Citation: Xiaoxiao Hu, Hongjing Wu, Qiang Zhang, Feng Gao. Dual-emission carbonized polymer dots for ratiometric sensing and imaging of L-lysine and pH in live cell and zebrafish[J]. Chinese Chemical Letters, ;2023, 34(5): 107846. doi: 10.1016/j.cclet.2022.107846 shu

Dual-emission carbonized polymer dots for ratiometric sensing and imaging of L-lysine and pH in live cell and zebrafish

Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Chemo/Biosensing, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China

fgao@mail.ahnu.edu.cn

Received Date: 6 May 2022
Revised Date: 11 September 2022
Accepted Date: 22 September 2022
Available Online: 27 September 2022

Figures(8)

It is highly desired to accurately and selectively detect and image intracellular L-lysine and pH in biological systems because they could act as the biomarkers in certain abnormal conditions and may give us a warning of the occurrence of diseases. It has been attracted more focuses to design new ratiometric fluorescent probe for monitoring L-lysine and pH to improve detection accuracy. Carbonized polymer dots (CPDs), which possess carbon/polymer hybrid structure rather than pure carbon structure and constitute of a carbon core and large amounts of functional groups/polymer chains on the surface, rise up as a new type of fluorescent nanomaterials and especially display many advantages for bioanalysis. In this study, o-phenylenediamine (o-PD) and poly(styrene-co-maleic anhydride) (PSMA) are used as the precursors to synthesize the desired CPDs through one-step hydrothermal amide method. The prepared CPDs display two well-resolved fluorescence emission bands, i.e., a very weak emission centered at 470 nm in blue region and a strong emission centered at 558 nm in yellow region. It is found that the two emissions are both responsive to L-lysine based on the surface passivation mechanism, whereas, only the yellow emission is responsive to pH due to the protonation/deprotonation process of the amino groups. Based on the different responsive behaviors, ratiometric detection and imaging of L-lysine and pH are achieved. The prepared ratiometric CPDs probe is successfully applied for L-lysine and pH sensing and imaging at two emission channels in live cell and zebrafish with satisfactory results.
- Carbonized polymer dots (CPDs),
- Ratiometric fluorescent probe,
- L-lysine,
- pH,
- Dual-emission
1. [1]
  C.S. Pundir, B. Nohwal, R. Chaudhary, Int. J. Biol. Macromol. 186 (2021) 445–461. doi: 10.1016/j.ijbiomac.2021.07.010
2. [2]
  J.R. Casey, S. Grinstein, J. Orlowski, Nat. Rev. Mol. Cell Biol. 11 (2010) 50–56. doi: 10.1038/nrm2820
3. [3]
  F. Gao, L. Wang, L.J. Tang, C.Q. Zhu, Microchim. Acta 152 (2005) 131–135. doi: 10.1007/s00604-005-0418-4
4. [4]
  F. Gao, L.J. Tang, L. Dai, L. Wang, Spectrochim. Acta A: Mol. Biomol. Spectrosc. 67 (2007) 517–521. doi: 10.1016/j.saa.2006.08.009
5. [5]
  F. Gao, X.X. Chen, Q.Q. Ye, et al., Microchim. Acta 172 (2011) 327–333. doi: 10.1007/s00604-010-0494-y
6. [6]
  P. Cui, X.K. Jiang, J.Y. Sun, Q. Zhang, F. Gao, Methods Appl. Fluoresc. 5 (2017) 024009. doi: 10.1088/2050-6120/aa69c7
7. [7]
  J.Y. Sun, P.H. Ling, F. Gao, Anal. Chem. 89 (2017) 11703–11710. doi: 10.1021/acs.analchem.7b03154
8. [8]
  Q. Zhang, J.Y. Sun, R.C. Zhang, et al., Chem. Commun. 56 (2020) 8647–8650. doi: 10.1039/D0CC01811B
9. [9]
  X.X. Hu, Q. Zhang, X.M. Dai, J.Y. Sun, F. Gao, ACS Appl. Bio Mater. 4 (2021) 7663–7672. doi: 10.1021/acsabm.1c00892
10. [10]
  W. Song, W.X. Duan, Y.H. Liu, et al., Anal. Chem. 89 (2017) 13626–13633. doi: 10.1021/acs.analchem.7b04211
11. [11]
  J.Y. Sun, H. Mei, S.F. Wang, F. Gao, Anal. Chem. 88 (2016) 7372–7377. doi: 10.1021/acs.analchem.6b01929
12. [12]
  J.Y. Sun, S.F. Wang, F. Gao, Langmuir 32 (2016) 12725–12731. doi: 10.1021/acs.langmuir.6b03002
13. [13]
  Y.Y. Ma, Y.H. Tang, Y.P. Zhao, S.Y. Gao, W.Y. Lin, Anal. Chem. 89 (2017) 9388–9393. doi: 10.1021/acs.analchem.7b02216
14. [14]
  W. Pan, H.H. Wang, L.M. Yang, et al., Anal. Chem. 88 (2016) 6743–6748. doi: 10.1021/acs.analchem.6b01010
15. [15]
  Q. Zhang, X.X. Hu, X.M. Dai, et al., ACS Nano 15 (2021) 13633–13645. doi: 10.1021/acsnano.1c04581
16. [16]
  Z.X. Liu, X. Zhou, Y. Miao, et al., Angew. Chem. Int. Ed. 56 (2017) 5812–5816. doi: 10.1002/anie.201702114
17. [17]
  X.L. Chen, J.Y. Sun, Q. Zhang, X.K. Jiang, F. Gao, Chem. Commun. 56 (2020) 3035–3038. doi: 10.1039/C9CC08912H
18. [18]
  J.J. He, X.K. Jiang, P.H. Ling, J.Y. Sun, F. Gao, ACS Omega 4 (2019) 8282–8289. doi: 10.1021/acsomega.9b00702
19. [19]
  D. Cheng, Y. Pan, L. Wang, et al., J. Am. Chem. Soc. 139 (2017) 285–292. doi: 10.1021/jacs.6b10508
20. [20]
  J.Y. Sun, N.N. Chen, X.L. Chen, Q. Zhang, F. Gao, Anal. Chem. 91 (2019) 12414–12421. doi: 10.1021/acs.analchem.9b03010
21. [21]
  Y.Y. Han, C.Q. Ding, J. Zhou, Y. Tian, Anal. Chem. 87 (2015) 5333–5339. doi: 10.1021/acs.analchem.5b00628
22. [22]
  J.Y. Sun, H. Mei, F. Gao, Biosens. Bioelectron. 91 (2017) 70–75. doi: 10.1016/j.bios.2016.12.034
23. [23]
  E. Ferrer, A. Alegria, R. Farre, et al., Food Nahr. 47 (2003) 403–407. doi: 10.1002/food.200390090
24. [24]
  M. Hikuma, M. Kawarai, Y. Tonooka, et al., Anal. Lett. 24 (1991) 2225–2236. doi: 10.1080/00032719108053047
25. [25]
  Y.F. Shi, Y.P. Jiang, P.P. Sun, et al., Spectrochim. Acta A: Mol. Biomol. Spectrosc. 249 (2021) 119214. doi: 10.1016/j.saa.2020.119214
26. [26]
  J. Dong, X.D. Zhang, X.F. Xie, et al., RSC Adv. 10 (2020) 37449–37455. doi: 10.1039/D0RA06879A
27. [27]
  Y.B. Song, S.J. Zhu, S.T. Zhang, et al., J. Mater. Chem. C 23 (2015) 5976–5984.
28. [28]
  K. Muthamma, D. Sunil, P. Shetty, App. Mater. Today 23 (2021) 101050. doi: 10.1016/j.apmt.2021.101050
29. [29]
  S.J. Zhu, X.H. Zhao, Y.B. Song, S.Y. Lu, B. Yang, Nano Today 2 (2016) 128–132.
30. [30]
  S.Y. Tao, T.L. Feng, C.Y. Zheng, S.J. Zhu, B. Yang, J. Phys. Chem. Lett. 17 (2019) 5182–5188.
31. [31]
  X.H. Zhao, J. Li, D.N. Liu, et al., iScience 23 (2020) 100982. doi: 10.1016/j.isci.2020.100982
32. [32]
  S.Y. Tao, S.J. Zhu, T.L. Feng, et al., Mater. Today Chem. 6 (2017) 13–25. doi: 10.1016/j.mtchem.2017.09.001
33. [33]
  C.L. Xia, S.J. Zhu, T.L. Feng, M.X. Yang, B. Yang, Adv. Sci. 6 (2019) 1901316. doi: 10.1002/advs.201901316
34. [34]
  B.E. Saji, M. Saji, N. Joseph, M. Balachandran, Biointerface Res. Appl. Chem. 12 (2022) 4662–4674.
35. [35]
  C.Y. Kang, S.Y. Tao, F. Yang, B. Yang, Aggregate 3 (2022) e169.
36. [36]
  F. Rigodanza, M. Burian, F. Arcudi, et al., Nat. Commun. 12 (2021) 1–9. doi: 10.1038/s41467-020-20314-w
37. [37]
  S.Y. Tao, S.Y. Lu, Y.J. Geng, et al., Angew. Chem. Int. Ed. 57 (2018) 2393–2398. doi: 10.1002/anie.201712662
38. [38]
  Y.B. Song, S.J. Zhu, J.R. Shao, B. Yang, J. Polym. Sci. Pol. Chem. 55 (2017) 610–615. doi: 10.1002/pola.28416
39. [39]
  S.Y. Tao, S.Y. Lu, Y.J. Geng, et al., Angew. Chem. Int. Ed. 57 (2018) 2393–2398. doi: 10.1002/anie.201712662
40. [40]
  W.Q. Gao, W.J. Wang, X.Y. Dong, Y. Sun, Small 16 (2020) 2002804. doi: 10.1002/smll.202002804
41. [41]
  Y.J. Jiang, M. Lin, T. Yang, et al., J. Mater. Chem. B 7 (2019) 2074–2080. doi: 10.1039/C8TB02998A
42. [42]
  M.X. Liu, S. Chen, N. Ding, Y.L. Yu, J.H. Wang, Chem. Commun. 56 (2020) 3050–3053. doi: 10.1039/C9CC10016D
43. [43]
  J.H. Liu, D.Y. Li, J.H. He, et al., ACS Appl. Mater. Interfaces 12 (2020) 4815–4820. doi: 10.1021/acsami.9b18934
44. [44]
  H. Liu, X. Geng, X. Wang, L. Wei, Z. Li, S. Lin, L. Xiao, CCS Chem. 3 (2021) 3081–3093.
45. [45]
  Z. Ye, X. Geng, L. Wei, Z. Li, S. Lin, L. Xiao, ACS Nano 15 (2021) 934–943. doi: 10.1021/acsnano.0c07555
46. [46]
  Z. Ye, L. Wei, X. Geng, X. Wang, Z. Li, L. Xiao, ACS Nano 13 (2019) 11593–11602. doi: 10.1021/acsnano.9b05354
47. [47]
  Z. Huo, G. Chen, Y. Geng, et al., Nanoscale 12 (2020) 9094–9103. doi: 10.1039/D0NR01543A
48. [48]
  E.B. Kang, J.E. Lee, Z.A.I. Mazrad, et al., Nanoscale 10 (2018) 2512–2523. doi: 10.1039/C7NR07900A
49. [49]
  R. Wang, W. Gu, Z. Liu, et al., ACS Omega 6 (2021) 32888–32895. doi: 10.1021/acsomega.1c04808
50. [50]
  Z.P. Huo, G. Chen, Y.J. Geng, et al., Nanoscale 12 (2020) 9094–9103. doi: 10.1039/D0NR01543A
51. [51]
  J.J. Liu, D.W. Li, K. Zhang, et al., Small 14 (2018) 1703919. doi: 10.1002/smll.201703919
52. [52]
  X.H. Zhao, Q.L. Tang, S.J. Zhu, et al., Nanoscale 11 (2019) 9526–9532. doi: 10.1039/C9NR01118H
53. [53]
  C. Liu, Y.Z. Jin, R.J. Wang, et al., iScience 23 (2020) 101546. doi: 10.1016/j.isci.2020.101546
54. [54]
  C. Dong, M.S. Xu, J.H. Huang, et al., ACS Appl. Nano Mater. 3 (2020) 10560–10564. doi: 10.1021/acsanm.0c02244
55. [55]
  F. Li, X. Wang, W. Liu, L.Q. Wang, G.Y. Wang, Opt. Mater. 86 (2018) 79–86. doi: 10.1016/j.optmat.2018.09.040
56. [56]
  T.L. Feng, S.J. Zhu, Q.S. Zeng, et al., ACS Appl. Mater. Interfaces 10 (2017) 12262–12277.
57. [57]
  S.Y. Lu, L.Z. Sui, M. Wu, et al., Adv. Sci. 6 (2019) 1801192. doi: 10.1002/advs.201801192
58. [58]
  C. Guo, Q.Q. Nie, S.Y. Xu, L.Y. Wang, Anal. Chem. 93 (2021) 13880–13885. doi: 10.1021/acs.analchem.1c02661
59. [59]
  B. Liu, Z. Chen, B. Chu, et al., Adv. Photonics Res. 2 (2021) 2000161. doi: 10.1002/adpr.202000161
1. [1]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
2. [2]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
3. [3]
  Xu Qu , Pengzhao Wu , Kaixuan Duan , Guangwei Wang , Liang-Liang Gao , Yuan Guo , Jianjian Zhang , Donglei Shi . Self-calibrating probes constructed on a unique dual-emissive fluorescence platform for the precise tracking of cellular senescence. Chinese Chemical Letters, 2024, 35(12): 109681-. doi: 10.1016/j.cclet.2024.109681
4. [4]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
5. [5]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
6. [6]
  Jianye Kang , Xinyu Yang , Xuhao Yang , Jiahui Sun , Yuhang Liu , Shutao Wang , Wenlong Song . Carbon dots-enhanced pH-responsive lubricating hydrogel based on reversible dynamic covalent bondings. Chinese Chemical Letters, 2024, 35(5): 109297-. doi: 10.1016/j.cclet.2023.109297
7. [7]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
8. [8]
  Donghui Wu , Qilin Zhao , Jian Sun , Xiurong Yang . Corrigendum to 'Fluorescence immunoassay based on alkaline phosphatase-induced in situ generation of fluorescent non-conjugated polymer dots' [Chin. Chem. Lett. 34 (2023) 107672]. Chinese Chemical Letters, 2024, 35(12): 109881-. doi: 10.1016/j.cclet.2024.109881
9. [9]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
10. [10]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
11. [11]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
12. [12]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
13. [13]
  Zhihui Zhang , Ru Sun , Chong Bian , Hongbo Wang , Zhen Zhao , Panpan Lv , Jianzhong Lu , Haixin Zhang , Hulie Zeng , Yuanyuan Chen , Zhijuan Cao . A dual-protease-triggered chemiluminescent probe for precise tumor imaging. Chinese Chemical Letters, 2025, 36(2): 109784-. doi: 10.1016/j.cclet.2024.109784
14. [14]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
15. [15]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
16. [16]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
17. [17]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
18. [18]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
19. [19]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778
20. [20]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1127)
HTML views(28)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142