Research Progress in the Fluorescent Probes for Alkaline Phosphatase

doi:10.6023/cjoc201903008

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3132-3144.DOI: 10.6023/cjoc201903008 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

碱性磷酸酶荧光探针的研究进展

张继东^a*(), 刘鸿泽^a, 孟丽^b

^a安康学院化学化工学院安康 725000
^b 中国富硒产业研究院农业农村部富硒产品开发与质量控制重点实验室安康 725000

收稿日期:2019-03-04 发布日期:2019-06-19
通讯作者: 张继东 E-mail:akuzjd@aku.edu.cn
基金资助:
陕西省科技厅重点(2018PT-31);安康市主导产业重大科研攻关(2016AKZDCY002);安康学院博士启动基金(2018AYQDZR06);农业部富硒产品开发国家地方联合工程实验室开放课题(Se-2018B02);陕西省大学生创新创业训练计划(201839032)

Research Progress in the Fluorescent Probes for Alkaline Phosphatase

Zhang Jidong^a*(), Liu Hongze^a, Meng Li^b

^a School of Chemistry & Chemical Engineering, Ankang Univerisity, Ankang 725000
^b Key Laboratory of Se-Enriched Products Development and Quality Control of Ministry of Agriculture, Se-Enriched Products Research Institute of China, Ankang 725000

Received:2019-03-04 Published:2019-06-19
Contact: Zhang Jidong E-mail:akuzjd@aku.edu.cn
Supported by:
the Key Projects of Shaanxi Provincial Science & Technology Department(2018PT-31);the Major Scientific Research Projects of the Leading Industry of Ankang City(2016AKZDCY002);the Doctor's Initial Funding of Ankang University(2018AYQDZR06);the Key Laboratory of Se-Enriched Products Development and Quality Control, Ministry of Agriculture(Se-2018B02);the Shaanxi Provincial Innovation Experiment Program for University Students(201839032)

Alkaline phosphatase (ALP) is an important enzyme for various mammalian tissues. As a biomarker and diagnostic indicator, ALP provides important information for the applied research of molecular biology and the treatment of human diseases. Due to its reliability of information in human health, the research on fluorescence detection as important detection method has become intense in recent years. The fluorescent chemosensors are categorized by different luminous feature involving excitedstate intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) chemosensors, aggregation-induced luminescent molecules (AIE), diminishes the electron donating ability (D d-E) and disruption of the π conjugated systems (D π-C), inner filter e?ect (IFE) chemosensors, and other sensing systems. In the end, the development tendency of the sensing ensembles for ALP is prospected.

Key words: alkaline phosphatase, fluorescence detection, biological imaging, aggregation-induced emission

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Zhang Jidong, Liu Hongze, Meng Li. Research Progress in the Fluorescent Probes for Alkaline Phosphatase[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3132-3144.

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Fig. & Tab. 14

Scheme 1. Mechanism of probe 2 reaction with ALP

Scheme 2. Reaction mechanism of probes 4 and 5 with ALP

Scheme 3. Mechanism of probe 10 reaction with ALP

Scheme 4. Mechanism of probe 12 reaction with ALP

Scheme 5. Mechanism of probe 13 reaction with ALP

Scheme 6. Mechanism of probe 14 reaction with ALP

Scheme 7. Mechanism of probe 19 reaction with ALP

Scheme 8. Mechanism of probe 20 reaction with ALP

Scheme 9. Mechanism of probe 21 reaction with ALP

Scheme 10. Mechanism of probe 22 reaction with ALP

Scheme 11. Mechanism of probe 24 reaction with ALP

Scheme 12. Mechanism of probe 25 reaction with ALP

Scheme 13. Mechanism of probe 26 reaction with ALP

Scheme 14. Mechanism of probe 28 reaction with ALP

References 45

[1]	ColemanJ. E. Annu. Rev. 1992, 21, 411.
[2]	ChristensonR. H. Clin. Biochem. 1997, 30, 573. doi: 10.1016/S0009-9120(97)00113-6
[3]	OoiK.; ShirakiK.; MorishitaY. J. Clin. Lab. Anal. 2007, 21, 133. doi: 10.1002/jcla.20178
[4]	WolfP. L. J. Clin. Lab. Anal. 1994, 8, 172. doi: 10.1002/jcla.1860080311
[5]	YeungM. C.-L.; YamV. W.-W. Chem. Sci. 2013, 4, 2928. doi: 10.1039/c3sc50383f
[6]	LiuY.; SchanzeK. S. Anal. Chem. 2008, 80, 8605. doi: 10.1021/ac801508y
[7]	RuanC.; WangW.; GuB. Anal. Chem. 2006, 78, 3379. doi: 10.1021/ac0522106
[8]	IqbalJ. Anal. Biochem. 2011, 414, 226. doi: 10.1016/j.ab.2011.03.021
[9]	MwiluS. K.; OkelloV. A.; OsongaF. J.; MillerS.; Sadik O. A. Analyst 2014, 139, 5472. doi: 10.1039/C4AN00931B
[10]	Yin, C.; Huo, F.; Zhang, J. Martínez-Má ez, R.; Yang, Y.; Lv, H.; Li, S. Chem. Soc. Rev. 2013, 42, 6032. doi: 10.1039/c3cs60055f
[11]	Xu, Q.; Jin, C.; Zhu, X. Chin. J. Org. Chem. 2014, 34, 647 (in Chinese). doi: 10.6023/cjoc201311043
	徐勤超, 金灿, 朱雪慧, 邢国文, 有机化学, 2014, 34, 647. doi: 10.6023/cjoc201311043
[12]	Huang, X.; Zhang, F.; Zhu, L.; Choi, K. Y.; Guo, N.; Guo, J.; Tackett, K.; Anilkumar, P.; Liu, G.; Sun, Y. P.; Lee, S.; Chen, X ACS Nano 2013, 7, 5684. doi: 10.1021/nn401911k
[13]	Wang, J.; Chu, H.; Chen, W. Chin. J. Org. Chem. 2016, 36, 2545 (in Chinese). doi: 10.6023/cjoc201605040
	王军, 初紅涛, 陈微微, 孙荣国, 有机化学, 2016, 36, 2545. doi: 10.6023/cjoc201605040
[14]	KimJ. S.; QuangD. T. Chem. Rev. 2007, 107, 3780. doi: 10.1021/cr068046j
[15]	BozdemirO. A.; GuliyevR.; BuyukcakirO.; SelcukS.; KolemenS.; GulserenG.; NalbantogluT.; BoyaciH.; AkkayaE. U. J. Am. Chem. Soc. 2010, 132, 8029. doi: 10.1021/ja1008163
[16]	HuQ.; ZengF.; YuC.; WuS. Sens. Actuators, B 2015, 220, 720. doi: 10.1016/j.snb.2015.05.111
[17]	SongZ.; KwokR. T.; ZhaoE.; HeZ.; HongY.; LamJ. W. Y.; LiuB.; TangB. Z. ACS Appl. Mater. Interfaces 2014, 6, 17245. doi: 10.1021/am505150d
[18]	KimT. I.; KimH.; ChoiY.; KimY. Chem. Commun. 2011, 47, 9825. doi: 10.1039/c1cc13819g
[19]	JiaY.; LiP.; HanK. Chem.-Asian J 2015, 10, 2444. doi: 10.1002/asia.201500280
[20]	FanC.; LuoS.; QiH. Luminescence 2016, 31, 423. doi: 10.1002/bio.2977
[21]	LuZ.; WuJ.; LiuW.; ZhangG.; WangP. RSC Adv. 2016, 6, 32046. doi: 10.1039/C6RA00983B
[22]	HongY.; LamJ. W. Y.; TangB. Z. Chem. Soc. Rev. 2011, 40, 5361. doi: 10.1039/c1cs15113d
[23]	LuoJ.; XieZ.; LamJ. W. Y.; ChengL.; ChenH.; QiuC.; KwokH. S.; ZhanX.; LiuY.; ZhuD.; TangB. Z. Chem. Commun. 2001, 1740
[24]	LiangJ.; KwokR. T.; ShiH.; TangB. Z.; LiuB. ACS Appl. Mater. Interfaces 2013, 5, 8784. doi: 10.1021/am4026517
[25]	GuX.; ZhangG.; WangZ.; LiuW.; XiaoL.; ZhangD. Analyst 2013, 138, 2427. doi: 10.1039/c3an36784c
[26]	LiuH.; LvZ.; DingK. J.; LiuX.; YuanL.; ChenH.; LiX. J. Mater. Chem. B 2013, 1, 5550. doi: 10.1039/c3tb21024c
[27]	LinM.; HuangJ.; ZengF.; WuS. Chem.-Asian J 2018, 14, 802. doi: 10.1002/asia.v14.6
[28]	ChenQ.; BianN.; CaoC.; QiuX. L.; QiA. D.; HanB. H. Chem. Commun. 2010, 46, 4067. doi: 10.1039/c002894k
[29]	ZhangW.; YangH.; LiN.; ZhaoN. RSC Adv. 2018, 8, 14995. doi: 10.1039/C8RA01786G
[30]	OwensE. A.; HenaryM.; El FakhriG.; SooC. H. Acc. Chem. Res. 2016, 49, 1731. doi: 10.1021/acs.accounts.6b00239
[31]	TanY.; ZhangL.; ManK. H.; PeltierR.; ChenG.; ZhangH.; ZhouL.; WangF.; HoD.; YaoS. Q.; HuY.; SunH. ACS Appl. Mater. Interfaces 2017, 9, 6796. doi: 10.1021/acsami.6b14176
[32]	LiS. J.; LiC. Y.; LiY. F.; FeiJ.; WuP.; YangB.; YangJ. O.; NieS. X. Anal. Chem 2017, 89, 6854. doi: 10.1021/acs.analchem.7b01351
[33]	ZhangQ.; LiS.; FuC.; XiaoY.; ZhangP. DingC. J. Mater. Chem. B 2019, 7, 443. doi: 10.1039/C8TB02799D
[34]	XuL.; HeX.; HuangY.; MaP.; JiangY.; LiuX.; TaoS.; SunY.; SongD.; WangX. J. Mater. Chem. B 2019, 7, 1284. doi: 10.1039/C8TB03230K
[35]	GaoZ.; SunJ.; GaoM.; YuF.; ChenL.; ChenQ. Sens. Actuators, B 2018, 265, 565. doi: 10.1016/j.snb.2018.03.078
[36]	FreemanR.; FinderT.; GillR.; WillnerI. Nano Lett. 2010, 10, 2192. doi: 10.1021/nl101052f
[37]	LiG.; FuH.; ChenX.; GongP.; ChenG.; XiaL.; WangH.; YouJ.; WuY. Anal. Chem. 2016, 88, 2720. doi: 10.1021/acs.analchem.5b04193
[38]	MaoG.; ZhangQ.; YangY.; JiX.; HeZ. Anal. Chim. Acta 2019, 1047, 208. doi: 10.1016/j.aca.2018.10.009
[39]	LiuH.; LiM.; XiaY.; RenX. ACS Appl. Mater. Interfaces 2017, 9, 120. doi: 10.1021/acsami.6b11920
[40]	DongL.; MiaoQ.; HaiZ.; YuanY.; LiangG. Anal. Chem. 2015, 87, 6475. doi: 10.1021/acs.analchem.5b01657
[41]	MeiY.; HuQ.; ZhouB.; ZhangY.; HeM.; XuT.; LiF.; KongJ. Talanta 2018, 176, 52. doi: 10.1016/j.talanta.2017.07.095
[42]	ZhangH.; XuC.; LiuJ.; LiX.; GuoL.; LiX. Chem. Commun. 2015, 51, 7031. doi: 10.1039/C5CC01005E
[43]	ChenJ.; JiaoH.; LiW.; LiaoD.; ZhouH.; YuC. Chem.-Asian J. 2013, 8, 8276.
[44]	HouX.; YuQ.; ZengF.; YeJ.; WuS. J. Mater. Chem. B 2015, 3, 1042. doi: 10.1039/C4TB01744G
[45]	GoraiT.; MaitraU. J. Mater. Chem. B 2018, 6, 2143. doi: 10.1039/C7TB02657A

碱性磷酸酶荧光探针的研究进展

Research Progress in the Fluorescent Probes for Alkaline Phosphatase

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