A fast-responsed fluorescent probe for the selective detection hydrogen sulfide and tert- butoxy radical

Article abstract of DOI:10.1016/j.tet.2020.131317

The fluorescent probe (1) for detecting hydrogen sulfide and tert-butoxy radical in aqueous environment and living cells was first developed. The probe 1 displayed excellent optical properties such as good selectivity, low detection limit (21 nM), quantitative detection (1–10 μM), and very fast response times (<50 s) for monitor of hydrogen sulfide in aqueous environment. Furthermore, the color of the probe 1 solution changed from yellow to colorless when hydrogen sulfide added. More importantly, the probe 1 is successfully used to real-time imaging for hydrogen sulfide and tert-butoxy radical in Hela cells. These merits play a significant role in the process for hydrogen sulfide detection considering the rapid metabolism in organisms.

Full text of DOI:10.1016/j.tet.2020.131317

Journal Pre-proof
A fast-responsed fluorescent probe for the selective detection hydrogen sulfide and
tert- butoxy radical
Junyang Dong, Jianfeng Hu, Hao Zhang
PII:
S0040-4020(20)30472-5
https://doi.org/10.1016/j.tet.2020.131317
TET 131317
DOI:
Reference:
To appear in: Tetrahedron
Received Date: 21 March 2020
Revised Date: 27 May 2020
Accepted Date: 29 May 2020
Please cite this article as: Dong J, Hu J, Zhang H, A fast-responsed fluorescent probe for the selective
detection hydrogen sulfide and tert- butoxy radical, Tetrahedron (2020), doi: https://doi.org/10.1016/
j.tet.2020.131317.
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Graphical abstracts
A novel fluorescent probe for detecting hydrogen sulfide and tert-butoxy radical in aqueous
environment and living cells was developed.

A fast-responsed fluorescent probe for the selective detection hydrogen
sulfide and tert- butoxy radical
Junyang Donga,d, Jianfeng Hua,b, Hao Zhanga,b,c*
aCollege of Chemical & Chemical Engineering, Inner Mongolia University, Hohhot 010021, P.
R. China.
bInner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot 010021, P. R. China.
cState Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied
Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China.
dState Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese
Academy of Sciences, Lanzhou 730000, P. R.China
*Corresponding Author, tel: +86-471-4994406, fax: +86-471-4994406, e-mail:
haozhang@imu.edu.cn; zh_hjf@hotmail.com.
1

Abstract: The fluorescent probe (1) for detecting hydrogen sulfide and tert-butoxy radical in
aqueous environment and living cells was first developed. The probe 1 displayed excellent
optical properties such as good selectivity, low detection limit (21 nM), quantitative detection
(1-10 μM), and very fast response times (< 50 s) for monitor of hydrogen sulfide in aqueous
environment. Furthermore, the color of the probe 1 solution changed from yellow to colorless
when hydrogen sulfide added. More importantly, the probe 1 is successfully used to real-time
imaging for hydrogen sulfide and tert-butoxy radical in Hela cells. These merits play a
significant role in the process for hydrogen sulfide detection considering the rapid metabolism
in organisms.
Keywords: carbazole, hydrogen sulfide, tert-butoxy radical, colorimetric probe, cell imaging.
2

1. Introduction
As the third most common gaseous signalling molecule, hydrogen sulfide is well known
in biology besides nitric oxide and carbon monoxide.1,2 Hydrogen sulfide is endogenously
produced in biology by enzymes such as cystathionine g-lyase,3 cystathionine b-synthase,4
cysteine aminotransferase,5 and 3-mercaptopyruvate sulfurtransferase.6 Moreover, some
international research team also have proved that the concentration of hydrogen sulfide is
related to Down syndrome,7 Alzheimer’s disease8 and liver cirrhosis.9 All these results
demonstrated the significance of hydrogen sulfide homeostasis in biosystems.
The catabolism of hydrogen sulfide is very fast, and the concentrations of endogenous
biological sulfides sometimes even lower than 10 μM in normal cells.9,10,11 The concentration
of H2S instantaneously in vitro is very hard to detect, because the response time of most
analytical methods always needs long time (> 20 min). Therefore, the development of
sensitive, fast, efficient, and quantitative methods for detection of hydrogen sulfide in living
systems is of considerable significance with further research on the physiological and
pathological functions of hydrogen sulfide.
Meanwhile, reactive oxygen species (ROS) is a collective term that includes hydroxyl
.
.
.
radicals (HO ), peroxyl radicals (ROO ), alkoxyl radicals (RO ), singlet oxygen (1O2),
.
-
superoxide radicals (O2 ), and peroxides (H2O2). Tert-butoxy radical is a kind of alkoxyl
radicals. Reactive oxygen species play important roles in a variety of physiological and
pathological processes, such as cancer, aging and many other health diseases.12,13 Furthermore,
some research team reports also have indicated that ROS could lead to sequential peroxidation
3

of lipids and fatty acid decomposition and then dissociate the membrane to kill the cells
because of their high reactivity.13,14
Table 1. Comparison of other reported fluorescent probes for H2S.
LOD
(nM)
Reaction
time
Analytical
applictions
Probe
References
NO2
2000
60 min
Living cells
27
O
N
N
NC CN
Living cells
and living mice
3050
790
60 min
30 min
28
29
O
N3
O
O
O
O
O
O
O
O
Living cells
and C.elegans
S
S
OHC
O
O
10
3 min
Living cells
30
N
N
S
S
N
OMe
O
O
120
21
2 min
Living cells
Living cells
31
N
S
O2N
NO2
50 s
This work
N
Many novel, effective and selective fluorescent probes have been reported for detection
of specific reactive oxygen species, because of Chemists and biologists have attached great
4

importance to this field.15,16 On the basis of literature reports, the fluorescent probes reported
.
.
-
so far are mainly designed and applied for detection of HO , O2 , 1O2, H2O2, ONOO- and so
on.15,17-26 There has been rare example of special fluorescent probe for tert-butoxy radical in
living cells. Thus, it is highly desired to develop fluorescent probes for selectively detecting
tert-butoxy radical in living cells.
.
Herein, we report the first fluorescent probe for the reversible detection of H2S and tBuO
in aqueous environment and living cells. Compared with some other fluorescent probes
(Table 1),27-31 the fluorescent probe 1 is found to be selective for the quantitative monitoring
of H2S with a detection limit of 21 nM in CH3CN/PBS buffer (2/8, v/v, pH 7.4) conditions.
The fluorescent response of probe 1 to H2S could complete within 50 s. These merits play a
crucial role in the H2S detection in consideration of the fast metabolism in homeostasis
regulation. Cell imaging studies have verified that the probe 1 could be used to detect H2S and
.
tBuO in living cells.
2. Results and discussion
2.1 Design and synthesis of fluorescent probe 1.
Scheme 1. Synthesis of probe 1.
In our study, the following properties should be satisfied for an excellent fluorescent
probe: rapidly response, high selectivity, quantitative detection and good biocompatibility. It
5

is great important for finding a specific reaction between hydrogen sulfide and reaction group
to design new and highly selective H2S fluorescent probes. The nitro group can be easily
reduced to amine group in the presence of H2S.27 Meanwhile, most carbazole derivatives have
some advantages, such as good stability, strong intramolecular charge-transfer, excellent
solubility and membrane permeability. Bearing these information in mind, a novel
colorimetric and fluorescent probe for H2S was developed based on the fundamental redox
reaction. Probe 1 was synthesized by one step with 84% yield (Scheme 1). The structure of
probe 1 was characterized by 1H NMR, 13C NMR spectra and HR-MS spectrometry.
2.2 UV−Visible absorption responses of probe 1 to H2S.
We researched many different sole and mix solvents to find most suitable solvent system
of water solubility experiment for probe 1 to detect H2S. It turned out that probe 1 could
respond to H2S well in CH3CN/PBS buffer (2/8, v/v, pH 7.4). The absorption and fluorescence
spectra properties of probe 1 were investigated under optimized conditions (CH3CN/PBS
buffer 2/8, v/v, pH 7.4). The absorption spectra of probe 1 did not show obvious changes in
the presence of other reductants and anions (Cys, Hcy, GSH, Fe2+, CO3 , AcO-, Br-, Cl-, F-, I-,
2-
-
-
-
-
2-
NO3 , HPO4 , HCO3 , HSO3 , SO4 ). As displayed in Figure 1 (a), upon the addition of H2S,
the color of the probe 1 solution changed from yellow to colorless. The absorption peaks at
331 nm and 423 nm decreased with the addition of NaHS (40 μM), which might cause the
color change (Figure 1 (b)). These results exhibited that probe 1 can act as a naked-eye probe
for the detection of hydrogen sulfide in aqueous environment.
6

Figure 1. (a) UV-vis spectra of 1 (10 μM) in CH3CN/PBS buffer (2/8, v/v, pH 7.4) with
different additions (100 μM ). The inset photo of 1 and HS- (40 μM). (b) UV-vis titration
spectra of 1 (10 μM) in the presence of HS- (0-40 μM) in CH3CN/PBS buffer (2/8, v/v, pH =
7.4).
.
2.3 Fluorescence responses of probe 1 to H2S and tBuO .
Then we examined the cytotoxicity of probe 1 (Figure S4) and the fluorescence
specificity of the probe 1 for H2S. As shown in Figure 2 (a), the fluorescence spectra of probe
1 did display hardly any changes with addition of other reductants and tested anions (Cys,
Hcy, GSH, Fe2+, CO3 , AcO-, Br-, Cl-, F-, I-, NO3 , HPO4 , HCO3 , HSO3 , SO4 ). Meanwhile,
the fluorescence spectra of probe 1 showed strong fluorescence in the presence of H2S.
Besides, the competitive experiments of the background species to the selectivity of probe 1
for H2S were carried out (Figure S5). The experiment result showed that the background
species had no interference with the detection of H2S for probe 1.
2-
-
-
-
-
2-
Next, we researched the response of probe 1 to different concentrations of H2S under the
optimized conditions. A gradual increase of the fluorescence intensity (quantum yield, Φ =
0.41) was found with the increase of H2S concentration (Figure 2 (b)) because of the
reduction of nitro group. Interestingly, the probe 1 showed a good linear response to H2S with
7

a low detection limit of 21 nM (S/N = 3) in the range of 1-10 μM (Figure 3). These results
indicated that the probe 1 could detect H2S quantitatively under CH3CN/PBS buffer (2/8, v/v,
pH 7.4) conditions.
Reaction time is a very important parameter to evaluate a good H2S probe in real time
detection. Therefore, we investigated the time dependent response and optical stability of
probe 1 to H2S. The fluorescence intensity increased immediately after the addition of (300
μM) NaHS (Figure 4). Meanwhile, the result showed that the reaction was almost completed
within 50 s. The fluorescence intensities of probe 1 and HS- (40 μM) displayed either no or
minimal change with time from 0 to 10 min (Figure S6). These data indicated that probe 1
had a very fast response and good optical stability to detect H2S.
Figure 2. (a) Fluorescence spectra of probe 1 (10 μM) in the presence of different additions
(100 μM) in CH3CN/PBS buffer (2/8, v/v, pH = 7.4). (b) Fluorescence spectra of probe 1 (10
μM) in the presence of HS- (0-40 μM) in CH3CN/PBS buffer (2/8, v/v, pH = 7.4),
(λex= 423
nm).
8

Figure 3. (a) Fluorescence spectra of probe 1 (10 μM) in the presence of HS- (0-10 μM) in
CH3CN/PBS buffer (2/8, v/v, pH = 7.4). (b) Linear relation between fluorescence
enhancement and HS- concentration (1-10 μM) in CH3CN/PBS buffer (2/8, v/v, pH = 7.4),
(
λex= 423 nm).
Figure 4. Time-dependent fluorescence intensity change at 525 nm of probe 1 (10 μM) in the
presence of HS- (300 μM) in CH3CN/PBS buffer (2/8, v/v, pH = 7.4) with the excitation at
423 nm.
.
To date, there is rare special fluorescent probe has been reported to detect tBuO in living
.
cells. Therefore, design and synthesis a fluorescent probe for sensoring H2S and tBuO
9

.
concentration changes would be very significative for understanding intracellular H2S / tBuO
redox cycle. This is still an unmet need in aqueous environment and biosystems.
We hypothesized that the reduced product of probe 1 treated with H2S might be
converted back to probe 1 by certain oxidants, which could be achieved the regeneration of
the probe. As shown in Figure S7, the process was investigated with a series of oxidants by
.
fluorescence spectrum experiments. The results suggested that tBuO was the most ideal
oxidant and it could recover the fluorescence intensity of probe 1 to almost the original level
.
2-
1
(Figure 5). Meanwhile, other oxidants, such as H2O2, ClO-, HClO4, S2O8 , OH, and O2,
could not regenerate the fluorescence intensity of probe 1. Therefore, the turn on fluorescence
.
intensity of probe 1 by H2S is reversible via tBuO . The redox cycles was repeated at least two
times under the optimized conditions (Figure S8). These results indicated that probe 1 could
.
be used to monitor the redox cycles between H2S and tBuO by fluorescence spectrum under
CH3CN/PBS buffer (2/8, v/v, pH 7.4) conditions.
10

Figure 5. Fluorescence recovery of probe 1 (10 μM) in CH3CN/PBS buffer (2/8, v/v, pH =
7.4). (1) Red line: L1 only. (2) Blue line: L1 with 4 equiv of HS-. (3) Black line: L1 + HS- and
.
1 min later treated with tBuO
(
Fe2+：TBHP, mol：mol=10：1)
(λex= 423 nm).
.
2.4 Proposed mechanism of probe 1 to H2S/ tBuO .
According to the previous reports and experimental results, we speculated that the nitro
group of probe 1 was reduced to amine group by H2S and the fluorescence of probe 1 turned
on (Figure S9).27 The sensing mechanism of probe 1 for H2S was checked by
high-resolution-mass spectrometry (HR-MS). The compound 2 can be verified by HR-MS, in
which [2 + H2O + H]+ peaked at 324.2092 (m/z calcd for C20H26N3O 324.2070). As shown in
Figure S10, the result verified the proposed mechanism. Enamine is an important and weakly
stable intermediate in chemistry. Therefore, enamine (compound 2, Figure S9) is very easily
oxidized. Considering these facts, we speculated that the compound 2 can be oxidized to
.
.
probe 1 by tBuO . Meanwhile, the addition of tBuO can reverse the color change in probe
visibility（Figure S11）proved that probe 1 is reversible. The sensing mechanism and
.
experimental results revealed the reversible process for probe 1 to H2S and tBuO .
.
2.5 Cellular imaging of H2S and tBuO by probe 1.
11

Figure. 6. (a1-c1) Fluorescence images of HeLa cells incubated with probe 1 (10 μM) for 0.5
h. (a2-c 2) Fluorescence images of cells treated with probe 1 (10 μM) for 0.5 h and
subsequently dealt with (40 μM) NaHS for 0.5 h. (a3-c3) Fluorescence images of cells treated
with probe 1 (10 μM) for 0.5 h and subsequently dealt with (40 μM) NaHS for 0.5 h, then
dealt with tBuO. for 10 min. Scale bar: 25 μm.
We further researched the fluorescence imaging of probe 1 in biological systems. The
.
fluorescence imaging of H2S and tBuO was conducted in live Hela (cervix carcinoma cell)
cell lines. As shown in Figure 6, Hela cells were treated with probe 1 (10 μM) and
displayed almost no fluorescence. While the live Hela cells were loaded with NaHS (40
μM) for another 30 min, a strong fluorescence in the intracellular was observed. Importantly,
hela cells pretreated with probe 1 and NaHS (40 μM) experienced a significant fluorescence
.
quenching after treatment with tBuO for 10 min. Therefore, the results of fluorescence
.
imaging indicated that the probe 1 can be used to monitor intracellular H2S and tBuO
activity.
12

3. Conclusions
In summary, probe 1 was developed as the first reversible fluorescent probe to detect H2S
.
and tBuO in living cells. Upon the addition of H2S, the color of the probe 1 solution changed
from yellow to colorless. The probe 1 displayed excellent properties such as good selectivity,
low detection limit, and very fast response times for detection of H2S. Importantly, the probe
.
1 is successfully used to real-time imaging the variation of H2S and tBuO in living cells. Our
results confirm that probe 1 is a reliable fluorescent probe for reversible detection of the
.
changes of H2S and tBuO in living cells.
4. Experimental section
4.1 Chemicals and spectrophotometric experiments
All chemicals were purchased from commercial sources, unless specified otherwise,
and used without further purification. All solvents were purified before using. The water used
in the experiments was the triple distilled water. Stock solution of probe 1 (1 mM) was
prepared in CH3CN. Stock solution (1 mM) of HS-, Cys, Hcy, GSH, Fe2+, CO3 , AcO-, Br-,
2-
-
-
-
-
2-
Cl-, F-, I-, NO3 , HPO4 , HCO3 , HSO3 , SO4 , Zn2+, Na+, K+, Ca2+, Mg2+, H2O2, ClO-, HClO4,
2-
and S2O8 was prepared in distilled water. All the detection experiments were performed in
CH3CN/PBS buffer solution (10 μM, 2:8, v/v, pH = 7.4) at room temperature. The HeLa cells
were grown in DMEM (High Glucose), supplemented with 10% FBS (Fetal Bovine Serum) at
◦
37 C in humidified atmosphere of 5% CO2. HeLa cells were seeded on 12-well plates and
allowed to adhere for 24 h. Before the experiments, HeLa cells were washed 3 times with
13

PBS. After HeLa cells are incubated with the probe 1, the cells were washed 3 times with
PBS.
4.2 Instruments.
NMR spectra experiments were measured with a Bruker Avance 500 spectrometer. Mass
(HR-MS) spectra were performed with a Bruker QTOF mass instrument. Melting points were
measured with melting points apparatus and were uncorrected. The UV−vis absorption
spectra experiments were performed with UV-2700 (Shimadzu) at room temperature.
Fluorescence spectra experiments were performed with a HitachiF-7000 spectrofluorimeter.
Cells imaged experiments were measured by the Zeiss Axiovert A1 fluorescence inverted
microscope.
4.3 Synthesis of fluorescent probe 1.
Aldehyde 2 (279.3 mg, 1.0 mmol), ammonium acetate (231.2 mg, 3.0 mmol), glacial
acetic acid (98%, 1.6 mL) were dissolved in nitromethane (6 mL) in a 50 mL round bottomed
flask. The flask was stirred at 80oC for 3 h (Scheme S1). Then the reaction mixture was
cooled to room temperature, 20 mL water were added, and the mixture was extracted with
ethyl acetate (25 mL, 3 times), then washed with saturated salt water. The organic layers were
combined and dried over Na2SO4. The solvents were concentrated under reduced pressure,
and the crude product was purified by chromatography on silica gel. Red solid, 306 mg (yield
o
1
84%); mp 188-189 C; Rf (dichloromethane/methyl alcohol = 10:1). H NMR (500 MHz,
CDCl3) δ 8.30 (s, 2H), 8.24 (s, 1H), 8.21 (s, 1H), 7.77 – 7.68 (m, 4H), 7.49 (d, J = 8.6 Hz, 2H),
4.36 (t, J = 7.2 Hz, 2H), 1.87 (dt, J = 5.2, 7.6 Hz, 2H), 1.41 (dt, J = 6.7, 7.5 Hz, 2H), 0.98 (t, J
14

= 7.4 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 143.3, 140.2, 135.2, 127.6, 123.4, 123.0, 122.2,
110.5, 43.6, 31.2, 20.6, 13.9. HR-MS (ESI-TOF) m/z: [M+] calcd for C20H19N3O4 365.1376;
found: 365.1371.
Acknowledgements
This study was financially supported by the National Natural Science Foundation of
China (No. 21861028), Natural Science Foundation of Inner Mongolia (2017MS0206),
Grassland Talent Innovative Teams of Inner Mongolia Autonomous Region, Open Research
Fund of State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of
Applied Chemistry, Chinese Academy of Sciences.
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17

Highlights
ꢀ The probe 1 displayed excellent properties for monitor of H2S in aqueous
environment.
ꢀ The probe 1 could be used to monitor the redox cycles between H2S and tBuO. by
fluorescence spectrum.
ꢀ The probe 1 is successfully used to real-time imaging the variation of H2S and
tBuO. in living cells.

Declaration of interests
☒ The authors declare that they have no known competing financial interests or personal relationships
that could have appeared to influence the work reported in this paper.
☐The authors declare the following financial interests/personal relationships which may be considered
as potential competing interests: