Citation: 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. doi: 10.6023/cjoc201905024 shu

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

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

Corresponding author: Zhang Jidong, akuzjd@aku.edu.cn
Received Date: 12 May 2019
Revised Date: 27 June 2019
Available Online: 17 November 2019
Fund Project: Project supported by the Youth Foundation of Shaanxi Provincial Science & Technology Department (No. 2019JQ-504), the Major Scientific Research Projects of the Leading Industry of Ankang City (No. 2016AKZDCY002), the Doctor's Initial Funding of Ankang University (No. 2018AYQDZR06), the Key Laboratory of Se-enriched Products Development and Quality Control, Ministry of Agriculture (No. Se-2018B02), and the Shaanxi Provincial Innovation Experiment Program for University Students (No. 201839032)the Major Scientific Research Projects of the Leading Industry of Ankang City 2016AKZDCY002the Doctor's Initial Funding of Ankang University 2018AYQDZR06the Key Laboratory of Se-enriched Products Development and Quality Control, Ministry of Agriculture Se-2018B02the Youth Foundation of Shaanxi Provincial Science & Technology Department 2019JQ-504the Shaanxi Provincial Innovation Experiment Program for University Students 201839032

Figures(14)

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.
- fluorescent chemosensor,
- adenosine triphosphate,
- biological imaging,
- small organic molecules
1. [1]
  Knowles, J. R. Annu. Rev. Biochem. 1980, 49, 877. doi: 10.1146/annurev.bi.49.070180.004305
2. [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. [3]
  Mishra, N. S.; Tuteja, R.; Tuteja, N. Arch. Biochem. Biophys. 2006, 452, 55. doi: 10.1016/j.abb.2006.05.001
4. [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. [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. [6]
  Gao, M.; Yu, F.; Lv, C.; Choo, J.; Chen, L. Chem. Soc. Rev. 2017, 46, 2237. doi: 10.1039/C6CS00908E
7. [7]
  Umezawa, K.; Yoshida, M.; Kamiya, M.; Yamasoba, T.; Urano, Y. Nat. Chem. 2017, 9, 279. doi: 10.1038/nchem.2648
8. [8]
  You, L.; Zha, D.; Anslyn, E. V. Chem. Rev. 2015, 115, 7840. doi: 10.1021/cr5005524
9. [9]
  Buccella, D.; Horowitz, J. A.; Lippard, S. J. J. Am. Chem. Soc. 2011, 133, 4101. doi: 10.1021/ja110907m
10. [10]
  Zhou, Y.; Xu, Z.; Yoon, J. Chem. Soc. Rev. 2011, 40, 2222. doi: 10.1039/c0cs00169d
11. [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. [12]
  Lu, B.; Meng, S.; Feng, Y. Chin. J. Org. Chem. 2018, 38, 350 (in Chinese).
13. [13]
  Qu, W.; Fang, H.; Huang, Q.; Zhang, Y.; Lin, Q.; Yao, H.; Wei, T. Chin. J. Org. Chem. 2019, 39, 1226 (in Chinese).
14. [14]
  Li, J.; Chen, L.; Du, L.; Li, M. Chem. Soc. Rev. 2013, 42, 662. doi: 10.1039/C2CS35249D
15. [15]
  Fan, Y.; Wang, S.; Zhang, F. Angew. Chem. Int. Ed. 2019, 58, 13208. doi: 10.1002/anie.201901964
16. [16]
  Li, M.; Wang, Y.; Liu, G.; Lü, H.; Xing, G. Chin. J. Org. Chem. 2017, 37, 356 (in Chinese).
17. [17]
  Kurishita, Y.; Kohira, T.; Ojida, A.; Hamachi, I. J. Am. Chem. Soc. 2010, 132, 13290. doi: 10.1021/ja103615z
18. [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. [19]
  Ojida, A.; Mito-oka, Y.; Sada, K.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 2454. doi: 10.1021/ja038277x
20. [20]
  Yamaguchi, S.; Yoshimura, I.; Kohira, T.; Tamaru, S.; Hamachi, I. J. Am. Chem. Soc. 2005, 127, 11835. doi: 10.1021/ja052838y
21. [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. [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. [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. [24]
  Mahato, P.; Ghosh, A.; Mishra, S. K.; Shrivastav, A.; Mishra, S.; Das, A. Inorg. Chem. 2011, 50, 4162. doi: 10.1021/ic200223g
25. [25]
  Duodu, E.; Kraskouskaya, D.; Gomez-Biagi, R. F.; Gunning, P. T. Analyst 2016, 141, 820. doi: 10.1039/C5AN01414J
26. [26]
  Butler, S. J. Chem. Eur. J. 2014, 20, 15768. doi: 10.1002/chem.201404499
27. [27]
  Minami, T.; Emami, F.; Nishiyabu, R.; Kubo, Y.; Anzenbacher, P. Jr. Chem. Commun. 2016, 52, 7838. doi: 10.1039/C6CC02923J
28. [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. [29]
  Zhang, M.; Ma, W. J.; He, C.T.; Jiang, L.; Lu, T. B. Inorg. Chem. 2013, 52, 4873. doi: 10.1021/ic302435g
30. [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. [31]
  Moro, A. J.; Cywinski, P. J.; Korsten, S.; Mohr, G. J. Chem. Commun. 2010, 46, 1085. doi: 10.1039/B919661G
32. [32]
  Xu, Z.; Spring, D. R.; Yoon, J. Chem. Asian. J. 2011, 6, 2114. doi: 10.1002/asia.201100120
33. [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. [34]
  Strianese, M.; Milione, S.; Maranzana, A.; Grassi, A.; Pellecchia, C. Chem. Commun. 2012, 48, 11419. doi: 10.1039/c2cc35730e
35. [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. [36]
  Kumari, N.; Zelder, F. Chem. Commun. 2015, 51, 17170. doi: 10.1039/C5CC07413D
37. [37]
  Kataev, E.; Arnold, R.; Rüffer, T.; Lang, H. Inorg. Chem. 2012, 51, 7948. doi: 10.1021/ic300805q
38. [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. [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. [40]
  Zhang, X.; Jiang, Y.; Xiao, N. Chem. Commun. 2018, 54, 12812. doi: 10.1039/C8CC06311G
41. [41]
  Wu, H.; He, C.; Lin, Z.; Liu, Y.; Duan, C. Inorg. Chem. 2009, 48, 408. doi: 10.1021/ic801350h
42. [42]
  Liu, X.; Xu, J.; Lv, Y.; Wu, W.; Liu, W.; Tang, Y. Dalton. Trans. 2013, 42, 9840. doi: 10.1039/c3dt50986a
43. [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. [44]
  Shuvaev, S.; Fox, M. A.; Parker, D. Angew. Chem., Int. Ed. 2018, 57, 7488. doi: 10.1002/anie.201801248
45. [45]
  Mailhot, R.; Traviss-Pollard, T.; Pal, R.; Butler, S. J. Chem. Eur. J. 2018, 24, 10745. doi: 10.1002/chem.201801008
46. [46]
  Xu, Z.; Kim, S. K.; Yoon, J. Chem. Soc. Rev. 2010, 39, 1457. doi: 10.1039/b918937h
47. [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. [48]
  Farshbaf, S.; Anzenbacher, P. Jr. Chem. Commun. 2019, 55, 1770. doi: 10.1039/C8CC09857C
49. [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. [50]
  Kwok, R. T.; Leung, C. W.; Lam, J. W.; Tang, B. Z. Chem. Soc. Rev. 2015, 44, 4228. doi: 10.1039/C4CS00325J
51. [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. [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. [53]
  Yang, Y.; Wang, X.; Cui, Q.; Cao, Q.; Li, L. ACS. Appl. Mater. Interfaces. 2016, 8, 7440. doi: 10.1021/acsami.6b00065
54. [54]
  Cheng, L.; Zhang, H.; Dong, Y.; Zhao, Y.; Yu, Y.; Cao, L. Chem. Commun. 2019, 55, 2372. doi: 10.1039/C9CC00599D
55. [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. [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. [57]
  Maity, D.; Li, M.; Ehlers, M.; Schmuck, C. Chem. Commun. 2016, 53, 208.
58. [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. [59]
  Tang, J. L.; Li, C. Y.; Li, Y. F.; Zou, C. X. Chem. Commun. 2014, 50, 15411. doi: 10.1039/C4CC08044K
60. [60]
  Fang, Y.; Shi, W.; Hu, Y.; Li, X.; Ma, H. Chem. Commun. 2018, 54, 5454. doi: 10.1039/C8CC02209G
61. [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. [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. [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. [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
1. [1]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
2. [2]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
3. [3]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
4. [4]
  Renyi Shao , Khurram Abbas , Vladimir Yu. Osipov , Haimei Zhu , Yuan Li , Usama , Hong Bi . Red-emitting carbon dots prepared from Epipremnum Aureum leaves extract for biological imaging. Acta Physico-Chimica Sinica, 2026, 42(2): 100134-0. doi: 10.1016/j.actphy.2025.100134
5. [5]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
6. [6]
  Xiaoyu YANG , Yejun ZHANG , Yu ZOU , Hongchao YANG , Jiang JIANG , Qiangbin WANG . Research progress of inorganic X-ray nanoscintillators. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1929-1952. doi: 10.11862/CJIC.20250122
7. [7]
  Lin′an CAO , Dengyue MA , Gang XU . Research advances in electrically conductive metal-organic frameworks-based electrochemical sensors. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1953-1972. doi: 10.11862/CJIC.20250160
8. [8]
  Qiaoqiao BAI , Anqi ZHOU , Xiaowei LI , Tang LIU , Song LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128
9. [9]
  Yang Meiqing , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 100018-0. doi: 10.3866/PKU.WHXB202310046
10. [10]
  Junmei FAN , Wei LIU , Ruitao ZHU , Chenxi QIN , Xiaoling LEI , Haotian WANG , Jiao WANG , Hongfei HAN . High sensitivity detection of baicalein by N, S co-doped carbon dots and their application in biofluids. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2009-2020. doi: 10.11862/CJIC.20240120
11. [11]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
12. [12]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
13. [13]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
14. [14]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
15. [15]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
16. [16]
  Ke Zhao , Zhen Liu , Luyao Liu , Changyuan Yu , Jingshun Pan , Xuguang Huang . Functionalized Reflective Structure Fiber-Optic Interferometric Sensor for Trace Detection of Lead Ions. Acta Physico-Chimica Sinica, 2024, 40(4): 2304029-0. doi: 10.3866/PKU.WHXB202304029
17. [17]
  Xiaogang YANG , Xinya ZHANG , Jing LI , Huilin WANG , Min LI , Xiaotian WEI , Xinci WU , Lufang MA . Synthesis, structure, and photoelectric properties of Zinc(Ⅱ)-triphenylamine based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2078-2086. doi: 10.11862/CJIC.20250167
18. [18]
  Wei Zheng , Yanyu Chen , Rizhong Gao , Chao Lu . Development and Application of Primary Battery-based Humidity Sensors: Advancing a New Paradigm for Integrated Experimental Teaching through Science-Education Synergy. University Chemistry, 2026, 41(4): 393-399. doi: 10.12461/PKU.DXHX202503009
19. [19]
  Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . Photomultiplication-Type All-Polymer Photodetectors and Their Applications in Photoplethysmography Sensor. Acta Physico-Chimica Sinica, 2025, 41(1): 100007-0. doi: 10.3866/PKU.WHXB202311021
20. [20]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351

Get Citation

PDF

XML

Metrics

PDF Downloads(40)
Abstract views(2872)
HTML views(526)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142