Communication
ChemComm
with APAP show a significant decrease of fluorescence with Notes and references
time, suggesting that Gal-NIR is capable of monitoring ONOOÀ
1 (a) A. Srivastava, J. L. Maggs, D. J. Antoine, D. P. Williams, D. A. Smith
and B. K. Park, Handb. Exp. Pharmacol., 2010, 196, 165–194;
(b) M. Holt and C. Ju, Handb. Exp. Pharmacol., 2010, 196, 3–27.
2 (a) L. Yuan and N. Kaplowitz, Clin. Liver Dis., 2013, 17, 507–518;
(b) W. Bernal and J. Wendon, N. Engl. J. Med., 2013, 369, 2525–2534.
3 Y. Zhou, L. Yang, Z. Liao, X. He, Y. Zhou and H. Guo, Eur. J.
Gastroenterol. Hepatol., 2013, 25, 825–829.
4 (a) P. Pacher, J. S. Beckman and L. Liaudet, Physiol. Rev., 2007, 87, 315–424;
(b) G. Ferrer-Sueta and R. Radi, ACS Chem. Biol., 2009, 4, 161–177.
5 (a) P. B. Watkins, Therapy, 2010, 7, 367–375; (b) C. Cover,
A. Mansouri, T. R. Knight, M. L. Bajt, J. J. Lemasters, D. Pessayre
and H. Jaeschke, J. Pharmacol. Exp. Ther., 2005, 315, 879–887.
6 (a) S. Xu, H.-W. Liu, X. Yin, L. Yuan, S.-Y. Huan and X.-B. Zhang,
Chem. Sci., 2019, 10, 320–325; (b) D. Cheng, J. Peng, Y. Lv, D. Su,
D. Liu, M. L. Yuan and X. Zhang, J. Am. Chem. Soc., 2019, 141,
6352–6361; (c) C.-X. Yin, K.-M. Xiong, F.-J. Huo, J. C. Salamanca and
R. M. Strongin, Angew. Chem., Int. Ed., 2017, 56, 13188–13198;
(d) A. Shao, Y. Xie, S. Zhu, Z. Guo, S. Zhu, J. Guo, P. Shi,
T. D. James, H. Tian and W.-H. Zhu, Angew. Chem., Int. Ed., 2015,
54, 7275–7280; (e) X. Han, X. Song, F. Yu and L. Chen, Adv. Funct.
Mater., 2017, 27, 1700769; ( f ) W. Feng, S. Feng and G. Feng, Anal.
Chem., 2019, 91, 8602–8606; (g) X. Li, X. Gao, W. Shi and H. Ma,
Chem. Rev., 2013, 114, 590–659; (h) M. H. Lee, J. S. Kim and
J. L. Sessler, Chem. Soc. Rev., 2015, 44, 4185–4191.
7 (a) H. Li, X. Li, X. Wu, W. Shi and H. Ma, Anal. Chem., 2017, 89,
5519–5525; (b) X. Li, J. Hou, C. Peng, L. Chen, W. Liu and Y. Liu, RSC
Adv., 2017, 7, 34287–34292; (c) H. Zhang, J. Liu, C. Liu, P. Yu, M. Sun,
X. Yan, J.-P. Guo and W. Guo, Biomaterials, 2017, 133, 60–69;
(d) D. Li, J. Cheng, C.-K. Wang, H. Ying, Y. Hu, F. Han and X. Li,
Chem. Commun., 2018, 54, 8170–8173; (e) H. Zhang, J. Liu, Y.-Q. Sun,
Y. Huo, Y. Li, W. Liu, X. Wu, N. Zhu, Y. Shi and W. Guo, Chem.
Commun., 2015, 51, 2721–2724; ( f ) X. Jia, Q. Chen, Y. Yang, Y. Tang,
R. Wang, Y. Xu, W. Zhu and X. Qian, J. Am. Chem. Soc., 2016, 138,
10778–10781; (g) Z. Li, S.-H. Yan, C. Chen, Z.-R. Geng, J.-Y. Chang,
C.-X. Chen, B.-H. Huang and Z.-L. Wang, Biosens. Bioelectron., 2017,
90, 75–82; (h) J. Peng, A. Samanta, X. Zeng, S. Han, L. Wang, D. Su,
D. B. Loong, N.-Y. Kang, S.-J. Park, A. All, W. Jiang, L. Yuan, X. Liu
and Y.-T. Chang, Angew. Chem., Int. Ed., 2017, 56, 4165–4169.
8 (a) A. M. Pujol, M. Cuillel, O. Renaudet, C. Lebrun, P. Charbonnier,
D. Cassio, C. Gateau, P. Dumy, E. Mintz and P. Delangle, J. Am.
Chem. Soc., 2010, 133, 286–296; (b) H.-L. Zhang, Y. Zang, J. Xie, J. Li,
G.-R. Chen, X.-P. He and H. Tian, Sci. Rep., 2014, 4, 5513; (c) Z. Li,
S.-S. Deng, Y. Zang, Z. Gu, X.-P. He, G.-R. Chen, K. Chen, T. D. James,
J. Li and Y.-T. Long, Sci. Rep., 2013, 4, 2293.
9 (a) Q. Duan, P. Jia, Z. Zhuang, C. Liu, X. Zhang, Z. Wang, W. Sheng,
Z. Li, H. Zhu, B. Zhu and X. Zhang, Anal. Chem., 2019, 91,
2163–2168; (b) D.-T. Shi, D. Zhou, Y. Zang, J. Li, G.-R. Chen,
T. D. James, X.-P. He and H. Tian, Chem. Commun., 2015, 51,
3653–3655; (c) P. Zhang, Y. Tian, H. Liu, J. Ren, H. Wang, R. Zeng,
Y. Long and J. Chen, Chem. Commun., 2018, 54, 7231–7234;
(d) C. Liu, Q. Duan, X. Zhang, Z. Li, P. Jia, H. Zhu, Y. Yu, Z. Wang,
B. Zhu and W. Sheng, Sens. Actuators, B, 2019, 289, 124–130.
10 (a) A. Bertolini, A. Ferrari, A. Ottani, S. Guerzoni, R. Tacchi and
S. Leone, CNS Drug Rev., 2006, 12, 250–275; (b) B. J. Anderson,
Pediatr. Anesth., 2008, 18, 915–921.
in mice with APAP-induced liver injury. And, three hepato-
protective medicines (GSH, NAC and DDB) were injected after
APAP-induced hepatotoxicity, and the obvious recovery of
fluorescence in the liver is observed. The results prove that
the three medicines could offset ONOOÀ produced by DILI.
Subsequently, the mice were sacrificed and the main organs
were recovered (Fig. 5c). The fluorescence imaging clearly
indicates that the selective localization of Gal-NIR is in the
liver over other organs including the heart, spleen, lungs and
kidney. In addition, histological analysis of liver tissues was
performed by hematoxylin and eosin (H&E) staining (Fig. 5d).
Just like the change in fluorescence, the liver tissues of mice
treated with hepatoprotective medicines are closer to the
normal state, while the vacuolization of the cells is observed
from the injured liver tissues of the APAP-injected mice. All the
above experiments confirm that Gal-NIR could not only be
hepatocyte-specific, but also be a useful indicator to monitor
the biological processes of APAP-induced hepatotoxicity and its
remediation by using the three kinds of hepatoprotective
medicines in vivo.
In conclusion, we have reported a hepatocyte-targeting NIR
fluorescent probe (Gal-NIR) for ratiometric detection of ONOOÀ.
The probe is prepared by linking a galactose moiety on a
coumarin-benzopyrylium-based fluorophore. Moreover, Gal-NIR
shows a large emission shift (220 nm), which is beneficial for
enhancing the signal-to-background ratio. Furthermore, the probe
exhibits high sensitivity for ONOOÀ with a 72-fold increasing ratio
and excellent selectivity for ONOOÀ over various potential biolo-
gical analytes. In addition, Gal-NIR can specifically target the
hepatocyte, and thus is used for assessing APAP-induced hepato-
toxicity and its remediation by using hepatoprotective medicines
in living cells and mice. These results enable the probe to be a
promising candidate for disclosing the roles of ONOOÀ in the
liver during drug-induced hepatotoxicity and its remediation.
This work was supported by the National Natural Science
Foundation of China (21775133 and 21874114), the Hunan
Provincial Natural Science Foundation (2018JJ2385), the Degree
& Postgraduate Education Reform Project of Hunan Province
(2019JGYB113) and the Degree & Postgraduate Education
Reform Project of Hunan Province (CX20190483).
11 (a) B. L. Woolbright and H. Jaeschke, J. Hepatol., 2017, 66, 836–848;
(b) M. Yan, Y. Huo, S. Yin and H. Hu, Redox Biol., 2018, 17, 274–283.
12 (a) K. de Andrade, F. Moura, J. dos Santos, O. de Arau´jo, J. de Farias
Santos and M. Goulart, Int. J. Mol. Sci., 2015, 16, 30269–30308;
(b) S. Gregory and N. D. Kelly, Altern. Med. Rev., 1998, 3, 114–127.
Conflicts of interest
There are no conflicts to declare.
14310 | Chem. Commun., 2019, 55, 14307--14310
This journal is ©The Royal Society of Chemistry 2019