Citation: Jiakun BAI, Ting XU, Lu ZHANG, Jiang PENG, Yuqiang LI, Junhui JIA. A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002 shu

A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid

Jiakun BAI ^1,, ,
Ting XU ¹ ,
Lu ZHANG ¹ ,
Jiang PENG ¹ ,
Yuqiang LI ^2,, ,
Junhui JIA ^1,,

1.
Key Laboratory of Magnetic Molecules and Magnetic Information Material, Ministry of Education, College of Chemistry and Material Science, Shanxi Normal University, Taiyuan 030032, China
2.
School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, China

Corresponding author: Jiakun BAI, jiakun_bai@163.com Yuqiang LI, yuqiangli@nuc.edu.cn Junhui JIA, jiajunhui@sxnu.edu.cn
Received Date: 1 January 2024
Revised Date: 5 April 2024

Figures(10)

An optical probe (3) with a donor-π-acceptor (D-π-A) structure for the detection of hypochlorous acid (HClO) was synthesized by a one-step reaction. It employed a barbituric acid derivative as the electron acceptor and 4-(dimethylamino)cinnamaldehyde as the electron donor. The probe exhibited high sensitivity and selectivity for the detection of HClO, rapidly responding with distinct colorimetric and fluorescent "on-off" signals (about 15 s). The probe displayed a linear relationship between fluorescence intensity and HClO concentration, with a low detection limit (LOD) of 14 nmol·L^-1, which made it suitable for quantitative HClO detection. Moreover, the probe exhibited red light emission (628 nm) with a significant Stokes shift (158 nm) and good photostability, which provided advantages for its application in cell imaging. The proposed reaction mechanism, which was deduced from high-resolution mass spectrometry data, involved electrophilic addition and oxidative cleavage of the C=C bond by ClO^-, which led to the disruption of the probe′s D-π-A structure. Consequently, this effectively halted the intramolecular charge transfer (ICT) process of the probe. MTT cytotoxicity assays demonstrated minimal toxicity of the probe following 12, 24, and 48 h of incubation with HepG2 cells. The probe was successfully applied to living cell imaging and enabled the detection of HClO via fluorescence quenching within the living cellular milieu.
- large Stokes shift,
- hypochlorite detection,
- colorimetric and fluorescent dual-response,
- red-emitting,
- cell imaging
1. [1]
  Yang B W, Chen Y, Shi J L. Reactive oxygen species (ROS)-based nanomedicine[J]. Chem. Rev., 2019,119(8):4881-4985. doi: 10.1021/acs.chemrev.8b00626
2. [2]
  Heyne B, Ahmed S, Scaiano J C. Mechanistic studies of fluorescent sensors for the detection of reactive oxygen species[J]. Org. Biomol. Chem., 2008,6(2):354-358. doi: 10.1039/B713575K
3. [3]
  Wang S H, Han M Y, Huang D J. Nitric oxide switches on the photoluminescence of molecularly engineered quantum dots[J]. J. Am. Chem. Soc., 2009,131(33):11692-11694. doi: 10.1021/ja904824w
4. [4]
  Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T. Development of an Si-rhodamine-based far-red to near-infrared fluorescence probe selective for hypochlorous acid and its applications for biological imaging[J]. J. Am. Chem. Soc., 2011,133(15):5680-5682. doi: 10.1021/ja111470n
5. [5]
  Özyürek M, Bekdeşer B, Güçlü K, Apak R. Resorcinol as a spectrofluorometric probe for the hypochlorous acid scavenging activity assay of biological samples[J]. Anal. Chem., 2012,84(21):9529-9536. doi: 10.1021/ac302369p
6. [6]
  Xiao Y N, Zhang R, Ye Z Q, Dai Z C, An H Y, Yuan J L. Lanthanide complex-based luminescent probes for highly sensitive time-gated luminescence detection of hypochlorous acid[J]. Anal. Chem., 2012,84(24):10785-10792. doi: 10.1021/ac3028189
7. [7]
  Liu S R, Vedamalai M, Wu S P. Hypochlorous acid turn-on boron dipyrromethene probe based on oxidation of methyl phenyl sulfide[J]. Anal. Chim. Acta, 2013,800:71-76. doi: 10.1016/j.aca.2013.09.018
8. [8]
  Park J, Kim H, Choi Y, Kim Y. A ratiometric fluorescent probe based on a BODIPY-DCDHF conjugate for the detection of hypochlorous acid in living cells[J]. Analyst, 2013,138(12):3368-3371. doi: 10.1039/c3an36820c
9. [9]
  Pattison D I, Davies M J. Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: implications for the prevention of hypochlorous-acid-mediated damage[J]. Biochemistry, 2006,45(26):8152-8162. doi: 10.1021/bi060348s
10. [10]
  Ashton T D, Jolliffe K A, Pfeffer F M. Luminescent probes for the bioimaging of small anionic species in vitro and in vivo[J]. Chem. Soc. Rev., 2015,44(14):4547-4595. doi: 10.1039/C4CS00372A
11. [11]
  Zhang C, Sun Y T, Gan S, Ren A, Milaneh S, Xiang D J, Wang W L. Recent progress of organic fluorescent molecules for bioimaging applications: Cancer-relevant biomarkers[J]. J. Mater. Chem. C, 2023,11:16859-16889. doi: 10.1039/D3TC03664B
12. [12]
  Ji X T, Wang N, Wang J K, Wang T, Huang X, Hao H X. Non‑ destructive real-time monitoring and investigation of the self-assembly process using fluorescent probes[J]. Chem. Sci., 2024,15:3800-3830. doi: 10.1039/D3SC06527H
13. [13]
  Chen G, Xu J, Ma S Y, Ji X R, Carney J B. , Wang C, Gao X Y, Chen P, Fan B L, Chen J, Yue Y F, James T D[J]. Visual monitoring of biocatalytic processes using small molecular fluorescent probes: Strategies-mechanisms-applications. Chem. Commun., 2024,60:2716-2731.
14. [14]
  YU Q, CHEN X L, LIU H, ZHANG Q L. Recent progress in colorimetric and fluorimetric probes for the detection of hypochlorous acid[J]. Chin. J. Org. Chem., 2020,40(5):1206-1231.
15. [15]
  Hu J J, Wong N K, Lu M Y, Chen X M, Ye S, Zhao A Q, Gao P, Kao R Y T, Shen J G, Yang D. HKOCl-3: A fluorescent hypochlorous acid probe for live-cell and in vivo imaging and quantitative application in flow cytometry and a 96-well microplate assay[J]. Chem. Sci., 2016,7:2094-2099. doi: 10.1039/C5SC03855C
16. [16]
  Wei P, Yuan W, Xue F F, Zhou W, Li R H, Zhang D T, Yi T. Deformylation reaction-based probe for in vivo imaging of HOCl[J]. Chem. Sci., 2018,9:495-501. doi: 10.1039/C7SC03784H
17. [17]
  Chen W, Xu S, Day J J, Wang D F, Xian M. A general strategy for development of near-infrared fluorescent probes for bioimaging[J]. Angew. Chem. Int. Ed., 2017,56(52):16611-16615. doi: 10.1002/anie.201710688
18. [18]
  Bai J K, Peng J, Xu T, Bu M, Chen W, Nie Y J, Jia J H. A tetraphenylethene-based Schiff base AIEgen with a large Stokes shift as probe for highly sensitive and selective detection of aqueous Cu²⁺ ions and its application in cell imaging[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2023,290122190. doi: 10.1016/j.saa.2022.122190
19. [19]
  QIU L, JI Y F, ZHU C C, CHEN Y C, HE W J, GUO Z J. A BODIPY-derived Zn²⁺ fluorescent sensor: The enhanced ICT effect[J]. Chinese J. Inorg. Chem., 2014,30(1):169-178.
20. [20]
  LIU C, SUN H, YANG X L, HE W J. A new benzothiazole-derived pH fluorescent sensor of large Stokes shift[J]. Chinese J. Inorg. Chem., 2011,27(11):2121-2127.
21. [21]
  ZHANG G Q, YIN C X. Application of fluorescent probe based on dicyanoisophorone in detection of thiophenol[J]. Chinese J. Inorg. Chem., 2021,37(7):1245-1250.
22. [22]
  Sonkaya Ö, Soylukan C, Algi M P, Algi F. Aza-BODIPY-based fluorescent and colorimetric sensors and probes[J]. Curr. Org. Synth., 2023,20(1):20-60. doi: 10.2174/1570179419666220216123033
23. [23]
  Jiang Q, Wang Z L, Li M X, Song J, Yang Y Q, Xu X, Xu H J, Wang S F. A novel nopinone-based fluorescent probe for colorimetric and ratiometric detection of hypochlorite and its applications in water samples and living cells[J]. Analyst, 2020,145(3):1033-1040. doi: 10.1039/C9AN01981B
24. [24]
  Shafiq N, Arshad U, Zarren G, Parveen S, Javed I, Ashraf A. A comprehensive review: Bio-potential of barbituric acid and its analogues[J]. Curr. Org. Chem., 2020,24(2):129-161. doi: 10.2174/1385272824666200110094457
25. [25]
  Bhattacharyya A, Makhal S C, Guchhait N. Comparative photophysical study of differently substituted cinnamaldehyde-based chalcones: From intramolecular charge transfer to fluorogenic solvent selectivity[J]. J. Phys. Chem. A, 2019,123(30):6411-6419. doi: 10.1021/acs.jpca.9b03437
26. [26]
  Zhang Z, Fan J L, Cheng G H, Ghazali S, Du J J, Peng X J. Fluorescence completely separated ratiometric probe for HClO in lysosomes[J]. Sens. Actuator B-Chem., 2017,246:293-299. doi: 10.1016/j.snb.2017.02.081
27. [27]
  Sun M T, Yu H, Zhu H J, Ma F, Zhang S, Huang D J, Wang S H. Oxidative cleavage-based near-infrared fluorescent probe for hypochlorous acid detection and myeloperoxidase activity evaluation[J]. Anal. Chem., 2014,86(1):671-677. doi: 10.1021/ac403603r
28. [28]
  Zhang Y Y, Chen X Z, Liu X Y, Zhang X Y, Gao G, Hou S C, Wang H M. A highly selective and ultrafast near-infrared fluorescent turn-on and colorimetric probe for hypochlorite in living cells[J]. Anal. Chim. Acta, 2019,1078:135-141. doi: 10.1016/j.aca.2019.06.014
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