Design of a FRET-based fluorescent probe for the reversible detection of SO2and formaldehyde in living cells and mice

Article abstract of DOI:10.1039/d0nj03071f

SO2 and formaldehyde (FA) are important signal molecules in physiological and pathological processes. It is particularly urgent to seek a method that can monitor SO2 and FA in real-time to study their role in organisms. Herein, we designed and synthesized

Full text of DOI:10.1039/d0nj03071f

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Design of a FRET-based fluorescent probe for reversible detection
of SO2 and formaldehyde in living cells and mice
Wenjie Gao, Yanyan Ma and Weiying Lin*
Received 00th January 20xx,
Accepted 00th January 20xx
SO2 and formaldehyde (FA) are important signal molecules in physiological and pathological processes. It is particularly
urgent to seek a method that can monitor SO2 and FA in real-time to study their role in organisms. Herein, we designed and
synthesized a ratiometric fluorescent probe NaP based on FRET mechanism for reversible detection of SO2 and FA. This
probe possessed, high sensitivity, good selectivity, excellent photostability, low cytotoxicity and an ultra-fast response to
SO2 (within 5s). Notably, the probe can be recoverd efficiently by FA. In addition, the biological experiments showed that
the novel probe NaP could reversibly image SO2 and FA in cells and mice.
DOI: 10.1039/x0xx00000x
detecting SO2 or FA have been reported,25-36 most of them have
some imperfections, such as shorter emission wavelength,
longer response time, intensity-based fluorescent probes,
meanwhile, SO2 and FA can only be identified separately. In
order to study the mechanism of SO2 and FA participating in cell
homeostasis in vivo, it is necessary to develop a reversible
fluorescent probe of SO2 and FA. To achieve this goal, the probe
should have several advantages including ratiometric
fluorescence signal, reversibility, deep penetration, high
sensitivity and good selectivity.
In this study, a reversible fluorescent probe NaP based FRET
for monitoring SO2 and FA was designed and synthesized.
Naphthalimide was selected as energy donor because of its
outstanding photostability and high fluorescence quantum
yield.37,38 In addition, we chose benzopyran with a long emission
wavelength as the energy acceptor and piperazine as the linking
group to connect the donor and acceptor.39 The probe has the
characteristics of rapid response to SO2, good selectivity and
photostability, and more importantly, it can be recovered by FA.
In addition, the probe NaP can also be used for reversible
imaging of SO2 and FA in cells and living animal, providing a
simple and fast method for dynamically monitoring SO2 and FA
in living bodies.
Introduction
In daily life, SO2 derivatives are widely used in industries such as
antibacterial agents, enzyme inhibitors, pharmaceutical
products, and basic preservatives for food and beverages.1-4 SO2
is an important gas signal molecule in complex biological
-
2- 5-7
systems, it exists as two forms HSO3 and SO3
.
Recently
studies have shown that SO2 plays an important role in the
nervous and cardiovascular system.8,9 It is mainly produced by
the metabolism of some sulfur-containing amino acids in
mitochondria.10
Formaldehyde (FA) is an important chemical raw material,
but excessive FA is harmful to living systems.11,12 At the same
time, FA is also a very important physiological signaling
molecule, involved in cell homeostasis.13 The production of
endogenous FA mainly comes from the metabolism of some
amines through semicarbazide-sensitive amine oxidase (SSAO),
or DNA methylation.14,15 Recent studies have shown that FA is
related to the pathogenesis of many major diseases, such as,
nervous system diseases.16 SO2 and FA are both important bio-
signal molecules and are closely related to many physiological
activities. In order to further explore their role in organisms, it
is an urgent need to develop a fast and reliable tool for
detecting the content of SO2 and FA in the body.
The traditional methods for monitoring SO2 and FA are
usually electrochemical analysis, titration, chromatography,
etc. However, these methods have the disadvantages of
complicated operation and high cost of detection. Fluorescence
analysis is widely concerned because of its advantages of simple
operation, high sensitivity, non-invasive, and in situ
monitoring.17-24 In recent years, some fluorescent probes for
Experimental section
Materials and instruments
Unless otherwise noted, the chemical reagents were acquired from
commercial suppliers and not purified. The experimental
instruments involved in this work are supplied in detail in the
supporting information.
Synthesis and characterization of NaP
Institute of Fluorescent Probes for Biological Imaging, School of Chemistry and
Chemical Engineering, School of Materials Science and Engineering, University of
Jinan, Jinan, Shandong 250022, P.R. China. E-mail: weiyinglin2013@163.com
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
Compound 2 (1.04 g, 25 mmol) and N, N diethylsalicylic aldehyde (4.8
g, 25 mmol) were dissolved in conc. H2SO4 (5 mL) and stirred at 90 °C
for 5 h. After cooling to room temperature, the solution was added
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sensitivity,45 so we chose it as the reaction site. NVaipewhAthrtiaclleimOnildinee
possesses excellent photostability, high molar absorptivity and
70% perchloric acid (0.5 mL) and ice water (100 mL). Then the
precipitated solid was filtered, and washed with water to afford
crude product. The crude product was purified by silica gel flash
chromatography (CH2Cl2/CH3OH, 20:1) to afford bluish violet solid
compound NaP (yield: 70%). 1H NMR (400 MHz, DMSO) δ 8.63 (d, J
= 8.5 Hz, 1H), 8.57 (d, J = 8.4 Hz, 1H), 8.51 (d, J = 6.7 Hz, 1H), 8.43 (d,
J = 8.1 Hz, 1H), 8.30 (d, J = 9.2 Hz, 2H), 7.98 (d, J = 8.5 Hz, 1H), 7.93 –
7.82 (m, 2H), 7.41 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 9.4 Hz, 1H), 7.28 (d,
J = 9.4 Hz, 3H), 4.01 (s, 2H), 3.91 (s, 4H), 3.67 (d, J = 7.1 Hz, 4H), 3.42
(s, 4H), 1.65 (q, J = 7.4 Hz, 2H), 1.25 (m, 6H), 0.92 (m, 3H). 13C NMR
(101 MHz, DMSO) δ 167.35, 163.93, 163.40, 158.57, 155.47, 155.38,
155.10, 148.26, 132.53, 132.20, 131.20, 131.15, 130.89, 129.50,
126.60, 125.67, 122.97, 117.47, 116.95, 116.84, 116.35, 115.63,
114.34, 108.62, 96.38, 52.52, 46.72, 45.68, 41.48, 21.36, 12.92,
11.84.
DOI: 10.1039/D0NJ03071F
high fluorescence quantum yield, thereby, it was chosen as an
energy donor. Benzopyran was chosen as the energy acceptor
due to its large emission wavelength and good light stability.
Importantly, the emission spectrum of naphthalimide and the
absorption spectrum of benzopyran basically overlaped. In
addition, the piperazine was selected as the connection group
between the energy donor and the acceptor. When NaHSO3
exists, it may attack the double bond position of the benzopyran
group, destroy the FRET structure, and cause the blue shift of
the emission and release the fluorescence of the
naphthalimide. When FA exists, it will react with free sodium
bisulfite, causing the Michael addition reaction to proceed in
reverse, leading to the recovery of the probe. Thus, the FRET
process would be restored and the fluorescence of the probe
would be recovered.
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Preparation for the spectral measurement
The probe NaP (1.0 mM) stock solution was dissolved in DMSO. NaP
(10 μM) and other ions were added to acetonitrile/PBS (V/V = 1:4,
PH = 7.4) buffer solution for spectral testing. The other analytes
including CuCl2, Hcy, Cys, GSH, Na2S, NaClO, H2O2, tert-butyl peroxide
(TBHP), KF, NaF, KI, FeSO4, KSCN, MgCl2, NaBr, NaHCO3, NaNO2,
NaNO3, , BaCl2, Na2HPO4, AgNO3, ZnCl2, NaOAc, HCHO, CaCl2, Na2SO3,
and NaHSO3 were prepared at 100 mM in distilled water, and the di-
t-butyl peroxide (DTBP) stock solution (100 mM) was prepared in the
DMSO. (λex = 425 nm, slit: 5 nm/5 nm)
Cells culture and imaging
HeLa cells were incubated in sterile confocal plates for 24 hours (37
°C, 5% CO2). Before imaging, the HeLa cells were washed three times
with PBS and then NaP (10 μM) was mixed. For imaging SO2
experiment, the cells were pre-loaded with NaP, and then incubated
with (70 μM) for 30 min. For the experiment of imaging FA, FA (350
μM) was added to the culture medium including 70 μM NaHSO3 and
10 μM NaP to incubate for 30 min and then imaged.
Scheme 1. The sensing mechanism of NaP.
Spectral properties of the probe NaP
Fluorescence imaging in living mice
In order to prove whether the probe NaP could reversibly
respond to SO2 and FA, we explored the spectral performance
of the probe. As shown in Fig. S1, the NaP shown a main
absorption peak at 550 nm, while in the presence of NaHSO3 (70
Before the experiment, the mouse belly hair was shaved and then
anesthetized by injection of chloral hydrate. For in vivo imaging, the
abdominal cavity of the mice was injected with 100 μL NaP (50 μM)
by syringe and imaged. Then, 100 μL NaHSO3 (500 μM) was injected μM), the absorption peak was changed from 550 nm to 425 nm.
Next, the fluorescence spectrum of NaP was investigated in the
presence or absence of NaHSO3. From Fig. 1a, with the
increasing concentration of NaHSO3, the fluorescence intensity
at the emission peak of 640 nm gradually decreased, while the
fluorescence intensity at 540 nm gradually increased, which is
consistent with the change of absorption spectra. It indicates
that SO2 may attack the energy acceptor and destroy the FRET
structure, thus releasing the fluorescence of the energy donor.
and imaged. Finally, the mice were injected intraperitoneally with
100 μL FA (2 mM) in the same location, and then used IVIS Lumina
XR system for imaging in vivo (λex = 580 nm, λem = 660 nm).
Results and discussion
Design and synthesis of probe NaP
1
HRMS and H-NMR titration experiment were used to further
In this paper, a reversible fluorescent probe which was
capable of detecting SO2 and FA was proposed (scheme 1). In
recent years, many reaction sites of SO2 have been reported.40-
verify the sensing mechanism. As shown in Fig. S2a, when the
probe interacted with SO2, the NaP-HSO3 peak at 599.3020 was
observed, which was basically consistent with the theoretical
peak. As shown in Fig. S2b, when NaHSO3 was present, a new
resonance signal loaded at around 5.6 ppm (Ha´) with the
44
Among them, the Michael addition reaction based on C = C
double bond is widely used because of its good selectivity and
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disappearance of the 7.8 ppm (Ha), however, the signal at 5.8 explained that the NaP is conducive to reversibly detect of SO2
ppm (Hb) did not change. According to experimental data, when and FA in biological systems. Moreover, we test the selectivity
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DOI: 10.1039/D0NJ03071F
NaHSO3 is present, the probe NaP will react with it and generate of the probe with various analytes. As shown in Fig. S6, only
a new compound NaP-HSO3. In addition, the fluorescence Na2SO3 and NaHSO3 caused the fluorescence signal ratio
intensity ratio of I540/I640 displayed a nice linear relationship significantly enhanced, indicating that the probe NaP can
with HSO3−concentration ranging from 2 μM to 5 μM (Fig. 1b) specifically sense for SO2. As shown in Fig. S7, FA could restore
and the detection limit was calculated to be 1.21 μM. These the probe effectively and the recovery efficiency almost
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results suggest that the NaP can be used to detect SO2
reached 100%. These results confirm that the probe can
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Next, we explored the reversible performance of FA for NaP- specifically detect SO2 and can be specifically recovered by FA.
HSO3. Different concentrations of FA were added to the probe
solution containing NaHSO3 (70 μM). As shown in Fig. S3a, the
fluorescence signal at 640 nm gradually increased, while the
signal at 540 nm gradually decreased. Notably, when 350 μM FA
was added, the fluorescence intensity ratio was reached
saturated and almost the same as that of the only probe. In
addition, the probe NaP can reversible sensing SO2 and FA for
four times (Fig. S3b). Notably, its absorption spectrum was
basically the same as that of NaP (Fig. S4), indicating that the
fluorescence of the NaP can be restore by FA. In addition,
sensing mechanism was further verified by HRMS (Fig. S5). The
experimental results indicate that the NaP can reversibly detect
SO2 and FA.
Fig. 2. (a) Fluorescence intensity ratio (I540/I640) change of probe
NaP after adding NaHSO3 (70 μM). (b) Fluorescence intensity
ratio (I540/I640) change of NaP-HSO3 after adding FA (350 μM). (c)
The photostability of the probe in the existence or absence of
NaHSO3 and FA. (d) Fluorescence signal ratio (I540/I640) of the
probe NaP in the existence or absence of NaHSO3 and FA at
different pH. λex = 425 nm.
Fig. 1. (a) Fluorescence spectra of probe NaP (10 μM) treated
with different concentrations of NaHSO3. (b) The linear
-
relationship between I540/I640 and the concentrations of HSO3 .
λex = 425 nm.
Next, the kinetic profiles of NaP sensing SO2 was discussed.
As shown in Fig. 2a, when 70 μM NaHSO3 was added to the
probe NaP test solution, it could be observed that the
fluorescence at the 640 nm decreased rapidly, while the
fluorescence at 540 nm increased, and the I540/I640 tended to
stabilize within 5 S. Moreover, when FA (350 μM) was added to
the test solution containing NaHSO3 (70 μM), its fluorescence
intensity ratio (I540/I640) tended to be stable within 50 S (Fig. 2b).
It shows that the probe NaP can quickly and reversibly detect
NaHSO3 and FA. In addition, the NaP was continuously laser
exposure for 1 h in the existence or absence of NaHSO3 and FA,
and the fluorescence intensity ratio (I540/I640) hardly changed
(Fig. 2c), explaining that the probe has a nice photostability.
Considering the complexity of the biological environment,
We explored the applicability of the probe NaP under different
pH conditions (Fig. 2d). The only probe NaP presented a stable
fluorescence intensity ratio (I540/I640) in a wide pH range. After
adding NaHSO3 (70 μM), the fluorescence intensity ratio
increased rapidly at pH 7.0-10.0, while when FA (350 μM) were
added, the fluorescence intensity ratio was the same as the
pure probe and stable in a wide pH range. These results
Fig.3 Fluorescence images of SO2 and FA in HeLa cells. (a1) - (a4)
HeLa cells were treated with NaP (10 μM) for 30 min. (b1) - (b4)
HeLa cells were treated with NaHSO3 (70 μM) and then treated
with NaP (10 μM) for 30 min. (c1) - (c4) HeLa cells were
incubated with NaHSO3 (70 μM) and NaP (10 μM), then treated
with FA (350 μM). Green channel: λex = 405 nm, λem = 500−550
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nm. Red channel: λex = 405 nm, λem = 663−738 nm. Fluorescence (b) The mice were injected with NaHSO3 (500 μVMiew) Aarnticdle Othnleinne
DOI: 10.1039/D0NJ03071F
ratio images of red channel and green channel. Scale bar: 20 μm. treated with NaP (50 μM). (c) The mice were injected with
NaHSO3 (500 μM) and incubated with NaP (50 μM), then
injected with FA (2 mM) for 1 min. (d) The mice were injected
with NaHSO3 (500 μM) and incubated with NaP (50 μM), then
injected with FA (2 mM) for 5 min.
Reversible fluorescence imaging of SO2 and FA with NaP in
living cells
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Encouraged by the above experiments, we studied the capacity
of the NaP to reversibly detect of SO2 and FA in living cells.
Initially, the cytotoxicity of NaP was tested by MTT assay. As
shown in Fig. S8, HeLa cells maintained 85% survival rates after
incubated with probe NaP (0-20 μM) for 24 h, indicating that
NaP has low toxicity and can be used in cell experiments. Next,
we performed cell imaging with a laser confocal microscope. As
shown in Fig. 3, When HeLa were treated with NaP (10 μM) for
30 min, a weak green fluorescence was shown in the green
channel and a strong red fluorescence was observed in the red
channel. On the contrary, when the cells cultured with NaHSO3
(70 μM) for 30 min, the green channel fluorescence increased
obviously and only a faint red fluorescence was observed. When
FA (350 μM) was added to the medium for 30 min, the green
fluorescence reduced and the red fluorescence recovered. The
results of this experiment show that the new probe NaP can
reversible sense SO2 and FA in living cells.
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Conclusions
In summary, we successfully designed and synthesized a new
fluorescent probe NaP for reversible detection of SO2 and FA.
The probe showed the advantages of fast response (within 5 S),
good selectivity, deep red emission and low cytotoxicity. It is
worth noting that FA can make NaP almost 100% recovered. In
addition, the probe NaP had successfully monitored SO2 and FA
reversibly in live cells and live mice. We believe that the novel
probe NaP have potential application prospects in exploring the
relevant pathological mechanisms of SO2 and FA in vivo.
Conflicts of interest
There are no conflicts to declare.
In vivo imaging of reversible recognition of SO2 and FA in mice
Acknowledgements
As the probe NaP possessed good selectivity and deep red
emission advantage, we explored the performance of the probe
NaP to reversibly detection SO2 and FA in vivo. As shown in Fig.
4, When 100 μL NaP (50 μM) was injected intraperitoneally in
mice, strong fluorescence was emitted at the injection site.
Conversely, when we inject 100 μL NaHSO3 (500 μM), the
fluorescence signal quickly disappeared. Then 100 μL FA (2 mM)
was injected, the fluorescence signal gradually enhanced and
tended to be stable after 5 min. These results show that the
probe NaP can reversibly track SO2 and FA in mice.
This work was financially supported by NSFC (21472067,
21672083, 21877048), Taishan Scholar Foundation (TS
201511041), and the startup fund of the University of Jinan
(309-10004)
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DOI: 10.1039/D0NJ03071F
Design of a FRET-based fluorescent probe for reversible detection of
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