Citation: Yu Jingwen, Lv Jia, Cheng Yiyun. Fluorination Significantly Improves the Antibacterial Activity of Carbon Dots[J]. Chemistry, ;2020, 83(4): 360-368. shu

Fluorination Significantly Improves the Antibacterial Activity of Carbon Dots

Yu Jingwen ¹ ,
Lv Jia ^2, ,
Cheng Yiyun ^1,2,

1.
School of Life Sciences, East China Normal University, Shanghai, 200241
2.
School of Molecular Science and Engineering, South China University of Technology, Guangzhou, 510640

Received Date: 13 November 2019
Accepted Date: 19 December 2019

Figures(5)

In this study, carbon dots were synthesized by branched polyethyleneimine and ethanol, and the cationic carbon dots were further grafted with fluoroalkane chains to obtain fluorinated carbon dots. They exhibited high antibacterial activity against both Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and relative low cytotoxicity on mammalian cells. The structure-activity relationship of fluorinated carbon dots showed that fluorination is critical for the high antibacterial activity of carbon dots, and the replacement of fluoroalkane chains with alkane containing the same number of carbon atom significantly reduces the antibacterial activity. This study can provide new insights into the rational design of nanomaterials for antibacterial applications.
- Carbon dots,
- Antibacterial materials,
- Fluroination,
- Polyethylenimine,
- Fluorinated polymers
1. [1]
  Shankar P R. Med. J. Australa., 2014, 7:237.
2. [2]
  Kawaharada Y, Kelly S, Nielsen M W, et al. Nature, 2015, 523:308.
3. [3]
  I L Medintz, H T Uyeda, E R Goldman, et al. Nat. Mater., 2005, 4(6):435~446.
4. [4]
  Wang J, Soisson S M, Young K, et al. Nature, 2006, 441(7091):358~361.
5. [5]
  Jampilek J. Curr. Med. Chem., 2018, 25(38):4972~5006.
6. [6]
  Ali Y, Muhamad Bunnori N, Susanti D, et al. Front. Chem., 2018, 6:210.
7. [7]
  Santajit S, Indrawattana N. BioMed Res. Int., 2016, 8:2475067.
8. [8]
9. [9]
  Hu J, Quan Y, Lai Y, et al. J. Control. Release, 2017, 247:145~152.
10. [10]
  Li M, Wang H, Hu J, et al. Chem. Mater., 2019, 31(18):7678~7685.
11. [11]
  Cheng X, Li M, Wang H, et al. Chin. Chem. Lett., 2019, doi:10.1016/j.cclet.2019.07.013.
12. [12]
  Hu J, Zheng Z, Liu C, et al. Biomater. Sci., 2019, 7(2):581~584.
13. [13]
  Wang H, Cheng Y. Mater. Chem. Front., 2019, 3(3):472~475.
14. [14]
  Hu J, Hu Q, He X, et al. Adv. Health. Mater., 2019, doi:10.1002/adhm.201901329.
15. [15]
  Vetterli S U, Moehle K, Robinson J A. Bioorg. Med. Chem., 2016, 24(24):6332~6339.
16. [16]
  Zimmermann L, Das I, Désiré J, et al. J. Med. Chem., 2016, 59(20):9350~9369.
17. [17]
  Chalopin T, Alvarez Dorta D, Sivignon A, et al. Org. Biomol. Chem., 2016, 14(16):3913~3925.
18. [18]
  Jung S A, Chapman C A, Ng W L. PLoS Pathogens, 2015, 11(4):e1004837.
19. [19]
  Andersson D I, Hughes D, Kubicek-Sutherland J Z. Drug Resist. Update, 2016, 26:43~57.
20. [20]
  Garneau-Tsodikova S, Labby K J. Med. Chem. Comm., 2016, 7(1):11~27.
21. [21]
  Pelaz B, Alexiou C, Alvarez-Puebla R A, et al. ACS Nano, 2017, 11(3):2313~2381.
22. [22]
  Chen G, Roy I, Yang C, et al. Chem. Rev., 2016, 116(5):2826~2885.
23. [23]
  Hoseinnejad M, Jafari S M, Katouzian I. Crit. Rev. Microbiol., 2018, 44(2):161~181.
24. [24]
  Raghunath A, Perumal E. Int. J. Antimicrob. Agents, 2017, 49(2):137~152.
25. [25]
  Wang D, Lin Z, Wang T, et al. J. Hazard. Mater., 2016, 308:328~334.
26. [26]
  Soenen S J, Parak W J, Rejman J, et al. Chem. Rev., 2015, 115(5):2109~2135.
27. [27]
  Zheng K, Setyawati M I, Leong D T, et al. Chem. Mater., 2018, 30(8):2800~2808.
28. [28]
  Zhou Z, Yan Y, Wang L, et al. Biomaterials, 2019, 203:63~72.
29. [29]
  Wang C, Wang D, Dai T, et al. Adv. Funct. Mater., 2018, 28(33):1802127.
30. [30]
  Namdari P, Negahdari B, Eatemadi A. Biomed. Pharmacother., 2017, 87:209~222.
31. [31]
  Peng Z, Han X, Li S, et al. Coord. Chem. Rev., 2017, 343:256~277.
32. [32]
  Zheng X T, Ananthanarayanan A, Luo K Q, et al. Small, 2015, 11(14):1620~1636.
33. [33]
  Lim S Y, Shen W, Gao Z. Chem. Soc. Rev., 2015, 44(1):362~381.
34. [34]
  Gaddam R R, Mukherjee S, Punugupati N, et al. Mater. Sci. Eng. C, 2017, 73:643~652.
35. [35]
  Cao L, Yang S T, Wang X, et al. Theranostics, 2012, 2(3):295~301.
36. [36]
  Dou Q, Fang X, Jiang S, et al. RSC Adv., 2015, 5(58):46817~46822.
37. [37]
  Meziani M J, Dong X, Zhu L, et al. ACS Appl. Mater. Interf., 2016, 8(17):10761~10766.
38. [38]
  Sun Y P, Zhou B, Lin Y, et al. J. Am. Chem. Soc., 2006, 128(24):7756~7757.
39. [39]
  Wang Q, Huang X, Long Y, et al. Carbon, 2013, 59:192~199.
40. [40]
  Zhong D, Zhuo Y, Feng Y, et al. Biosens. Bioelectron., 2015, 74:546~553.
41. [41]
  Bing W, Sun H, Yan Z, et al. Small, 2016, 12(34):4713~4718.
42. [42]
  Jian H J, Wu R S, Lin T Y, et al. ACS Nano, 2017, 11(7):6703~6716.
43. [43]
  Harroun S G, Lai J Y, Huang C C, et al. ACS Infect. Dis., 2017, 3(11):777~779.
44. [44]
  Jiang F, Chen D, Li R, et al. Nanoscale, 2013, 5(3):1137~1142.
45. [45]
  Sun H, Gao N, Dong K, et al. ACS Nano, 2014, 8(6):6202~6210.
46. [46]
  Ristic B Z, Milenkovic M M, Dakic I R, et al. Biomaterials, 2014, 35(15):4428~4435.
47. [47]
  Sattarahmady N, Rezaie-Yazdi M, Tondro G H, et al. J. Photoch. Photobiol. B, 2017, 166:323~332.
48. [48]
  Wang L, Zhou H S. Anal. Chem., 2014, 86(18):8902~8905.
49. [49]
  Sahu S, Behera B, Maiti T K, et al. Chem. Commun., 2012, 48(70):8835~8837.
50. [50]
  Jiang C, Wu H, Song X, et al. Talanta, 2014, 127:68~74.
51. [51]
  Du F, Zhang M, Li X, et al. Nanotechnology, 2014, 25(31):315702.
52. [52]
  Zhang Z, Shen W, Ling J, et al. Nat. Commun., 2018, 9(1):1377.
53. [53]
  Shen W, Wang Q, Shen Y, et al. ACS Cent. Sci., 2018, 4(10):1326~1333.
54. [54]
  Fox S J, Fazil M, Dhand C, et al. Acta Biomater., 2016, 37:155~164.
55. [55]
  Wang M, Liu H, Li L, et al. Nat. Commun., 2014, 5(1):3053.
56. [56]
  Li L, Song L, Liu X, et al. ACS Nano, 2017, 11(1):95~111.
57. [57]
  Li L, Song L, Yang X, et al. Biomaterials, 2016, 111:124~137.
58. [58]
  Liu H, Wang Y, Wang M, et al. Biomaterials, 2014, 35(20):5407~5413.
59. [59]
  Lv J, He B, Yu J, et al. Biomaterials, 2018, 182:167~175.
60. [60]
  Wang H, Wang Y, Wang Y, et al. Angew. Chem. Int. Ed., 2015, 54(40):11647~11651.
61. [61]
  Wang L H, Wu D C, Xu H X, et al. Angew. Chem. Int. Ed., 2016, 55(2):755~759.
62. [62]
  Wang M, Cheng Y. Biomaterials, 2014, 35(24):6603~6613.
63. [63]
  Yang J, Zhang Q, Chang H, et al. Chem. Rev., 2015, 115(11):5274~5300.
64. [64]
  Kretzmann J A, Ho D, Evans C W, et al. Chem. Sci., 2017, 8(4):2923~2930.
65. [65]
  Lv J, Fan Q, Wang H, et al. Biomaterials, 2019, 218:119358.
66. [66]
67. [67]
  Liu C, Wan T, Wang H, et al. Sci. Adv., 2019, 5:eaaw8922.
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