Development of a triple channel detection probe for hydrogen peroxide

Article abstract of DOI:10.1016/j.cclet.2015.10.022

The rapid and reliable measurement of hydrogen peroxide (H₂O₂) is imperative for many areas of technology, including pharmaceutical, clinical, food industry and environmental applications. In this work, a novel multifunctional complex, [Ru(bpy)₂(luminol-bpy)](PF₆)₂ (bpy: 2,2′-bipyridine), was designed and synthesized by incorporating a Ru(II) complex with a luminal group. In the presence of horseradish peroxidase (HRP), reaction of [Ru(bpy)₂(luminol-bpy)]²⁺ with H₂O₂ can be monitored by three sensing channels including photoluminescence (PL), chemiluminiscence (CL) and eletrochemiluminiscence (ECL). The quantitative assays for H₂O₂ in aqueous solutions using [Ru(bpy)₂(Luminal-bpy)](PF₆)₂ as a probe were established with PL, ECL and CL signal output modes, respectively.

Full text of DOI:10.1016/j.cclet.2015.10.022

G Model
CCLET 3469 1–5
Chinese Chemical Letters xxx (2015) xxx–xxx
Contents lists available at ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
1
2
Original article
3
4
Development of a triple channel detection probe for hydrogen
peroxide
5
6
Q1 Wen-Zhu Zhang, Zhong-Bo Du, Bo Song, Zhi-Qiang Ye *, Jing-Li Yuan
State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116024, China
A R T I C L E I N F O
A B S T R A C T
Article history:
The rapid and reliable measurement of hydrogen peroxide (H O ) is imperative for many areas of
2
2
Received 17 August 2015
Received in revised form 23 October 2015
Accepted 27 October 2015
Available online xxx
technology, including pharmaceutical, clinical, food industry and environmental applications. In this
0
work, a novel multifunctional complex, [Ru(bpy)
2
(Luminol-bpy)](PF
6
)
2
(bpy: 2,2 -bipyridine), was
designed and synthesized by incorporating a Ru(II) complex with a luminal group. In the presence of
2
+
horseradish peroxidase (HRP), reaction of [Ru(bpy)
three sensing channels including photoluminescence (PL), chemiluminiscence (CL) and eletrochem-
iluminiscence (ECL). The quantitative assays for H in aqueous solutions using [Ru(bpy) (Luminal-
bpy)](PF as a probe were established with PL, ECL and CL signal output modes, respectively.
2 2 2
(Luminol-bpy)] with H O can be monitored by
Keywords:
2
O
2
2
Hydrogen peroxide
Multifunctional complex
Three sensing channels
Photoluminescence
Chemiluminiscence
Eletrochemiluminiscence
6 2
)
ß 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Published by Elsevier B.V. All rights reserved.
7
8
1. Introduction
microelectrode by fast scan cyclic voltammetry in vitro and in 29
brain slices. Recently, several boronate-based fluorescence 30
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
Reactive oxygen species (ROS) are a class of radical or
nonradical oxygen-containing molecules that show high reactivity
to biomolecules [1]. Although generation of ROS is often simply
regarded as representing oxidative stress, each ROS has unique
chemical characteristics in terms of chemical reactivity and
lifetime in aqueous solution and, therefore, may play a distinct
2 2
probes capable of detecting H O have been reported, such as 31
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
peroxyfluor-1, peroxyresorufin-1 and peroxyxanthone-1 [13–17]. 32
These fluorescent probes are cell membrane-permeable, and able 33
2 2
to monitor the intracellular H O concentration changes in living 34
cells. At the same time, chemiluminescence (CL)-based assays 35
possess several advantages such as simplicity in instrumentation 36
[18], high sensitivity, and wide linear range. Since no external light 37
source is used for excitation in chemiluminescent approaches, 38
nonspecific signals caused by external light excitation as often 39
observed in fluorescence-based measurements can be minimized. 40
Suzuki et al. has reported a luciferin-based long-wavelength 41
chemiluminescent based probe, KEIO-BODIPY-imidazopyrazine, 42
2 2
role in biological systems [2]. Hydrogen peroxide (H O ) exhibits
relatively mild reactivity among ROS and has attracted intense
interest in recent years. It appears to be involved in signal
transduction by reversible oxidation of proteins, such as phos-
phatases and thioredoxins, in a tightly regulated manner. The fast
2 2
and accurate detection of H O has profound applications in
pharmaceutical, clinical, food industry, environmental analysis
and other fields [3,4]. Thus, numerous analytical methods have
which exhibited the strong response toward H
2
O
2
.
43
Although various techniques in H sensing have been 44
2 2
O
been applied for the detection of H
2
O
2
such as fluorescence [5,6],
installed to enhance sensitivity, selectivity, and the dynamic 45
working range, these approaches mainly follow the paradigm that 46
is still dominating traditional probe design: one probe for one 47
detection method. Therefore, the application of the probe will be 48
significantly limited by the requirement of instrument and 49
complicated samples containing the different interfering species. 50
As an alternative strategy, here we reported a mutli-signaling 51
chemiluminescence [7,8], and electrochemical methods [9–11].
Among these methods, the electrochemical technique is the
most studied because of its simplicity, fast response for analysis,
low detection limit, and low costs [12]. Sombers and co-workers
2 2
have detected rapid H O fluctuations at an uncoated carbon fiber
probe, Ru[(bpy)
sensing channels including photoluminescence, chemiluminis- 53
cence and eletrochemiluminiscence. 54
2 6 2 2 2
luminol-bpy](PF ) , that can detect H O in three 52
*
Corresponding author.
E-mail address: yezq@dlut.edu.cn (Z.-Q. Ye).
http://dx.doi.org/10.1016/j.cclet.2015.10.022
1
001-8417/ß 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
Please cite this article in press as: W.-Z. Zhang, et al., Development of a triple channel detection probe for hydrogen peroxide, Chin.
Chem. Lett. (2015), http://dx.doi.org/10.1016/j.cclet.2015.10.022

G Model
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W.-Z. Zhang et al. / Chinese Chemical Letters xxx (2015) xxx–xxx
5
5
6
2. Experimental
analysis (%) calcd. for C40
N 11.33; found (%): C 43.12, H 3.03, N, 11.13.
H
31
F
12
N
9
O
3
P
2
Ruꢀ2H
2
O: C 43.17, H 3.17,
101
102
5
2.1. Materials and instrumentation
2.3. Chemiluminiscence measurements
103
5
5
5
6
6
6
6
6
6
6
6
6
6
7
7
7
7
7
7
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
5-Amino-2,3-dihydrophthalazine-1,4-dione, hydrogen perox-
ide, horseradish peroxidase (HRP) were purchased from Aladdin. 4-
A
mixture of [Ru(bpy)
mol/L), HRP (1.0 mol/L) and different concentrations of
(0.1 mol/L, 1.0
mol/L, 10 mol/L, 12
mol/L, 70 m mol/L) was injected into injection
2
(Luminol-bpy)](PF
6
)
2
solution
104
105
106
107
108
109
110
111
0
0
methyl-4 -methyl-2,2 -bipyridine were purchased from Sigma-
Aldrich. [Ru(bpy) (COOH-bpy)](PF were synthesized by using
(1.0
m
m
2
6
)
2
H
8.0
50
2
O
2
m
m
mol/L, 2.0
m
mol/L, 4.0
m
mol/L, 6.0 mol/L,
m
the literature methods [19]. Unless otherwise stated, all chemical
materials were purchased from commercial sources and used
without further purification.
m
m
m
m
mol/L, 28
m
mol/L, 40 mmol/L,
mol/L, 60
m
port, respectively. The rotate speed of main and vice-peristaltic
pump were set as 20 and 15 r/min, respectively, and CL intensities
of the solutions were determined on chemiluminescence analyzer.
1
13
H NMR and C NMR spectra were measured on a Bruker
1
13
Avance spectrometer (400 MHz for H NMR and 100 MHz for
C
NMR). Mass spectra were recorded on a HP1100 LC/MSD MS
spectrometer. Absorption spectra were measured on a Perkin-
Elmer Lambda 35 UV–Vis spectrometer. Elemental analysis was
carried out on a Vario-EL analyser. Photoluminescence spectra
were measured on a Perkin-Elmer LS-50 luminescence spectrom-
eter. All the ECL measurements were carried out on an ECL insECL
cell at room temperature. All measurements of chemiluminiscence
were carried out IFFM-D flow injection chemiluminescence
analyzer and IFFS-A instrument system (Remex Electronics
Instrument Co., Ltd.).
2.4. ECL measurements
112
[Ru(bpy)
(1.0 mol/L) was stirred with different concentrations of H
(0 mol/L, 5 mol/L, 15 mol/L, 20 mol/L, 25 mol/L) at room
2
(Luminol-bpy)](PF
6
)
2
(10
m
mol/L)
and
HRP
113
114
115
116
117
118
119
120
121
122
123
124
125
m
2 2
O
m
m
m
m
m
temperature for 30 min in the PBS buffer (25 mmol/L, pH 7.4),
respectively. The glassy carbon (3.0 mm in diameter) electrode and
KCl saturated Ag/AgCl electrode were used working electrode and
reference electrode, respectively, and a platinum wire (0.3 mm in
diameter) was used as the auxiliary electrode. Before measure-
ments, the glassy carbon working electrode was soaked in 10%
7
6
2 6 2
2.2. Synthesis of [Ru(bpy) (Luminol-bpy)](PF )
HNO in an ultrasonic water bath for 1 min, then polished by an
2 3
Al O slurry, and thoroughly rinsed with deionized water for
3
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
A
solution of [Ru(bpy)
0.1 mmol) in 5 mL SOCl was refluxed for 5 h under an argon
atmosphere. After removing the excess SOCl by distillation
under reduced pressure, the residue was dried in vacuum for 2 h,
and dissolved in 30 ml absolute CH CN. The solution was added
to a mixture of luminal (17.5 mg, 0.1 mmol) and Et N (21 L,
2
(COOH-bpy)](PF
6
)
2
(93.6 mg,
2
1 min. The voltage of the photomultiplier tube was set at 900 V in
the detection process while collecting the ECL signals.
2
3
3. Results and discussion
126
127
3
0.15 mmol). The mixture was refluxed 12 h. The solvent was
evaporated, and the residue was purified by silica gel column
3.1. Design and synthesis of the mutli-signaling probe
A novel multi-signaling probe for H O , Ru[(bpy) luminol-
chromatography using CH
3
CN–H
2
O–KNO
3
(sat.) (100:20:1, v/v/v)
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
143
2
2
2
as eluent. The fractions containing the target product were
collected, and the solvent was evaporated. The resulting solid
6 2
bpy](PF ) , was developed by conjugating luminal with a
luminescent Ru(II) complex. The luminescent Ru(II)-polypyridyl
complexes has attracted much attention due to their abundant
photophysical, photochemical, and electrochemical properties,
such as visible-light excitation and emission with large Stokes
shifts, high photo- and chemical stabilities, low cytotoxicity, good
water-solubility, and high PL and ECL response efficiency [20–23].
In addition, the output signals of Ru(II)-polypyridyl complexes can
be modulated by appropriate modification of the pyridine moiety.
At the same time, it is well known that luminal is a specifically
reactive group for H O , and has been widely used for the
was dissolved in a small amount of CH
saturated solution of NH PF was added to give a red precipitate.
The product was filtered and washed with small amount of water.
Compound [Ru(bpy) (Luminol-bpy)](PF was obtained as a red
powder (75.89 mg, 70.4% yield). H NMR (400 MHz, CD CN):
3 2
CN–H O(1:1), and a
4
6
2
6 2
)
1
3
d
2.54 (s, 3H), 7.27(m, 1H), 7.38–7.43(m, 4H), 7.57(m, 1H), 7.70(s,
1H), 7.74(m, 3H), 7.78(s, 1H), 7.81(m, 2H), 7.97(m, 1H), 8.04–
8.09(m, 4H), 8.51(d, J(H,H) = 4 Hz, 5H), 8.97(s, 1H), 8.99(m, 1H).
1
3
3
C NMR (100 MHz, CD CN): d 19.97, 117.04, 118.96, 121.24,
2
2
123.44, 124.00, 124.03, 124.08, 125.32, 127.29, 127.34, 127.37,
127.39, 128.59, 134.81, 137.70, 150.54, 150.59, 151.28, 151.47,
151.49, 152.63, 155.63, 156.51, 156.62, 156.73, 158.25, 161.52.
2 2
development of chemiluminescent probe for H O detection.
Ru[(bpy) luminol-bpy](PF ) was successfully synthesized as
shown in Scheme 1, and the structure of the probe was well
confirmed by NMR spectroscopy, MS, and elementary analyses.
2
6 2
+
2+
6 6
ESI-MS (m/z): 932.0 ([M-PF ] ), 393.4 ([M-2PF ] ). Elemental
2 6 2
Scheme 1. Synthesis of Ru[(bpy) luminol-bpy](PF ) .
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Chem. Lett. (2015), http://dx.doi.org/10.1016/j.cclet.2015.10.022

G Model
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W.-Z. Zhang et al. / Chinese Chemical Letters xxx (2015) xxx–xxx
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Fig. 1. Reaction of Ru[(bpy)
2
luminol-bpy](PF
6
)
2
2 2
with H O in the presence of HRP.
6
5
0
5
B
Y=17.251+0.9531X r=0.9949
7
6
5
4
3
2
1
0
0
0
0
0
0
0
A
Conc. of H O (µmol/L)
2 2
50
35
4
4
3
5
0
5
3
2
2
1
1
8
6
4
2
0
0
5
0
5
0
30
25
2
0
15
1
0
0
0
10
20
2 2
30
40
5
00
600
700
Conc. of H O (µmol/L)
Wevelength(nm)
Fig. 2. A. Luminescence emission of [Ru(bpy)
2 6 2 2 2
(Luminal-bpy)](PF ) (10 mmol/L) upon addition of H O (0–35 mmol/L) and HRP (1 mmol/L) for 5 min at 25 8C in 25 mmol/L PBS
buffer (pH = 12.0). ex = 450 nm. B. The calibration curve for luminescence detection of H O .
l
2 2
1
44
3.2. Luminescence measurements H
2
O
2
Furthermore, [Ru(bpy)
good selectivity for H . As shown in Fig. 3, the probe did not 170
give any observable luminescence responses to the addition of 171
2
(Luminal-bpy)](PF
6
)
2
exhibited the 169
2 2
O
145
146
147
148
149
150
151
152
153
154
155
156
157
158
159
160
161
162
163
164
165
166
167
168
After conjugated with a luminal moiety, the metal-to-ligand
charge transfer (MLCT) emission of the Ru(II) complex is effectively
corrupted by the electron of N atoms via an intramolecular
ꢁ
ꢁ
ꢁ
ꢁ 1
other ROS/RNS, such as ClO , NO
O
3
,ꢀOH, NO, NO
ꢁ
2
, while the luminescence intensity was remarkably increased 173
2
, ONOO , O and 172
2
.
photoinduced electron transfer (PET) process. Ru[(bpy)
bpy](PF exhibited weak luminescence at 645 nm. It is well
known that the luminal moiety can react with ROS, which are
generated by the reaction of H with HRP, to generate a high
energy species that decomposes to give an excited molecule with
loss of nitrogen molecule [24]. Therefore, after reacting with H
2
luminol-
after [Ru(bpy)
2
(Luminal-bpy)](PF
6
)
2
was reacted with H
2
O
2
. These 174
6 2
)
2 2
O
1
0
0
.0
.8
.6
2 2
O
in the presence of HRP to trigger the cleavage of the N atoms, the
PET process is eliminated, so that the luminescence of the Ru(II)
complex can be turned on (Fig. 1).
To investigate the luminescence response of the Ru(II) complex
to H
(10
concentrations of H
12.0. As shown in Fig. 2A, the complex [Ru(bpy)
bpy)](PF exhibited weak luminescence at 645 nm. Upon
reaction with different concentrations of H , the luminescence
intensity of the complex was increased gradually. In addition, the
2
O
2
, the emission spectra of [Ru(bpy)
2
(Luminal-bpy)](PF
6 2
)
m
mol/L) in the presence of HRP (1.0
m
mol/L) and different
0.4
2
O
2
were recorded in 25 mM PBS buffer of pH
(Luminal-
2
0
0
.2
.0
6 2
)
2 2
O
-
-
-
-
k
-
.
2
n
O
2
3
2
.
H
1
O
2
O
dose-dependent luminescence enhancement showed
linearity in the concentration range of 0–40
(Fig. 2B), suggesting [Ru(bpy) (Luminal-bpy)](PF
tively detect H by using luminescence methods.
a
good
la
H 2
OO
O
b
ClO
NO
N
NO
NO
O
H
2
O
2
m
mol/L
2
6
)
2
can quantita-
Fig. 3. PL intensities of Ru[(bpy)
with various ROS/RNS (60
luminol-bpy](PF
)
(10
m
mol/L) upon reaction
2
6
2
2
O
2
m
mol/L) in 25 mmol/L PBS buffer with pH 12.0.
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6
5
5
4
4
3
3
2
2
1
1
500
000
500
000
500
000
500
000
500
000
500
000
A
6000
B
5
000
4000
3
2
000
000
500
0
1000
0
5
10
15
20
25
5
10
15
20
25
30
Scan time (s)
Scan time (s)
Fig. 4. A. ECL intensity responses of [Ru(bpy)
2 6 2 2 2
(Luminal-bpy)](PF ) (10 mmol/L) upon addition of H O (0–25 mmol/L) and HRP (1.0 mmol/L) at room temperature in 25 mmol/
2 2
L PBS buffer (pH = 12.0) containing 10 mmol/L of TPrA. Photomultiplier tube voltage: 900 V; B. The calibration curve for the ECL detection of H O .
10000
2
2
600
400
B
Y=730.6670+24.3814X r=0.9933
A
8
000
000
000
000
0
2200
000
1800
2
6
4
2
1
1
1
1
600
400
200
000
8
6
00
00
1
10 20 4060 80 120160 200280 400 500 600 700
0
10
20
30
40
50
-7
60
70
80
-7
Conc. of H O (10 mol/L)
2
2
Conc. of H2O2
(
10 mol/L
)
Fig. 5. A. Chemilunminescence spectra of Ru[(bpy)
2 6 2 2 2
luminol-bpy](PF ) (1.0 mmol/L) upon addition of H O (0.1–70 mmol/L) and HRP (1.0 mmol/L) in 25 mmol/L PBS buffer
(
pH = 12.0); B. The calibration curve for the chemiluminescence detection of H O .
2 2
1
1
75
76
results demonstrate that the response of the probe to H
highly specific by using luminescence methods.
2
O
2
is
chemiluminescence detection, and the signal interferences from
the background fluorescence that is triggered by an external
excitation source can be avoided. The most widely used
198
199
200
201
202
203
204
205
206
207
208
209
210
211
212
213
214
215
216
1
77
3.3. ECL measurements for H
2
O
2
chemiluminescence system is
reaction catalyzed by horseradish peroxidase. Here a Ru(II)
complex containing luminal moiety, Ru[(bpy) luminol-
bpy](PF , was evaluated for the chemiluminescence detection
of H . The chemiluminescence spectra of Ru[(bpy) luminol-
bpy](PF (1.0 mol/L) was recorded in the presence of H (0.1–
70 mol/L) and HRP (1.0 mol/L) in 25 mmol/L PBS buffer
(pH = 12.0). As shown in Fig. 5A, upon addition of
chemiluminescence intensity of Ru[(bpy) luminol-bpy](PF
was clearly increased. The dose-dependent luminescence en-
hancement followed good linear relationship with
concentrations in a range of 0–7.0 mol/L, and a detection limit
of 0.6 mol/L was obtained (Fig. 5B). This result indicates that
Ru[(bpy) luminol-bpy](PF can be also used as a chemilumines-
a luminol/hydrogen peroxide
178
179
180
181
182
183
184
185
186
187
188
189
190
191
192
193
In the ECL case, the similar phenomenon might also occur since
the excited-state electron can be also withdrawn by the electron
acceptor group to retain the complex in the ECL-off state, while its
ECL behavior should be turned on after the cleavage reaction
a
2
6 2
)
2
O
2
2
6
)
2
m
2 2
O
induced by H
bpy)][PF was investigated upon addition of different concen-
tration of H in 25 mmol/L PBS buffer (pH = 12.0) containing
2
O
2
and HRP. The ECL intensity of [Ru(bpy)
2
(luminol-
m
m
6
]
2
2 2
H O ,
2
O
2
2
6 2
)
10 mmol/L of TPrA. As shown in Fig. 4A, when the cyclic potential
was scanned from 0.2 V to 1.8 V and then backed from 1.8 V to
0.2 V, a typical ECL emission from the excited-state of the Ru(II)
complex appeared at ꢂ1.27 V, which was increased followed by
a
2 2
H O
m
m
the increase of H
versus the H
a dynamic range of 0–25
indicates that [Ru(bpy) (luminol-bpy)][PF
ECL probe for the quantitative detection of H
2
O
2
concentration. By plotting the ECL intensity
2
6 2
)
2
O
2
concentration, a good linear calibration curve with
mol/L was obtained (Fig. 4B). This result
can be also used as a
2 2
cence probe for the quantitative detection of H O at a low
m
micromolar concentration level.
2
6 2
]
2
O
2
.
4. Conclusion
217
1
94
3.4. Chemiluminiscence measurements for H
2
O
2
In conclusion, a multifunction Ru(II) complex, [Ru(bpy)
2
(Lum-
218
219
220
221
222
inal-bpy)](PF , has been developed as a probe for H by using
6
)
2
2 2
O
195
196
197
A unique advantage of chemiluminescence detection technique
is that can effectively lower the signal-to-noise ratio and improve
the sensitivity due to an excitation source is not needed for
triple-channel detection. Based on a luminal mioety/hydrogen
peroxide reaction catalyzed by horseradish peroxidase, the novel
2 2
probe can detect H O in the three sensing channels including
Please cite this article in press as: W.-Z. Zhang, et al., Development of a triple channel detection probe for hydrogen peroxide, Chin.
Chem. Lett. (2015), http://dx.doi.org/10.1016/j.cclet.2015.10.022

G Model
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W.-Z. Zhang et al. / Chinese Chemical Letters xxx (2015) xxx–xxx
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[
10] J.J. Zhang, Y.G. Liu, L.P. Jiang, et al., Synthesis, characterizations of silica-coated 258
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2 2
cence. The quantitative assays for H O in aqueous solutions using
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260
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2
6
)
2
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with PL, ECL and CL signal output modes, respectively and its
feasibility of practical application was studied on. We believe that
the present approach could provide a useful strategy to design and
synthesize multifunctional probes for biomolecules.
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Acknowledgment
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2
2
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31 Q2
32
33
This project was supported by the National Natural Science
Foundation of China (NO. 21205009) and the Fundamental
Research Funds for the Central Universities (No. DUT15ZD116).
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Please cite this article in press as: W.-Z. Zhang, et al., Development of a triple channel detection probe for hydrogen peroxide, Chin.
Chem. Lett. (2015), http://dx.doi.org/10.1016/j.cclet.2015.10.022