A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging

doi:10.6023/cjoc202008005

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 719-725.DOI: 10.6023/cjoc202008005 Previous Articles Next Articles

Article

基于萘酰亚胺的次氯酸荧光探针的合成及细胞成像性能研究

王欣宇^a^,^c, 戚少龙^a^,^c, 杜建时^a^,^c^,^*(), 李强^b^,^c, 祝录宝^b^,^c,
薛龙启^b^,^c, 赵晴^a^,^d, 杨清彪^b^,^c^,^*(), 李耀先^b, 丛宪玲^a

a 吉林大学中日联谊医院长春 130033
b 吉林大学化学学院长春 130061
c 吉林大学中日联谊医院吉林省淋巴外科重点实验室吉林省淋巴外科工程实验室长春 130033
d 吉林大学中日联谊医院吉林省记忆与认知障碍疾病工程实验室长春 130031

收稿日期:2020-08-06 修回日期:2020-09-01 发布日期:2020-09-22
通讯作者: 杜建时, 杨清彪
作者简介:
* Corresponding authors. E-mail: dujs@jlu.edu.cn; yangqb@jlu.edu.cn
† 共同第一作者(These authors contributed equally to this work).
基金资助:
吉林省重点实验室建设项目(20190901002JC); 吉林省自然科学基金(20200201169JC); 吉林省创新能力建设(2019C007)

A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging

Xinyu Wang^a^,^c, Shaolong Qi^a^,^c, Jianshi Du^a^,^c^,^*(), Qiang Li^b^,^c, Lubao Zhu^b^,^c, Longqi Xue^b^,^c, Qing Zhao^a^,^d, Qingbiao Yang^b^,^c^,^*(), Yaoxian Li^b, Xianling Cong^a

a China-Japan Union Hospital of Jilin University, Changchun 130061
b College of Chemistry, Jilin University, Changchun 130061
c Key Laboratory of Lymphatic Surgery Jilin Province, Engineering Laboratory of Lymphatic Surgery Jilin Province, China-Japan Union Hospital of Jilin University, Changchun 130031
d Engineering Laboratory of Memory and Cognitive Impairment Disease Jilin Province, China-Japan Union Hospital of Jilin University, Changchun 130031

Received:2020-08-06 Revised:2020-09-01 Published:2020-09-22
Contact: Jianshi Du, Qingbiao Yang
Supported by:
the Key Laboratory Construction Project of Jilin Province(20190901002JC); the Natural Science Foundation of Jilin Province(20200201169JC); the Innovation Building Projects of Jilin Province(2019C007)

1. cjoc202008005.pdf(453KB)

Abstract

A novel naphthalimide-based fluorescence probe ethyl (E)-3-(2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo- [de]isoquinolin-5-yl)-2-cyanoacrylate (NAEC) containing C=C double bond group with intramolecular charge transfer (ICT) effect for hypochloric acid detection was synthesized, which could selectively and sensitively respond to hypochloric acid within 10 s in phosphate buffer saline (PBS) buffer solution [N,N-dimethylformamide (DMF)/PBS (V∶V=1∶19), pH=7.4]. The mechanism is that the C=C double bond in the probe can be oxidized and turned to aldehyde group, then the original ICT effect of probe is destroyed, and the fluorescence of naphthalimide restores. The spectroscopic properties of the probe NAEC towards ClO^– were studied through UV-vis absorption and ?uorescence emission spectroscopies. The results showed that the probe NAEC possessed a large pseudo Stokes shift (100 nm) and the limit of detection (LOD) for NAEC has been estimated to be 2.4 nmol/L. In addition, the probe exhibited good response and anti-interference performance for hypochloric acid in the presence of 22 kinds of interferences, such as other reactive oxygen, small molecule biosulphol and common anions. And probe NAEC exhibited good cell permeability and was successfully applied in living cells by fluorescence imaging. The method is expected to be extended to the diagnosis of diseases and the detection in environmental samples, etc.

Key words: naphthalimide, hypochlorous acid, fluorescence probe, cellular imaging

Cite this article

Xinyu Wang, Shaolong Qi, Jianshi Du, Qiang Li, Lubao Zhu, Longqi Xue, Qing Zhao, Qingbiao Yang, Yaoxian Li, Xianling Cong. A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 719-725.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

Scheme 1. Synthetic route of the probe NAEC

Figure 1. (A) Fluorescence spectra of NAEC (5.0×10–6 mol/L) before (a) and after (b) addition of ClO– in different pH conditions [DMF/PBS (V∶V=1∶19), λex=420 nm, λ em=520 nm, slit: 5/5 nm] and (B) time-dependent fluorescence intensity changes of NAEC (5.0×10–6 mol/L) after addition of ClO– [DMF/PBS (V∶V=1∶19), pH=7.4, λex=420 nm, λ em=520 nm, slit: 5/5 nm]

. Insert: emission color changes of probe NAEC (5.0×10–6 mol/L) before and after addition of ClO– (9 equiv.) under a 365 nm light

Figure 3. (A) Fluorescence spectra of probe NAEC (5.0×10–6 mol/L) upon addition of different concentrations of ClO– (0~9 equiv.) [DMF/PBS (V∶V=1∶19), pH=7.4, λex=420 nm, slit: 5/5 nm] and (B) Linear fit curve of fluorescence intensity of NAEC vs ClO– concentration [DMF/PBS (V∶V=1∶19), pH=7.4, λex=420 nm, λ em=520 nm, slit: 5/5 nm]

Figure 4. Variation in the fluorescence of NAEC (5.0×10–6 mol/L) before and after adding 9 equiv. ClO– in the presence of 90 equiv. of various interferents [DMF/PBS (V∶V=1∶19), pH=7.4]

Figure 5. (A) Fluorescence spectra of molecule 4 and NAEC and (B) proposed reaction mechanism of probe NAEC towards ClO–

Figure 6. Viability of HUVEC cell after incubated with probes NAEC by methyl thiazolyl tetrazolium (MTT) method (C represents control sample,, and the viability is 100%)

Figure 7. Optical confocus microscopic images of HUVEC cells incubated 30 min with the NAEC probe (5.0×10–6 mol/L) (A, B, C); pretreated for 2 h with PMA (1 mg/mL) and incubated with the NAEC probe (5.0×10–6 mol/L) for 30 min (D, E, F) and incubated 30 min with the NAEC probe (5.0×10–6 mol/L), followed by treatment with 9.0 equiv. ClO– for another 30 min (G, H, I) (left: fluorescence images, middle: bright-field images, right: merge images)

References 21

[1]	Rutala W.A; Weber D.J. Clin. Microbiol. Rev. 1997, 10, 597. pmid: 9336664
[2]	Ye Z.; Zhang R.; Song B.; Dai Z.; Jin D.; Goldys E.M.; Yuan J. Dalton Trans. 2014, 43, 8414. doi: 10.1039/c4dt00179f
[3]	Sultana S.; Foti A.; Dahl J.U. Infect. Immun. 2020, 88, e00964- 19.
[4]	Aiken M.L.; Painter R.G.; Zhou Y.; Wang G. Free Radicals Biol. Med. 2012, 53, 2308. doi: 10.1016/j.freeradbiomed.2012.10.542
[5]	Wu Y.; Wang J.; Zeng F.; Huang S.; Huang J.; Xie H.; Yu C.; Wu S. ACS Appl. Mater. Interfaces 2016, 8, 1511. doi: 10.1021/acsami.5b11023
[6]	Guo B.; Nie H.; Yang W.; Tian Y.; Jing J.; Zhang X. Sens. Actuators, B 2016, 236, 459. doi: 10.1016/j.snb.2016.06.004
[7]	Yuan L.; Wang L.; Agrawalla B.K.; Park S.J.; Zhu H.; Sivaraman B.; Peng J.; Xu Q.H.; Chang Y.T. J. Am. Chem. Soc. 2015, 137, 5930. doi: 10.1021/jacs.5b00042
[8]	Shi D.; Chen S.; Dong B.; Zhang Y.; Sheng C.; James T.D.; Guo Y. Chem. Sci. 2019, 10, 3715. doi: 10.1039/C9SC00180H
[9]	Xing P.; Zhang Z.; Niu Y.; Qi Y.; Dong L.; Wang C. Chem. Commun. 2018, 54, 9889. doi: 10.1039/C8CC04631J
[10]	Pak Y.L.; Park S.J.; Wu D.; Cheon B.; Kim H.M.; Bouffard J.; Yoon J. Angew. Chem., Int. Ed. 2018, 57, 1567. doi: 10.1002/anie.v57.6
[11]	Liu S.; Yang D.; Liu Y.; Pan H.; Chen H.; Qu X.; Li H. Sens. Actuators, B 2019, 299, 126937. doi: 10.1016/j.snb.2019.126937
[12]	Wang J.; Guo J.; Dou L.; Wang R.; Song Y.; Yang Q.; Du J.; Li Y. Chem. Res. Chin. Univ. 2019, 35, 570. doi: 10.1007/s40242-019-9109-2
[13]	Wang J.J.; Qi S.L.; Du J.S.; Yang Q.B.; Song Y.; Li Y.X. Chem. J. Chin. Univ. 2019, 40, 1397. (in Chinese)
	王金金, 戚少龙, 杜建时, 杨清彪, 宋岩, 李耀先, 高学校化学学报 2019, 40, 1397.).
[14]	Cheng G.; Fan J.; Sun W.; Sui K.; Jin X.; Wang J.; Peng X. Analyst 2013, 138, 6091. doi: 10.1039/c3an01152f
[15]	Duan C.; Won M.; Verwilst P.; Xu J.; Kim H.S.; Zeng L.; Kim J.S. Anal. Chem. 2019, 91, 4172. doi: 10.1021/acs.analchem.9b00224
[16]	Yao S.F.; Yao Y.S.; Zheng W.B.; Ye C.Z.; Ying J.; Lü G.L.; Li C.X. Chin. J. Lumin. 2020, 41, 791. (in Chinese)
	姚书帆, 尧雨斯, 郑武斌, 叶晨喆, 应杰, 吕光磊, 李春霞, 发光学报, 2020, 41, 791.).
[17]	Xiong H.; He L.; Zhang Y.; Wang J.; Song X.; Yang Z. Chin. Chem. Lett. 2019, 30, 1075. doi: 10.1016/j.cclet.2019.02.008
[18]	Setsukinai K.; Urano Y.; Kakinuma K.; Majima H.J.; Nagano T. J. Biol. Chem. 2003, 278, 3170. pmid: 12419811
[19]	Gampp H.; Lippard S.J. Inorg. Chem. 1983, 22, 357. doi: 10.1021/ic00144a033
[20]	Yang Y.-K.; Cho H.J.; Lee J.; Shin I.; Tae J. Org. Lett. 2009, 11, 859. doi: 10.1021/ol802822t
[21]	Qi S.L.; Du J.S.; Li R.H.; Li Q.; Zhu L.B.; Shi Y.N.; Wang X.Y.; Yang Q.B.; Zhang G.R.; Li Y.X. Chin. J. Anal. Chem. 2020, 48, 347. (in Chinese)
	戚少龙, 杜建时, 李容杭, 李强, 祝录宝, 时亚男, 王欣宇, 杨清彪, 张桂荣, 李耀先, 分析化学, 2020, 48, 347.).

基于萘酰亚胺的次氯酸荧光探针的合成及细胞成像性能研究

A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 21

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	Wu Zhou, Min Peng, Qingxiang Liang, Aibin Wu, Wenming Shu, Weichu Yu. A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4277-4283.
[3]	Siyi Zhou, Xu Ding, Yongmei Zhao, Jinghua Li, Wen Luo. A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 178-185.
[4]	Chuntian Shi, Mei Yu, Aibin Wu, Jiangxiong Luo, Xiaojun Li, Ningchen Wang, Wenming Shu, Weichu Yu. A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2806-2813.
[5]	Huixu Lu, Yonghe Tang, Hongmei Zhou, Weiying Lin. Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1163-1169.
[6]	Yongmei Zhao, Yeshu Mu, Wen Luo, Zhiyong Tian. Synthesis of Naphthalimide Derivatives as Cholinesterase Inhibitors with Aggregation Induced Emission Properties [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 819-829.
[7]	Pengpeng Xia, Jiangtai Chen, Gaofan Shi, Mengmeng Zhang, Wanchen Yao, Xiangde Lin, Dongdong Zeng. Research Progress of Naphthalimide Derivatives Optical Probes for Monitoring Physical and Chemical Properties of Microenvironment and Active Sulfur Substances [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3620-3639.
[8]	Yun Zhao, Yanfang Li, Rongxiao Li, Yaqing Wang, Xiaoxia Fan. A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1974-1981.
[9]	Ruixue Rong, Jimin Li, Yaowen Li, Xiaoyu Guo, Chong Wang, Yanjun Li, Jinmei Li, Baojun Han, Zhiran Cao, Kerang Wang, Xiaoliu Li. Synthesis and Anti-tumor Effects of Naphthalimide Derivatives Targeted in Cell Nucleus [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1599-1606.
[10]	Enqing Chen, Yonghe Tang, Lei Wang, Jiangbo Ren, Weiying Lin. Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1200-1206.
[11]	Yu Qing, Chen Xiaoli, Liu Hua, Zhang Qilong. Recent Progress in Colorimetric and Fluorimetric Probes for the Detection of Hypochlorous Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1206-1231.
[12]	Chen Yu, Bi Keying, Hao Ruiting, Xie Ping, Huang Lina, Wang Yumin, Zhang Junfeng, Xu Rui, Wu Xianghua. Near-Infrared Ratiometric Fluorescent Probe for Detection of Peroxynitrite in HeLa Cells Based on Dicyanomethylene-4H-pyran Coumarin System [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 511-515.
[13]	Wang Ruixianga, Lai Xiaojinga, Qiu Guanyinsheng, Liu Jinbiao. Recent Advances in Reaction-Based Excited State Intramolecular Proton Transfer (ESIPT) Fluorescence Probe [J]. Chin. J. Org. Chem., 2019, 39(4): 952-960.
[14]	Jiao Chunpeng, Liu Yuanyuan, Lu Wenjuan, Zhang Pingping, Wang Yanfeng. Molecular Fluorescence Probe for Detecting Reactive Nitrogen/Reactive Oxygen [J]. Chin. J. Org. Chem., 2019, 39(3): 591-616.
[15]	Wang Yafei, Zhang Tao, Guo Xudong, Hu Rui, Wang Shuangqing, Yang Guoqiang. Preparation of Hydrophobic SiO₂ Aerogel by Rapid Solvents Exchange Method and Its Application Loaded with Organic Fluorescence Probe [J]. Chin. J. Org. Chem., 2019, 39(2): 550-554.