A water soluble ratiometric fluorescent probe for targeting SO2in mitochondria based on conjugated biquinolines

Article abstract of DOI:10.1039/d0nj04484a

Despite the unprecedented development of SO2 fluorescent probes in the past five years, the water-solubility of these probes is still an important factor related to their practical application. In previous work, we have studied SO2 detection by coupling quinoline and coumarin. Although the water solubility of the probe was improved, SO2 detection in a 100% aqueous medium was not fully achieved. Therefore, based on the previous system, we conjugated two quinolines to realize a 100% water-soluble sulfur dioxide fluorescent probe. The Probe showed a large Stokes shift (170 nm). Besides, the Probe could respond to SO2 within 1.5 min with high selectivity and sensitivity (LOD = 0.29 μM). In addition, fluorescence co-localization studies suggested that the Probe could be used for monitoring SO2 in the mitochondria of HeLa cells and living mice. It is believed that such an excellent probe will have a wide application prospect in the future. This journal is

Full text of DOI:10.1039/d0nj04484a

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Chechia Hu, Tzu-Jen Lin et al.
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Water soluble ratiometric fluorescent probe to
mitochondrial targeted SO2 based on conjugated
biquinolines
Received 00th January 20xx,
Accepted 00th January 20xx
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Jialu Yanga, Caixia Yin, a,* Kaiqing Ma, aYongkang Yue, a Fangjun Huob,*
DOI: 10.1039/x0xx00000x
Despite the unprecedented development of SO2 fluorescent probes in the past five years, the water-solubility of probes is
still an important factor related to their practical application. In previous work, we have studied SO2 detection by coupling
quinoline and coumarin. Although the water solubility of probe was improved, the detection in the 100% aqueous medium
was not fully achieved. Therefore, based on the previous system, we conjugated two quinolines to realize a 100%
water-soluble sulfur dioxide fluorescent probe. The Probe showed a large Stokes-shift (170 nm). Besides, the Probe could
respond to SO2 within 1.5 min with high selectively and sensitively (LOD = 0.29 μM). In addition, fluorescence
co-localization studies suggested that the Probe could be used for monitoring SO2 in the mitochondria of HeLa cells and
living mice. It is believed that such an excellent probe will have a wide application prospect in the future
.
nucleophilic addition of SO2 to aldehyde group,25-26 decomposition
1. Introduction
- 27
of levulinic acid mediated by HSO3 , Michael addition and
For a long time, environmental and health issues have received
great attention. Sulfur dioxide (SO2) is used as
coordination.28-29 However, these fluorescent probes have some
defects, poor water solubility (Table 1) and are often interfered by
other mercaptan competitive substances. In addition, the single
emission type fluorescent probe has a single emission wavelength
and the SO2 in the sensor body will be interfered by other
environmental factors.30 In contrast, the ratio type fluorescence
probe uses its fluorescence emission ratio at different
wavelengths as the detection signal, which can be more
accurate.31-34
a global
atmospheric pollutant frequently, but it is widely used as food
additive due to its excellent antioxidant properties, corrosion
protection, and color retention.1 Therefore, SO2 has great effect
on human health. However, articles show that the emission of SO2
is not only aggravating the air pollution, but also related to the
occurrence of many diseases.2-5 Endogenous SO2 mainly exists in
6-7
the mitochondria of cells. It is formed by the oxidation of H2S
and some sulfur-containing amino acids.8-13 After being absorbed
into the human body, it is first converted into its derivatives-sulfite
and bisulfite in body fluids.14-15 These derivatives can not only
damage the respiratory system, but also enter the blood in the
form of ions and distribute to the whole body, causing a variety of
organ damage. Therefore, it is necessary to track and detect SO2
and its derivatives in the mitochondria of subcellular organelles.
As a powerful visual biological imaging method, fluorescent
probe is widely used because of its strong designability, high
spatial-temporal resolution and high sensitivity.16-24 A lot of
fluorescent probes are used to detect SO2 derivatives in vitro and
vivo in recent years. The detection mechanism includes:
In our previous research, we designed a SO2 fluorescent probe
through the conjugation of quinoline and coumarin, which greatly
improved the water solubility of the probe.35 However, the
detection system still required organic solvents to help dissolve.
Based on this foundation, two quinolines were conjugated by
double bonds to construct Probe.36 Moreover, the common
mitochondrial targeting probes usually show small Stokes shift and
are affected by external factors. Compared to this, after the Probe
reacted with NaHSO3 in water, the Probe responded quickly and
showed proportional fluorescence emission. In addition, the Probe
showed a large Stokes shift (170 nm), which was more likely to
avoid background fluorescence interference. In living cell imaging,
Probe accumulated in mitochondria. In addition, Probe had been
made use of imaging in mice successfull.
a. Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of
Education, Institute of Molecular Science, Shanxi University, Taiyuan, 030006,
China.
b. Research Institute of Applied Chemistry, Shanxi University, Taiyuan, 030006,
China..
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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DOI: 10.1039/D0NJ04484A
O
N
SeO2
5
OCH3
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9
N
80°C 4h
1
O
O
N
OCH3
N
Piperidine
100°C
NH2
CH3I
OCH3
H3CO
C2H5OH 90°C
N
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100°C 12h
Probe
OCH3
2
Scheme 1. The synthetic route of the Probe.
2 Result and Discussion
0.20
400 nm
2.1. Characterization data of the Probe
-
0-120 μM HSO3
Scheme 1 shows the Probe synthesis route. Probe was synthesized
according to the literature.37 The synthetic routes of other
compounds are listed in the supporting information.
0.15
0.10
0.05
0.00
330nm
The Probe was characterized by NMR and HR-MS..1H NMR (600
MHz, DMSO-d6) δ 9.00 (d, J = 8.8 Hz, 1H), 8.62 (d, J = 8.8 Hz, 1H),
8.56 (d, J = 10.3 Hz, 1H), 8.44 (d, J = 8.4 Hz, 1H), 8.31 (d, J = 15.8 Hz,
1H), 8.16 (dd, J = 21.2, 12.2 Hz, 2H), 8.02 (d, J = 9.1 Hz, 1H), 7.87 (d,
J = 5.7 Hz, 2H), 7.51 – 7.45 (m, 2H), 4.61 (s, 3H), 4.02 (s, 3H), 3.95
(s, 3H).13C NMR (151 MHz, DMSO-d6) δ 159.44 (s), 158.83 (s),
153.31 (s), 151.20 (s), 144.80 (s), 144.22 (s), 143.72 (s), 136.18 (d, J
= 42.4 Hz), 135.27 (s), 131.26 (s), 130.76 (s), 129.85 (s), 127.18 (s),
123.73 (s), 123.67 (s), 122.49 (s), 122.27 (s), 121.75 (s), 108.77 (s),
106.21 (s), 56.76 (d, J = 3.4 Hz), 56.18 (d, J = 4.0 Hz), 40.82 (d, J =
300
325
350
375
400
425
450
Wavelength (nm)
8.7 Hz).The HR-MS spectrum of Probe: calc. for C23H21N2O2 [M]+,
357.15975, found 357.15973.
+
2.2. Optical characteristics of the Probe
In the PBS test system, we evaluated the response of the Probe to
SO2 through ultraviolet spectrophotometer and fluorescence
spectrophotometer. As shown in Figure 1a, after the continuous
mixing of NaHSO3, the strong absorption peak gradually decreased
until the peak disappeared (400 nm). Meanwhile, a peak appeared
at 330nm gradually. As for the fluorescence spectrum (Figure 1b),
under the excitation of 330 nm, with the addition of 120 μM SO2,
the strong fluorescent emission of the Probe at 570 nm continued
to decline and reached a saturation, and a emission peak arised at
445 nm, which proved that the new substance was produced in
the reaction process. At the same time, we also conducted a
spectral test on the stability of the Probe (Figure S5), which
showed that the Probe had excellent photostability. In addition,
the Probe showed a large Stokes shift of 170 nm (Figure 1c),
effectively avoiding excitation backscattering effects.
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Whether it has a single excellent selectivity is veryViimewpAortritcalenOtnflioner
DOI: 10.1039/D0NJ04484A
Probe, so we evaluated it by fluorescence spectroscopy. First,
0
Probe interacted with other amino acids in PBS buffer, which can
-
be compared with the HSO3 treated system. The fluorescence
6
intensity emission ratio was significantly higher than the ratio
after other amino acid treatments (Figure 3a). Similarly, under the
same external additional conditions, Probe interacted with other
anions. The ratio of fluorescence intensity was still much lower
than the ratio with HSO3 action (Figure 3b). When HSO3 was
added to other amino acids, it can be clearly seen that the ratios
have increased by different amplitudes in the competition graph.
(Figure S6-7) Therefore, from all these results, we can conclude
that the Probe has outstanding selectivity for SO2.
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-
1.0
Figure 1 (a) In the PBS, the Ultraviolet spectrum of the Probe (10
μM) coexisted with different concentrations of NaHSO3 (0-120 μ
M). pH = 7.4 (b) The fluorescence spectrum of the Probe (10 μM)
coexisted with different concentrations of NaHSO3 (0-120 μM) in
PBS solution (pH = 7.4), λex = 330 nm, slit width: 5 nm / 10 nm. (c)
The normalized absorption (green) and fluorescence (blue) spectra
a
0.8
0.6
0.4
0.2
0.0
of
Probe.
-
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3
4
5 6 7 8 9 10 11 12 13 14 15 16 17
During the contact of the Probe with HSO3 , the reaction was
rapidly and the reaction was almost completed in a short time (1.5
min). The fluorescence intensity was basically flat in the system
where only Probe existed. This indicated that Probe had the ability
to respond quickly to SO2, and had the potential to detect SO2 in
real time in living organisms.
analytes
1.0
0.5
0.0
b
600
1.5 min
Probe+HSO3-
Probe
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4
5
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7
8
9 10 11 12 13 14 15
analytes
400
200
Figure 3. (a) In the existence of other amino acids each (5 mM),
the ratio value of the Probe (10 μM) in PBS solution (pH=7.4), slit
width:
5
nm/10 nm. 1.NaHSO3, 2.H2S, 3.L-Threonine,
4.L-Methionine, 5.L-Proline, 6.L-Aspartic acid, 7.L-Valine,
8trans-4-Hydroxy-L-proline, 9.L-Asparagine, 10.L-Glutamic acid,
11.L-phenylalanine, 12.L-Arginine, 13.L-Isoleucine, 14.Cys, 15.GSH,
16.Hcy, 17.L-Leucine. All data were obtained after waiting for 3
minutes. (b) In the existence of other anions each (5 mM), the
fluorescence intensity of the Probe (10 μM) in PBS solution
(pH=7.4), slit width: 5 nm/10 nm. 1.NaHSO3, 2.CH3COO-, 3.Cl-,
1
2
3
4
5
Time/min
Figure 2 In PBS solution, the fluorescence intensity changes at 445
nm with time when excess NaHSO3 (120 μM) coexisted with the
Probe (10.0 μM). pH = 7.4, λex = 330 nm, slit width: 5 nm / 10 nm
-
-
2-
4.CO32-, 5.F-, 6.H2PO4 , 7.ClO-, 8.HCO3 , 9.HPO42-, 10.SO4 11.Br-,
at
room
temperature.
12.NO2 , 13.SCN-, 14.S2O3 , 15.H2O2, All data were obtained after
-
-
waiting for 3 minutes.
2.3 Selectivity of the Probe
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that the Probe exhibited strong fluorescence emission in the
2.4 pH dependence and the detection limit of the Probe
View Article Online
DOI: 10.1039/D0NJ04484A
yellow channel and almost no light in the blue channel. After
We explored the physiological and environmental effects of
coexistence of Probe and SO2 under different pH conditions. It is
obvious from the figure (Figure S8) that the fluorescence intensity
ratio between pH 7-10 has a large increase. This is good for
detecting SO2 in a physiological environment. Furthermore, the
detection limit is also an important content that cannot be ignored
in evaluating probe functionality. After precise tests and
calculations, on the basis of the definition of IUPAC (CDL= 3 Sb/m),
the detection limit of the Probe was 0.29 μM. It showed that in
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incubated 50 μM and 100 μM HSO3 into the cells, it can be seen
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from the Figure 5b-5c that with the increase of HSO3 , the
fluorescence of yellow channel was gradually weaken and the
fluorescence of blue channel was further enhanced. These results
demonstrated that Probe can respond to exogenous SO2. After
implemented the exogenous cell experiment, we detected the
endogenous SO2. HeLa cells were cultured with Probe (10 μM) for
20 min, and cultured with 200 μM Cys [30]. After washed with
PBS, we found that the fluorescence of the yellow channel was
significantly decreased and that of the blue channel was enhanced
compared with the Probe only. This also illustrated that the Probe
can be a powerful testing means to detect endogenous SO2 in
living cells.
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the PBS test solution, the Probe has a high sensitivity to HSO3 .
R2=0.98144
1.0
Y=0.01209X-0.0566
0.8
0.6
0.4
0.2
0.0
20
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60
80
100
HSO3-/10-6M
Figure 4. The relationship between fluorescence intensity and
NaHSO3 concentration was linear.
2.5 Detection mechanism
The design initially intended to form a conjugated system for two
large quinoline rings. The Probe showed a certain fluorescence
intensity at 570 nm under the excitation of 330 nm when the
double bond was not added. After the addition of NaHSO3, the
double bond addition and the large conjugated system were
destroyed, showing the fluorescence of the quinoline ring at
445nm. In Figure S4, we verified its mechanism. The product
[C23H22N2NaO5S+] in high-resolution mass spectrometry should be
m/z:461.11416 and the product m/z:461.11359 confirmed our
assumption.
Figure 5 (a) The Probe (10 μM) and Hela cells were co-cultured for
20 min for cell imaging; (b) incubation with NaHSO3 (50 μM); (c)
After pretreatment of the Probe (10 μM) with Hela cells for 20
min, the cell images obtained after 20 min of incubation with
NaHSO3 (100 μM); (d) Cys (200 μM) was incubated for 15 min after
the Probe (10 μM) incubated with Hela cells for 20 min. Yellow
channel, λem= 540-600 nm, λex = 488 nm; Blue channel: λem
=
420-480 nm, λex 405 nm. Scale bar: 20 μm.
=
2.6 The cytotoxicity and live cell imaging.
After the spectral experiment, because of the excellent spectral
properties of the Probe, we carried out further biological imaging
experiments to prove that the Probe can detect small molecular
sulfur in cells. First, we measured the cytotoxicity of the Probe.
We incubated different concentrations of Probe for 5 h and 10 h in
Hela cells, and found that the survival percentage of Hela cells was
91% (Figure S9). The excellent low toxicity of the Probe can pave
the way for our next cell imaging experiment.
We further explored the function of the Probe targeting the
subcellular organelle mitochondria. We incubated the Probe into
HeLa cells for 20 min, and then added with mitochondrial
dye-Mito Tracker Red (MTR) (1 μM) for 20 min after washing with
PBS. It can be seen in the combined images that the mitochondrial
dye and the Probe were well overlapped (R=0.91), indicated that
the Probe can exist in the mitochondria after entering the cell.
These results indicated that the Probe has a targeting function on
mitochondria and can be used for cell imaging of SO2 in
In the exogenous experiment of cell imaging, we incubated the
Probe (10 μM) into HeLa cells at 37 °C for 20 min. It was obvious
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mitochondria.
In summary, we have designed and developed a ratiometric
DOI: 10.1039/D0NJ04484A
Probe based on the quinoline ring large conjugated
View Article Online
architecture, which exhibited an Stokes shift of 170 nm, and
had rapid response capability and low detection limit in
aqueous phase. In biological imaging experiments, the Probe
can be well accumulated in the mitochondria and successfully
carry out internal and external experiments and mouse
imaging.
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Figure 6 The co-localization image of the cells co-cultured with the
Probe (10 μM) and Mitotracker red (1 μM). (a) Indicates the red
channel (mitochondrial dye staining); (b) Indicates yellow channel
(probe staining); (c) Indicates bright field; (d) Indicates merged
images; (e) Correlation R=0.91. (f) Intensity profile of linear region
of interest across the HeLa cell costained with Yellow channel of
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Conflicts of interest
There are no conflicts to declare.
Acknowledgments
Probe and Mitotracker Red; Red channel, λem= 660-720 nm, λex
=
We thank the National Natural Science Foundation of China (No.
21775096, 21907062, 21878180,), One hundred people plan of
Shanxi Province, Shanxi Province"1331 project" key innovation
team construction plan cultivation team (2018-CT-1), 2018
Xiangyuan County Solid Waste Comprehensive Utilization Science
and Technology Project (2018XYSDJS-05), Shanxi Province
Foundation for Returness (2017-026), Shanxi Collaborative
Innovation Center of High Value-added Utilization of Coal-related
Wastes (2015-10-B3), the Shanxi Province Foundation for Selected
(No. 2019), Innovative Talents of Higher Education Institutions of
Shanxi, Scientific and Technological Innovation Programs of Higher
Education Institutions in Shanxi (2019L0031), Key R&D Program of
Shanxi Province (201903D421069), the Shanxi Province Science
Foundation (No. 201901D111015), Key R&D and transformation
plan of Qinghai Province (No. 2020-GX-101 and Scientific
Instrument Center of Shanxi University (201512).
633 nm; Yellow channel: λem= 540-600 nm, λex = 488 nm. Scale bar:
20
μm.
3.7 The imaging of Probe in mice
Then we studied the SO2 imaging of Probe in mice. Before the
-
injection of Probe and HSO3 , we photographed the blank mice
and found that there was no fluorescence signal. After injected
Probe into the abdominal cavity of mice, a strong fluorescent
-
signal was observed. After intraperitoneal injection of HSO3
solution, photographs were taken at different times. It can be
seen from the Figure7c-7d that the fluorescence signal gradually
weakened after 30 min. We added an experiment, only the probe
was shot at different times when the probe was injected into the
abdominal cavity of the mouse. From Figure 7e-7h, it can be
clearly seen that within 120 min, the fluorescence signal in the
mouse's abdominal cavity is weakened to a certain extent under a
certain metabolic effect. It showed that the Probe can track SO2
directly in vivo.
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Figure 7. (a) Blank shooting. (b-d) After 10 min of NaHSO3 (200
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