Citation: Yang-Yang Huang, Meng-Jia Wang, Zheng Yang, Meng-Yao She, Shu Wang, Ping Liu, Jian-Li Li, Zhen Shi. High effi cient probes with Schiff base functional receptors for hypochlorite sensing under physiological conditions[J]. Chinese Chemical Letters, ;2014, 25(7): 1077-1081. doi: 10.1016/j.cclet.2014.05.011 shu

High effi cient probes with Schiff base functional receptors for hypochlorite sensing under physiological conditions

1.
Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, China

Corresponding author: Ping Liu, Jian-Li Li,
Received Date: 18 March 2014
Available Online: 22 April 2014
Fund Project: the Northwest University Science Foundation for Postgraduate Students (Nos. YZZ12030, YZZ13042) (No. 2012JQ2007) and the Chinese National Innovation Experiment Program for University Students (No. 201210697011). (Nos. YZZ12030, YZZ13042)

A series of novel and convenient fluorescent probes with Schiff base functionality were presented for direct detection of OCl^- via the irreversible OCl^--promoted oxidation and hydrolyzation reaction in formation of the ring-opened product, fluorescein. Prominent high sensitivity, selectivity and antiinterference OCl^--induced fluorescence and color change over a wide range of tested metal ions performance were observed for each probe under physiological conditions, thus making the probes well suitable for sensing of OCl^-in living cells.
- Fluorescent probe,
- Schiff base,
- Hypochlorite,
- Cinnamyl aldehyde,
- Cell imaging
1. [1]
  [1] (a) M. Vendrell, D.T. Zhai, J.C. Er, Y. Chang, Combinatorial strategies in fluorescent probe development, Chem. Rev. 112 (2012) 4391-4420; (b) Y.Y. Huang, M.J. Wang, M.Y. She, et al., Recent progress in the fluorescent probe based on spiro ring opening of xanthenes and related derivatives, Chin. J. Org. Chem. 34 (2014) 1-25; (c) L. Chen, Q. Zhao, X.Y. Zhang, G.H. Tao, Determination of silver ion based on the redshift of emission wavelength of quantum dots functionalized with rhodanine, Chin. Chem. Lett. 25 (2014) 261-264; (d) Q. Liu, L. Xue, D.J. Zhu, et al., Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells, Chin. Chem. Lett. 25 (2014) 19-23.
2. [2]
  [2] (a) H. Woo, S. Cho, Y. Han, et al., Synthetic control over photoinduced electron transfer in phosphorescence zinc sensors, J. Am. Chem. Soc. 135 (2013) 4771-4787; (b) X.Y. Qu, C.J. Li, H.C. Chen, A red fluorescent turn-on probe for hydrogen sulfide and its application in living cells, Chem. Commun. 49 (2013) 7510-7512; (c) M.Z. Tian, L.B. Liu, Y.J. Li, et al., An unusual OFF-ON fluorescence sensor for detecting mercury ions in aqueous media and living cells, Chem. Commun. 50 (2014) 2055-2057; (d) W.T. Yin, H. Cui, Z. Yang, et al., Facile synthesis and characterization of rhodamine-based colorimetric and off-on fluorescent chemosensor for Fe³⁺, Sens. Actuators B: Chem. 157 (2011) 675-680; (e) M.Y. She, Z. Yang, B. Yin, et al., A novel rhodamine-based fluorescent and colorimetric "off-on" chemosensor and investigation of the recognizing behavior towards Fe³⁺, Dyes Pigments 92 (2012) 1337-1343; (f) Q. Liu, G.P. Li, D.J. Zhu, et al., Design of quinolone-based fluorescent probe for the ratiometric detection of cadmium in aqueous media, Chin. Chem. Lett. 24 (2013) 479-482.
3. [3]
  [3] (a) Z.Q. Guo, S. Park, J. Yoon, I. Shin, Recent progress in the development of nearinfrared fluorescent probes for bioimaging applications, Chem. Soc. Rev. 43 (2014) 16-29; (b) Z. Yang, L.K. Hao, B. Yin, et al., Six-membered spirocycle triggered probe for visualizing Hg²⁺ in living cells and bacteria-EPS-mineral aggregates, Org. Lett. 15 (2013) 4334-4337; (b) Z. Yang, L.K. Hao, B. Yin, et al., Six-membered spirocycle triggered probe for visualizing Hg²⁺ in living cells and bacteria-EPS-mineral aggregates, Org. Lett. 15 (2013) 4334-4337.
4. [4]
  [4] V. Dujols, F. Ford, A.W. Czarnik, A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water, J. Am. Chem. Soc. 119 (1997) 7386-7387.
5. [5]
  [5] H.N. Kim, M.H. Lee, H.J. Kim, et al., A new trend in rhodamine based chemosensors: application of spirolactam ring-opening to sensing ions, Chem. Soc. Rev. 37 (2008) 1465-1472.
6. [6]
  [6] X.Q. Chen, T. Pradhan, F. Wang, et al., Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives, Chem. Rev. 112 (2012) 1910-1956.
7. [7]
  [7] X.H. Li, X.H. Gao, W. Shi, H.M. Ma, Design strategies for water-soluble small molecular chromogenic and fluorogenic probes, Chem. Rev. 114 (2014) 590-659.
8. [8]
  [8] (a) S. Kundu, P. Ghosh, S. Datta, et al., Oxidative stress as a potential biomarker for determining disease activity in patients with rheumatoid arthritis, Free Radical Res. 46 (2012) 1482-1489; (b) D.M. Tabima, S. Frizzell, M.T. Gladwin, Reactive oxygen and nitrogen species in pulmonary hypertension, Free Radical Biol. Med. 2 (2012) 51970-51986.
9. [9]
  [9] M.J. Gray, W.Y. Wholey, U. Jakob, Bacterial responses to reactive chlorine species, Annu. Rev. Microbiol. 67 (2013) 141-160.
10. [10]
  [10] (a) M.R. Ramsey, N.E. Sharpless, ROS as a tumor suppressor? Nat. Cell Biol. 8 (2006) 1213-1215; (b) C. Nussbaum, A. Klinke, M. Adam, et al., Myeloperoxidase: a leukocytederived protagonist of inflammation and cardiovascular disease, Antioxid. Redox Sign. 18 (2013) 692-713.
11. [11]
  [11] (a) Q.L. Xu, K. Lee, S. Lee, et al., A highly specific fluorescent probe for hypochlorous acid and its application in imaging microbe-induced HOCl production, J. Am. Chem. Soc. 135 (2013) 9944-9949; (b) X.J. Wu, Z. Li, L. Yang, et al., A self-referenced nanodosimeter for reaction based ratiometric imaging of hypochlorous acid in living cells, Chem. Sci. 4 (2013) 460-467; (c) M. Emrullahoğlu, M. Üçüncü, E. Karakus, A BODIPY aldoxime-based chemodosimeter for highly selective and rapid detection of hypochlorous acid, Chem. Commun. 49 (2013) 7836-7838; (c) M. Emrullahoğlu, M. Ü çüncü, E. Karakus, A BODIPY aldoxime-based chemodosimeter for highly selective and rapid detection of hypochlorous acid, Chem. Commun. 49 (2013) 7836-7838.
12. [12]
  [12] L. Yuan, W.Y. Lin, Z.M. Cao, L.L. Long, J.Z. Song, Photocontrollable analyte-responsive fluorescent probes: a photocaged copper-responsive fluorescence turn-on probe, Chem. Eur. J. 17 (2011) 689-696.
13. [13]
  [13] (a) Z. Yang, M.Y. She, J. Zhang, et al., Highly sensitive and selective rhodamine Schiff base "off-on" chemosensors for Cu²⁺ imaging in living cells, Sens. Actuators B: Chem. 176 (2013) 482-487; (b) Z. Yang, M.Y. She, B. Yin, et al., Three rhodamine-based "off-on" chemosensors with high selectivity and sensitivity for Fe³⁺ imaging in living cells, J. Org. Chem. 77 (2012) 1143-1147.
14. [14]
  [14] (a) X.Q. Chen, X.C. Wang, S.J. Wang, et al., A highly selective and sensitive fluorescence probe for the hypochlorite anion, Chem. Eur. J. 14 (2008) 4719-4724; (b) G.W. Chen, F.L. Song, J.Y. Wang, et al., FRET spectral unmixing: a ratiometric fluorescent nanoprobe for hypochlorite, Chem. Commun. 48 (2012) 2949-2951.
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沈阳化工大学材料科学与工程学院沈阳 110142