Citation: WANG Xiao-Bo, XIONG Hui-Juan, WU Sha-Sha, GENG Zhi-Rong, WANG Zhi-Lin. Progress of Fluorescent Probes Based on Macrocyclic Polyamine[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(6): 1035-1048. doi: 10.11862/CJIC.2020.143 shu

Progress of Fluorescent Probes Based on Macrocyclic Polyamine

1.
School of Pharmacy, Hubei University of Science and Technology, Xianning, Hubei 437100, China
2.
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China

Corresponding author: GENG Zhi-Rong, gengzr@nju.edu.cn WANG Zhi-Lin, wangzl@nju.edu.cn
Received Date: 17 February 2020
Revised Date: 13 April 2020

Figures(12)

Macrocyclic polyamines are intriguing electron donors for constructing fluorescent probes due to their characteristics of ring configuration and a few nitrogen atoms. For example, typical tetraazamacrocycle such as cyclen (1, 4, 7, 10-tetraazacyclododecane), cyclam (1, 4, 8, 11-tetraazacyclotetradecane) and pyclen (1, 4, 7, 10-tetraaza-2, 6-pyridinophane), and triazamacrocycle tacn (1, 4, 7-triazacyclononane) which are widely employed as receptors or functional groups in fluorescent probes for recognition of metal ions, onions, small molecules and biomacromolecules. In this review, we highlight the many different detection targets and summarize the latest prominent research achievements in the design, preparation and application of fluorescent probes based on macrocyclic polyamines. Additionally, the future research interests and perspectives in the field of fluorescence analysis are also addressed.
- macrocyclic polyamine,
- fluorescent probes,
- cyclen,
- cyclam,
- cell imaging
1. [1]
  Sousa L R, Larson J M. J. Am. Chem. Soc., 1977, 99(1):307- 310 doi: 10.1021/ja00443a084
2. [2]
  De Silva A P, De Silva S A. J. Chem. Soc. Chem. Commun., 1986, 23:1709-1710
3. [3]
  Czarnik A W. Acc. Chem. Res., 1994, 27(10):302-308 doi: 10.1021/ar00046a003
4. [4]
  Huo Y, Miao J, Han L, et al. Chem. Sci., 2017, 8(10):6857- 6864 doi: 10.1039/C7SC02608K
5. [5]
  Jung Y, Ju I G, Choe Y H, et al. ACS Sens., 2019, 4(2):441- 449 doi: 10.1021/acssensors.8b01429
6. [6]
  Wang J, Hao Y, Wang H, et al. J. Agric. Food Chem., 2017, 65(13):2883-2887 doi: 10.1021/acs.jafc.7b00353
7. [7]
  Duan C, Zhang J, Hu Y, et al. Dyes Pigments, 2019, 162:459 -465 doi: 10.1016/j.dyepig.2018.10.057
8. [8]
  Yin C, Xiong K, Huo F. et al. Angew. Chem. Int. Ed., 2017, 56(43):13188-13198 doi: 10.1002/anie.201704084
9. [9]
  Yin J, Jiao Y, Peng X, et al. Biosens. Bioelectron., 2020, in press. DOI: 10.1016/j.bios.2020.112026
10. [10]
  Daly B, Ling J, de Silva A P. Chem. Soc. Rev., 2015, 44(13): 4203-4211 doi: 10.1039/C4CS00334A
11. [11]
  Jia X, Chen Q, Yang Y, et al. J. Am. Chem. Soc., 2016, 138 (34):10778-10781 doi: 10.1021/jacs.6b06398
12. [12]
  QIU Lin, JI Yi-Fan, ZHU Cheng-Cheng, et al. Chinese J. Inorg. Chem., 2014, 30 (1):169-178
13. [13]
  Liu T, Huang Z, Feng R, et al. Dyes Pigments, 2020, 174, 108102. DOI:10.1016/j.dyepig. 2019.108102 doi: 10.1016/j.dyepig.2019.108102
14. [14]
  Yu Q, Zhang X, Wu S T, et al. Chem. Commun., 2020, 56 (15):2304-2307 doi: 10.1039/C9CC09540C
15. [15]
  Gao M, Tang B. ACS Sensors, 2017, 2(10):1382-1399 doi: 10.1021/acssensors.7b00551
16. [16]
  WANG Xiao-Yong, TAN Ren-Xiang, GUO Zi-Jian. Chin. J. Org. Chem., 2003, 2: 129-138
17. [17]
  Athey P S, Kiefer G E. J. Org. Chem., 2002, 67(12):4081-4085 doi: 10.1021/jo016111d
18. [18]
  Richman J E, Atkins T J. J. Am. Chem. Soc., 1974, 96(7): 2268-2270 doi: 10.1021/ja00814a056
19. [19]
  Su J, Liu Y, Zheng Z, et al. Chinese Chem. Lett., 2007, 18 (10):1166-1168 doi: 10.1016/j.cclet.2007.08.021
20. [20]
  Barefield E K. Inorg. Chem., 1972, 11(9):2273-2274 doi: 10.1021/ic50115a065
21. [21]
  Tempkin O, Kapa P. US Patent, 5811544. 1998-09-22
22. [22]
  Costa J, Delgado R. Inorg. Chem., 1993, 32(23):5257-5265 doi: 10.1021/ic00075a052
23. [23]
  Stetter H, Frank W, Mertens R. Tetrahedron, 1981, 37(4): 767-772 doi: 10.1016/S0040-4020(01)97695-1
24. [24]
  Carvalho J F, Crofts S P, Rocklage S M. WO Patent, 9110645. 1991-07-25.
25. [25]
  WU Cheng-Tai, HE Yong-Bing. Chin. J. Org. Chem., 1983, 6:437-439
26. [26]
27. [27]
  Hoye R C, Richman J E, Dantas G A, et al. J. Org. Chem., 2001, 66(8):2722-2725 doi: 10.1021/jo001639o
28. [28]
  Rohini, Baral M, Kanungo B K. New J. Chem., 2018, 42(19): 16040-16059 doi: 10.1039/C8NJ02217H
29. [29]
  Huang Y, Liu Y, Liu S, et al. Eur. J. Org. Chem., 2018, 13: 1546-1551
30. [30]
  Majzoub A E, Cyril C, Isabelle D O, et al. Inorg. Chem., 2011, 50(9):4029-4038 doi: 10.1021/ic102521g
31. [31]
  Tamanini E, Flavin K, Motevalli M, et al. Inorg. Chem., 2010, 49(8):3789-3800 doi: 10.1021/ic901939x
32. [32]
  Yasuhiro S, Yoshinao M, Takayuki H. J. Phys. Chem. A, 2013, 117(16):3387-3395 doi: 10.1021/jp4013009
33. [33]
  Steve C, Sarah A T, Laura K T, et al. Inorg. Chem., 2012, 51 (19):10158-10168 doi: 10.1021/ic300697w
34. [34]
  Wang M, Zhang D, Li M, et al. J. Fluoresc., 2013, 23(3):417- 423 doi: 10.1007/s10895-013-1159-0
35. [35]
  Fang L, Trigiante G, Kousseff C, et al. Chem. Commun., 2018, 54(69):9619-9622 doi: 10.1039/C8CC05425H
36. [36]
  Aurore T, Valerie C P. J. Am. Chem. Soc., 2008, 131(2):434- 435
37. [37]
  Guo R, Wang Q, Lin W. J. Fluoresc., 2017, 27(5):1655-1660 doi: 10.1007/s10895-017-2102-6
38. [38]
  Wang X, Ma X, Yang Z, et al. Chem. Commun., 2013, 49 (96):11263-11265 doi: 10.1039/c3cc46585c
39. [39]
  Zhou R, Li B, Wu N, et al. Chem. Commun., 2011, 47(23): 9619-9622
40. [40]
  Xu H, Li K, Liu Q, et al. Analyst, 2013, 138(8):2329-2334 doi: 10.1039/c3an36789d
41. [41]
  Wen J, Geng Z, Yin Y, et al. Dalton Trans., 2011, 40(38): 9737-9745 doi: 10.1039/c1dt10362h
42. [42]
  Mercury Update: Impact on Fish Advisories, EPA Fact Sheet EPA-823-F-01-011; EPA, Office of Water, Washington, DC, 2001.
43. [43]
  Bazzicalupi C, Caltagirone C, Cao Z, et al. Chem. Eur. J., 2013, 19(43):14639-14653 doi: 10.1002/chem.201302090
44. [44]
  Choi J, Lee S K, Bae J, et al. Tetrahedron Lett., 2014, 55 (38):5294-5297 doi: 10.1016/j.tetlet.2014.07.095
45. [45]
  Kim S H, Kim J S, Park S M, et al. Org. Lett., 2006, 8(3): 371-374 doi: 10.1021/ol052282j
46. [46]
  Liu T, Nonat A, Beyler M, et al. Angew. Chem. Int. Ed., 2014, 53(28):7259-7263 doi: 10.1002/anie.201404847
47. [47]
  Zhang Y, Gao Y, Shi Y, et al. Chin. Chem. Lett., 2015, 26 (7):894-898 doi: 10.1016/j.cclet.2015.05.032
48. [48]
  Ding A, Shi Y, Zhang K, et al. Sensor Actuat. B: Chem., 2018, 255:440-447 doi: 10.1016/j.snb.2017.08.037
49. [49]
  Wen J, Geng Z, Yin Y, et al. Dalton Trans., 2011, 40(9): 1984-1989 doi: 10.1039/C0DT01262A
50. [50]
  Wang X, Zhang Z, Ma X, et al. Talanta, 2015, 137:156-160 doi: 10.1016/j.talanta.2015.01.028
51. [51]
  McMahon B K, Gunnlaugsson T. J. Am. Chem. Soc., 2012, 134(26):10725-10728 doi: 10.1021/ja300887k
52. [52]
  Wang X, Ma X, Wen J, et al. Talanta, 2020, 207:120311 doi: 10.1016/j.talanta.2019.120311
53. [53]
  Li Z, Geng Z, Zhang C, et al. Biosens. Bioelectron., 2015, 72:1-9 doi: 10.1016/j.bios.2015.04.085
54. [54]
  CHEN Yun-Long, WANG Ming-Hui. J. Qingdao Uni. Sci. Tech: Natural Science Edition, 2012, 33(4):372-376
55. [55]
  Sasakura K, Hanaoka K, Shibuya N, et al. J. Am. Chem. Soc., 2011, 133(45):18003-18005 doi: 10.1021/ja207851s
56. [56]
  Liu J, Guo X, Hu R, et al. Anal. Chem., 2016, 88(1):1052- 1057 doi: 10.1021/acs.analchem.5b04248
57. [57]
  Wu H, Krishnakumar S, Yu J, et al. Chem. Asia J., 2014, 9 (12):3604-3611 doi: 10.1002/asia.201402860
58. [58]
  Palanisamy S, Lee L, Wang Y, et al. Talanta, 2016, 147:445- 452 doi: 10.1016/j.talanta.2015.10.019
59. [59]
  Mirra S, Strianese M, Pellecchia C. Eur. J. Inorg. Chem., 2017, 33:3900-3907
60. [60]
  Inclan M, Guijarro L, Pont I, et al. Chem. Eur. J., 2017, 23 (63):15966-15973 doi: 10.1002/chem.201702934
61. [61]
  Zhu Z, Wang S, Wei D, et al. Biosens. Bioelectron., 2016, 85:792-797 doi: 10.1016/j.bios.2016.05.085
62. [62]
  Viehweger K, Barbaro L, Garcia K P, et al. Bioconjugate Chem., 2014, 25(5):1011-1022 doi: 10.1021/bc5001388
63. [63]
  Song S, Liu D, Peng J, et al. Int. J. Pharm., 2008, 363(1/2): 155-161
64. [64]
  Kikuchi K, Hashimoto S, Mizukami S, et al. Org. Lett., 2009, 11(13):2732-2735 doi: 10.1021/ol9006508
65. [65]
  Akiba H, Sumaoka J, Komiyama M. Chem. Eur. J., 2009, 16 (17):5018-5025
66. [66]
  Liu J, Zhang S, Zhang C, et al. Chem. Commun., 2017, 53 (83):11476-11479 doi: 10.1039/C7CC06045A
67. [67]
  Shen Z, Zhang C, Yu X, et al. J. Mater. Chem. C, 2018, 6 (36):9636-9641 doi: 10.1039/C8TC02982B
68. [68]
  Aoki S, Kawatani H, Goto T, et al. J. Am. Chem. Soc., 2001, 123(6):1123-1132 doi: 10.1021/ja0033786
69. [69]
  Li Z, Zhu Z, Sun Z, et al. Sensor Actuat. B: Chem., 2019, 282:541-548 doi: 10.1016/j.snb.2018.11.119
70. [70]
  Chen H, Cao J, Zhou P, et al. Biosens. Bioelectron., 2018, 122:1-7 doi: 10.1016/j.bios.2018.09.029
1. [1]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
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]
  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
4. [4]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
5. [5]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
6. [6]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
7. [7]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
8. [8]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
9. [9]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
10. [10]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
11. [11]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
12. [12]
  Jinwang Wu , Qijing Xie , Chengliang Zhang , Haifeng Shi . 自旋极化增强ZnFe_1.2Co_0.8O₄/BiVO₄ S型异质结光催化性能降解四环素. Acta Physico-Chimica Sinica, 2025, 41(5): 100050-. doi: 10.1016/j.actphy.2025.100050
13. [13]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
14. [14]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
15. [15]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
17. [17]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
18. [18]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
19. [19]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
20. [20]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(2042)
HTML views(282)

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