Citation: HUANG Zi-Heng, ZOU Jian-Mei, LI Xiao-Qing, HE Qing, NIE Jin-Fang. Research Progress of Fluorescent Probe for G-quadruplex[J]. Chinese Journal of Analytical Chemistry, ;2021, 49(8): 1258-1269. doi: 10.19756/j.issn.0253-3820.201797 shu

Research Progress of Fluorescent Probe for G-quadruplex

College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China

Corresponding author: ZOU Jian-Mei, NIE Jin-Fang,
Received Date: 28 December 2020
Revised Date: 14 May 2021

Fund Project: Supported by the National Natural Science Foundation of China (No.21765007), the Guangxi Key Research Project (No.GuikeAB17129003), and the Natural Science Foundation of Guangxi, China (No.2020GXNSFBA297114).

G-quadruplex is a kind of secondary structure of nucleic acids that is formed by the stacking of guanine-rich oligonucleotides. It has been reported that G-quadruplexes widely locate in the human genome (Telomere, gene promoter and so on) and play important roles in regulation of gene transcription and expression, stabilization of gene and synthesis of telomere. This indicates that the structure, quantity and distribution of G-quadruplex in organism are related to the occurrence and development of various diseases to some extent. Therefore, the real-time monitoring of G-quadruplex in organism has great significance for the diagnosis and treatment of diseases. Fluorescence spectrometry technique shows many advantages such as high sensitivity and convenience in practice, and has become one of the main tools for detection and identification of G-quadruplex. Herein, the recent development of G-quadruplex fluorescent probes (including porphyrins, thiazole orange, Thioflavin T, etc.) and the research progress of biosensors and fluorescence cell imaging based on the specific recognition reaction between G-quadruplex and probes are reviewed.
- G-quadruplex,
- Fluorescent probe,
- Biosensor,
- Fluorescence cell imaging,
- Review
1. [1]
  WATSON J D, CRICK F H. Nature, 1953, 171(4356): 737-738.
2. [2]
  SWADLING J B, ISHII K, TAHARA T, KITAO A. Phys. Chem. Chem. Phys., 2018, 20(5): 2990-3001.
3. [3]
  DAYN A, MALKHOSYAN S, MIRKIN S M. Nucleic Acids Res., 1992, 20(22): 5991-5997.
4. [4]
  LIMONGELLI V, TITO S D, CEROFOLINI L, FRAGAI M, PAGANO B, TROTTA R, COSCONATI S, MARINELLI L, NOVELLINO E, BERTINI I. Angew. Chem., Int. Ed., 2013, 52(8): 2269-2273.
5. [5]
  GELLERT M, LIPSETT M N, DAVIES D R. Proc. Natl. Acad. Sci. U. S. A., 1962, 48(12): 2013-2018.
6. [6]
  KETTANI A, BOUAZIZ S, GORIN A, ZHAO H, JONES R A, PATEL D J. J. Mol. Biol., 1998, 282(3): 619-636.
7. [7]
  RHODES D, LIPPS H J. Nucleic Acids Res., 2015, 43(18): 8627-8637.
8. [8]
  VERDUN R E, KARLSEDER J. Nature, 2007, 447(7147): 924-931.
9. [9]
  AWADASSEID A, MA X D, WU Y L, ZHANG W. Biomed. Pharmacother., 2021, 139: 111550.
10. [10]
  CHILKA P, DESAI N, DATTA B. Molecules, 2019, 24(4): 752-767.
11. [11]
  WINNERDY F R, BAKALAR B, MAITY A, VANDANA J J, MECHULAM Y, SCHMITT E, PHAN A T. Nucleic Acids Res., 2019, 47(15): 8272-8281.
12. [12]
  ADRIAN M, HEDDI B, PHAN A T. Methods, 2012, 57(1): 11-24.
13. [13]
  TOTHOVA P, KRAFCIKOVA P, VIGLASKY V. Biochemistry, 2014, 53(45): 7013-7027.
14. [14]
  OLSEN C M, MARKY L A. Methods Mol. Biol., 2010, 608: 147-158.
15. [15]
  YIN S, LOO J A. Int. J. Mass spectrom., 2011, 300(2-3): 118-122.
16. [16]
  ZHENG K W, CHEN Z, HAO Y H, TAN Z. Nucleic Acids Res., 2010, 38(1): 327-338.
17. [17]
  JIN B, ZHANG X, ZHENG W, LIU X J, QI C, WANG F Y, SHANGGUAN D H. Anal. Chem., 2014, 86(1): 943-952.
18. [18]
  HE H Z, CHAND S H, LEUNG C H, MA D L. Nucleic Acids Res., 2013, 41(8): 4345-4359.
19. [19]
  UMAR M I, JI D Y, CHAN C Y, KWOK C K. Molecules, 2019, 24(13): 2416.
20. [20]
  BURGE S, PARKINSON G N, HAZEL P, TODD A K, NEIDLE S. Nucleic Acids Res., 2006, 34(19): 5402-5415.
21. [21]
  ZIMMERMAN S B, COHEN G H, DAVIES D R. J. Mol. Biol., 1975, 92(2): 181-192.
22. [22]
  DAVIS J T. Angew. Chem., 2010, 43(6): 668-698.
23. [23]
  SIMONSSON T. Biol. Chem., 2001, 382(4): 621-628.
24. [24]
  KINGSBURY C J, SENGE M O. Coord. Chem. Rev., 2021, 431: 213760.
25. [25]
  DUFOUR E, MARDEN M C, TOMASZ H. FEBS Lett., 1990, 277(1-2): 223-226.
26. [26]
  LI Y F, GEYER C R, DIPANKAR S. Biochemistry, 1996, 35(21): 6911-6922.
27. [27]
  LI T, WANG E K, DONG S J. Anal. Chem., 2010, 82(18): 7576-7580.
28. [28]
  HUO Y F, ZHU L N, LIX Y, HAN G M, KONG D M. Sens. Actuators, B, 2016, 237: 179-189.
29. [29]
  ZHU L N, ZHAO S J, WU B, LI X Z, KONG D M. PloS One, 2012, 7(5): e35586.
30. [30]
  ZHANG R, CHENG M, ZHANG L M, ZHU L N, KONG D M. ACS Appl. Mater. Interfaces, 2018, 10(16): 13350-13360.
31. [31]
  MATHEW D, SUJATHA S. J. Inorg. Biochem., 2021, 219: 111434.
32. [32]
  KEANE P M, KELLY J M. Coord. Chem. Rev., 2018, 364: 137-154.
33. [33]
  RYAZANOVA O, ZOZULYA V, VOLOSHIN I, DUBEY L, DUBEY I, KARACHEVTSEV V. J. Fluoresc., 2015, 25(6): 1897-1904.
34. [34]
  SABHARWAL N C, MENDOZA O, NICOLUDIS J M, RUAN T, MERGNY J L, YATSUNYK L A. JBIC, J. Biol. Inorg. Chem., 2016, 21(2): 227-239.
35. [35]
  SABATER L, FANG P J, CHANG C F, DE RACHE A D, PRADO E, DEJEU J, GAROFALO A, LIN J H, MERGNY J L, DEFRANCQ E. Dalton Trans., 2015, 44(8): 3701-3707.
36. [36]
  MUSETTI C, SPAGNUL C, MION G, ROS S D, GIANFERRARA T, SISSI C. ChemPlusChem, 2015, 80(1): 158-168.
37. [37]
  NYGREN J, SVANVIK N, KUBISTA M. Biopolymers, 1998, 46(1): 39-51.
38. [38]
  MOHANTY J, BAROOAH N, DHAMODHARAN V, HARIKRISHNA S, PRADEEPKUMAR P I, BHASIKUTTAN A C. J. Am. Chem. Soc., 2013, 135(1): 367-376.
39. [39]
  BHOWMIK S, TAKAHASHI S, SUGIMOTO N. ACS Omega, 2019, 4(2): 4325-4329.
40. [40]
  WANG Y Q, HU M H, GUO R J, CHEN S B, HUANG Z S, TAN J H. Sens. Actuators, B, 2018, 266: 187-194.
41. [41]
  YANG P, CIAN A D,TEULADE-FICHOU M P, MERGNY J L, MONCHAUD D. Angew. Chem., Int. Ed., 2009, 48(12): 2188-2191.
42. [42]
  OHEIM M, MICHAEL D J, GEISBAUER M, MADSEN D, CHOW R H. Adv.Drug Delivery Rev., 2006, 58(7): 788-808.
43. [43]
  ZHANG F, LI G, LV F L, JIANG G B, WANG H X, WANG M Q, LI S. Tetrahedron Lett., 2018, 59(34): 3272-3278.
44. [44]
  LI Y, XU S, WU X, XU Q, ZHAO Y H, LOU X H, YANG X B. Anal. Bioanal. Chem., 2016, 408(28): 8025-8036.
45. [45]
  KATAOKA Y, FUJITA H, KASAHARA Y, YOSHIHARA T, TOBITA S, KUWAHARA M. Anal. Chem., 2014, 86(24): 12078-12084.
46. [46]
  GUAN A J, ZHANG X F, SUN X, LI Q, XIANG J F, WANG L X, LAN L, YANG F M, XU S J, GUO X M, TANG Y L. Sci. Rep., 2018, 8: 2666.
47. [47]
  YIN J L, MA Y Y, LI G H, PENG M, LIN W Y. Coord. Chem. Rev., 2020, 412: 213257.
48. [48]
  CHANG C C, WU J Y, CHANG T C. J. Chin. Chem. Soc., 2003, 50(2): 185-188.
49. [49]
  DENG Q R, WANG N, SU J K, LIU A J, ZHANG J, LONG L P, QI F P, TANG R R, LIU C H. Anal. Methods, 2019, 11(20): 2630-2633.
50. [50]
  DAI H, HUANG M L, QIAN J Q, LIU J, MENG C, LI Y Y, MING G X, ZHANG T, WANG S L, SHI Y J. Eur. J. Med. Chem., 2019, 166: 470-479.
51. [51]
  AMIN K M, RAHMAN D E A, ALLAM H A, EL-ZOHEIRY H H. Bioorg. Chem., 2021, 110: 104792.
52. [52]
  JUNG H S, KWON P S, LEE J W, KIM J I, HONG C S, KIM J W, YAN S, LEE J Y, LEE J H, JOO T, KIM J S. J. Am. Chem. Soc., 2009, 131(5): 2008-2012.
53. [53]
  KWON H, LEE K, KIM H J. Chem. Commun., 2011, 47(6): 1773-1775.
54. [54]
  WANG K N, MA L, LIU G Q, CAO D X, GUAN R F, LIU Z Q. Dyes Pigm., 2016, 126: 104-109.
55. [55]
  XIE X, REZNICHENKO O, CHAPUT L, MARTIN P, TEULADE-FICHOU M P, GRANZHAN A. Chemistry, 2018, 24(48): 12638-12651.
56. [56]
  DEORE P S, COMAN D S, MANDERVILLE R A. Chem. Commun., 2019, 55(24): 3540-3543.
57. [57]
  NARAYANASWAMY N, KUMAR M, DAS S, SHARMA R, SAMANTA P K, PATI S K, DHAR S K, KUNDU T K, GOVINDARAJU T. Sci. Rep., 2014, 4: 6476.
58. [58]
  JIANG N, FAN J L, XU F, PENG X J, MU H Y, WANG J Y, XIONG X Q. Angew. Chem., Int. Ed., 2015, 54(8): 2510-2514.
59. [59]
  PAJONK F, SCHOLBER J, FIEBICH B. Cancer Chemoth. Pharm., 2005, 55(5): 439-446.
60. [60]
  ZHANG X, JIN B, ZHENG W, ZHANG N, LIU X J, BING T, WEI Y B, WANG F Y, SHANGGUAN D H. Dyes Pigm., 2016, 132: 405-411.
61. [61]
  DEORE P S, MANDERVILLE R A. New J. Chem., 2019, 43(13): 4994-4997.
62. [62]
  GRANDE V, SHEN C A, DEIANA M, DUDEK M, OLESIAK-BANSKA J, MATCZYSZYN K, WURTHNER F. Chem. Sci., 2018, 9(44): 8375-8381.
63. [63]
  LIU L L, SHAO Y, PENG J, HUANG C B, LIU H, ZHANG L H. Anal. Chem., 2014, 86(3): 1622-1631.
64. [64]
  KONG D M, GUO J H, YANG W, MA Y E, SHEN H X. Biosens. Bioelectron., 2009, 25(1): 88-93.
65. [65]
  NAGATOISHI S, NOJIMA T, JUSKOWIAK B, TAKENAKA S. Angew. Chem., Int. Ed., 2005, 44(32): 5067-5070.
66. [66]
  HE H Z, WANG M D, CHAND S H, LEUNG C H, LIN X X, LIN J M, MA D L. Methods, 2013, 64(3): 212-217.
67. [67]
  ZHOU X, KHUSBU F Y, CHEN H C, MA C B. Talanta, 2020, 208: 120453.
68. [68]
  ZHAO H Z, LIU Q, LIU M, JIN Y, LI B X. Talanta, 2017, 165: 653-658.
69. [69]
  SUN X, LI Q, XIANG J F, WANG L X, ZHANG X F, LAN L, XU S J, YANG F M, TANG Y L. Analyst, 2017, 142(18): 3352-3355.
70. [70]
  GUO L Q, NIE D D, QIU C Y, ZHENG Q S, WU H Y, YE P R, HAO Y L, FU F F, CHEN G N. Biosens.Bioelectron., 2012, 35(1): 123-127.
71. [71]
  ZHU Q, LIU L H, XING Y P, ZHOU X H. J. Hazard. Mater., 2018, 355: 50-55.
72. [72]
  XU L J, CHEN Y, ZHANG R H, GAO T, ZHANG Y J, SHEN X Q, PEI R J. J. Fluoresc., 2017, 27(2): 569-574.
73. [73]
  ZHOU Z X, ZHU J B, ZHANG L B, DU Y, DONG S J, WANG E K. Anal. Chem., 2013, 85(4): 2431-2435.
74. [74]
  YANG C L, HU R, LI Q, LI S, XIANG J F, GUO X D, WANG S Q, ZENG Y, LI Y, YANG G Q. ACS Omega, 2018, 3(9): 10487-10492.
75. [75]
  ZHANG S G, SUN H X, WANG L X, LIU Y, CHEN H B, LI Q, GUAN A J, LIU M R, TANG Y L. Nucleic Acids Res., 2018, 46(15): 7522-7532.
76. [76]
  ANJONG T F, KIM G, JANG H Y, YOON J, KIM J. New J. Chem., 2017, 41(10): 4241-4241.
77. [77]
  LU Y J, HU D P, ZHANG K, WONG W L, CHOW C F. Biosens. Bioelectron., 2016, 81: 373-381.
78. [78]
  MURRAY J M, CARR A M. Curr. Opin. Cell Biol., 2018, 52: 120-125.
79. [79]
  DEZ C, TOLLERVEY D. Curr. Opin. Cell Biol., 2004, 7(6): 631-637.
80. [80]
  SHIVALINGAM A, IZQUIERDO M A, LE MAROIS A, VYSNIAUSKAS A, SUHLING K, KUIMOVA M K, VILAR R. Nat. Commun., 2015, 6: 8718.
81. [81]
  LI L L, XU H R, LI K, YANG Q, PAN S L, YU X Q. Sens. Actuators, B, 2019, 286: 575-582.
82. [82]
  CHEN H B, SUN H X, ZHANG S G, YAN W P, LI Q, GUAN A J, XIANG J F, LIU M R, TANG Y L. Chem. Commun., 2019, 55(35): 5060-5063.
1. [1]
  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
2. [2]
  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
3. [3]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
4. [4]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
5. [5]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
6. [6]
  Meiqing Yang , 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-. doi: 10.3866/PKU.WHXB202310046
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
12. [12]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
17. [17]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112
18. [18]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
19. [19]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
20. [20]
  Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010

Get Citation

PDF

XML

Metrics

PDF Downloads(31)
Abstract views(2020)
HTML views(405)

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