A fluorescence chemosensor based on imidazo[1,2-a]quinoline for Al3+ and Zn2+ in respective solutions

Article abstract of DOI:10.1039/c5ra21055k

A new chemosensor, N′-[(2-hydroxyphenyl)methylidene]imidazo[1,2-a]quinoline-2-carbohydrazide (L2), was developed, which could detect Al³⁺ in DMSO/H₂O HEPES buffer and Zn²⁺ in EtOH/H₂O HEPES buffer. The chemosensor exhibits high selectivity and sensitivity for sensing Al³⁺ and Zn²⁺ with a fluorescence "turn-on" mode.

Full text of DOI:10.1039/c5ra21055k

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A fluorescent chemsensor based on imidazo[1,2-a]quinoline for
3
+
2+
Al and Zn in respective solutions
Received 00th January 20xx,
Accepted 00th January 20xx
Junhua Sun, Zheng Liu, Ying Wang, Shihua Xiao, Meishan Pei, Xiuxian Zhao, and Guangyou Zhang*
DOI: 10.1039/x0xx00000x
A new chemsensor N'-[(2-hydroxyphenyl)methylidene]imidazo[1,2-a]quinoline-2-carbohydrazide (L2) was developed
3
+
2+
which could detect Al in DMSO/H
2 2
O HEPES buffer and detect Zn in EtOH/H O HEPES buffer. The chemsensor exhibits
www.rsc.org/
3+
2+
high selectivity and sensitivity for sensing Al and Zn with a fluorescense “turn-on” mode.
Introduction
THF, DMSO and EtOH, etc. So far, the effect of different
solvents on chemosensors for the selective and sensitive
Serving as the most abundant metal on earth and the second
most abundant transition metal in human body, aluminium
and zinc carry irreplaceable weight in livings. As a potential
toxic ion, aluminium is a non-essential element for biological
processes that has been implicated in various
neurodegenerative and neurological disorders, such as
Alzheimer's disease, dialysis encephalopathy, and problems
[25]
metal-ion detection has been rarely reported . Therefore,
there is still a urgent need to develop new sensors that
render to recognize different metal ions selectively in
dependent solvent. Based on the above needs and the
[
26-33]
studies about quinoline-based ligands
, a new and simple
sensor (L2) for Al and Zn was designed and synthesized
Scheme 1), which show distinctly different optical properties
in different solvent systems. Sensor L2 exhibits enhanced
3
+
2+
[1-3]
in bone, muscles, etc . According to WHO (World Health
Organization) report, the average daily intake of aluminium is
approximately 3-10 mg per day for human beings, which has
been widely used in food additive, aluminium-based
pharmaceuticals, and aluminium containers and cooking
(
3
+
fluorescence with high selectivity upon binding to Al in
2
+
DMSO/H
2 2
O HEPES buffer, but to Zn in EtOH/H O HEPES
[4]
buffer.
utensils . Zinc is an essential element for life and plays
critical roles in many biochemical processes, such as gene
expression, apoptosis, immune system response and
[5-8]
neurotransmission . However, the disordered cellular zinc
level can induce various diseases, for instance, Alzheimer
’
s
[9-10]
disease, epilepsy and infantile diarrhea
. Consequently,
the recognition and quantification of aluminium and zinc ions
are significant goals in both biological and environmental
research fields.
With regard to the detection of environmentally and
biologically relevant ions, fluorescence measurement is
considered to be a versatile technique with high sensitivity,
[
11-12]
rapid response, and easy performance
. In particular,
molecular chemosensors that show fluorescence responses
upon selective binding with metal ions have received great
interest since it is cost-effective, rapid, real time-monitoring
[13]
and facile . In recent years, the fluorescent chemsensors for
[21-24]
[14-20]
the detection of zinc
or aluminium ions
are
emerging continually. But most of fluorescence
chemosensors are studies in single organic solvents, such as
Scheme 1 Synthetic route of L1 and L2. Conditions: (1)
o
3 3 3 4
CH CN, catalyst MoO , H PO , at 50 C for 12h; (2)
o
benzotrifluoride, at 70 C for 5h; (3) THF, reflux for 16h; (4)
MeOH, at room temperature for 1h; (5) EtOH, at room
temperature for 12h.
School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022,
China. E-mail: chm_zhanggy@ujn.edu.cn; Tel: +86-13296449182
Electronic
DOI: 10.1039/x0xx00000x
Supplementary
Information
(ESI)
available.
See
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9:1, v/v). Stock solutions of various ions were prepared in
deionized water.
Experimental section
Results and discussion
Materials and instruments
2
The properties of L2 in DMSO/H O HEPES buffer
All organic reagents were obtained from commercial
suppliers and used without purification. UV-vis spectra were
recorded on a Shimadzu 3100 spectrometer. Fluorescence
measurements were carried out using Edinburgh Instruments
As shown in Fig. S9, the complexation time in the system of
DMSO/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v) was
investigated by monitoring the fluorescent emission intensity
2
3
+
1
of L2 (20
μM) bonding with Al (10 equiv.) at an excitation
Ltd-FLS920 fluorescence spectrophotometer. H NMR spectra
3
+
wavelength of 305 nm. After the addition of Al , the
fluorescent intensity of L2 at λ=450 nm was enhanced to a
relatively stable value after 6 h. Therefore, the complexation
time of 6 h was used for this system.
were recorded on Bruker AV III 400 MHz NMR spectrometer
1
3
and C NMR spectra were recorded on a Bruker AV III 100
MHz NMR spectrometer with tetramethysilane (TMS) as an
internal standard. Infrared spectra were recorded using a
Bruker Vertex 70 FT-IR spectrometer with KBr pellets.
2
+
+
The selectivity of L2 for different metal ions (Cu , Ag ,
2
+
2+
Cd , Hg , Na , K , Co , Pb , Mn , Li , Ni , Fe , Ca , Cr ,
+
+
2+
2+
2+
+
2+
3+
2+
3+
2
+
2+
3+
Zn , Mg , Al ) was investigated by fluorescence emission
spectroscopy. L2 (20 M) exhibited a weak fluorescence
intensity at 375 nm when it was excited at 305 nm in
DMSO/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v). The
Methods for the preraration of the receptor
μ
Synthesis
carbohydrazide (L1) The compoud
a]quinoline-2-carboxylate) was synthesized following a series
of
compound
imidazo[1,2-a]quinoline-2-
L
(ethyl imidazo[1,2-
2
3
+
[
34-36]
addition of Al to the solution induced a remarkable increase
in the fluorescence intensity along with a significant red shift
of 75 nm (Fig. 1A). Meanwhile, there was a sharp change
of previously reported methods
4
. Hydrazine hydrate (80%,
mL) was added dropwise to methanol solution (20 mL) of
ethyl imidazo[1,2-a]quinoline-2-carboxylate (0.91 mmol, 0.22
g). The reaction mixture was stirred for 12 h at room
temperature. Solvent was then removed under reduced
pressure, and the residue was dissolved in chloroform (10 ml).
The organic layer was washed with water, dried over
3
+
from colorless to blue in the presence of Al ions (Fig. 1A
inset). In contrast, addition of other metal ions caused almost
negligible fluorescence increase. To further understand the
3+
properties of L2 as a receptor for Al , a titration experiment
3+
anhydrous Na
purified by silica gel chromatography with chloroform
methanol (v/v, 15:1) as developing solvent to give
2
SO
4
, filtered, and condensed. The residue was
was performed with increasing concentration of Al (Fig. 1B).
3+
Upon incremental addition of Al , the fluorescence emission
/
1
maximum at 450 nm gradually increased and reached a
compound L1 as gray solid (0.16 g, 77%). H NMR [400 MHz,
DMSO-d , J=Hz, (ppm)]: 9.58 (1 H, s), 9.16 (1 H, s), 8.50 (1 H,
d, J=8.4), 8.01 (1 H, dd, J=7.9, 1.2), 7.76 (2 H, ddd, J=12.3, 9.7,
3
+
plateau when the concentration of Al was 25 equiv.. The
fluorescence intensity of L2 (20 M) at λ=450 nm increased
linearly with the concentration of Al from 1 up to 10
good linear relationship was observed between the
6
δ
μ
3
+
1
3
μM. A
5
.5), 7.61
DMSO, (ppm) ]: 161.81, 142.99, 138.78, 132.86, 129.93,
29.63, 128.13, 126.03, 123.42, 117.14, 116.74, 114.76.
–7.51 (2 H, m), 4.56 (2 H, s). C NMR [101 MHz,
δ
3
+
1
fluorescence intensity and [Al ] (Fig. S10). The detection limit
3+
+
-7
[M+H] : 227.1.
(3σ/slope) for Al was calculated to be 1.73
fluorescence quantum yield of L2 in DMSO/H O HEPES buffer
×10 M. The
Synthesis of compound N'-[(1E)-(2-hydroxyphenyl)methylidene]
imidazo[1,2-a]quinolie-2-carbohydrazide (L2) Salicylic aldehyde
2
3
was 0.36 and was increased to 0.77 by Al addition.
+
(
0.98 mmol, 0.12 g) was added to an ethanol solution (30 mL)
of imidazo[1,2-a]quinoline-2-carbohydrazide (0.43 mmol,
.10 g). Then the solution was stirred for 12 h at room
To further check the selectivity of receptor L2 towards
3+
2
Al , competitive experiment was carried out in DMSO/H O
0
HEPES buffer (10 mM, pH=7.4, 9:1, v/v). When L2 was treated
3+
with 1 equiv. of Al in the presence of the same
temperature and white precipitate appeared. The precipitate
was filtered and then washed with ethanol to isolate L2 in
1
pure form (0.09 g, 62%); H NMR [400 MHz, DMSO-d , J=Hz,
concentration of other metal ions (Fig. S12), several metal
6
2
ions (Ni ,Cu and Cd ) decreased the emission intensity and
+
2+
2+
δ
(ppm)]: 12.39 (1 H, s), 11.51 (1 H, s), 9.38 (1 H, s), 8.80 (1 H,
s), 8.59 (1 H, d, J=8.3), 8.05 (1 H, d, J=7.9), 7.87 (1 H, d, J=9.6),
.78 (1 H, t, J=7.8), 7.62 (2 H, dd, J=12.6, 5.9), 7.47 (1 H, d,
2
+
3+
2+
2+
some other metal ions (Pb , Fe , Zn and Mg ) increased
the emission intensity obviously. Even so, the result of Fig. 1A
had confirmed the solely addition of other metal ions caused
no significant florescence increase.Thus, L2 can be used
7
1
3
J=8.0), 7.32 (1 H, t, J=7.8), 6.94 (2 H, t, J=7.6). C NMR [101
MHz, DMSO, (ppm) ]: 158.85, 158.03, 149.41, 143.17,
37.98, 132.84, 131.75, 130.37, 130.11, 129.72, 128.74,
26.36, 123.52, 119.81, 119.13, 117.02, 116.93, 116.67. ESI-
δ
3
+
1
1
potentially to qualitatively detect Al in specified condition.
The UV-vis spectrum of L2 in DMSO/H O HEPES buffer (20
M) in the prescence of 10 equiv. of a variety of metal ions
2
+
MS: [M+H] : 331.1.
μ
2
+
+
2+
2+
+
+
2+
2+
2+
+
2+
3+
(
Cu , Ag , Cd , Hg , Na , K , Co , Pb , Mn , Li , Ni , Fe ,
2
+
3+
2+
2+
Ca , Cr , Zn , Mg , Al ) was detected as shown in Fig. S14.
3+
Preparation of test solution
3
+
2+
2+
5
The result show that these metal ions (Fe , Ni , Cu ) could
be distinguished easily over other ones using UV-vis
3
spectroscopy. In addition, the activity of L2 toward Al was
−
Stock solutions of the probe L2 (2.0
×
10 M) were prepared
O HEPES buffer (10 mM,
O HEPES buffer (10 mM, pH=7.4,
in two solvent systems: DMSO/H
pH=7.4, 9:1, v/v) , EtOH/H
2
+
2
2
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examined solely with absorption spectroscopy. The sensor L2
The effect of pH was studied dependently. Over the pH
range tested, L2 has nearly no fluorescence. Sharp decline
was observed at acidic (pH < 7) and basic (pH > 8) conditions
displayed four characteristic peaks at 291, 301, 326 and 339
2
nm in DMSO/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v).
3
+
in presence of Al . At lower pH (2-7), the decline probably
attribute to the protonation of the imidazole nitrogen, which
interfere the coordination between metal ions and the
nitrogen. At pH greater than 8, the fall of the fluorescence
intensity possibly due to formation of salt.
Fig. 2 Changes in absorption spectra of L2 (20
+
μ
M) with the
3
incremental addition of Al in DMSO/H
mM, pH=7.4, 9:1, v/v).
2
O HEPES buffer (10
Fig. 1 (A) Fluorescence spectra of L2 (20
μM) upon the
2
+
+
addition of metal salts (10equiv.) of Cu , Ag , Cd , Hg , Na ,
2+
2+
+
+
2+
2+
2+
+
2+
3+
2+
3+
K , Co , Pb , Mn , Li , Ni , Fe , Ca , Cr , Zn , Mg , and
2+
2+
3
+
Al in DMSO/H
ex=305nm.Inset: color of L2 and L2+Al system under UV
lamp. (B) Fluorescence titration spectra of L2 (20 M) upon
an incremental addition of Al (up to 25equiv.) in DMSO/H
HEPES buffer (10 mM, pH=7.4, 9:1, v/v). ex=305nm.
2
O HEPES buffer (10 mM, pH=7.4, 9:1, v/v). λ
3
+
μ
3
Fig. 3 Optimized structure of L2+Al at B3LYP/6-31+ G(d,p)
+
3
+
2
O
λ
3
+
Titration experiments with incremental addition of Al
ions resulted in the decline of the four intrinsic peaks along
with the emergence of two new peak at 382 nm and 407 nm.
A distinct isosbestic point at 354 nm implied the complete
3
+
conversion of L2 to its Al complex (Fig. 2). To confirm the
chelation structure, DFT calculations were carried out with
B3LYP/6-31G(d) basis sets using a suite of Gaussian 09
programs. Structure optimization and energy calculations
3
+
provide the best binding mode between L2 and Al (Fig. 3).
The DFT calculations also revealed that there is a reasonable
decrease in the HOMO to LOMO energy gap from L2 to its
aluminium complex (Fig. 4), which is consistent with the
emerging of the new red shifted absorbance peaks on the
3
+
addition of Al to L2
.
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The UV-vis spectrum of L2 (20
2
μM) in EtOH/H O HEPES
buffer (10 mM, pH=7.4, 9:1, v/v) in the prescence of 7 equiv.
2
+
+
2+
2+
+
+
2+
of a variety of metal ions (Cu , Ag , Cd , Hg , Na , K , Co ,
2
+
2+
+
2+
3+
2+
3+
2+
2+
3+
Pb , Mn , Li , Ni , Fe , Ca , Cr , Zn , Mg , Al ) was
detected as shown in Fig. S15. It is not easy to differentiate
various metal ions using UV-vis spectroscopy. The UV-spectra
2
+
properties of L2 and L2+Zn were researched in EtOH/H
HEPES buffer. The receptor L2 also has four absorption peaks
respectively at 290, 298, 322, and 333 nm in EtOH/H O HEPES
buffer, which is similar with L2 in DMSO/H O HEPES buffer.
Titration experiments with incremental amounts of Zn
2
O
2
2
2
+
ions resulted in the decreasing of the four intrinsic peaks
along with the emergence of a new peak at 390 nm. A distinct
isosbestic point at 354 nm established the transformation of
a free receptor in its zinc complex (Fig. 6). The DFT
2
+
3+
calculations of L2+Zn have similar results with L2+Al (Fig. 7
Fig. 4 Energy diagrams of HOMO and LOMO orbitals of L2 and
3
and Fig. 8).
+
L2+Al complex calculated at the DFT level using a B3LYP/6-
1G(d) basis set within the Gaussian 09 programs.
3
The properties of L2 in EtOH/H
The complexation time in the system of EtOH/H
buffer was very short which can be ignored. The selectivity of
2
O HEPES buffer
2
O HEPES
2
+
+
2+
2+
+
+
2+
L2 for different metal ions (Cu , Ag , Cd , Hg , Na , K , Co ,
2
+
2+
+
2+
3+
2+
3+
2+
2+
3+
Pb , Mn , Li , Ni , Fe , Ca , Cr , Zn , Mg , Al ) in
EtOH/H O HEPES buffer was detected by fluorescence
spectra. As is evident from Fig. 5A, a solution of L2 (20 M)
showed a low intensity at 345 nm when it was excited at 315
nm in EtOH/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v). The
2
μ
2
2
+
addition of Zn to the solution induced a large increase in the
fluorescence intensity, along with a significant red shift of
1
44 nm. There was also a dramatic color change from
2
+
colorless to yellow green in the presence of Zn ions (Fig. 5A
inset). While other metal ions induced unconspicuous
fluorescence increase. Similarly, fluorescent titration was also
2
+
conducted (Fig. 5B). Upon incremental addition of Zn , the
fluorescence emission maximum at 489 nm gradually
increased and reached a plateau when the concentration of
2
+
Zn was 7 equiv.The fluorescence intensity of L2 (20
λ=489 nm increased linearly with the concentration of Zn
from 0.1 up to 1 M. A good linear relationship was
observed between the fluorescence intensity and [Zn ] (Fig.
μM) at
2
+
μ
2
+
2
+
S11). The detection limit (3σ/slope) for Zn was calculated to
-8
be 6.36
×
10 M. The fluorescence quantum yield of L2 in
EtOH/H
2
O HEPES buffer was 0.25 and was increased to 0.41
2
by Zn addition.
+
2
Competitive experiment was carried out in EtOH/H O
Fig. 5 (A) Fluorescence spectra of L2 (20
μM) upon the
2
+
+
2+
2+
+
addition of metal salts (7 equiv.) of Cu , Ag , Cd , Hg , Na ,
HEPES buffer (10 mM, pH=7.4, 9:1, v/v). When L2 was treated
2
+
+
2+
2+
2+
+
2+
3+
2+
3+
2+
2+
3+
with 1 equiv. of Zn in the presence of the same
concentration of other metal ions (Fig. S13), several metal
K , Co , Pb , Mn , Li , Ni , Fe , Ca , Cr , Zn , Mg , Al in
EtOH/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v).
λ
2
2
+
ions (Ni , Fe and Cu ) decreased the emission intensity
3+
2+
2
+
ex=315nm. Inset: color of L2 and L2+Zn system under UV
lamp. (B) Fluorescence titration spectra of L2 (20 M) upon
an incremental addition of Zn (up to 7 equiv.) in EtOH/H O
2
+
2+
+
2+
and most of the metal ions (Pb , Co , Ag , Hg , Al , Cr
3+
3+
μ
2
+
2
+
and Mg ) increased the emission intensity. Nonetheless, the
result of Fig. 5A had confirmed the solely addition of other
metal ions caused no significant florescence enhancement.
2
HEPES buffer (10 mM, pH=7.4, 9:1, v/v).
λex=315nm.
2+
Thus, L2 can be used potentially to qualitatively detect Zn in
specified condition.
4
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2
The influence of pH for L2 and L2+Zn in EtOH/H
+
2
O solution
3
was analogous to L2 and L2+Al in DMSO/H
+
2
O solution. The
2
fluorescent effect of L2+Zn is best when pH values get close
+
to neutrality, which could have a similar explaination like
3
+
L2+Al
.
The proposed mechanism
The low fluorescence of the free receptor may be attributed
to a large extent of intramolecular charge transfer (ICT). Upon
interaction with the target anaystes, the intramolecular
charge transfer (ICT) changed following the principle of
forming a stable structure. Hence, the chelation enhanced
fluorescence (CHEF) process occured in the presence of the
analysts, accompanying with a large Stokes shift. Moreover, a
difference in the charge density of the cations and solvent
effect are likely to affect the ICT mechanism. This may
account for the different emission spectra of the probe upon
Fig. 6 Changes in absorption spectra of L2 (20
μM) with the
2
+
incremental addition of Zn in EtOH/H O HEPES buffer (10
2
mM, pH=7.4, 9:1, v/v).
3
+
2+
interaction with Al and Zn in different solvent (Scheme 2).
Conclusions
In summary, we designed and synthesized a new fluorescent
3
+
2+
probe, L2, which selectively senses Al and Zn ions with a
switch ON response in its fluorescence spectra. L2 shows an
3
prominent fluorescent selectivity toward Al over other
+
common metal ions in DMSO/H O HEPES buffer (10 mM,
2
2
Fig. 7 Optimized structure of L2+Zn at B3LYP/6-31+ G(d,p)
+
pH=7.4, 9:1, v/v) and shows an excellent fluorescent
2
+
selectivity toward Zn over other common metal ions in
EtOH/H O HEPES buffer (10 mM, pH=7.4, 9:1, v/v). The
detection limits for Al and Zn were found to be as low as
2
3
+
2+
-
7
-8
1
.73×10 M and 6.36×10 M, respectively.
Fig. 8 Energy diagrams of HOMO and LOMO orbitals of L2 and
2
+
L2+Zn complex calculated at the DFT level using a B3LYP/6-
1G(d) basis set within the Gaussian 09 programs.
3
The fluorescence changes of L2 (20
μM) in the absence
2
and presence of Zn in different pH values were examined.
+
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3
Scheme 2 The proposed mechanism of L2 with Al in DMSO and Zn in EtOH.
+
2+
Takahiro Mukai, and Hideo Saji, Sensors and Actuators B,
015, 213, 45 52.
Aasif Helal , Mohammad Harun Or Rashid , Cheol-Ho Choi
and Hong-Seok Kim, Tetrahedron, 2012, 68, 647-653.
20 Kang Shen, Xia Yang, Yixiang Cheng, and Chengjian Zhu,
Tetrahedron, 2012, 68, 5719-5723.
2
–
1
9
Acknowledgements
,
The authors thank Henan Sanmenxia Aoke Chemical Industry
Co., Ltd. for financial support.
2
1
Hyungjoo Kim, Boddu Ananda Rao, Jong Woo Jeong,
Sudipta Mallick,Sung-Min Kang, Joon Sig Choi, Chang-Soo
Lee, and Young-A. Son, Sensors and Actuators B, 2015,
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| J. Name., 2012, 00, 1-3
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RSC Advances
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DOI: 10.1039/C5RA21055K
Journal Name ARTICLE
Johnson, Richard D. Tanaka, Heinz E. Moser, and Roland
W. Burli, J. Med. Chem., 2003, 46, 3914-3929.
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RSC Advances
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DOI: 10.1039/C5RA21055K
Abstract
A new chemsensor N'-[(2-hydroxyphenyl)methylidene]imidazo[1,2-a]
3+
quinoline-2-carbohydrazide (L2) was developed which could detect Al
2+
in DMSO/H O HEPES buffer and detect Zn in EtOH/H O HEPES
2
2
buffer. The chemsensor exhibits high selectivity and sensitivity for
3+
2+
sensing Al and Zn with a fluorescense “turn-on” mode.