Fuller Nanotub Car N 12:155–158

    Article  Google Scholar 

  • Schneider NS, Darwish AD, Kroto HW, Taylor R, Walton DRM (1994) Formation of fullerols via hydroboration of fullerene C60. J Chem Soc Chem Comm 4:463–464

  • Shalata A, Neumann PM (2001) Exogenous ascorbic acid (vitamin C) increases resistance to salt stress and reduces lipid peroxidation. J Exp Bot 52:2207–2211

    Google Scholar 

  • Singh R, Goswami T (2011) Understanding of thermo-gravimetric analysis to calculate number of addends in multifunctional hemi-ortho ester derivatives of fullerenol. Thermochim Acta 513:60–67

    Article  Google Scholar 

  • Vileno B, Marcoux PR, Lekka M, Sienkiewicz A, Feher T, Forro L (2006) Spectroscopic and photophysical properties of a highly derivatized C60 fullerol. Adv Funct Mater 16:120–128

    Article  Google Scholar 

  • Wang CT, Yuan ZH, Li SP, Wang W, Xue RL, Tai FJ (2014) Characterization of eight CBL genes expressions in maize early seeding development. Acta Physiol Plant 36:3307–3314

    Article  Google Scholar 

  • Wang FF, Li N, Tian D, Xia GF, Xiao N (2010) Efficient synthesis of fullerenol in anion form for the preparation of electrodeposited films. ACS Nano 4:5565–5572

    Article  Google Scholar 

  • Wang S, He P, Zhang JM, Jiang H, Zhu SZ (2005) Novel and efficient synthesis of water-soluble [60]fullerenol by solvent-free reaction. Synthetic Commun 35:1803–1808

    Article  Google Scholar 

  • Wang XZ, Li XC, Chen DF (2011) Evaluation of antioxidant activity of isoferulic acid in vitro. Nat Prod Commun 6:1285–1288

    Google Scholar 

  • Wang ZZ, Lu ZH, Zhao YL, Gao XF (2015a) Oxidation-induced water-solubilization and chemical functionalization of fullerenes C60, Gd@C60 and Gd@C82: atomistic insights into the formation mechanisms and structures of fullerenols synthesized by different methods. Nanoscale 7:2914–2925

    Article  Google Scholar 

  • Wang ZZ, Wang SK, Lu ZH, Gao XF (2015b) Syntheses, structures and antioxidant activities of fullerenols: knowledge learned at the atomistic level. J Clust Sci 26:375–388

    Article  Google Scholar 

  • Xing GM et al (2004) Influences of structural properties on stability of fullerenols. J Phys Chem B 108:11473–11479

    Article  Google Scholar 

  • Xiong FX, Li J, Wang HZ, Xing GM, He R (2016) Evaluation of a series of different surface charged fullerenol nanoparticles as reactive oxygen species scavengers and potential cytoprotective agents. J Nanosci Nanotechno 16:7170–7174

    Article  Google Scholar 

  • Xue TT, Li XZ, Zhu W, Wu CA, Yang GD, Zheng CC (2009) Cotton metallothionein GhMT3a, a reactive oxygen species scavenger, increased tolerance against abiotic stress in transgenic tobacco and yeast. J Exp Bot 60:339–349

    Article  Google Scholar 

  • Yao L, Kang F, Peng QY, Yang XL (2010) An improved method for fullerol preparation based on dialysis. Chinese J Chem Eng 18:876–879

    Article  Google Scholar 

  • Zhang JM, Yang W, He P, Zhu SZ (2004) Efficient and convenient preparation of water-soluble fullerenol. Chinese J Chem 22:1008–1011

    Article  Google Scholar 

  • Zhang P, Pan HL, Liu DF, Guo ZX, Zhang FS, Zhu DB (2003) Effective mechanochemical synthesis of [60]fullerols. Synthetic Commun 33:2469–2474

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the financial supports of the Natural Science Foundation of China (21305027, 11405185), the Public Welfare (Agriculture) Research Project of China (201303030), and the Key Project of Henan Educational Committee of China (16A210007 and 14A180005).

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Authors and Affiliations

  1. Collaborative Innovation Center of Henan Grain Crops, State Key Laboratory of Wheat and Maize Crop Science, College of Life Science, Henan Agricultural University, Zhengzhou, 450002, China

    Fu-yang Liu & Fu-ju Tai

  2. NanoAgro Center, College of Plant Protection, Henan Agricultural University, 63 Nongye Road, Zhengzhou, 450002, China

    Feng-xia Xiong, Yi-kang Fan, He-zhong Wang, Feng-ming Yan & Rui He

  3. Lab. for Bio-Environmental Health Sciences of Nanoscale Materials, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing, 100049, China

    Juan Li & Geng-mei Xing

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  1. Fu-yang Liu
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  2. Feng-xia Xiong
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  4. Juan Li
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Correspondence to Fu-ju Tai or Rui He.

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Fu-yang Liu and Feng-xia Xiong contributed equally to this work.

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Liu, Fy., Xiong, Fx., Fan, Yk. et al. Facile and scalable fabrication engineering of fullerenol nanoparticles by improved alkaline-oxidation approach and its antioxidant potential in maize. J Nanopart Res 18, 338 (2016). https://doi.org/10.1007/s11051-016-3642-4

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  • DOI: https://doi.org/10.1007/s11051-016-3642-4

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