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Analytical and Bioanalytical Chemistry

, Volume 411, Issue 12, pp 2715–2727 | Cite as

Green synthesis of carbon dots using the flowers of Osmanthus fragrans (Thunb.) Lour. as precursors: application in Fe3+ and ascorbic acid determination and cell imaging

  • Min Wang
  • Yuyan Wan
  • Kailian Zhang
  • Qifeng Fu
  • Lujun Wang
  • Jing Zeng
  • Zhining XiaEmail author
  • Die GaoEmail author
Research Paper
  • 86 Downloads

Abstract

In this work, dried flowers of Osmanthus fragrans Lour. were applied as green precursors to synthesize carbon dots (CDs) by a green hydrothermal method for the first time. The CDs showed strong blue fluorescence at 410 nm under 340-nm excitation with a quantum yield of approximately 18.53%. Furthermore, the CDs were applied for the sensitive detection of Fe3+. The linear response of Fe3+ ranged from 10 nM to 50 μM with a limit of detection as low as 5 nM. In addition, other ions were used as competitive substances to explore the selectivity of CDs for Fe3+. The fluorescence quenching effect of Fe3+ was much stronger, which demonstrated that the CDs had high selectivity for Fe3+ and they can be employed for the selective detection of Fe3+. The potential fluorescence quenching mechanism between CDs and Fe3+ was identified as the inner filter effect. The CDs were then used as a fluorescent sensor for the detection of Fe3+ in water samples and human serum; the recovery range was 93.76–113.80% (relative standard deviation less than 0.79%). These results indicate that the CDs can be applied for the sensitive and selective detection of Fe3+ in real samples. Moreover, on the basis of the redox reaction between Fe3+ and ascorbic acid (AA), the CD–Fe3+ system can be used as a fluorescent “off–on” sensor for the detection of AA with a limit of detection of 5 μM. What is more, because of their low toxicity and biocompatibility, the CDs can also be used for cell imaging and acted as a fluorescent probe for fluorescence imaging of Fe3+ and AA in living cells. These results demonstrate that the CDs have great potential for application in the fields of sensing, bioimaging, and even disease diagnosis.

Keywords

Carbon dots Flowers of Osmanthus fragrans Lour. Fe3+ Inner filter effect Fluorescent “off–on” sensor Ascorbic acid 

Notes

Funding information

This work was supported by the university level fund of Southwest Medical University (no. 2017-ZRQN-032) and a joint program of Luzhou Government and Southwest Medical University [no. 2015LZCYD-S07(2/5)].

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Ethics approval and consent to participate

This study was approved by the Ethical Committee of Southwest Medical University. All blood samples were from healthy persons with their informed consent.

Human and animal rights

No violation of human or animal rights occurred during this investigation.

Supplementary material

216_2019_1712_MOESM1_ESM.pdf (657 kb)
ESM 1 (PDF 657 kb)

References

  1. 1.
    Ankireddy SR, Kim J. Highly selective and sensitive detection of calcium (II) ions in human serum using novel fluorescent carbon dots. Sensors Actuators B Chem. 2018;255:3425–33.CrossRefGoogle Scholar
  2. 2.
    Karthik S, Saha B, Ghosh SK, Pradeep Singh ND. Photoresponsive quinoline tethered fluorescent carbon dots for regulated anticancer drug delivery. Chem Commun. 2013;49:10471–3.CrossRefGoogle Scholar
  3. 3.
    Zhu S, Meng Q, Wang L, Zhang J, Song Y, Jin H, et al. Highly photoluminescent carbon dots for multicolor patterning, sensors, and bioimaging. Angew Chem Int Ed. 2013;52:3953–7.CrossRefGoogle Scholar
  4. 4.
    Li W, Zhang HR, Chen S, Liu YL, Zhuang JL, Lei BF. Synthesis of molecularly imprinted carbon dot grafted YVO4:Eu3+ for the ratiometric fluorescent determination of paranitrophenol. Biosens Bioelectron. 2016;86:706–13.CrossRefGoogle Scholar
  5. 5.
    Yang YX, Huo DQ, Wu HX, Wang XF, Yang JS, Bian MH, et al. N, P-doped carbon quantum dots as a fluorescent sensing platform for carbendazim detection based on fluorescence resonance energy transfer. Sensors Actuators B Chem. 2018;274:296–303.CrossRefGoogle Scholar
  6. 6.
    Li HX, Yan X, Qiao SP, Lu GY, Su XG. Yellow-emissive carbon dot-based optical sensing platforms: cell imaging and analytical applications for biocatalytic reactions. ACS Appl Mater Interfaces. 2018;10:7737–44.CrossRefGoogle Scholar
  7. 7.
    Gong PW, Sun L, Wang F, Liu XC, Yan ZQ, Wang MZ, et al. Highly fluorescent N-doped carbon dots with two-photon emission for ultrasensitive detection of tumor marker and visual monitor anticancer drug loading and delivery. Chem Eng J. 2019;356:994–1002.CrossRefGoogle Scholar
  8. 8.
    Liu YS, Li W, Wu P, Liu SX. Preparation and applications of carbon quantum dots prepared via hydrothermal carbonization method. Prog Chem. 2018;30:349–64.Google Scholar
  9. 9.
    Du FF, Li G, Gong XJ, Guo ZH, Shuang SM, Xian M, et al. Facile, rapid synthesis of N,P-dual-doped carbon dots as a label-free multifunctional nanosensor for Mn(VII) detection, temperature sensing and cellular imaging. Sensors Actuators B Chem. 2018;277:492–501.CrossRefGoogle Scholar
  10. 10.
    Xu JC, Miao YQ, Zheng JX, Wang H, Yang YZ, Liu XG. Carbon dot-based white and yellow electroluminescent light emitting diodes with a record-breaking brightness. Nanoscale. 2018;10:11211–21.CrossRefGoogle Scholar
  11. 11.
    Bano D, Kumar V, Singh VK, Hasan SH. Green synthesis of fluorescent carbon quantum dots for the detection of mercury(II) and glutathione. New J Chem. 2018;42:5814–21.CrossRefGoogle Scholar
  12. 12.
    Miao X, Qu D, Yang DX, Nie B, Zhao YK, Fan HY, et al. Synthesis of carbon dots with multiple color emission by controlled graphitization and surface functionalization. Adv Mater. 2018;30:1–8.Google Scholar
  13. 13.
    Zhou N, Zhang XW, Shi YP, Li ZL, Feng ZB. Nitrogen-doped carbon dot mediated fluorescence on-off assay for highly sensitive detection of I- and Br- ions. New J Chem. 2018;42:14332–9.CrossRefGoogle Scholar
  14. 14.
    Bai ZJ, Yan FY, Xu JX, Zhang J, Wei JF, Luo YM, et al. Dual-channel fluorescence detection of mercuric (II) and glutathione by down- and up-conversion fluorescence carbon dots. Spectrochim Acta A. 2018;205:29–39.CrossRefGoogle Scholar
  15. 15.
    Liu YA, Zhang TX, Wang R, Cui HN, Song HW. A facile and universal strategy for preparation of long wavelength emission carbon dots. Dalton Trans. 2017;46:16905–10.CrossRefGoogle Scholar
  16. 16.
    Chen LY, Zhang YY, Duan BH, Gu ZZ, Guo YT, Wang HF, et al. Carbon dots prepared in different solvents with controllable structures: optical properties, cellular imaging and photocatalysis. New J Chem. 2018;42:1690–7.CrossRefGoogle Scholar
  17. 17.
    Wang L, Zhou HS. Green synthesis of luminescent nitrogen-doped carbon dots from milk and its imaging application. Anal Chem. 2014;86:8902–5.CrossRefGoogle Scholar
  18. 18.
    Vandarkuzhali SAA, Jeyalakshmi V, Sivaraman G, Singaravadivel S, Krishnamurthy KR, Viswanathan B. Highly fluorescent carbon dots from pseudo-stem of banana plant: applications as nanosensor and bio-imaging agents. Sensors Actuators B Chem. 2017;252:894–900.CrossRefGoogle Scholar
  19. 19.
    Bandi R, Gangapuram BR, Dadigala R, Eslavath R, Singh SS, Guttena V. Facile and green synthesis of fluorescent carbon dots from onion waste and their potential applications as sensor and multicolour imaging agents. RSC Adv. 2016;6:28633–9.CrossRefGoogle Scholar
  20. 20.
    Bandi R, Dadigala R, Gangapuram BR, Guttena V. Green synthesis of highly fluorescent nitrogen-doped carbon dots from Lantana camara berries for effective detection of lead(II) and bioimaging. J Photochem Photobiol B. 2018;178:330–8.CrossRefGoogle Scholar
  21. 21.
    Bhatt S, Bhatt M, Kumar A, Vyas G, Gajaria T, Paul P. Green route for synthesis of multifunctional fluorescent carbon dots from Tulsi leaves and its application as Cr(VI) sensors, bio-imaging and patterning agents. Colloids Surf B: Biointerfaces. 2018;167:126–33.CrossRefGoogle Scholar
  22. 22.
    Xu J, Jie X, Xie FF, Yang HM, Wei WL, Xia ZN. Flavonoid moiety-incorporated carbon dots for ultrasensitive and highly selective fluorescence detection and removal of Pb2+. Nano Res. 2018;11:3648–57.CrossRefGoogle Scholar
  23. 23.
    Kumar A, Chowdhuri AR, Laha D, Mahto TK, Karmakar P, Sahu SK. Green synthesis of carbon dots from Ocimum sanctum for effective fluorescent sensing of Pb2+ ions and live cell imaging. Sensors Actuators B Chem. 2017;242:679–86.CrossRefGoogle Scholar
  24. 24.
    Li LS, Jiao XY, Zhang Y, Cheng C, Huang K, Xu L. Green synthesis of fluorescent carbon dots from Hongcaitai for selective detection of hypochlorite and mercuric ions and cell imaging. Sensors Actuators B Chem. 2018;263:426–35.CrossRefGoogle Scholar
  25. 25.
    Wang L, Tan NN, Hu JY, Wang H, Duan DZ, Ma L, et al. Analysis of the main active ingredients and bioactivities of essential oil from Osmanthus fragrans var. thunbergii using a complex network approach. BMC Syst Biol. 2017;11:144.CrossRefGoogle Scholar
  26. 26.
    Wang LM, Li MT, Jin WW, Li S, Zhang SQ, Yu LJ. Variations in the components of Osmanthus fragrans Lour. essential oil at different stages of flowering. Food Chem. 2009;114:233–6.CrossRefGoogle Scholar
  27. 27.
    Li HL, Chai Z, Shen GX, Li CY. Polyphenol profiles and antioxidant properties of ethanol extracts from Osmanthus fragrans (Thunb.) Lour. flowers. Pol J Food Nutr Sci. 2017;67:317–25.CrossRefGoogle Scholar
  28. 28.
    Jiang YR, Mao SQ, Huang WS, Lu BY, Cai ZX, Zhou F, et al. Phenylethanoid glycoside profiles and antioxidant activities of Osmanthus fragrans Lour. flowers by UPLC/PDA/MS and simulated digestion model. J Agric Food Chem. 2016;64:2459–66.CrossRefGoogle Scholar
  29. 29.
    Ilboudo O, Tapsoba I, Bonzi-Coulibaly YL, Gerbaux P. Targeting structural motifs of flavonoid diglycosides using collision-induced dissociation experiments on flavonoid/Pb2+ complexes. Eur J Mass Spectrom. 2012;18:465–73.CrossRefGoogle Scholar
  30. 30.
    Perez CA, Wei YB, Guo ML. Iron-binding and anti-Fenton properties of baicalein and baicalin. J Inorg Biochem. 2009;103:326–32.CrossRefGoogle Scholar
  31. 31.
    Murugan N, Sundramoorthy AK. Green synthesis of fluorescent carbon dots from Borassus flabellifer flowers for label-free highly selective and sensitive detection of Fe3+ ions. New J Chem. 2018;42:13297–307.CrossRefGoogle Scholar
  32. 32.
    Zhou JL, Fang XY, Wang JQ, Zhao LG, Li Y, Tang F, et al. Structures and bioactivities of seven flavonoids from Osmanthus fragrans 'Jinqiu' essential oil extraction residues. Nat Prod Res. 2018;32:588–91.CrossRefGoogle Scholar
  33. 33.
    Diao H, Li T, Zhang R, Kang Y, Liu W, Cui Y, et al. Facile and green synthesis of fluorescent carbon dots with tunable emission for sensors and cells imaging. Spectrochim Acta A. 2018;200:226–34.CrossRefGoogle Scholar
  34. 34.
    Amjadi M, Hallaj T, Mayan MA. Green synthesis of nitrogen-doped carbon dots from lentil and its application for colorimetric determination of thioridazine hydrochloride. RSC Adv. 2016;6:104467–73.CrossRefGoogle Scholar
  35. 35.
    Xu Q, Su RG, Zhong J, Zhang LP, Guo YJ, Street J, et al. Synthesis of highly fluorescent yellow-green N-doped carbon nanorings for pH variation detection and bioimaging. Part Part Syst Charact. 2018;35:1800276.CrossRefGoogle Scholar
  36. 36.
    Gao ZH, Lin ZZ, Chen XM, Zhong HP, Huang Z-y. A fluorescent probe based on N-doped carbon dots for highly sensitive detection of Hg2+ in aqueous solutions. Anal Methods. 2016;8:2297–304.CrossRefGoogle Scholar
  37. 37.
    Li H, He H, Huang J, Wang CZ, Gu X, Gao Y, et al. A novel molecularly imprinted method with computational simulation for the affinity isolation and knockout of baicalein from Scutellaria baicalensis. Biomed Chromatogr. 2016;30:117–25.CrossRefGoogle Scholar
  38. 38.
    Jiang K, Sun S, Zhang L, Wang Y, Cai C, Lin H. Bright-yellow-emissive N-doped carbon dots: preparation, cellular imaging, and bifunctional sensing. ACS Appl Mater Interfaces. 2015;7:23231–8.CrossRefGoogle Scholar
  39. 39.
    Liu W, Diao H, Chang H, Wang H, Li T, Wei W. Green synthesis of carbon dots from rose-heart radish and application for Fe3+ detection and cell imaging. Sensors Actuators B Chem. 2017;241:190–8.CrossRefGoogle Scholar
  40. 40.
    Bandi R, Devulapalli NP, Dadigala R, Gangapuram BR, Guttena V. Facile conversion of toxic cigarette butts to N,S-codoped carbon dots and their application in fluorescent film, security ink, bioimaging, sensing and logic gate operation. ACS Omega. 2018;3:13454–66.CrossRefGoogle Scholar
  41. 41.
    Shi QQ, Li YH, Xu Y, Wang Y, Yin XB, He XW, et al. High-yield and high-solubility nitrogen-doped carbon dots: formation, fluorescence mechanism and imaging application. RSC Adv. 2014;4:1563–6.CrossRefGoogle Scholar
  42. 42.
    Liang Q, Wang YL, Lin FC, Jiang MS, Li PF, Huang B. A facile microwave-hydrothermal synthesis of fluorescent carbon quantum dots from bamboo tar and their application. Anal Methods. 2017;9:3675–81.CrossRefGoogle Scholar
  43. 43.
    Zhang J, Yang L, Yuan Y, Jiang J, Yu S-H. One-pot gram-scale synthesis of nitrogen and sulfur embedded organic dots with distinctive fluorescence behaviors in free and aggregated states. Chem Mater. 2016;28:4367–74.CrossRefGoogle Scholar
  44. 44.
    Galande C, Mohite AD, Naumov AV, Gao W, Ci L, Ajayan A, et al. Quasi-molecular fluorescence from graphene oxide. Sci Rep. 2011;1:85.CrossRefGoogle Scholar
  45. 45.
    Vezza T, Rodriguez-Nogales A, Algieri F, Utrilla MP, Rodriguez-Cabezas ME, Galvez J. Flavonoids in inflammatory bowel disease: a review. Nutrients. 2016;8:1–22.CrossRefGoogle Scholar
  46. 46.
    Zhang S, Li J, Zeng M, Xu J, Wang X, Hu W. Polymer nanodots of graphitic carbon nitride as effective fluorescent probes for the detection of Fe3+ and Cu2+ ions. Nanoscale. 2014;6:4157–62.CrossRefGoogle Scholar
  47. 47.
    Li S, Li Y, Cao J, Zhu J, Fan L, Li X. Sulfur-doped graphene quantum dots as a novel fluorescent probe for highly selective and sensitive detection of Fe3+. Anal Chem. 2014;86:10201–7.CrossRefGoogle Scholar
  48. 48.
    Guo XR, Yue GQ, Huang JZ, Liu C, Zeng Q, Wang LS. Label-free simultaneous analysis of Fe(III) and ascorbic acid using fluorescence switching of ultrathin graphitic carbon nitride nanosheets. ACS Appl Mater Interfaces. 2018;10:26118–27.CrossRefGoogle Scholar
  49. 49.
    Akhgari F, Samadi N, Farhadi K. Fluorescent carbon dot as nanosensor for sensitive and selective detection of cefixime based on inner filter effect. J Fluoresc. 2017;27:921–7.CrossRefGoogle Scholar
  50. 50.
    Li YH, Cai JB, Liu FJ, Yu HW, Lin F, Yang H, et al. Highly crystalline graphitic carbon nitride quantum dots as a fluorescent probe for detection of Fe(III) via an inner filter effect. Microchim Acta. 2018;185:1–7.CrossRefGoogle Scholar
  51. 51.
    Chatzimarkou A, Chatzimitakos TG, Kasouni A, Sygellou L, Avgeropoulos A, Stalikas CD. Selective FRET-based sensing of 4-nitrophenol and cell imaging capitalizing on the fluorescent properties of carbon nanodots from apple seeds. Sensors Actuators B Chem. 2018;258:1152–60.CrossRefGoogle Scholar
  52. 52.
    Luo X, Zhang W, Han Y, Chen X, Zhu L, Tang W, et al. N,S co-doped carbon dots based fluorescent "on-off-on" sensor for determination of ascorbic acid in common fruits. Food Chem. 2018;258:214–21.CrossRefGoogle Scholar
  53. 53.
    Liu J, Wang L, Bao H. A novel fluorescent probe for ascorbic acid based on seed-mediated growth of silver nanoparticles quenching of carbon dots fluorescence. Anal Bioanal Chem. 2019;411:877–83.CrossRefGoogle Scholar
  54. 54.
    Khan WU, Wang D, Zhang W, Tang Z, Ma X, Ding X, et al. High quantum yield green-emitting carbon dots for Fe(III) detection, biocompatible fluorescent ink and cellular imaging. Sci Rep. 2017;7:14866.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of PharmacySouthwest Medical UniversityLuzhouChina
  2. 2.School of Pharmaceutical SciencesChongqing UniversityChongqingChina

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