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SCIENCE CHINA Chemistry, Volume 61, Issue 8: 882-891(2018) https://doi.org/10.1007/s11426-018-9300-5

Biothiol-specific fluorescent probes with aggregation-induced emission characteristics

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  • ReceivedApr 3, 2018
  • AcceptedJun 5, 2018
  • PublishedJul 18, 2018

Abstract

Biothiols are important species in physiological processes such as regulating protein structures, redox homeostasis and cell signalling. Alternation in the biothiol levels is associated with various pathological processes, therefore non-invasive fluorescent probes with high specificity to biothiols are highly desirable research utilities. Meanwhile, fluorescent probes with aggregation-induced emission properties (AIEgens) possess unique photophysical properties that allow modulation of the sensing process through controlling the aggregation-disaggregation or the intramolecular rotational motions of the fluorophores. Herein we review the recent progress in the development of biothiol-specific AIEgens. In particular, the molecular design principles to target different types of biothiols and the corresponding sensing mechanisms are discussed, along with the potential of the future design and development of multi-functional bioprobes.


Funded by

Australian Research Council(DE170100058)

Rebecca L. Cooper Medical Research Foundation.


Acknowledgment

This work was supported by Australian Research Council (DE170100058) and Rebecca L. Cooper Medical Research Foundation.


Interest statement

The authors declare that they have no conflict of interest.


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  • Figure 1

    Chemical reactions involved in the detection mechanism of biothiol-specific fluorescent probes (color online).

  • Figure 2

    (a) Strategy for assaying protein foldedness via access to buried Cys thiols utilising TPE-MI; (b) confocal microscopy images for TPE-MI staining of HeLa cells with ER Tracker counterstain; (c) unfolding of the proteome by heat shock as assessed by denaturation of Renilla luciferase and luciferase activity; (d) heat shock treatment of HeLa cells at 42 °C for 45 min and subsequent time course of recovery at 37 °C; (e) effect of overnight tunicamycin treatment on HeLa cells; (f) effects of hsp90 inhibitor novobiocin (800 μM for 6 h) and free radical generator, hydrogen peroxide (100 μM for 1 h) on HEK293 cells [38] (color online).

  • Figure 3

    Molecular structures of probes 2 and 3 (color online).

  • Figure 4

    Emission ratio changes of probe 4 (10 μM) upon addition of 1 mM different amino acids or GSH in pH buffer. Inset: solution of 10 μM 4 in blank buffer or 100 mM GSH, Cys and Hcy (left to right) under UV lamp; molecular structure of probe 4 [41] (color online).

  • Figure 5

    Molecular structures of probes 5, 6, and 7 (color online).

  • Figure 6

    Molecular structure of probe 8 (color online).

  • Figure 7

    Fluorescence intensity changes of probe 9 (5 μM) in the presence of a gradually varied concentration of Cys (0–15 μM) in HEPES buffer. Inset: solution of 9 in blank buffer and 15 μM Cys under UV lamp; molecular structure of probe 9 [45] (color online).

  • Figure 8

    (a) Molecular structure of probe 10; (b) inverted SDS-PAGE fluorescence image of 10 labeled proteins (BSA, Enolase, and Myoglobin, left to right) with various contents of Cys residue; (c) image of the same gel post-stained with Coomassie R-250 [46] (color online).

  • Figure 9

    Molecular structures of probe 11, 12 and 13 (color online).

  • Figure 10

    Molecular structures of probes 1418 (color online).

  • Figure 11

    (A) Molecular structures of probe 19 and 20; (B) confocal microscopy images of U87-MG (a, b) and MCF-7 (c, d) cells after incubation with 20 (a, c) and 19 (b, d). The nuclei were stained with propidium iodide [54,55] (color online).

  • Figure 12

    (a) H2S detecting mechanism of 21; (b) plot of PL intensity ratio versus the number of scan in a total time of 25 min. Inset: fluorescence of 21 before and after reacting with NaHS; (c) plot of PL intensity ratio versus NaHS concentration [56] (color online).

  • Figure 13

    (a) Molecular structure of 22; (b) fluorescence images of H2S: 22-loaded C. elegans, sensor for H2S under stimulation with SNP, and 22-loaded zebrafish stimulated with H2S. (c) Fluorescence and (d) absorbance responses of 10 mM TPE-NP to various analytes in aqueous solution: (1) control, (2) I, (3) Br, (4) Cl, (5) CO32−, (6) HCO3, (7) H2PO4, (8) HPO42−, (9) NO3, (10) VC, (11) Zn2+, (12) Mg2+, (13) K+, (14) Ca2+, (15) Ac, (16) S2O32−, (17) S2O42−, (18) S2O52−, (19) SO32−, (20) SO42−, (21) ButOOH, (22) ClO, (23) H2O2, (24) NO, (25) O1, (26) O2, (27) OH, (28) ONOO, (29) GSH, (30) Hcy, (31) S2−, (32) HS [58] (color online).

  • Figure 14

    The reduction reaction of 23 by H2S (color online).

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