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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

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Frontiers of Chemical Science and Engineering  2022, Vol. 16 Issue (1): 34-63   https://doi.org/10.1007/s11705-021-2050-1
  本期目录
Recent advances of small-molecule fluorescent probes for detecting biological hydrogen sulfide
Lei Zhou1, Yu Chen1, Baihao Shao2, Juan Cheng2, Xin Li1,2()
1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China
2. College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
 全文: PDF(4312 KB)   HTML
Abstract：

H2S is well-known as a colorless, acidic gas, with a notoriously rotten-egg smell. It was recently revealed that H2S is also an endogenous signaling molecule that has important biological functions, however, most of its physiology and pathology remains elusive. Therefore, the enthusiasm for H2S research remains. Fluorescence imaging technology is an important tool for H2S biology research. The development of fluorescence imaging technology has realized the study of H2S in subcellular organelles, facilitated by the development of fluorescent probes. The probes reviewed in this paper were categorized according to their chemical mechanism of sensing and were divided into three groups: H2S reducibility-based probes, H2S nucleophilicity-based probes, and metal sulfide precipitation-based probes. The structure of the probes, their sensing mechanism, and imaging results have been discussed in detail. Moreover, we also introduced some probes for hydrogen polysulfides.
Key words： hydrogen sulfide    fluorescent probe    reducibility    nucleophilicity    copper sulfide precipitate    hydrogen polysulfides
收稿日期: 2020-12-30      出版日期: 2021-12-27
Corresponding Author(s): Xin Li   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2022, 16(1): 34-63.
Lei Zhou, Yu Chen, Baihao Shao, Juan Cheng, Xin Li. Recent advances of small-molecule fluorescent probes for detecting biological hydrogen sulfide. Front. Chem. Sci. Eng., 2022, 16(1): 34-63.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-021-2050-1
https://academic.hep.com.cn/fcse/CN/Y2022/V16/I1/34
Probe Selectivity Ex/Em/nm Reported change
in fluorescence		 Limit of detection
(LOD)		 Biological system
H2S reducibility-based probes
1 (DDP-1) H2S/H2Sn 360/452,542 100 nmol·L−1
24 nmol·L−1		 HeLa cells
2 (Flu-N3) H2S 470/538 50-fold 0.031 μmol·L−1 HepG-2 cells and nude mice
3 (RPC-1) H2S/HClO 360/445
545/580		 192.1 nmol·L−1
19.8 nmol·L−1		 HeLa cells, HepG-2 cells, RAW264.7 cells and drug-induced liver injury mice
4 (Lyso-HA-HS) H2S/HOCl 380/448
550/580		 490-fold 3.4 × 10–7 mol·L−1
7.3 × 10–8 mol·L−1		 HepG-2 cells and RAW264.7 cells
5 (Mito-HS) H2S 345/540 21-fold HeLa cells and BALB/C nude mice with xenograft breast cancer tumor
6 (Lyso-HS) H2S 345/540 15-fold HeLa cells and BALB/C nude mice with xenograft breast cancer tumor
7 (MT-HS) H2S 440/540 40-fold 1.65 µmol·L−1 HeLa cells and fresh rat liver slices
8 (Na-H2S-ER) H2S 440/545 45-fold 7.77 × 10–6 mol·L−1 HeLa cells, living liver tissue slices and zebrafish
9 (ASNHN-N3) H2S 454/545 0.75 µmol·L−1 HeLa cells, RAW264.7 cells, the fresh liver tissues and heart arteries
10 (BN-H2S) H2S 440/544 71 nmol·L−1 HeLa cells and NIH 3T3 cells
11 (CouN3-BC) H2S 405/450 35-fold HeLa cells
12 H2S 370/490 0.67 µmol·L−1 HEK293A cells
13–14 H2S
15 (Mito-HS) H2S 380/450 ~43-fold 24.3 nmol·L−1 HeLa cells, MDA-MB-231 cells, DU145 cells and 3T3-L1 cells
16 (Lyso-C) H2S 355/458 >20-fold 47 nmol·L−1 HepG-2 cells
17 (1-H2S) H2S 580/635 7-fold ~4.7 × 10–5 mol·L−1 HeLa cells, zebrafish and fresh liver tissue slices of Kunming mice
18 (AC-N3) H2S 360/500 18 nmol·L−1 HeLa cells
19 (QME-N3) RSH/H2S 350/– MCF-7 cells
20 (TPC-N3) H2S –/498 HepG-2 cells and fresh liver and muscle slices of liver cirrhosis induction mice
21 (Lyso-HS) H2S 365/505 95-fold 214.5 nmol·L−1 A549 cells, HepG-2 cells and rat renal tubular epithelial cells
22 (QL-Gal-N3) H2S 365/521 102-fold 126 nmol·L−1 HeLa, A549 cells and HepG-2 cells
23 (Gol-H2S) H2S 405/515 0.11 µmol·L−1 HeLa, EK293A cells and SMMC-7721 cells
24 (Diketopyrrolopyrrole, DPP-NO2) H2S 506/550 800-fold 5.2 nmol·L−1 HeLa cells
25 H2S 485/522 2.55 µmol·L−1 HepG-2 cells
26 (azo1)
27 (azo2) H2S 468/517 103-fold 5 µmol·L−1 Fresh male Sprague-Dawley (SD) rat blood plasma and tissues
28 (azo3) H2S 468/517 148-fold 500 nmol·L−1 Fresh male SD rat blood plasma and tissues
29–32
33 (PHS1) H2S 393/486 8.87 nmol·L−1 HeLa cells
H2S nucleophilicity-based probes
34 190 nmol·L−1 (buffer) 380 nmol·L−1 (serum)
35 (Cy-Cl) H2S 760/795 HeLa cells
36 (CyCl-1) HS− 0.16 µmol·L−1 Living mice
37 (CyCl-2) HS− 0.37 µmol·L−1 Living mice
38 (BH-HS) H2S 450/535 57-fold 1.7 × 10–6 mol·L−1 HeLa cells
39 (CPC) H2S 410/474, 582 56-fold 40 nmol·L−1 HeLa cells
40 (TP-PMVC) H2S 405/550 3.2 µmol·L−1 A549 cells
41 (CP-H2S) H2S 355/454, 573 252.7-fold 2.2 × 10–7 mol·L−1 SMMC-7721 hepatoma cells
42 (Mi) H2S 520/596 15 nmol·L−1 HeLa cells
43 (CyT) H2S 575/595, 655 7.33 nmol·L−1 HeLa cells
44 (Indo-TPE-Indo) H2S 488/560, 710 0.19 µmol·L−1 HeLa, MCF-7 and HUVEC cells
45 (TP-MIVC) RNA/H2S 488/625
405/550		 12-fold 1.0 × 10–6 mol·L−1
3.2 × 10–6 mol·L−1		 HeLa cells, zebrafish, normal mice and tumor mice
46 (CTN) H2S 370/424 200-fold 90 nmol·L−1 HeLa cells
47 (Near-infrared (NIR)-HS) H2S 670/723 50-fold 38 nmol·L−1 MCF-7 cells and living mice
48 (TPE-3) H2S 452/550 0.09 µmol·L−1 HeLa cells, zebrafish
49 (TP-NIR-HS) H2S 800/675 83 nmol·L−1 A375 cells and nude rat liver frozen slices
50 (2-CHO-OH) H2S 550/655 32-fold 8.3 × 10–8 mol·L−1 HeLa cells
51 (NDCM-2) H2S 490/655 160-fold 58.797 nmol·L−1 MCF-7 cells, the kidney tissue slices and living Kunming mice
52 (NIPY-DNP, 2,4-dinitrophenyl) H2S 340/505 273-fold 0.36 µmol·L−1 A549 cells
53 (TMSDNPOB) H2S 574/592 30-fold 1.27 µmol·L−1 HeLa cells and raw 264.7 macrophage cells
54 (LC-H2S) H2S 571/664 27-fold 4.05 µmol·L−1 HeLa cells
55 (A) H2S 440/537 49 nmol·L−1 LoVo cells and SW480 cells
56 (DMC) H2S 384/547 0.069 µmol·L−1 HeLa cells
57 (Cda-DNP) H2S 405/450 120-fold 0.18 µmol·L−1 HeLa cells, A549 cells, HFL1 cells, and zebrafish
58 (NR-NO2) H2S 675/710 L929 cells, HeLa cells, HCT-116 cells and BALB/c nude mice
59 (Mito-NIR-SH) H2S 670/720 14-fold 89.3 nmol·L−1 HeLa cells
60 (DMOEPB) H2S
61 (DMONPB) H2S 543/625 1.3 µmol·L−1 RAW264.7 macrophages and HeLa cells and liver tissues of Kunming mice
62 H2S 570/623 HCT-116 and CT-26 cells
63 H2S 590/680 115-fold 11 nmol·L−1 HCT16, HT29, A549, H1944, MCF-7, MDA-MB-468, MDA-MB-231, PANC1, HeLa, HepG-2 cells and Kunming living mice
64 (QCy7-HS) H2S 580/715 25-fold 1 µmol·L−1 HeLa, HepG-2 cells and female BALB/c mice
65 (Z1) H2S 480/537 0.15 µmol·L−1 Ec1 cells
66 (L) H2S 496/607 1.05 × 10–5 mol·L−1 MCF-7 cells
67 H2S, Cys/homocysteine (Hcy), GSH 415/465
415/465
415/465		 0.10 µmol·L−1
0.08 µmol·L−1
0.06 µmol·L−1		 HeLa cells
68 H2S 382/550 HeLa cells
69 H2S 382/455 150 nmol·L−1 HeLa cells
70 H2S 502/530 65-fold 0.057 µmol·L−1 HEK293A cells
71 H2S 530/589 4.5-fold 0.58 µmol·L−1 HEK293A cells
72 H2S 565/585 19-fold 0.36 µmol·L−1 HEK293A cells and zebrafish
73 H2S 405/480 45-fold 9 µmol·L−1 HEK293 cells and HeLa cells
74 H2S 405/496 200-fold 0.9 µmol·L−1 HEK293A cells, A549 cells and zebrafish
75 H2S 394/486 45-fold 56 nmol·L−1 HEK293 cells
76 (Endoplasmic reticulum (ER)-CN) H2S 383/490 6.5-fold 4.9 µmol·L−1 HeLa cells
77 H2S 395/532 68-fold 2.46 µmol·L−1 HeLa cells
78 H2S 346/516 25-fold 20 nmol·L−1 A431 cells
79 (BDP-N1) H2S 540/587 150-fold 0.06 µmol·L−1 A549 cells and zebrafish
80 (BDP-N2) H2S 625/587 170-fold 0.08 µmol·L−1 A549 cells and zebrafish
81 H2S/GSH Cys/Hcy 620/685
460/540		 253-fold/448-fold 70 µmol·L−1/0.38 µmol·L−1
52 nmol·L−1/38 nmol·L−1		 HeLa cells and living mice
82 H2S 539/565 160-fold 4.80 × 10–8 mol·L–1 HeLa cells
83 (NIR-H2S) H2S 730/830 68-fold 2.7 × 10–7 mol·L−1 MCF-7 cells, athymic nude mice and Kunming mice
84 (L) H2S 780/468 29-fold 24 nmol·L−1 HeLa cells
85 (RHP) H2S 410/550, 475 4-fold A549 cells
86 (RHP-2) H2S 415/467, 532 27-fold 270 nmol·L−1 MCF-7 cells and mouse hippocampus
87 H2S 465/520 80-fold 0.15 µmol·L−1 HeLa cells
88 (NS1) H2S 365/539, 444 1.7 × 10–6 mol·L−1 MCF-7 cells
89 (MeRho-TCA) H2S 476/520 65-fold
90 (LR-H2S) H2S 410/541, 475 (one-photon)
840/541,475 (two-photo)		 80-fold 0.70 µmol·L−1 SGC-7901 cells
91 (PyN3) H2S 410/455 158 nmol·L−1 MCF-7 cells, HeLa cells, zebrafish
92 (NIR-Az) H2S 680/720 200-fold 0.26 µmol·L−1 HeLa cells, RAW 264.7 murine macrophages and BALB/c nude mice
93 (Mito-VS) H2S 370/510 7-fold 0.17 µmol·L−1 HeLa cells
94 (BDP-N3) H2S 475/515 10-fold 2.05 µmol·L−1 HepG-2 cells
95 (Mito-N3) H2S 680/736 20 nmol·L−1 MCF-7 cells and BALB/c(nu/nu) mice
96 H2S 485/610 5.7 nmol·L−1 HeLa cells
97 (MF-N3) H2S 530/560 16-fold 0.09 µmol·L−1 HepG-2 cells
98 (HF-PBA) H2S/biothiols 345/520, 400 75 nmol·L−1 HeLa cells
99 (HS-1) H2S 350/403, 519 0.020±0.001 mmol·L−1 A549 cells
100 (DCM-PBA) H2S 560/680 1.1 nmol·L−1 HeLa cells
101 (Cy-PBA) H2S 675/725 21 nmol·L−1 A549 cells and nude mice
102 H2S 380/495, 525 91 nmol·L−1 HeLa cells
103 H2S 560/633 25-fold 8.37 µmol·L−1 Hi5 insect cells and Caenorhabditis elegans
104 (DCN-S) H2S 420/550, 580 5.7-fold 88 nmol·L−1 HeLa cells
105 (HBTSeSe) H2S 380/460 47-fold 0.19 µmol·L−1 RAW264.7 cells
106 (SFP-1) H2S 300/391 HeLa cells
107 (SFP-2) H2S 465/510 16-fold HeLa cells
108 (ZS1) H2S 520/561 62-fold 2.5 µmol·L−1 RAW 264.7 macrophage cells
109 (P1) H2S 378/524 HeLa cells
110 (P2) H2S 370/450
111 (P3) H2S 375/500 50 nmol·L−1 HeLa cells
112 (P5) H2S 485/638 0.9 µmol·L−1 HeLa cells
113 (RB-PE-1) H2S 560/590 HeLa cells
114 (RB-PE-2) H2S 560/590 HeLa cells
115 (RB-PE-3) H2S 560/590 HeLa cells
116 (FEPO-1) H2S 455/522 14 µmol·L−1 HeLa cells and zebrafish
117 (FLVN-OCN) H2S 415/525 0.25 µmol·L−1 A-549 cells
118 (ZX-NIR) H2S 520/600
650/700		 37 nmol·L−1 HCT116 cells, HepG-2 tumor-bearing mouse model and HCT116 tumor-bearing mice
119 (Coumarin-tetrazine (Tz)) H2S 375/456 16-fold
120 (boradiazaindacene (BODIPY)-Tz-I) H2S 580/660 22.7-fold 0.68 µmol·L−1 3T3 fibroblast cells
121 (BODIPY-Tz-II) H2S 580/660 31-fold 0.66 µmol·L−1 3T3 fibroblast cells
122 H2S 18.2 µmol·L−1
123 (PTZ-P1) H2S –/488 25-fold
124 (PTZ-P2) H2S
125 (PTZ-P3) H2S 330/480, 540
126 (PTZ-P4) H2S 580/638 HeLa cells and Caenorhabditis elegans
H2S metal sulfide-based fluorescent probes
127 H2S 470/517 420 nmol·L−1
128 Cu2+/H2S 410/505 1.3 × 10–7 mol·L−1 HeLa cells
129 H2S 456/612 0.25 µmol·L−1
130 (CuHCD) S2– and HNO 484/595
484/595		 0.7 µmol·L−1
23 µmol·L−1
131 (TACN) H2S
132 (Cyclam) H2S
133 (Hsip-1) H2S 491/516 50-fold HeLa cells
134 (TMCyclen) H2S
135 H2S 680/765 80 nmol·L−1 RAW264.7 cells and HEK 293 cells
136 H2S 600/680 MCF-7 cells
137 H2S 446/605 ~130-fold 21.6 nmol·L−1
138 [Cu(MaT-cyclen)2] H2S 375/430 205 nmol·L−1 HeLa cells and zebrafish
139 H2S –/794 27-fold 280 nmol·L−1
140 (L1Cu) H2S 495/534 HeLa cells and L929 mouse fibroblast cell lines
141 (L1) H2S 494/523 25-30-fold 1.7 µmol·L−1 HepG-2 cells
142 (L1-Cu) H2S 495/557 HeLa cells
143 (L2)
144 (L) Cu2+/H2S 310/373,495 9.12 × 10–7 mol·L−1
145 (NJ1) Cu2+/H2S 360/492 HeLa cells
146 (NL) Cu2+/H2S 430/519 0.17 µmol·L−1 MDA-MB-231 cells
147 Cu2+/HS− 340/480 25-fold 2.24 µmol·L−1 HepG-2 cells
148 Cu2+/H2S 345/540
149 Cu2+/H2S 405/540 47 nmol·L−1 NIH/3T3 cells
150 (TAB-3)
151 (CAH-Cu2+) H2S 350/425 31-fold 65 nmol·L−1
152 (L-Cu) H2S 495/525 31 nmol·L−1 HeLa cells and zebrafish
153 (DPD-Cu2+) Cu2+/S2– 440/510
440/510		 0.73 nmol·L−1
0.87 nmol·L−1		 A549 cells
154 (Cu-1) HS− 543/600 14-fold HeLa cells
155 (Cu(BB)2) H2S 384/590 0.11 µmol·L−1
156 (aggregation-induced emission (AIE)-S) Cu2+/H2S 350/533 HeLa cells
157 (6-CdII) H2S 550/599, 619 HeLa cells
158 H2S 365/500 ~13-fold 30 nmol·L−1
Fluorescent probes for H2Sn
159 (Cy-Sn) H2Sn 680/720 2.2 × 10–8 mol·L−1 RAW264.7 cells and living mice
160 (KB1) H2Sn 535/682 >30-fold 8.2 nmol·L−1 MCF-7 cells
161 (RPHS1) H2Sn 395/482, 655 5.8-fold 43 nmol·L−1 HeLa cells
162 H2Sn 397/534 328-fold 26 nmol·L−1 A549 cells and zebrafish
163 (PZC-Sn) H2Sn 480/620 1 nmol·L−1 RAW 264.7 cells and zebrafish
164 (Re-SS) H2Sn 550/589 24 nmol·L−1 RAW 246.7 cells
165 (BDP-PHS) H2Sn 525/574, 618 57 nmol·L−1 HeLa cells
166 (JCCF) H2Sn 480/543 52-fold 98.3 nmol·L−1 MCF-7 cells and zebrafish
167 H2Sn 360/502 18-fold 5.0 × 10–7 mol·L−1 HepG-2 cells
168 H2Sn
H2S		 410/468, 606
410/519, 606		 194-fold
37-fold		 21 nmol·L−1
34 nmol·L−1		 RAW264.7 cells, living mice liver tissue and zebrafish
169 (NIPY-NF) H2Sn 340/520 69-fold 84 nmol·L−1 A549 cells
170 (Lyso-NRT-HP) H2Sn 405/548 10 nmol·L−1 HeLa cells and the freezing kidney slices
171 (BCy-FN) H2Sn 653/727 46 nmol·L−1 RAW264.7 cells, ZF4 cells, zebrafish larvae and BALB/c mice
172 H2Sn 680/708 44-fold 35 nmol·L−1 HeLa cells, RAW264.7 cells and BALB/c mice
173 (τ-Probe) H2Sn 2 nmol·L−1 HeLa cells and zebrafish
174 (MB-Sn) H2Sn 530/584 26.01 nmol·L−1 RAW 264.7 cells
175 (HQO-PSP) H2Sn 520/633 86-fold 95.2 nmol·L−1 A549 cells and mouse lung tissues
176 (SPS-M1) H2Sn 372/430, 506 0.1 µmol·L−1 HeLa cells, transgenic mice expressing human A53 T α-syn, SH-SY5Y cells and fresh mice brain slices
177 (PP-PS) H2Sn 300/478 20.3-fold 1 nmol·L−1 A549 cells, mouse tumor tissues and inflamed mouse models
Tab.1  
Fig.1  
Fig.2  
Fig.3  
Fig.4  
Fig.5  
Fig.6  
Fig.7  
Fig.8  
Fig.9  
Fig.10  
Fig.11  
Fig.12  
Fig.13  
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