An AIE probe for imaging mitochondrial SO2-induced stress and SO2levels during heat stroke

Article abstract of DOI:10.1039/d0cc05803c

A probe, MITO-TPE, was developed for imaging mitochondrial SO2 with good selectivity, high sensitivity, and a fast response time. Cell imaging indicated that SO2-induced oxidative stress may cause damage to cells through O2- bursting. MITO-TPE has here be

Full text of DOI:10.1039/d0cc05803c

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An AIE probe for imaging mitochondria SO -induced stress and its
2
level in heat stroke
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
b
a
a
a
a,c
a
Xiaopeng Yang , Jun Tang , Di Zhang,* Xiaojing Han , Jianfei Liu , Jinsa Li , Yufen Zhao , Yong Ye*
DOI: 10.1039/x0xx00000x
A probe MITO-TPE was developed for imaging mitochondrial SO
with good selectivity, high sensitivity, and fast response. Cell also to other organs including brain, heart, liver, kidney .
2
causes severe oxidative damage to the respiratory system, but
6
imaging indicated that SO
damage to cells through O
achieved imaging the misregulation of SO
during heat stroke for the first time.
2
induced oxidative stress may cause Therefore, it is an urgent need to develop an effective method
·
−
2
bursting. MITO-TPE has been for monitoring the SO
2
-induced oxidative stress, which is very
level in mitochondria meaningful to study biological toxicity mechanism of SO to
the body.
Heat stroke was induced by exposing to a high ambient
2
2
2
Sulfur dioxide (SO ), which traditionally recognized as a toxic
o 7
temperature of 40.6 C . In the case of severe heat stroke,
heart rate and respiration rate will increase as blood pressure
drops and the heart attempts to supply enough oxygen to the
gas or environmental pollutant, may be a new member of the
growing family of gaseous signaling molecules in addition to
1
NO, CO and H
2
S . In biological system, SO
2
is one of the
8
o
body . When the body temperature is higher than 41 C, the
enzyme becomes denatured and mitochondrial dysfunction
important metabolites of SH-containing amino acids such as
cysteine (Cys). Additionally, SO
2
is dissociated into its two
) in humoral
is related to lung
9
occurs . The cell membrane is unstable and the oxygen-
2
−) and bisulfite (HSO −
derivatives sulfite (SO
3
3
dependent metabolic pathway is destroyed. But in spite of
these associations, the mitochondrial behavior during a heat
2
environment . However, excessive SO
2
cancer, and many neurological diseases, including strokes,
migraine headaches, and brain cancers . The role of SO
physiological environment has received increased attention
across a number of disciplines in recent years . More evidence
2
shock process is still little known. Moreover, SO plays an
important role in oxidative stress and cell homeostasis . It is
worth studying the relationship between the mis-regulation of
3
in
10
2
4
SO
2
level in mitochondria and temperature. Consequently,
changes in mitochondria during
2
suggests that SO has corrosive and irritating effects on the
accurately monitoring the SO
2
respiratory mucosa, and lead to airway obstructive diseases.
Researchers have attempted to explore toxicological effect of
heat shock is essential to understanding the mechanism of
heat cytotoxicity.
SO
damage of SO
After SO is inhaled into the human body, various sulfur-
2
associated with respiratory system, but ignored the
Owing to the advantages of simple operation, high
sensitivity, low cost, and non-destructive, fluorescent probes
have been widely used in biological fields such as living cells
2
to other organisms and systems in the body.
2
centered radicals and oxygen-centered radicals can be formed
through metabolic transformation, leading to the formation of
11
and tissues to monitor chemical substances . Because
aggregation-induced emission (AIE)-based fluorescent probes
could work well at high concentrations, more and more AIE
molecules were used for fluorescence analysis. There will be
corresponding changes in the fluorescence signal for detection
of analytes which can adjust the dispersion and aggregation
·−
2
superoxide anions radicals (O ). These free radicals can cause
oxidative damage to the body, which may be one of the main
5
mechanisms of SO
2
-induced cytotoxicity . So far, there has
2
been agreement about the excessive inhalation of SO causes
peroxidation of lipids in different organs, which not only
12
state of AIE molecules . In addition, AIE molecules also
1
3
provide new strategy for designing fluorescent probes . To
date, lots of fluorescent probes have been developed for SO
2
a. Green Catalysis Center, and College of Chemistry, Zhengzhou University,
Zhengzhou 450001, China. E-mail: yeyong03@tsinghua.org.cn.
derivatives detection based on aldehyde, levulinate, Michael
14
addition and metal coordination complex . However, a fast,
b.
Institute of Agricultural Quality Standards and Testing Technology, Henan
Academy of Agricultural Sciences, Zhengzhou 450002, China. E-mail:
pandy811@163.com
Institute Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang,
sensitive and selective AIE fluorescence probe for SO
detection is still missing.
2
c.
Herein, our group constructed
a
novel AIE and
China
†
Electronic Supplementary Information (ESI) available: Materials and methods; mitochondrion-targeted fluorescent probe (MITO-TPE)
photophysical data; bioimaging; synthetic details, NMR and HR-MS spectra. See
DOI: 10.1039/x0xx00000x
combining tetraphenylethene (TPE) and benzopyrylium as
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illustrated in Scheme 1. Notably, MITO-TPE showed strong tested the fluorescence change of the probe under excitation
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DOI: 10.1039/D0CC05803C
green fluorescence after SO
2
derivatives react with C=C bonds at 490 nm, and the probe MITO-TPE showed negligible
−
of benzopyrylium by 1, 4-conjugate addition. Through the fluorescence emission(Figure S6). When HSO
specific reaction with SO
highly selective and fast-responsive detection for SO
3
was added, the
2
, the probe showed ultrasensitive, fluorescence decreased slightly. We then checked the
. In fluorescence of free MITO-TPE under excitation at 400 nm
2
addition, MITO-TPE was successfully employed for imaging (Figure 1a) and a weak fluorescence emission at 455 nm was
−
mitochondrial SO
was able to modulate oxidative stress by increasing the O
levels and further cause tissues and organs damage. We found known to all that the content of SO
2
. Cell imaging indicated that the extra SO
2
observed. With the increasing of concentration of HSO
3
, the
·−
2
fluorescence emission at 455 nm gradually enhanced. It is
derivatives in the human
2
that the mis-regulation of mitochondrial SO
stroke in MCF-7 cells for the first time.
2
levels under heat body is low, so the detection limit of the probe is an important
indicator to determine whether the probe can be used in a
-O3S
H
physiological environment. The fluorescence intensity at 455
−
O
N
nm was linearly related to the concentration of HSO (Figure
3
O
N
2
S7) with a good linear relationship (R =0.9884). The detection
NaHSO
3
limit was calculated to be 27.22 µM (DL=3σ/k) which indicated
N
N
N
N
−
that probe MITO-TPE is highly sensitive to HSO
3
and exhibited
−
the potential use for quantitative determination of HSO
3
. The
Mito-TPE
Mito-TPE-SO2
−
response of the probe toward HSO
3
was fast (Figure S8). The
Scheme 1. Proposed reaction mechanism of MITO-TPE with NaHSO
3
.
maximum plateau was reached within 20 s. To the contrary,
the emission of probe MITO-TPE exhibited almost negligible
changes indicating that the probe was stable in PBS solution.
The fluorescent probe MITO-TPE was easily prepared
through a few steps according to the route in Scheme S1.
Intermediate M4 was synthesized by lithiation of M3 with n-
Next, we examined the selectivity of MITO-TPE to HSO
3
−. As
Butyllithium and acetylation with dimethylacetamide. shown in Figure S9, the probe MITO-TPE (10 µM) exhibited
Compound M4 reacted with 4- (Diethylamino) salicylaldehyde central absorption at 490 nm. No significantly change in the
in concentrated sulfuric acid to give designed probe MITO-TPE. max absorption was observed upon the addition of different
1
And the structure of probe was confirmed by HR-MS, H NMR
−
biologically relevant molecules except HSO
3
. In addition, only
1
3
and C NMR spectra (Figures S1-3). At first, we examined the
−
introduction of HSO
3
to the MITO-TPE solution could trigger
the fluorescence emission at 455 nm significantly enhanced
Figure 1b). The addition of 10 equiv other biologically relevant
molecules did not induce any changes in the fluorescence
emission. Moreover, it is also worth noting that even in the
presence of other analytes shown in Figure S10, probe MITO-
−
response of MITO-TPE toward HSO
3
with AIE property which has
almost no fluorescence in distinct polar solvents, but have strong
fluorescence in polar solvents or solid states. We used compound
(
MITO-TPE-SO
2
(an analog of the reaction product of the probe
−
molecule with HSO
TPE-SO
However, fluorescence intensity of the MITO-TPE-SO
3
) for verification. As shown in Figure S4, MITO-
showed negligible fluorescence in the pure DMSO solution.
gradually
2
−
TPE still could specifically respond toward HSO
3
. Clearly, those
2
increased with the enhancement of water ratio. The fluorescent results demonstrated that probe MITO-TPE performed
intensity of MITO-TPE-SO
2
in 99% water solution was 15 times excellent selectivity and potential applications for detection of
−
higher than that in pure DMSO. The results demonstrate that MITO- HSO3 without any distinct interference from other biologically
TPE-SO is a fluorescent material with AIE property.
2
relevant species in complex biological environments.
In order to investigate whether MITO-TPE can meet the
original design purpose of detecting SO derivatives, the
2
fluorescence emission spectra of probe MITO-TPE in different
pH environments were tested in the absence or presence of
−
HSO
3
(Figure S11). The maximal emission intensity was
observed with pH ranging 6-11. In addition, we studied the
fluorescence emission of probe MITO-TPE (10 µM) in different
temperature environments in the absence or presence of
−
HSO
3
(Figure S12). The probe alone showed weak emission,
Figure 1. (a) Fluorescence emission spectra of MITO-TPE (10.0 µM)
upon the addition of increasing concentrations NaHSO (0 – 100 µM).
b) The selectivity of MITO-TPE (10 µM) to NaHSO (100 µM) and 100
and the fluorescence emission at 455 nm significantly
3
−
enhanced after the addition of HSO
3
(0-100 µM). Those
(
3
–
–
–
–
–
–
2–
µM other various relevant species (F , Cl , Br , I , AcO , HCO
3
–
, CO
3
,
results indicated that the probe could be applied for SO2
derivatives imaging in physiological environment as designed.
To explore the addition reaction mechanism of probe MITO-
–
–
–
–
3 2 2 2 2
GSH, Hcy, Cys , NO , NO , NO, HNO, ONOO , O , H O , ClO , TBHP,
1
2–
–
2–
2–
3–
–
–
·
OH, O
2
, S , HS , SO
4
, S
O
2 3
, PO
4
, N
3
, SCN ) in the PBS buffer (10
pH=7.4).
mM,
TPE depicted in Scheme 1, HR-MS was used to analyze the
−
process of the reaction between MITO-TPE and HSO
3
. The
Then, we studied the sensing ability of probe MITO-TPE
−
−
mass spectral analysis of probe treated with HSO3 displayed a
towards HSO
µM) exhibited
benzopyrylium absorption band at 490 nm markedly
3
in PBS buffer (10 mM, pH 7.4). MITO-TPE (10
new peak at m/z 698.3073 corresponded to the addition
a
strong absorption at 490 nm. The
-
product MITO-TPE-SO
2
(C43
H
44
N
3
O
4
−
S ) (Figure S13). These
−
results demonstrated that the HSO3 was reacted with C=C of
3
decreased upon the addition of of HSO (Figure S5). We first
2
| J. Name., 2012, 00, 1-3
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benzopyrylium via Michael addition, the conjugate structure been proved that can freely enter the cell and dehydrogenate
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DOI: 10.1039/D0CC05803C
was effectively blocked, which lead to the probe MITO-TPE to form ethidium bromide under the oxidation of intracellular
·
−
favourable for the SO
2
derivatives imaging.
O
2
(Scheme S2). Here, we had successfully applied probe
-induced oxidative stress
In order to investigate whether the probe MITO-TPE has MITO-TPE to real time image the SO
2
good bioavailability, the cytotoxicity of the probe MITO-TPE process under the red channel. As shown in Figure 2a, cells
was evaluated. First, the MCF-7 cell suspension was dropped showed almost no fluorescence in green and red channel upon
on a 96-well culture plate, and then cultured in a cell incubator treatment with probe MITO-TPE and HE (10 μM). After the
at 37 °C and 5% CO for 24 h. MITO-TPE solutions of different MCF-7 cells were pretreated with 500 μM Na SO for 2 h, then
2 2 3
concentrations (0, 5, 10, 15, 20 μM) were added, and the cells cells were stained with probe MITO-TPE and HE (10 μM) for
were cultured in the cell incubator for 24 h. Then, CCK8 (10 μL) another 0.5 h. The fluorescence was simultaneously enhanced
was added and incubated for 2 h. The absorbance at 450 nm in green and red channel (Figure 2b). This illustrated that SO
2
·−
was determined with enzyme-labelled instrument. As shown in induced the production of O
2
. As Figure 2c shown, the cells
Figure S14, the experimental data showed that the cell viability were first treated with N-acetyl-L-cysteine (NAC) 1 mM for 1 h,
is still around 90% after treated with 20 μM probe MITO-TPE. then added with 500 μM Na SO and incubated for 2 h. When
The experimental results illustrated that the toxicity of the the cells were further treated with probe MITO-TPE and HE
2
3
probe is basically negligible to cells.
We further investigated the application of probe for SO
(10 μM), the fluorescence of the green channel exhibited
significantly enhancement, while the fluorescence of the red
2
–
3
imaging in living cells. In the beginning, MCF-7 cells were channel showed a negligible change. The results showed that
·−
pretreated with the probe MITO-TPE (10 μM) solution for 0.5 NAC can effectively inhibit the production of O
2
caused by
h, and imaged by confocal fluorescence microscope after SO . In addition, SO -induced oxidative stress may cause
2
2
·−
washing three times with PBS buffer solution, displayed weak damage to cells through O
2
bursting.
fluorescence emission as illustrated in Figure S15a. In contrast,
probe-pretreated cells were incubation with exogenous 100
2
–
μM SO
3
for another 0.5 h, the imaging of cell showed strong
fluorescence (Figure S15b). FA (formaldehyde), known as a
1
0
bisulfite inhibitor, was used to clear the bisulfite in the cell .
2
–
The probe-pretreated cells with 100 μM SO
00 μM FA for 0.5 h, the cells showed negligible fluorescence
Figure S15c). Time-dependent confocal images of MITO-TPE
toward SO was investigated. Upon the addition of Na SO , the
fluorescence intensity of cells increased in a short period time
Figure S16). Taken together, those results demonstrated that
the probe can effectively imaging SO derivatives with good
3
were treated
2
(
2
2
3
(
2
biocompatibility and membrane permeability in the cell.
To further investigate the probe MITO-TPE can be used for
mitochondria SO
2
detection, we conducted co-localization Figure 2. Fluorescence images of SO -induced oxidative stress in MCF-
2
7
cells. (a) cells treated with probe MITO-TPE (10 μM) and HE(10 μM).
b) cells incubated with Na SO (500 μM) then treated with probe
MITO-TPE (10 μM) and HE (10 μM). (c) NAC-pretreated (1 mM) cells
incubated with Na SO (100 μM) and then treated with MITO-TPE (10
experiment in MCF-7 cells. The cells were incubated probe
MITO-TPE (10 μM) and commercial mitochondria indicator
Mito-Tracker Red (100 nM) for 0.5 h. Then MCF-7 cells
(
2
3
2
3
continue to be incubated upon the addition of another 100 μM μM) and HE (10 μM). (d) Relative optical density of the respect wells.
Na
2
SO
3
for 0.5 h. Cell imaging studies were taken on confocal (Chanel 1: λex = 405 nm, emission: 425-485 nm, Chanel 2: λex = 488 nm,
emission: 575-635 nm, Scale bar: 20 μm).
fluorescence microscopy after washed three times with PBS
buffer solution as illustrated in Figure S17. The probe MITO-
TPE showed obviously green fluorescence emission in channel
(Figure S17a). Meanwhile, the Mito-Tracker Red also
displayed strong red fluorescence emission in channel 2
Figure S17b). The overlay image demonstrated that the
fluorescence emission of probe MITO-TPE and Mito-Tracker
Red overlapped well (Figure S17c). The Pearson coefficient and
overlap coefficient are 0.9147 and 0.9032, respectively. Co-
localization experiments indicated that probe MITO-TPE can
specifically located to mitochondria with the potential for real-
Heat stroke response is an important cytoprotective process
in regulating cell homeostasis against not only environmental
stresses (e.g. temperature, ROS and pathogens infection), but
also the intracellular stresses (cell proliferation and
1
(
·−
differentiation). So, we studied SO
2
and O
2
concentration
changes under heat stroke in MCF-7 cells. Cells were first
o
treated with MITO-TPE (10 μM) for 0.5 h at 37 C. Next, the
cells were placed at 37, 39, 41, 43 and 45 °C and incubated for
1
h. As shown in Figure 3a, there is almost no fluorescence in
o
the cells under the incubation condition at 37 C. Weak
fluorescence can be observed in the cell under the incubation
condition at 39 and 41 C (Figure 3b, c). Under the incubation
condition of 43 and 45 oC, obvious fluorescence can be
observed (Figure 3d, e). The results indicate that the
time imaging mitochondria SO
SO -induced oxidative stress may be one of the mechanisms
to cause damage to cells. Monitoring oxidative stress caused
2
derivatives in vivo.
2
o
·−
by SO
2
in cells which still faces great challenge. O
the markers of oxidative stress, and hydroethidine (HE) has
2
is one of
1
5
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generation of SO
Journal Name
2
is related to the cell culture temperature. In tool for deeply understanding pathogenic mechanism of
View Article Online
DOI: 10.1039/D0CC05803C
a control experiment, FA was used to inhibit the production of excessive SO and mis-regulation of SO levels in heat stroke.
2
2
SO
2
in heat shock. Pretreated of MCF-7 cells with MITO-TPE
This work was financially supported by the NSFC (21907025),
o
were incubated with FA (200 μM) for 0.5 h at 37 C, and then Scientific and Technological Project of Henan Province of China
incubated at 45 C for another 1 h. Unsurprisingly, cells (192102310140), and Scientific and Technological Innovation
o
showed negligible fluorescence emission under the presence Project of Henan Academy of Agricultural Sciences (2020CX05).
of FA. The results indicate that the level of SO
with cell temperature increasing, and there is a direct
relationship between cell temperature and SO concentration
in mitochondria. More importantly, we have successfully
2
increase along
Conflicts of interest
There are no conflicts to declare.
2
·−
monitored the O
2
burst with the increase of temperature (37
o
·−
-
45 C) as shown in Figure S18. The level of O
2
increased
during heat shock. Above results suggested that up-regulation Notes and references
2
of SO in the mitochondria may be dependent on the oxidative
stress induced by heat shock.
1
2
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Figure 3. Fluorescence images of MCF-7 cells (a-f) incubated with
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°
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As a very good vertebrate model, zebrafish is of great
significance for biological imaging. The zebrafish first
incubated with MITO-TPE (10 μM) for 0.5 h, and then used for
fluorescence imaging. No fluorescence was found (Figure
S19a). Zebrafish was pretreated with MITO-TPE (10 μM) for
1
2
020, 49, 21-31; (b) H. Li, W. Shi, X. Li, Y. Hu, Y. Fang and H.
0
.5 h, and then 100 μM Na
another 0.5 h. There was obvious fluorescence enhancement
Figure S19b). Further, on the basis of the previous step, 200
μM FA was added to incubate for 1 h to clear SO , and weak
fluorescence enhancement was found (Figure S19c). It shows
2 3
SO was added to incubate for
Ma, J. Am. Chem. Soc., 2019, 141, 18301-18307. (c) W.
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1
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2
the advantages of novel structure, good selectivity, high
sensitivity and fast response. The probe realized the imaging of
2
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SO
2
in mitochondria of MCF-7 cells. In addition, we firstly
·−
reported imaging the O
2
2
caused by SO -induced oxidative
3
stress in mitochondria. The results indicated that oxidative
stress is closely related to the pathogenic mechanism of
1
excessive SO
SO produced in mitochondria during heat stroke for the first
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. Furthermore, MITO-TPE was applied to monitor 14. Y. Yue, F. Huo, P. Ning, Y. Zhang, J. Chao, X. Meng and C. Yin,
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