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Progress in Chemistry 2020, Vol. 32 Issue (2/3): 204-218 DOI: 10.7536/PC190513 Previous Articles   Next Articles

Molecular Fluorescent Probe for Monitoring Cellular Microenvironment and Active Molecules

Yang Wang, Chusen Huang**(), Nengqin Jia**()   

  1. Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Material, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China
  • Received: Online: Published:
  • Contact: Chusen Huang, Nengqin Jia
  • About author:
    ** e-mail: (Chusen Huang);
    (Nengqin Jia)
  • Supported by:
    National Natural Science Foundation of China(21672150); National Natural Science Foundation of China(21302125); Alexander von Humboldt Foundation (AvH) the Shanghai Rising-Star Program(19QA1406400); Doctoral Fund of Ministry of Education of China(20133127120005); Shanghai Science and Technology Committee(18DZ2254200); Shanghai Science and Technology Committee(17070503000); Program for Changjiang Scholars and Innovative(IRT_16R49); Shanghai Key Laboratory of Rare Earth Functional Material, and the Shanghai Engineering Research Center of Green Energy Chemical Engineering.()
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Small molecular fluorescent probe technology has become a potential tool for biosensing and bioimaging since it can realize real-time dynamic tracking and monitoring of active molecules and microenvironment changes in living organisms with advantages of less disturbance to biological samples, extremely high sensitivity and specificity. In this review, we summarize some characteristics of cellular microenvironment and related bioactive molecules commonly found in them. The design strategies of the molecular fluorescent probes utilized to monitor changes of cellular microenvironments and active molecules are also discussed. Some recently developed molecular fluorescent probes used to monitor microenvironmental changes and active molecules in organisms have also been listed in this review. Additionally, sensing behavior and potential application of these fluorescent probes have also been discussed.

Key words: cellular microenvironment, bioactive molecule, bioimaging, molecular fluorescent probe
Fig.1 Structures of cysteine(Cys), homocysteine(Hcy), and glutathione(GSH)
Fig.2 Structures of the fluorescence probe[64]
Fig.3 Structures of common fluorophores[65]
Fig.4 Mechanism of PET process[67]
Fig.5 Mechanism of ICT[69]
Fig.6 Mechanism of ESIPT process[72]
Fig.7 Mechanism of FRET process[82]
Fig.8 (a)Proposed mitochondrion-specific pH sensing mechanism for probe 1.(b)The structure of probe 1.(c)nutrient-deprived cells. The images were recorded at time points consisting of t=0, 90, 180, 270 and 360 s[84]. Reprinted with permission from ref 84. Copyright 2014, American Chemical Society
Fig.9 (a)Design strategies of fluorescent probes 2(CN-pH). (b)Proposed sensing mechanism and the fluorescence photographs of 5 μM probes 2(CN-pH) at pH 4.5, 6.5, and 8.5 under 365 nm.(c)The structure of fluorescent probe 2(CN-pH) and Confocal fluorescence images of probe 2(CN-pH)[85]. Reprinted with permission from ref 85. copyright 2016, American Chemical Society
Fig.10 The mechanism of probe 3(CPH) to pH and dual-modal colorimetric/fluorescence images[29]. Reprinted with permission from ref 29. copyright 2016, American Chemical Society
Fig.11 (a) The mechanism of probe 4(CPY) to pH.(b) The fluorescence response of probe 4(CPY) towards different pH values.(c) Relationship between lysosomal pH changes and heat stroke in HeLa cells[86]. Reprinted with permission from ref 86. copyright 2018, the Royal Society of Chemistry
Fig.12 (a) Design of the dual-site fluorescent probe 5 for Cys metabolism.(b) Confocal images of probe 5 responding to exogenous Cys and S O 3 2 - and endogenous thiols in 5-day-old zebrafish.(c) Cys metabolism imaging with probe 5 in A549 cells[20]. Reprinted with permission from ref 20. copyright 2017, American Chemical Society
Fig.13 Schematic representation of hepatocyte targeted imaging of probe 6[87]. Reprinted with permission from ref 87. copyright 2012, American Chemical Society
Fig.14 The mechanism of probe 7(VTAF) to VDPs and ratiometric fluorescence images[88]. Reprinted with permission from ref 88. copyright 2014, American Chemical Society
Fig.15 (a) Schematic of probe 8(C7H) and control probe 9(Con-C7H).(b) Time-dependent fluorescence imaging in larval zebrafish with probe 8(C7H)[89]. Reprinted with permission from ref 89. copyright 2019, the Royal Society of Chemistry
Fig.16 (a)Proposed sensing mechanisms of probe 10(PTZ-Cy2). (b)Changes in fluorescence and adsorption spectra of probe 10(PTZ-Cy2) upon addition of ·OH.(c)Changes in fluorescence and adsorption spectra of probe 10(PTZ-Cy2) upon addition of ClO-. (d)Confocal fluorescence images of probe 10(PTZ-Cy2)[14]. Reprinted with permission from ref 14. copyright 2013, the Royal Society of Chemistry
Fig.17 (a)Proposed sensing mechanisms of probe 11(MitoClO).(b)Confocal fluorescence images of probe 11(MitoClO)[93]. Reprinted with permission from ref 93. copyright 2013, the Royal Society of Chemistry
Fig.18 The structure of lysosome-targetable H2O2 probe 12[94]. Reprinted with permission from ref 94. copyright 2015, scientific reports
Fig.19 Structure of probe 13 and the mechanism of its response to ONO O - [ 95 ] . Reprinted with permission from ref 95. copyright 2014, the Royal Society of Chemistry
Fig.20 The structure of mito-targetable H2O2 and viscosity probe 14[96]. Reprinted with permission from ref 96. copyright 2017, American Chemical Society
Fig.21 Schematic representation of the synthesis procedures of probe 15(EIN) and its working principle[97]. Reprinted with permission from ref 97. copyright 2016, the Royal Society of Chemistry
Fig.22 Working principle of lysosomal viscosity probe 16(Lyso-V)[23]. Reprinted with permission from ref 23. copyright 2013, American Chemical Society
Fig.23 (a) Design procedures for the viscosity probe 17(Lys-V); (b) Fluorescence spectrum of probe 17(Lys-V) with increasing solvent viscosity;(c) Maximum fluorescence intensity of probe 17(Lys-V) in the different pH buffer solutions at various viscosities;(d) The lysosome-targeting properties of probe 17(Lys-V) in live MCF-7 cells;(e) Real-time monitoring of fluorescence changes in probe 17(Lys-V) labelled live MCF-7 after the cells were treated with dexamethasone[98]. Reprinted with permission from ref 98. copyright 2018, the Royal Society of Chemistry
Fig.24 Structures of fluorescent probe 18~21[102,103,104,105]
Fig.25 Structures of fluorescent probe 22 and its reaction with NTP, ATP and NTP/ATP[106]. Reprinted with permission from ref 106. copyright 2018, the Royal Society of Chemistry
Fig.26 ESIPT probe 23 for discrimination between live and dead cells[113]. Reprinted with permission from ref 113. copyright 2018, American Chemical Society
Fig.27 (a)Chemical structure of probe 24. (b)The fluorescence spectra of probe 24 in the presence of different concentrations of ATP. (c)Images of HeLa cell treated with apyrase from 0 to 60 min[114]. Reprinted with permission from ref 114. copyright 2014, the Royal Society of Chemistry
Fig.28 (a)Proposed response mechanism of probe 25 to ATP.(b)Colocation imaging of HeLa cells staining with probe 25 and Mtio-Tracker Green[115]. Reprinted with permission from ref 115. copyright 2017, American Chemical Society
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