First Dual Responsive “Turn-On” and “Ratiometric” AIEgen Probe for Selective Detection of Hydrazine Both in Solution and the Vapour Phase

Article abstract of DOI:10.1002/chem.201900003

A new dual responsive “turn-on” and “ratiometric” aggregation-induced emission luminogen (AIEgen) 3-formyl-5-(piperidin-1-yl)biphenyl-4-carbonitrile 6 a (FPBC 6 a) for selective detection of hydrazine in solution as well as in vapour phase is described. A

Full text of DOI:10.1002/chem.201900003

A Journal of
Accepted Article
Title: First Dual Responsive ‘Turn-on’ and ‘Ratiometric’ AIEgen Probe
for Selective Detection of Hydrazine both in Solution and Vapour
Phase
Authors: Deepak Purohit, Chandra P. Sharma, Ashutosh Raghuvanshi,
Ankita Jain, Kundan S. Rawat, Neeraj M. Gupta, Jagriti Singh,
Monika Sachdev, and Atul Goel
This manuscript has been accepted after peer review and appears as an
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content of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.201900003
Link to VoR: http://dx.doi.org/10.1002/chem.201900003
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COMMUNICATION
First Dual Responsive ‘Turn-on’ and ‘Ratiometric’ AIEgen Probe
for Selective Detection of Hydrazine both in Solution and Vapour
Phase
[
a]
[a]
[a]
[b]
[a][c]
Deepak Purohit, Chandra P. Sharma, Ashutosh Raghuvanshi, Ankita Jain, Kundan S. Rawat,
[a]
[a]
[b]
[a] [c]
Neeraj M. Gupta, Jagriti Singh, Monika Sachdev and Atul Goel*
Abstract:
aggregation induced emission luminogen (AIEgen) 3-formyl-5-
piperidin-1-yl)biphenyl-4-carbonitrile 6a (FPBC 6a) for selective
A new dual responsive ‘turn-on’ and ‘ratiometric’
(
detection of hydrazine in solution as well as in vapour phase has
been described. At low concentration of 2.5 M, the probe FPBC 6a
is non-fluorescent (turn-off) but remarkably lights up (turn-on with
blue emission) in the presence of hydrazine solution (0.25-25M).
Interestingly, at higher concentration the nano-aggregates of FPBC
6a (>25 M, 99% HEPES in DMSO) displayed ratiometric response
Figure 1. Various approaches for designing of fluorescent probes for
in the presence of hydrazine with a remarkable hypsochromic shift
from green region (500-550 nm) to blue region (440-480 nm).
Furthermore, the real application of FPBC 6a was successfully
demonstrated to detect and visualize hydrazine in live cervical
cancer cells as well as using portable test strips.
hydrazine detection.
Fluorescence imaging is an emerging and reliable
technique for analyte sensing because of high selectivity,
sensitivity, biological compatibility and direct visualization.9
Numerous probes (Table S1, SI) for hydrazine detection have
1
0
been reported, which are mostly prepared by deprotection,
1
1
12
Colourless, water soluble, flammable liquid hydrazine is an
important reagent in pharmaceutical as well as in chemical
industry.1 It is a powerful reducing agent and widely used as
catalyst, corrosion inhibitor, textile dye, pharmaceutical
intermediate and reagent.2 Its flammability and detonable
properties make it a high energy propellant for rocket and
spacecraft.3 Despite its widespread applications, it is a highly
toxic chemical with mutagenic and carcinogenic properties, and
could damage lungs, liver, kidney and human central nervous
system.4 U.S Environmental Protection Agency (EPA) has
considered hydrazine as probable human carcinogen and set
low threshold limit value of 10 ppb.5
hydrazinolysis,
peptides
self-assembly,
14
hydrazone
1
3
formation , substitution-cyclization and aggregation-induced
15
emission
approaches (Figure 1). The reported hydrazine
either exhibit turn-on response or ratiometric
probes1
0-16
fluorescence signals, however it has been challenging to realize
both these advantages in a single molecular framework. Herein,
we report first single molecular luminogen FPBC 6a with dual
mode of action (turn-on and ratiometric) for selective detection of
hydrazine both in solution and vapour phase. The ratiometric
detection of hydrazine was successfully demonstrated in live
cervical cancer HeLa cells. The practical applicability of the
probe FPBC 6a was demonstrated by preparing the test strip
which showed high sensitivity to the vapours of hydrazine
leading to bright blue emission under UV light.
The utility of hydrazone formation has been well
estabilshed in bioconjugation as well as in polymer and applied
chemistry. However, there is a significant challenge to construct
hydrazones under aqueous conditions at neutral pH particularly
in the absence of catalyst and in cellular settings where
concentrations of reactants are low.17 In order to increase the
reactivity of aldehyde functionality and keeping these limitations
in mind, we designed a new series of donor-acceptor based
activated benzaldehydes by incorporation of a strong electron
withdrawing group adjacent to aldehyde group (Figure 1). The
synthetic methodology adopted for the synthesis of activated
Due to carcinogenic nature of hydrazine and widespread
use in chemical industry, there is indeed a need for the
development of new efficient and portable techniques for its
6
detection. Analytical techniques like electrochemical analysis ,
7
mass spectrometry , high performance liquid chromatography
and gas chromatography8 are most commonly used tools for
hydrazine detection. However, these methods are not suitable
for real time monitoring of hydrazine in biological systems.
[
a]
Deepak Purohit, Chandra P. Sharma, Ashutosh Raghuvanshi,
Kundan S. Rawat, Neeraj M. Gupta, Jagriti Singh, Prof Atul Goel
Fluorescent Chemistry Lab, Department of Medicinal and Process
Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031
benzaldehydes is depicted in Scheme 1. The key acetophenone
18
1a-c and ketene-S,S-acetal 2 as previously reported. Further,
Michael addition of the conjugate base of methylglyoxal 1,1-
dimethyl-acetal to the 6-aryl-2-oxo-4-piperidin-1-yl-2H-pyran-3-
carbonitriles (4a-c) at position 6 followed by intramolecular
(
India).
E-mail: atul_goel@cdri.res.in
[
[
b]
c]
Ankita Jain, Dr Monika Sachdev
Endocrinology Division, CSIR-Central Drug Research Institute,
Lucknow 226031 (India).
cyclization
afforded
3-(dimethoxymethyl)-5-(piperidin-1-
yl)biphenyl-4-carbonitriles (5a-c) in good yields. Then
compounds 5a-c were converted into respective aldehydes 3-
formyl-5-(piperidin-1-yl)biphenyl-4-carbonitriles (FPBC) 6a-c by
deacetalation using acidic resin Amberlyst-15.
Kundan S. Rawat, Prof Atul Goel
Academy of Scientific and Innovative Research, Ghaziabad 201002
(
India).
Supporting information for this article is given via a link at the end of
the document.
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nano-aggregates leading to restriction in intramolecular motion
resulting in radiative decay with remarkable red shift. In order to
confirm the aggregation-induced emission property of the
compound 6a, the emission in classical DMSO/water mixtures
with varying water fractions (f
). We found that upon increasing the water fraction (f
in DMSO, the fluorescence intensity increased dramatically in
aqueous buffer mixtures at water fraction (f ) = 85-99% (Figure
). When the f reached 99%, the system became highly
w
) of 0-99% was examined (Figure
3
w
, HEPES)
w
3
w
emissive with emission maximum at 509 nm due to aggregation-
induced emission19 property. In this case the intensity enhanced
remarkably upto 50-fold as compared to the pure DMSO solution
possibly due to formation of nano-aggregates leading to
restriction in intramolecular motion resulting to radiative decay.
Scheme 1. Synthesis of activated benzaldehydes 6a-c.
The absorption and emission characteristics of the
compounds 6a-c were investigated in HEPES (4-(2-
hydroxyethyl)-1-piperazineethanesulfonic acid buffer) / DMSO
(
2.5 M, 1:1, v/v, pH 7.2) in the absence and presence of
hydrazine (Figure 2, Figure S1, Table S2). Compounds 6a-c
showed absorption maxima at 386, 390 and 390 nm,
respectively. Correspondingly, at this concentration, very weak
emission was observed in the blue region. Upon addition of
hydrazine, all the compounds 6a-c showed dramatic increase in
fluorescence intensity (Figure 2). The fluorescence maxima for
compounds 6a-c in the presence of hydrazine were obtained at
Figure 2. Emission spectra of 6a-c at 2.5 M in HEPES/DMSO (1:1, v/v, pH
7.2) at 25 °C; Inset shows turn-on response. Hydrazine at 25 M.
478, 476 and 483 nm respectively with 6-10 fold enhancements
in fluorescence intensity. This tremendous ‘turn-on’ fluorescence
response was observed due to the formation of hydrazone by
the reaction of activated aldehyde functionality of 6a-c with
hydrazine. The hydrazone of 6a showed maximum (10-fold)
increase in emission intensity with emission maximum at 478 nm,
which matched with the fluorescence maximum of synthesized
hydrazone 7 (Figure 2, Figure S2). Absorption and fluorescence
spectra of probe 6a were measured in solvents of varying
polarity (Figure S2). On increasing the polarity of solvents,
fluorescence band showed bathochromic shift which
demonstrated the intramolecular charge transfer (ICT)
characteristics of 6a and thus it was selected for further detailed
study.
In order to obtain limit of detection for hydrazine sensor,
the titration studies of 6a with increasing concentrations of
hydrazine (0.1-10 equiv.) were conducted which revealed a
good linearity between the fluorescence intensity and hydrazine
concentration (Figure S3, SI). The probe 6a potentially detected
hydrazine with a detection limit of approximately 0.19 M (6.08
ppb) (Figure S3) which is lower than the low threshold limit value
Figure 3. Fluorescence spectra of 6a (25 M) in DMSO with increasing
concentration of HEPES (0-99%, v/v) showing aggregation-induced green
emission, λex = 378 nm.
(
(
TLV) of 10 ppb set by U.S Environmental Protection Agency
EPA).
We observed that upon increasing the concentration of the
Time-correlated single photon counting (TCSPC) analysis
of 6a in the pure DMSO and 99% HEPES in DMSO mixture
showed an average fluorescence lifetime of 0.44 ns, and 15.16
probe 6a from 2.5 M to 2.5 mM in HEPES/DMSO, the
fluorescence intensity increased with emission maximum shifted
from 451 nm to 513 nm (Figure S4a, SI) due to formation of
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ns respectively due to the formation of nano-aggregates
confirming the AIE character of compound 6a in HEPES/DMSO
mixture (Figure S4). We observed that the compound 6a at
higher concentration (25 M-250 M) in DMSO showed
emission in green region with maximum in the range 525 + 25
nm (Figure S5). Upon addition of increasing concentration of
hydrazine (0-10 equiv), a new peak around 451 nm emerged
which increased gradually with respect to increase in hydrazine
equivalents. The titration curve showed ratiometric response
with good linearity and showed nearly 8 fold increase in intensity
ratio (I451/I531) at 10 equiv of hydrazine (Figure 4).
with the results shown in Figure 2. By contrast, in the cells
incubated with compound after the treatment of hydrazine (50
µM), strong fluorescence at 460±20 nm was observed also
suggesting that 6a was living cell membrane permeable (Figure
6).
Interestingly, when live HeLa cells were incubated with 50
µM of the compound 6a alone for 1 h (Figure 7), it exhibited
strong green fluorescence in the range 525±25 nm due to
formation of nano-aggregates at higher concentration, while the
blue fluorescence image obtained at 460±20 nm was hardly
visible. In contrast; incubation of compound 6a in hydrazine (100
µM) treated live cells, the fluorescence intensity increased
remarkably in the blue channel, whereas the green fluorescence
at 525±25 nm diminished simultaneously, suggesting that 6a
was capable to detect hydrazine in nano-aggregated form as
well. It was also confirmed by preparing nano-aggregates in
90% HEPES in DMSO. The nano-aggregate solution showed
emission maximum at 509 nm in the absence of hydrazine, while
in the presence of 10 equiv of hydrazine, the emission maximum
of the nano-aggregates solution was shifted from 509 nm to 480
nm (Figure S7).
Figure 4. Fluorescence spectra of 6a (2.5x10-4 M) in DMSO with increasing
concentration of hydrazine (0 to 10 equiv), inset shows ratiometric response
(I451/I531) of 6a in the presence of hydrazine.
The selectivity study of 6a was conducted in the presence
of high concentrations (10 equiv.) of perchlorate salts of various
metal cations, anions, amines and amino acids (Figure 5).
These experiments revealed that only hydrazine triggered a
dramatic increase in the emission with maxima at 478 nm while
other species as shown in Figure 5 were either silent or showed
minor effects. Competitive experiments of 6a with hydrazine in
the presence of various metal ions, anions, amines and amino
acids also confirmed that probe 6a is highly selective for
hydrazine (Figure S6).
Figure 6. Confocal fluorescence images of probe 6a in Live HeLa cells. Cells
were treated with: [A to C] 1 μM 6a for 1 hour without any hydrazine treatment;
[D to F]: 50 μM hydrazine for 30 minutes followed by treatment of 1 μM of 6a
for 1 hour. [A, D] blue emission (460±20nm); [B, E] nuclear stain, 7AAD
(647±20nm); [C, F] merge images. Scale bar: 75 μm.
Figure 5. Emission intensity of probe 6a (2.5X10-5 M) at 478 nm in
HEPES/DMSO (1:1, v/v, pH 7.2) in the presence of various metal ions, anions,
amines and amino acids (10 equiv. each), λex = 378 nm.
The selectivity of 6a for hydrazine over other biologically
relevant metal cations stimulated us to explore 6a for detection
of hydrazine in live cancer cells. The compound was
systematically assessed for its capability to infuse and stain the
intracellular space in HeLa cells both in presence and absence
of hydrazine. For this purpose, live HeLa cells were first treated
with hydrazine and then the cells were stained with 6a. Hela
cells incubated with 6a (1M) alone for 1 h showed no
fluorescence at 460±20 nm (blue emission), which is consistent
Figure 7. Confocal microscopy images of probe 6a in Live HeLa cells. [A] cells
treated with 6a (50 μM) only, [B] Cells were incubated with 100 μM hydrazine
for 30 minutes followed by 6a (50 μM) incubation for 1 hour. [C] control cells
without incubation with 6a or hydrazine showing no background fluorescence.
Nucleus was stained with 7AAD dye. λex = 405 nm. Blue channel: 460±20 nm;
green channel: 525±25 nm; red channel: 647±20nm.
We next examined the toxicity of 6a to check its
biocompatibility. The cytotoxicity of the dye was assessed using
MTT[3-(4,5-dimethyl-2-thiazolyl)2,5-diphenyltetrazoliumbromide]
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assay. HeLa cells showed more than 99% viability uptill 50 µM
concentration of 6a treatment (Figure S8).
Acknowledgements
The selective and sensitive nature of the probe 6a for
hydrazine prompted us to develop a simple, rapid and portable
method for hydrazine detection in vapour phase. The test strip
AG thanks Department of Atomic Energy (DAE-SRC) for
Outstanding Investigator Award (21/13/2015-BRNS/35029).
Authors thank CSIR, New Delhi for research fellowships. We
acknowledge Mrs. Rima A. Sarkar for confocal imaging of HeLa
Cells and SAIF-CDRI for providing spectral data. CDRI
communication number is 9804.
(
‘
TLC plate, Silica gel 60 F254) was engraved with the word
CDRI’ using the probe 6a (2.5x10- M) solution in DCM and then
4
the plate was air-dried. The changes in fluorescent response as
shown in Figure 8 were observed in the absence and presence
of 99 % hydrazine hydrate vapours. When engraved strip with
hydrazine vapour (panel C), highly bright blue emission under
UV light was observed (Figure 8, for direct visualization: see
Movie clip link in SI). This portable experiment suggested that
the probe 6a can be used potentially as chemosensor for
hydrazine.
Keywords: Dual Fluorescent Probe • Hydrazine Sensor •
AIEgen • Cell Imaging • Hydrazine vapour sensing
[
[
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Figure 8. Test strips engraved with the word ‘CDRI’ using the compound 6a,
(A) under ordinary light; and under UV light (B) in the absence of hydrazine
vapour, (C) in the presence of hydrazine vapour.
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In conclusion, we have designed and developed a new dual
acting (turn-on and ratiometric) donor-acceptor fluorescent
compound FPBC 6a for selective detection of hydrazine both in
solution and vapour phase. At low concentration of 2.5 M,
FPBC 6a showed turn-on reponse in the presence of hydrazine,
while at higher concentration (> 25 M at 99% HEPES in
DMSO), the probe FPBC 6a exhibited ratiometric signal due to
aggregation induced emission property. The probe FPBC 6a
displayed high selectivity to hydrazine with a detection limit of
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6.08 ppb (less than the threshold limit value (TLV) of 10 ppb).
The real application of the probe FPBC 6a for detection and
direct visualization of hydrazine was successfully demonstrated
in live cancer cells. The practical applicability of the probe as
hydrazine chemosensor was evidenced using test strip
engraved with the word ‘CDRI’ exposed with the vapours of
hydrazine leading to highly bright blue emission. To the best of
our knowledge, FPBC 6a is the first dual responsive probe for
selective detection of hydrazine that may potentially be utilized
in chemical and biomedical research fields in either low or higher
concentrations depending upon the need of the experiments.
Furthermore, the test strips coated with FPBC 6a can be used
as sensor for hydrazine-vapors leakage in industrial areas for
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Movie Clip Link:
https://mega.nz/#!fb4V2Ijb!r96TFqVHEi11IDi177fN_FWr26GaU
NfEg_euinpTuIw
2
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Experimental Section
Supporting Information is available and includes Supplementary
Figures S1–S8, as well as all experimental details, synthetic
procedures, analytical data, and NMR spectra of all compounds.
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Entry for the Table of Contents
COMMUNICATION
[a]
A
novel dual-acting ‘turn-on’ and
Deepak Purohit,[a] Chandra P. Sharma
Ashutosh Raghuvanshi, [ Ankita Jain, [b]
Kundan S. Rawat,[a],[c] Neeraj M.
a]
‘
ratiometric’
aggregation
induced
emission
luminogen
3-formyl-5-
[a]
(
piperidin-1-yl)biphenyl-4-carbonitrile
Gupta,[a]
Jagriti
Singh,
Monika
* [a], [c]
6a for selective detection of hydrazine
Sachdev[b] and Atul Goel
in solution as well as in vapour phase
has been described.
Page No. – Page No.
First Dual Responsive ‘Turn-on’ and
Ratiometric’ AIEgen Probe for
‘
Selective Detection of Hydrazine both
in Solution and Vapour Phase
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