高选择性比率型荧光探针用于急性肺损伤中次氯酸的检测

doi:10.6023/cjoc202301003

摘要/Abstract

检测急性肺损伤中过表达的次氯酸要求荧光探针具有很高的选择性. 合成了一种羟基萘香豆素探针NaphCou, 可以高选择性比值型检测次氯酸, 响应速度快, 发射波长长(从绿色到红色变化), Stokes位移大(从107 nm到155 nm). 利用该荧光探针, 成功监测了脂多糖诱导急性肺损伤小鼠中次氯酸的浓度变化.

关键词: 急性肺损伤, 次氯酸, 荧光探针, 比值型

The fluorescent probe for the detection of overexpressed ClO^－ in acute lung injury is required to have high selectivity against other reactive species. A hydroxybenzo[g]coumarin, NaphCou, was synthesized as a ratiometric fluorescent probe to detect ClO^－ with ultra-high selectivity, a fast response, long-wavelength emissions (from green to red) and large Stokes shifts (from 107 nm to 155 nm). Using probe NaphCou as a fluorescence sensing tool, the lipopolysaccharide (LPS)-induced acute lung injury in mouse model was investigated by monitoring the hypochlorous acid concentration variation.

Key words: acute lung injury, hypochlorous acid, fluorescent probe, ratiometric measurement

引用此文

丁炳辉, 韩少辉, 熊海青, 王本花, 左伯军, 宋相志. 高选择性比率型荧光探针用于急性肺损伤中次氯酸的检测[J]. 有机化学, 2023, 43(8): 2878-2884.

Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 9

Scheme 1. Synthetic route of probe NaphCou

Scheme 2. Proposed sensing mechanism of 7-hydroxycoumarin and probe NaphCou towards ClO－ at pH 7.4

Figure 1. Absorption (a) and emission (b) spectra of probe NaphCou (10.0 μmol/L) without (black line) and with (red line) of ClO－ (120.0 μmol/L) Insets: color (a) and fluorescence (b) images of probe NaphCou (10.0 μmol/L) with/without of ClO－ (120.0 μmol/L).

Figure 2. Emission spectra (a) and the fluorescence intensity ratio (I640 nm/I507 nm) (b) of probe NaphCou (10.0 μmol/L) with ClO－ (0~12 equiv.) and parallel tests 3 times Inset: the linear relationship between the ratio of I640 nm/I507 nm and the concentration of ClO－

Figure 3. Ratio of I640 nm/I507 nm vs time after 4.0, 8.0 and 12.0 equiv. of ClO－ were added into the solution of probe NaphCou

Figure 4. (a) Emission spectra of probe NaphCou (10.0 μmol/L) with various interferential analytes. (b) The ratio of I640 nm/I507 nm of probe NaphCou (10.0 μmol/L) in response to ClO－ in the presence of other interfering analytes 1, blank; 2, HO?; 3, 1O2; 4, H2O2; 5, KO2; 6, NO?; 7, ONOO－; 8, ROO?; 9, TBHP; 10, t-BuO?; 11, $\text{O}_{\text{2}}^{}$; 12, BrO－; 13, H2S; 14, SO2.

Figure 5. Bright (the first column), fluorescence (the second and third columns) and merged (the fourth column) images of A549 cells Top row: cells incubated with probe NaphCou (10.0 μmol/L) for 30 min; bottom row: cells treated with ClO－ (120.0 μmol/L) for 30 min and then incubated with probe NaphCou (10.0 μmol/L) for 30 min. Emission was collected at 490~520 nm for the green channel and 620~650 nm for the red channel. λex=435~460 nm. Scale bar=50 μm.

Figure 6. Bright (the first column), fluorescence (the second and third columns) and merged (the fourth column) images and of zebrafish Top row: zebrafish incubated with probe NaphCou (10.0 μmol/L) for 30 min; bottom row: zebrafish treated with ClO－ (120.0 μmol/L) for 30 min and then incubated with probe NaphCou (10.0 μmol/L) for 30 min. Emission was collect at 490~520 nm for the green channel and 620~650 nm for the red channel. λex=435~460 nm. Scale bar=200 μm.

Figure 7. (A) Bright (the first column) and fluorescence (the second and third columns) images of lung histology slides of the normal (a~c) and ALI (d~f) mice treated with probe NaphCou (10.0 μmol/L) for 30 min. (B) Pathological changes of the lung tissue of normal and ALI mice (H&E staining) Scale bar=200 μm.

参考文献 11

[1]	(a) Mitchell, W. B. Paediatr. Respir. Rev. 2020, 35, 20. doi: S1526-0542(20)30089-0 pmid: 32653469
	(b) Gallelli, L.; Zhang, L. M.; Wang, T.; Fu, F. H. J. Clin. Pharmacol. 2020, 60, 815. doi: 10.1002/jcph.v60.7 pmid: 32653469
[2]	((a) Mowery, N. T.; Terzian, W. T. H.; Nelson, A. C. Curr. Prob. Surg. 2020, 57, 100777. doi: 10.1016/j.cpsurg.2020.100777
[3]	(a) Kellner, M.; Noonepalle, S.; Lu, Q.; Srivastava, A.; Zemskov, E.; Black, S. M. Adv. Exp. Med. Biol. 2017, 967, 105. pmid: 24845678
	(b) Schieber, M.; Chandel, N. S. Curr. Biol. 2014, 24, 453. doi: 10.1016/j.cub.2014.03.034 pmid: 24845678
[4]	(a) Pattison, D. I.; Davies, M. J. Biochemistry 2004, 43, 4799. pmid: 29028288
	(b) Fukuyama, T.; Martel, B. C.; Linder, K. E.; Ehling, S.; Ganchingco, J. R.; Bäumer, W. Clin. Exp. Allergy 2018, 48, 78. doi: 10.1111/cea.13045 pmid: 29028288
	(c) Rayner, B. S.; Zhang, Y. J.; Brown, B. E.; Reyes, L.; Cogger, V. C.; Hawkins, C. L. Free Radic. Biol. Med. 2018, 129, 25. doi: 10.1016/j.freeradbiomed.2018.09.001 pmid: 29028288
[5]	(a) Qin, T. Y.; Zhao, X. F.; Song, C.; Chen, S. H.; Xu, Z. Y.; Zhang, Z. X.; Lv, T. Y. Z.; Xun, Z. Q.; Liu, B.; Peng, X. J. Chem. Eng. J. 2023, 451, 139022. doi: 10.1016/j.cej.2022.139022
	(b) Luo, Z. J.; Lv, T. Y. Z.; Zhu, K. N.; Li, Y.; Wang, L.; Gooding, J. J.; Liu, G. Z.; Liu, B. Angew. Chem., Int. Ed. 2020, 59, 3131. doi: 10.1002/anie.v59.8
[6]	Zhao, Y.; Li, Y. F.; Li, R. X.; Wang, Y. Q.; Fan, X. X. Chin. J. Org. Chem. 2021, 41, 1974. (in Chinese)
	( 赵云, 李艳芳, 李蓉晓, 王雅卿, 樊晓霞, 有机化学, 2021, 41, 1974.) doi: 10.6023/cjoc202101038
[7]	(a) Yue, X. X.; Wang, J. P.; Han, J. L.; Wang, B. H.; Song, X. Z. Chem. Commun. 2020, 56, 2849. doi: 10.1039/C9CC10028H pmid: 35014335
	(b) Zang, S. P.; Kong, X. X.; Cui, J.; Su, S.; Shu, W.; Jing, J.; Zhang, X. L. J. Mater. Chem. B 2020, 8, 2660. doi: 10.1039/C9TB02919B pmid: 35014335
	(c) Zhang, Y.; Yang, H. Y.; Li, M. X.; Gong, S.; Song, J.; Wang, Z. L.; Wang, S. F. Dyes Pigm. 2022, 197, 109861. doi: 10.1016/j.dyepig.2021.109861 pmid: 35014335
	(d) Liang, L. J.; Sun, Y. M.; Liu, C.; Zeng, X. S.; Zhao, J. L. Dyes Pigm. 2021, 190, 109344. doi: 10.1016/j.dyepig.2021.109344 pmid: 35014335
	(e) Chen, Y.; Lim, J. Y.; Wu, X. H.; Heo, J. S.; Yuan, F. Y.; Zhang, J. F.; Yoon, D. W.; Ren, W. X. Dyes Pigm. 2021, 195, 109666. doi: 10.1016/j.dyepig.2021.109666 pmid: 35014335
	(f) Han, J. L.; Yang, S.; Wang, B. H.; Song, X. Z. Anal. Chem. 2021, 93, 5194. doi: 10.1021/acs.analchem.0c05266 pmid: 35014335
	(g) Lamb, B. M.; Barbas Iii, C. F. Chem. Commun. 2015, 51, 3196. doi: 10.1039/C4CC09040C pmid: 35014335
	(h) Xu, Q. L.; Lee, K. A.; Lee, S.; Lee, K. M.; Lee, W. J.; Yoon, J. J. Am. Chem. Soc. 2013, 135, 9944. doi: 10.1021/ja404649m pmid: 35014335
	(i) Xiao, H. D.; Li, J. H.; Zhao, J.; Yin, G.; Quan, Y. W.; Wang, J.; Wang, R. Y. J. Mater. Chem. B 2015, 3, 1633. doi: 10.1039/C4TB02003K pmid: 35014335
	(j) Wu, M. Y.; He, T.; Li, K.; Wu, M. B.; Huang, Z.; Yu, X. Q. Analyst 2013, 138, 3018. doi: 10.1039/c3an00172e pmid: 35014335
	(k) Han, J. L.; Liu, X. J.; Xiong, H. Q.; Wang, J. P.; Wang, B. H.; Song, X. Z.; Wang, W. Anal. Chem. 2020, 92, 5134. doi: 10.1021/acs.analchem.9b05604 pmid: 35014335
	(l) Shen, Y. M.; Liu, X.; Zhang, X. Y.; Zhang, Y. Y.; Gu, B. Spectrochim. Acta, Part A 2020, 239, 118515. doi: 10.1016/j.saa.2020.118515 pmid: 35014335
	(m) Mao, Z. Q.; Ye, M. T.; Hu, W.; Ye, X. X.; Wang, Y. Y.; Zhang, H. J.; Li, C. Y.; Liu, Z. H. Chem. Sci. 2018, 9, 6035. doi: 10.1039/C8SC01697F pmid: 35014335
	(n) Xia, Q. N.; Wang, X. Y.; Liu, Y. N.; Shen, Z. F.; Ge, Z. G.; Huang, H.; Li, X.; Wang, Y. G. Spectrochim. Acta, Part A 2020, 229, 117992. doi: 10.1016/j.saa.2019.117992 pmid: 35014335
	(o) Zhang, J.; Kan, J. F.; Sun, Y. Y.; Won, M.; Kim, J. H.; Zhang, W. F.; Zhou, J.; Qian, Z. S.; Kim, J. S. ACS Appl. Bio Mater. 2021, 4, 2080. doi: 10.1021/acsabm.0c01178 pmid: 35014335
[8]	Ge, F.; Zhu, L. Z.; Chen, H. R. J. Hazard. Mater. 2006, 133, 99. doi: 10.1016/j.jhazmat.2005.09.062
[9]	Liptak, M. D.; Gross, K. C.; Seybold, P. G.; Feldgus, S.; Shields, G. C. J. Am. Chem. Soc. 2002, 124, 6421. doi: 10.1021/ja012474j
[10]	Moriya, T. Bull. Chem. Soc. Jpn. 1988, 61, 1873. doi: 10.1246/bcsj.61.1873
[11]	Sarkar, S.; Santra, M.; Singha, S.; Jun, Y. W.; Reo, Y. J.; Kim, H. R.; Ahn, K. H. J. Mater. Chem. B 2018, 6, 4446. doi: 10.1039/C8TB01144C

[1]	张莹珍, 江丹丹, 李娟华, 王菁菁, 刘昆明, 刘晋彪. 高选择性硒代半胱氨酸荧光探针的构建策略及成像[J]. 有机化学, 2024, 44(1): 41-53.
[2]	杨维清, 葛宴兵, 陈元元, 刘萍, 付海燕, 马梦林. 1,8-萘酰亚胺衍生物的设计、合成及其对半胱氨酸的识别研究[J]. 有机化学, 2024, 44(1): 180-194.
[3]	李焕清, 陈兆华, 陈祖佳, 邱琪雯, 张又才, 陈思鸿, 汪朝阳. 基于有机小分子的汞离子荧光探针研究进展[J]. 有机化学, 2023, 43(9): 3067-3077.
[4]	刘甜甜, 张鸿鹏, 焦晓梦, 白银娟. 多信号同时检测生物硫醇荧光探针的研究进展[J]. 有机化学, 2023, 43(6): 2081-2095.
[5]	刘飞冉, 敬静, 张小玲. 细胞器靶向型半胱氨酸荧光探针研究进展[J]. 有机化学, 2023, 43(6): 2053-2067.
[6]	李宜芳, 王耀, 牛华伟, 陈秀金, 李兆周, 王永国. 线粒体靶向的二氧化硫荧光探针研究进展[J]. 有机化学, 2023, 43(6): 1952-1962.
[7]	陈志华, 胡艳, 马丽丽, 张子怡, 刘传祥. 基于氢化吡啶辅助氨基氧化策略的次氯酸根荧光探针的设计、合成及其性能研究[J]. 有机化学, 2023, 43(2): 718-724.
[8]	唐宏伟, 王超, 钟克利, 侯淑华, 汤立军, 边延江. 一种裸眼和荧光双通道快速检测Hg²⁺的探针及其多种应用[J]. 有机化学, 2023, 43(2): 712-717.
[9]	周五, 彭敏, 梁庆祥, 吴爱斌, 舒文明, 余维初. 高选择和高灵敏检测溶液和气相中硫化氢的新型萘酰亚胺类开启型荧光探针[J]. 有机化学, 2023, 43(12): 4277-4283.
[10]	马延慧, 武宇乾, 王晓旭, 高贵, 周欣. 基于1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)的近红外荧光探针研究进展[J]. 有机化学, 2023, 43(1): 94-111.
[11]	杨雅馨, 陈琳, 胡晓玲, 钟克利, 李世迪, 燕小梅, 张璟琳, 汤立军. 一种点亮型硫化氢荧光探针的合成及其在红酒和细胞中的应用[J]. 有机化学, 2023, 43(1): 308-312.
[12]	周思仪, 丁旭, 赵永梅, 李景华, 罗稳. 基于黄酮的长波长荧光探针用于检测体外和体内生物硫醇[J]. 有机化学, 2023, 43(1): 178-185.
[13]	刘梦, 黄延茹, 孙小飞, 汤立军. 一种基于“聚集诱导发光+激发态分子内质子转移”机制的苯并噻唑衍生物荧光探针及其对次氯酸根的识别[J]. 有机化学, 2023, 43(1): 345-351.
[14]	李阳阳, 孙小飞, 胡晓玲, 任源远, 钟克利, 燕小梅, 汤立军. 三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别[J]. 有机化学, 2023, 43(1): 320-325.
[15]	张继东, 颜婉琳, 胡文强, 郭典, 张大龙, 权校昕, 卜贤盼, 陈思宇. 一种具有聚集诱导发光性能的Zn²⁺荧光探针的设计合成[J]. 有机化学, 2023, 43(1): 326-331.