基于有机小分子的三磷酸腺苷荧光传感器研究进展

doi:10.6023/cjoc201905024

有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3051-3064.DOI: 10.6023/cjoc201905024 上一篇下一篇

所属专题：荧光探针-生物传感合辑；有机超分子化学合辑

综述与进展

基于有机小分子的三磷酸腺苷荧光传感器研究进展

张继东^a*(), 张俊^b, 严瞻^c, 谢娟平^c

^a 安康学院化学化工学院陕西省富硒食品质量监督检验中心陕西安康 725000
^b 西北大学化学与材料科学学院合成与天然功能分子化学教育部重点实验室西安 710127
^c 安康学院医学院陕西安康 725000

收稿日期:2019-05-12 发布日期:2019-07-17
通讯作者: 张继东 E-mail:akuzjd@aku.edu.cn
基金资助:
陕西省科技厅青年基金(2019JQ-504);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)

Recent Progress in Fluorescent Probes for Adenosine Triphosphate Based on Small Organic Molecules

Zhang Jidong^a*(), Zhang Jun^b, Yan Zhan^c, Xie Juanping^c

^a Quality Supervision and Inspection Centre of Se-enriched Food of Shaanxi Province, School of Chemistry & Chemical Engineering, Ankang Univerisity, Ankang, Shaanxi 725000
^b Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127
^c School of Medicine, Ankang Univerisity, Ankang, Shaanxi 725000

Received:2019-05-12 Published:2019-07-17
Contact: Zhang Jidong E-mail:akuzjd@aku.edu.cn
Supported by:
the Youth Foundation of Shaanxi Provincial Science & Technology Department(2019JQ-504);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)

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摘要/Abstract

三磷酸腺苷（ATP）是各种活细胞内普遍存在的一种高能磷酸化合物，在能量的储存，细胞呼吸作用和酶催化反应等生物活动过程中扮演着重要作用.因此，对于ATP在生物体内的研究至关重要.荧光检测技术具有操作方便、选择性好和灵敏度高等优点，设计合成高效的ATP荧光传感器是近年来生物化学和分析化学领域的研究热点.根据ATP荧光传感器的结构特点和识别原理，将ATP荧光传感器分为金属Zn（Ⅱ）作为键合位点型识别，其它金属离子作为键合位点型识别和静电或氢键作用型识别.基于有机小分子荧光传感器，综述了近年来国内外ATP荧光传感器在分子设计与应用方面的研究进展，并展望了其发展趋势.

关键词: 荧光传感器, 三磷酸腺苷, 生物成像, 有机小分子

Adenosine triphosphate (ATP) is a high-energy phosphate compound commonly existing in various living cells, which plays important roles in the biological activities such as energy storage, cell respiration and enzyme catalytic reactions. Therefore, it is very crucial to ATP research in bio-organism. Fluorescence detection techniques has the advantages of convenient operation, good selectivity and high sensitivity, etc. In recent years, the design and synthesis of efficient ATP fluorescence sensors have become a research focus in the fields of biochemistry and analytical chemistry. According to the structure characteristics, ATP fluorescence chemosensors are categorized as Zn(Ⅱ) metal ions as recognition of bonding site type, other metal ions as recognition of bonding site type and electrostatic or hydrogen bond as interaction type. Based on organic small molecule fluorescence sensors, the recent progress in research of ATP fluorescence sensors in molecular design and application is reviewed, and the prospects for their development are discussed.

Key words: fluorescent chemosensor, adenosine triphosphate, biological imaging, small organic molecules

引用此文

张继东, 张俊, 严瞻, 谢娟平. 基于有机小分子的三磷酸腺苷荧光传感器研究进展[J]. 有机化学, 2019, 39(11): 3051-3064.

Zhang Jidong, Zhang Jun, Yan Zhan, Xie Juanping. Recent Progress in Fluorescent Probes for Adenosine Triphosphate Based on Small Organic Molecules[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3051-3064.

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图/表 14

图式 1. 传感器4, 5与ATP的识别机理

Scheme 1. Structures of 4 and 5, and illustration of the dual-emission sensing mechanism with ATP

图式 2. 传感器10, 11与ATP结合模式与识别机理

Scheme 2. Sensing mechanism and proposed binding mode between chemosensor 10, 11 and ATP

图式 3. 传感器12与ATP的结合模式和识别机理

Scheme 3. Sensing mechanism and proposed binding mode between chemosensor 12 and ATP

图式 4. 传感器13与PPi的结合模式与识别机理

Scheme 4. Sensing mechanism and proposed binding mode between chemosensor 13 and PPi

图式 5. 传感器14与ATP的结合模式与识别机理

Scheme 5. Sensing mechanism and proposed binding mode between chemosensor 14 and ATP

图式 6. 传感器29和30的结构图

Scheme 6. Structures of 29 and 30

图式 7. 传感器36对ATP的结合模式和识别机理

Scheme 7. Signalling mechanism and proposed binding mode between chemosensor 36 and ATP

图式 8. 传感器37与ATP的结合模式

Scheme 8. Proposed binding mode between chemosensor 37 with ATP

图式 9. 传感器46与ATP的作用机理

Scheme 9. Proposed response mechanism of chemosensor 46 to ATP

图式 10. 传感器48的结构与NTR, ATP和NTR/ATP的反应机理

Scheme 10. Structure of the chemosensor 48 and its reaction with NTR, ATP and NTR/ATP

图式 11. 传感器49识别ATP的机理

Scheme 11. Proposed mechanism of chemosensor 49 for sensing ATP

图式 12. 加入cAMP和ATP引起传感器50荧光的变化

Scheme 12. Fluorescence changes of 50 upon addition of cAMP and ATP

图式 13. 传感器51, 52和53的结构图

Scheme 13. Structures of chemosensors 51, 52 and 53

图式 14. 近红外传感器54的化学结构及ATP识别示意图

Scheme 14. Chemical structures of chemosensor 54; schematic diagram of sensing ATP by near-IR ?uorescent chemosensor

参考文献 64

[1]	Knowles J. R. Annu. Rev. Biochem. 1980 49 877. doi: 10.1146/annurev.bi.49.070180.004305
[2]	Higgins C. F. Hiles I. D. Salmond G. P. C. Gill D. R. Downie J. A. Evans I. J. Holland I. B. Gray L. Buckel S. D. Bell A. W. Hermodson M. A. Nature 1986 323 448. doi: 10.1038/323448a0
[3]	Mishra N. S. Tuteja R. Tuteja N. Arch. Biochem. Biophys. 2006 452 55. doi: 10.1016/j.abb.2006.05.001
[4]	Ghosh A. Shrivastav A. Jose D. A. Mishra S. K. Chandrakanth C. K. Mishra S. Das A. Anal. Chem. 2008 80 5312. doi: 10.1021/ac8005022
[5]	Beyeh N. K. Diez I. Taimoory S. M. Meister D. Feig A. I. Trant J. F. Ras R. H. A. Rissanen K. Chem. Sci. 2018 9 1358. doi: 10.1039/C7SC05167K
[6]	Gao M. Yu F. Lv C. Choo J. Chen L. Chem. Soc. Rev. 2017 46 2237. doi: 10.1039/C6CS00908E
[7]	Umezawa K. Yoshida M. Kamiya M. Yamasoba T. Urano Y. Nat. Chem. 2017 9 279. doi: 10.1038/nchem.2648
[8]	You L. Zha D. Anslyn E. V. Chem. Rev. 2015 115 7840. doi: 10.1021/cr5005524
[9]	Buccella D. Horowitz J. A. Lippard S. J. J. Am. Chem. Soc. 2011 133 4101. doi: 10.1021/ja110907m
[10]	Zhou Y. Xu Z. Yoon J. Chem. Soc. Rev. 2011 40 2222. doi: 10.1039/c0cs00169d
[11]	Weitz E. A. Chang J. Y. Rosenfield A. H. Pierre V. C. J. Am. Chem. Soc. 2012 134 16099. doi: 10.1021/ja304373u
[12]	Lu B. Meng S. Feng Y. Chin. J. Org. Chem 2018 38 350. doi: 10.6023/cjoc201706018
	卢博为孟舒献冯亚青有机化学 2018 38 350. doi: 10.6023/cjoc201706018
[13]	Qu W. Fang H. Huang Q. Zhang Y. Lin Q. Yao H. Wei T. Chin. J. Org. Chem. 2019, 39 2019 39 1226.
	曲文娟房虎黄青张有明林奇姚虹魏太保有机化学 2019 39 1126.
[14]	Li J. Chen L. Du L. Li M. Chem. Soc. Rev. 2013 42 662. doi: 10.1039/C2CS35249D
[15]	Fan Y. Wang S. Zhang F. Angew. Chem. Int. Ed. 2019 58 13208. doi: 10.1002/anie.201901964
[16]	Li M. Wang Y. Liu G. Lü H. Xing G. Chin. J. Org. Chem. 2017 37 356. doi: 10.6023/cjoc201607004
	李美含王宇童刘广建吕海娟邢国文有机化学 2017 37 356. doi: 10.6023/cjoc201607004
[17]	Kurishita Y. Kohira T. Ojida A. Hamachi I. J. Am. Chem. Soc. 2010 132 13290. doi: 10.1021/ja103615z
[18]	Wu Y. Wen J. Li H. Sun S. Xu Y. Chin. Chem. Lett. 2017 28 1916. doi: 10.1016/j.cclet.2017.09.032
[19]	Ojida A. Mito-oka Y. Sada K. Hamachi I. J. Am. Chem. Soc. 2004 126 2454. doi: 10.1021/ja038277x
[20]	Yamaguchi S. Yoshimura I. Kohira T. Tamaru S. Hamachi I. J. Am. Chem. Soc. 2005 127 11835. doi: 10.1021/ja052838y
[21]	Ojida A. Miyahara Y. Wongkongkatep J. Tamaru S. Sada K. Hamachi T. Chem. Asian J. 2006 1 555. doi: 10.1002/asia.200600137
[22]	Ojida A. Nonaka H. Miyahara Y. Tamaru S. Sada K. Hamachi I. Angew. Chem. Int. Ed. 2006 45 5518. doi: 10.1002/anie.200601315
[23]	Jose D. A. Mishra S. Ghosh A. Shrivastav A. Mishra S. K. Das A. Org. Lett. 2007 9 1979. doi: 10.1021/ol0705797
[24]	Mahato P. Ghosh A. Mishra S. K. Shrivastav A. Mishra S. Das A. Inorg. Chem. 2011 50 4162. doi: 10.1021/ic200223g
[25]	Duodu E. Kraskouskaya D. Gomez-Biagi R. F. Gunning P. T. Analyst 2016 141 820. doi: 10.1039/C5AN01414J
[26]	Butler S. J. Chem. Eur. J. 2014 20 15768. doi: 10.1002/chem.201404499
[27]	Minami T. Emami F. Nishiyabu R. Kubo Y. Anzenbacher P. Jr. Chem. Commun. 2016 52 7838. doi: 10.1039/C6CC02923J
[28]	Rao A. S. Kim D. Nam H. Jo H. Kim K. H. Ban C. Ahn K. H. Chem. Commun. 2012 48 3206. doi: 10.1039/c2cc17629g
[29]	Zhang M. Ma W. J. He C.T. Jiang L. Lu T. B. Inorg. Chem. 2013 52 4873. doi: 10.1021/ic302435g
[30]	Fang W. Liu C. Yu F. Liu Y. Li Z. Chen L. Bao X. Tu T. ACS. Appl. Mater. Interfaces 2016 8 20583. doi: 10.1021/acsami.6b05804
[31]	Moro A. J. Cywinski P. J. Korsten S. Mohr G. J. Chem. Commun. 2010 46 1085. doi: 10.1039/B919661G
[32]	Xu Z. Spring D. R. Yoon J. Chem. Asian. J. 2011 6 2114. doi: 10.1002/asia.201100120
[33]	Xu Q. Lv H. Lv Z. Liu M. Li Y. Wang X. Zhang Y. Xing G. RSC Adv. 2014 4 47788. doi: 10.1039/C4RA07923J
[34]	Strianese M. Milione S. Maranzana A. Grassi A. Pellecchia C. Chem. Commun. 2012 48 11419. doi: 10.1039/c2cc35730e
[35]	Patra C. Bhanja A. K. Mahapatra A. Mishra S. Saha K. D. Sinha C. RSC Adv. 2016 6 76505. doi: 10.1039/C6RA12369D
[36]	Kumari N. Zelder F. Chem. Commun. 2015 51 17170. doi: 10.1039/C5CC07413D
[37]	Kataev E. Arnold R. Rüffer T. Lang H. Inorg. Chem. 2012 51 7948. doi: 10.1021/ic300805q
[38]	Gao Y. G. Tang Q. Shi Y. D. Zhang Y. Lu Z. L. Talanta 2016 152 438. doi: 10.1016/j.talanta.2016.02.040
[39]	Xiao L. Sun S. Pei Z. Pei Y. Pang Y. Xu Y. Biosens. Bioelectron. 2015 65 166. doi: 10.1016/j.bios.2014.10.038
[40]	Zhang X. Jiang Y. Xiao N. Chem. Commun. 2018 54 12812. doi: 10.1039/C8CC06311G
[41]	Wu H. He C. Lin Z. Liu Y. Duan C. Inorg. Chem. 2009 48 408. doi: 10.1021/ic801350h
[42]	Liu X. Xu J. Lv Y. Wu W. Liu W. Tang Y. Dalton. Trans. 2013 42 9840. doi: 10.1039/c3dt50986a
[43]	Weitz E. A. Chang J. Y. Rosenﬁeld A. H. Pierre V. C. J. Am. Chem. Soc. 2012 134 16099. doi: 10.1021/ja304373u
[44]	Shuvaev S. Fox M. A. Parker D. Angew. Chem., Int. Ed. 2018 57 7488. doi: 10.1002/anie.201801248
[45]	Mailhot R. Traviss-Pollard T. Pal R. Butler S. J. Chem. Eur. J. 2018 24 10745. doi: 10.1002/chem.201801008
[46]	Xu Z. Kim S. K. Yoon J. Chem. Soc. Rev. 2010 39 1457. doi: 10.1039/b918937h
[47]	Xu Z. Singh N. J. Lim J. Pan J. Kim H. N. Park S. Kim K. K. Yoon J. J. Am. Chem. Soc. 2009 131 15528. doi: 10.1021/ja906855a
[48]	Farshbaf S. Anzenbacher P. Jr. Chem. Commun. 2019 55 1770. doi: 10.1039/C8CC09857C
[49]	Luo J. Xie Z. Lam J. W. Y. Chen L. Chen H. Qiu C. Kwok H. S. Zhan X. Liu Y. Zhu D. Tang B. Z. Chem. Commun. 2001 1740
[50]	Kwok R. T. Leung C. W. Lam J. W. Tang B. Z. Chem. Soc. Rev. 2015 44 4228. doi: 10.1039/C4CS00325J
[51]	Xu W. Lee M. M. S. Zhang Z. Sung H. H. Y. Williams I. D. Kwok R. T. K. Lam J. W. Y. Wang D. Tang B. Z. Chem. Sci. 2019 10 3494. doi: 10.1039/C8SC05805A
[52]	Li X. Guo X. Cao L. Xun Z. Wang S. Li S. Li Y. Yang G. Angew. Chem. Int. Ed. 2014 53 7809. doi: 10.1002/anie.201403918
[53]	Yang Y. Wang X. Cui Q. Cao Q. Li L. ACS. Appl. Mater. Interfaces. 2016 8 7440. doi: 10.1021/acsami.6b00065
[54]	Cheng L. Zhang H. Dong Y. Zhao Y. Yu Y. Cao L. Chem. Commun. 2019 55 2372. doi: 10.1039/C9CC00599D
[55]	Jiang G. Zhu W. Chen Q. Shi A. Wu Y. Zhang G. Li X. Li Y. Fan X. Wang J. Analyst 2017 142 4388. doi: 10.1039/C7AN01336A
[56]	Noguchi T. Shiraki T. Dawn A. Tsuchiya Y. Lien L. T. N. Yamamoto T. Shinkai S. Chem. Commun. 2012 48 8090. doi: 10.1039/c2cc33262k
[57]	Maity D. Li M. Ehlers M. Schmuck C. Chem. Commun. 2016 53 208. doi: 10.1039/C6CC08386B
[58]	Tan K. Y. Li C. Y. Li Y. F. Fei J. Yang B. Fu Y. J. Li F. Anal. Chem. 2017 89 1749. doi: 10.1021/acs.analchem.6b04020
[59]	Tang J. L. Li C. Y. Li Y. F. Zou C. X. Chem. Commun. 2014 50 15411. doi: 10.1039/C4CC08044K
[60]	Fang Y. Shi W. Hu Y. Li X. Ma H. Chem. Commun. 2018 54 5454. doi: 10.1039/C8CC02209G
[61]	Wang L. Yuan L. Zeng X. Peng J. Ni Y. Er J. C. Xu W. Agrawalla B. K. Su D. Kim B. Chang Y. T. Angew. Chem. Int. Ed. 2016 55 1773. doi: 10.1002/anie.201510003
[62]	Das S. Sarkar H. S. Uddin M. R. Rissanen K. Madal S. Sahoo P. Chem. Commun. 2017 53 7600. doi: 10.1039/C7CC02935G
[63]	Liu Y. Lee D. Wu D. Swamy K. M. K. Yoon J. Sensors Actuators, B 2018 265 429. doi: 10.1016/j.snb.2018.03.081
[64]	Zhang P. Zhu M. Luo H. Zhang Q. Guo L. E. Li Z. Jiang Y. B. Anal. Chem. 2017 89 6210. doi: 10.1021/acs.analchem.7b01175

基于有机小分子的三磷酸腺苷荧光传感器研究进展

Recent Progress in Fluorescent Probes for Adenosine Triphosphate Based on Small Organic Molecules

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