Study of the Fluorescence based Applications of Water Soluble (N, P) Doped Carbon Dots Synthesized via Microwave Assisted Green Pyrolysis

Rajshree       Singh; Shikha       Singh; Sudipta      Senapati; Kheyanath      Mitra; Jaydeep	      Singh; Susanta 	   K.S.   Gupta; Nira      Misra; Pralay      Maiti; Biswajit	      Ray

doi:10.2174/2210681209666190807151604

Abstract

Background: Water soluble nitrogen and phosphorus doped carbon dots (CD) have been synthesized using citric acid, tris(2-aminoethyl)amine and orthophosphoric acid via one step microwave assisted pyrolytic method.

Methods: The CD synthesized has been characterized using FTIR, UV-Vis, fluorescence spectroscopy and EDAX coupled with SEM techniques.

Results: SEM study has shown the formation of nanosized CD with an average size of ~18 nm. Elemental analysis via EDAX has confirmed successful incorporation of nitrogen (30.8% wt) and phosphorus (5.7% wt) atoms in it. The steady state and 3D fluorescence spectroscopic studies have shown its efficient fluorescence emission with emission maxima in the region of ~450 nm. It has shown efficient “turn off” fluorescence behaviour towards transition metal ions like Fe2+ and Co2+ ions and toxic nitrophenolic compounds like p-nitrophenol and picric acid. Its efficient interaction with BSA has been revealed in terms of fluorescence quenching of BSA by steady state, synchronous and 3D fluorescence spectroscopy. It has shown very good in vitro biocompatibility and enhanced cell adhesion properties towards NIH 3T3 fibroblast cells. Moreover, fluorescence microscopy has shown significant uptake of CD by the tested cell line.

Conclusion: Such bio-compatible nitrogen and phosphorous doped CD can be potentially useful to estimate metal ions, p-nitrophenol and picric acid using fluorescence spectroscopy and for fluorescence based bio-imaging.

Keywords: Carbon dots, green pyrolysis, cell adhesion, fibroblast cells, nano-materials, bioimaging.

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J Mater Chem C Mater Opt Electron Devices Wang Y. 2 6921 2014 10.1039/C4TC00988F Wang Y.; Hu A.; Carbon quantum dots: Synthesis, properties and applications. J Mater Chem C Mater Opt Electron Devices 2014,2(34),6921-6939 J Mater Chem B Mater Biol Med Wang W. 2 46 2014 10.1039/C3TB21370F Wang W.; Li Y.; Cheng L.; Cao Z.; Liu W.; Water-soluble and phosphorus-containing carbon dots with strong green fluorescence for cell labelling. J Mater Chem B Mater Biol Med 2014,2(1),46-48 Chemistry Xu Y. 19 2276 2013 10.1002/chem.201203641 Xu Y.; Wu M.; Liu Y.; Feng X.Z.; Yin X.B.; He X.W.; Zhang Y.K.; Nitrogen-doped carbon dots: A facile and general preparation method, photoluminescence investigation, and imaging applications. Chemistry 2013,19(7),2276-2283 RSC Advances Shi D. 5 98492 2015 10.1039/C5RA18800H Shi D.; Yan F.; Zheng T.; Wang Y.; Zhou X.; Chen L.; P-doped carbon dots act as nanosensor for trace 2,4,6-trinitrophenol detection and fluorescent reagent for biological imaging. RSC Advances 2015,5(119),98492-98499 Carbon Sadhanala H.K. 96 166 2016 10.1016/j.carbon.2015.08.096 Sadhanala H.K.; Nanda K.K.; Boron-doped carbon nanoparticles: size-independent color tunability from red to blue and bioimaging applications. Carbon 2016,96,166-173 ACS Appl Mater Interfaces Song Y. 9 7399 2017 10.1021/acsami.6b13954 Song Y.; Zhu C.; Song J.; Li H.; Du D.; Lin Y.; Drug-derived bright and color-tunable N-doped carbon dots for cell imaging and sensitive detection of Fe3+ in living cells. ACS Appl Mater Interfaces 2017,9(8),7399-7405 Nano-Objects Chandra S. 12 10 2017 10.1016/j.nanoso.2017.08.001 Chandra S.; Chowdhuri A.R.; Mahto T.K.; Laha D.; Sahu S.K.; Sulphur and nitrogen doped carbon dots: A facile synthetic strategy for multicolour bioimaging, tiopronin sensing, and Hg2+ ion detection. Nano-Struc. Nano-Objects 2017,12,10-18 Luminescence Chandra S. 31 81 2016 10.1002/bio.2927 Chandra S.; Laha D.; Pramanik A.; Ray Chowdhuri A.; Karmakar P.; Sahu S.K.; Synthesis of highly fluorescent nitrogen and phosphorus doped carbon dots for the detection of Fe(3+) ions in cancer cells. Luminescence 2016,31(1),81-87 ACS Appl Mater Interfaces Gong X. 8 11288 2016 10.1021/acsami.6b01577 Gong X.; Zhang Q.; Gao Y.; Shuang S.; Choi M.M.F.; Dong C.; Phosphorus and nitrogen dual-doped hollow carbon dot as a nanocarrier for doxorubicin delivery and biological imaging. ACS Appl Mater Interfaces 2016,8(18),11288-11297 J Mater Chem B Mater Biol Med Xu Q. 4 7204 2016 10.1039/C6TB02131J Xu Q.; Kuang T.; Liu Y.; Cai L.; Peng X.; Sreeprasad T.S.; Zhao P.; Yu Z.; Li N.; Heteroatom-doped carbon dots: synthesis, characterization, properties, photoluminescence mechanism and biological applications. J Mater Chem B Mater Biol Med 2016,4(45),7204-7219 J Mater Chem B Mater Biol Med Chandra S. 1 2375 2013 10.1039/c3tb00583f Chandra S.; Patra P.; Pathan S.H.; Roy S.; Mitra S.; Layek A.; Bhar R.; Pramanik P.; Goswami A.; Luminescent S-doped carbon dots: An emergent architecture for multimodal applications. J Mater Chem B Mater Biol Med 2013,1(18),2375-2382 Carbon Sun D. 64 424 2013 10.1016/j.carbon.2013.07.095 Sun D.; Ban R.; Zhang P.H.; Wu G.H.; Zhang J.R.; Zhu J.J.; Hair fiber as a precursor for synthesizing of sulfur and nitrogen-co-doped carbon dots with tunable luminescence properties. Carbon 2013,64,424-434 RSC Advances Guo Y. 7 48386 2017 10.1039/C7RA09785A Guo Y.; Chen Y.; Cao F.; Wang L.; Wang Z.; Leng Y.; Hydrothermal synthesis of nitrogen and boron doped carbon quantum dots with yellow-green emission for sensing Cr(VI), anti-counterfeiting and cell imaging. RSC Advances 2017,7(76),48386-48393 Biosens Bioelectron Gong Y. 79 822 2016 10.1016/j.bios.2016.01.022 Gong Y.; Yu B.; Yang W.; Zhang X.; Phosphorus, and nitrogen co-doped carbon dots as a fluorescent probe for real-time measurement of reactive oxygen and nitrogen species inside macropha-ges. Biosens Bioelectron 2016,79,822-828 Nanoscale Sun X. 7 17278 2015 10.1039/C5NR05549K Sun X.; Brückner C.; Lei Y.; One-pot and ultrafast synthesis of nitrogen and phosphorus co-doped carbon dots possessing bright dual wavelength fluorescence emission. Nanoscale 2015,7(41),17278-17282 Mikrochim Acta Li H. 183 821 2016 10.1007/s00604-015-1714-2 Li H.; Shao F.Q.; Zou S.Y.; Yang Q.J.; Huang H.; Feng J.J.; Wang A.J.; Microwave-assisted synthesis of N,P-doped carbon dots for fluorescent cell imaging. Mikrochim Acta 2016,183(2),821-826 J Phys Chem C Barman M.K. 118 20034 2014 10.1021/jp507080c Barman M.K.; Jana B.; Bhattacharyya S.; Patra A.; Photophysical properties of doped carbon dots (N, P, and B) and their influence on electron/hole transfer in carbon dots−nickel (II) phthalocyanine conjugates. J Phys Chem C 2014,118(34),20034-20041 Mikrochim Acta Li J. 184 2933 2017 10.1007/s00604-017-2314-0 Li J.; Jiao Y.; Feng L.; Zhong Y.; Zuo G.; Xie A.; Dong W.; Highly N.; P-doped carbon dots: Rational design, photoluminescence and cellular imaging. Mikrochim Acta 2017,184(8),2933-2940 R Inst Chem Rev Williams R.J.P. 1 13 1968 10.1039/rr9680100013 Williams R.J.P.; Role of transition metal ions in biological pro-cesses. R Inst Chem Rev 1968,1,13-38 Interdiscip Toxicol Jaishankar M. 7 60 2014 10.2478/intox-2014-0009 Jaishankar M.; Tseten T.; Anbalagan N.; Mathew B.B.; Beeregowda K.N.; Toxicity, mechanism and health effects of some heavy metals. Interdiscip Toxicol 2014,7(2),60-72 Environ Sci Technol Dean J.G. 6 518 1972 10.1021/es60065a006 Dean J.G.; Bosqui F.L.; Lanouette K.H.; Removing heavy metals from waste water. Environ Sci Technol 1972,6(6),518-522 Wittmann G.T.W. Wittmann G.T.W.; In: Metal Pollution in the Aquatic Environment, 2nd rev. ed.; Förstner, U.; Wittmann, G.T.W., Eds.; Springer- Verlag Press: Berlin, Heidelberg, 1983, pp. 30-57 Nano Today Zhang J. 11 309 2016 10.1016/j.nantod.2016.05.010 Zhang J.; Cheng F.; Li J.; Zhu J.J.; Lu Y.; Fluorescent nanoprobes for sensing and imaging of metal ions: Recent advances and future perspectives. Nano Today 2016,11(3),309-329 J Appl Toxicol Kovacic P. 34 810 2014 10.1002/jat.2980 Kovacic P.; Somanathan R.; Nitroaromatic compounds: Environmental toxicity, carcinogenicity, mutagenicity, therapy and mechanism. J Appl Toxicol 2014,34(8),810-824 Mar Pollut Bull Nipper M. 50 1205 2005 10.1016/j.marpolbul.2005.04.019 Nipper M.; Carr R.S.; Biedenbach J.M.; Hooten R.L.; Miller K.; Fate and effects of picric acid and 2,6-DNT in marine environments: Toxicity of degradation products. Mar Pollut Bull 2005,50(11),1205-1217 The Chemistry of Explosives Akhavan J. 2004 Akhavan J.; The Chemistry of Explosives 2004 Chem Soc Rev Salinas Y. 41 1261 2012 10.1039/C1CS15173H Salinas Y.; Martínez-Máñez R.; Marcos M.D.; Sancenón F.; Costero A.M.; Parra M.; Gil S.; Optical chemosensors and reagents to detect explosives. Chem Soc Rev 2012,41(3),1261-1296 J Phys Chem B Ghosh S. 119 7804 2015 10.1021/acs.jpcb.5b00965 Ghosh S.; Dey J.; Binding of fatty acid amide amphiphiles to bovine serum albumin: Role of amide hydrogen bonding. J Phys Chem B 2015,119(25),7804-7815 Biochem Pharmacol Jannin B. 68 1113 2004 10.1016/j.bcp.2004.04.028 Jannin B.; Menzel M.; Berlot J.P.; Delmas D.; Lançon A.; Latruffe N.; Transport of resveratrol, a cancer chemopreventive agent, to cellular targets: plasmatic protein binding and cell uptake. Biochem Pharmacol 2004,68(6),1113-1118 Pharmacol Rev Kragh-Hansen U. 33 17 1981 Kragh-Hansen U.; Molecular aspects of ligand binding to serum albumin. Pharmacol Rev 1981,33(1),17-53 IUBMB Life Fasano M. 57 787 2005 10.1080/15216540500404093 Fasano M.; Curry S.; Terreno E.; Galliano M.; Fanali G.; Narciso P.; Notari S.; Ascenzi P.; The extraordinary ligand binding properties of human serum albumin. IUBMB Life 2005,57(12),787-796 Cytotechnology Francis G.L. 62 1 2010 10.1007/s10616-010-9263-3 Francis G.L.; Albumin and mammalian cell culture: implications for biotechnology applications. Cytotechnology 2010,62(1),1-16 Hepatology Quinlan G.J. 41 1211 2005 10.1002/hep.20720 Quinlan G.J.; Martin G.S.; Evans T.W.; Albumin: Biochemical properties and therapeutic potential. Hepatology 2005,41(6),1211-1219 Carbon Sopotnik M. 95 560 2015 10.1016/j.carbon.2015.08.018 Sopotnik M.; Leonardi A.; Križaj I.; Dušak P.; Makovec D.; Mesarič T.; Ulrih N.P.; Junkar I.; Sepčić K.; Drobne D.; Comparative study of serum protein binding to three different carbon-based nanomaterials. Carbon 2015,95,560-572 J Lumin Hao A. 170 90 2016 10.1016/j.jlumin.2015.10.002 Hao A.; Guo X.; Wu Q.; Sun Y.; Cong C.; Liu W.; Exploring the interactions between polyethyleneimine modified fluorescent carbon dots and bovine serum albumin by spectroscopic methods. J Lumin 2016,170(1),90-96 J Control Release Senapati S. 224 186 2016 10.1016/j.jconrel.2016.01.016 Senapati S.; Thakur R.; Verma S.P.; Duggal S.; Mishra D.P.; Das P.; Shripathi T.; Kumar M.; Rana D.; Maiti P.; Layered double hydroxides as effective carrier for anticancer drugs and tailoring of release rate through interlayer anions. J Control Release 2016,224,186-198 ACS Biomater Sci Eng Patel D.K. 3 3351 2017 10.1021/acsbiomaterials.7b00342 Patel D.K.; Senapati S.; Mourya P.; Singh M.M.; Aswal V.K.; Ray B.; Maiti P.; Functionalized graphene tagged polyurethanes for corrosion inhibitor and sustained drug delivery. ACS Biomater Sci Eng 2017,3(12),3351-3363 ACS Appl Mater Interfaces Li H. 7 10004 2015 10.1021/acsami.5b02386 Li H.; Guo S.; Li C.; Huang H.; Liu Y.; Kang Z.; Tuning laccase catalytic activity with phosphate functionalized carbon dots by visible light. ACS Appl Mater Interfaces 2015,7(18),10004-10012 Nano Res Zhu S. 8 355 2015 10.1007/s12274-014-0644-3 Zhu S.; Song Y.; Zhao X.; Shao J.; Zhang J.; Yang B.; Thephotoluminescence mechanism in carbon dots (graphene quantum dots, carbon nanodots, and polymer dots): Current state and future perspective. Nano Res 2015,8(2),355-381 J Phys Chem C LeCroy G.E. 121 28180 2017 10.1021/acs.jpcc.7b10129 LeCroy G.E.; Messina F.; Sciortino A.; Bunker C.E.; Wang P.; Fernando K.A.S.; Sun Y.P.; Characteristic excitation wavelength dependence of fluorescence emissions in carbon quantum dots. J Phys Chem C 2017,121(50),28180-28186 Angew Chem Int Ed Engl Li H. 49 4430 2010 10.1002/anie.200906154 Li H.; He X.; Kang Z.; Huang H.; Liu Y.; Liu J.; Lian S.; Tsang C.H.A.; Yang X.; Lee S.T.; Water-soluble fluorescent carbon quantum dots and photocatalyst design. Angew Chem Int Ed Engl 2010,49(26),4430-4434 Biochem Biophys Res Commun Hirayama K. 173 639 1990 10.1016/S0006-291X(05)80083-X Hirayama K.; Akashi S.; Furuya M.; Fukuhara K.; Rapid confirmation and revision of the primary structure of bovine serum albumin by ESIMS and Frit-FAB LC/MS. Biochem Biophys Res Commun 1990,173(2),639-646 Albumin: Structure, Function and Uses Brown J.R. 27 1977 10.1016/B978-0-08-019603-9.50009-0 Brown J.R.; Albumin: Structure, Function and Uses 1977,27-51 RSC Advances Ahirwar R. 5 100077 2015 10.1039/C5RA20750A Ahirwar R.; Bariar S.; Balakrishnana A.; Nahar P.; BSA blocking in enzyme-linked immunosorbent assays is a non-mandatory step: a perspective study on mechanism of BSA blocking in common ELISA protocols. RSC Advances 2015,5(121),100077-100083 ACS Biomater Sci Eng Mitra K. 2 1630 2016 10.1021/acsbiomaterials.6b00397 Mitra K.; Singh S.; Hira S.K.; Patel V.K.; Singh D.; Vishwakarma S.; Singh R.; Kumari A.; Manna P.P.; Ray B.; Study of the fluorescence based applications of pyrene-tagged poly(N vinyl-2-pyrrolidone). ACS Biomater Sci Eng 2016,2(9),1630-1640 RSC Advances Bortolotti A. 6 112870 2016 10.1039/C6RA23426G Bortolotti A.; Wong Y.H.; Korsholm S.S.; Bahring N.H.B.; Bobone S.; Tayyab S.; Weert M.; Stella L.; On the purported “backbone fluorescence” in protein three dimensional fluorescence spectra. RSC Advances 2016,6(114),112870-112876 Principles of fluorescence spectroscopy Lakowicz J.R. 2006 10.1007/978-0-387-46312-4 Lakowicz J.R.; Principles of fluorescence spectroscopy 2006 J Biomol Struct Dyn Shi J.H. 35 1529 2017 10.1080/07391102.2016.1188416 Shi J.H.; Wang Q.; Pan D.Q.; Liu T.T.; Jiang M.; Characterization of interactions of simvastatin, pravastatin, fluvastatin, and pitavastatin with bovine serum albumin: multiple spectroscopic and molecular docking. J Biomol Struct Dyn 2017,35(7),1529-1546 Chem Select Mukhopadhyay S. 2 6000 2017 Mukhopadhyay S.; Mitra K.; Paitandi R.P.; Singh R.S.; Singh S.; Ray B.; Pandey D.S.; Polymerization of 1-(2-Propynyl)-3-methylimidazolium bromide using cyclometalatedPd(II) catalysts and study of the interaction of ensuing oligomer with BSA. Chem Select 2017,2(21),6000-6008 Pharm Res Bhardwaj V. 26 2495 2009 10.1007/s11095-009-9965-4 Bhardwaj V.; Ankola D.D.; Gupta S.C.; Schneider M.; Lehr C.M.; Kumar M.N.V.R.; PLGA nanoparticles stabilized with cationic surfactant: Safety studies and application in oral delivery of paclitaxel to treat chemical-induced breast cancer in rat. Pharm Res 2009,26(11),2495-2503 Int J Mol Sci Dávila-Grana Á. 19 2018 10.3390/ijms19010246 Dávila-Grana Á.; Diego-González L.; González-Fernández Á.; Simón-Vázquez R.; Synergistic effect of metal oxide nanoparticles on cell viability and activation of MAP kinases and NFκB. Int J Mol Sci 2018,19(1) J Am Chem Soc Lesniak A. 135 1438 2013 10.1021/ja309812z Lesniak A.; Salvati A.; Santos-Martinez M.J.; Radomski M.W.; Dawson K.A.; Åberg C.; Nanoparticle adhesion to the cell membrane and its effect on nanoparticle uptake efficiency. J Am Chem Soc 2013,135(4),1438-1444

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DOI https://dx.doi.org/10.2174/2210681209666190807151604	Print ISSN 2210-6812
Publisher Name Bentham Science Publisher	Online ISSN 2210-6820

Nanoscience & Nanotechnology-Asia

Study of the Fluorescence based Applications of Water Soluble (N, P) Doped Carbon Dots Synthesized via Microwave Assisted Green Pyrolysis

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