Isonicotinoylhydrazide modified 3-acetylcoumarin scaffold as an efficient chemical reversible sensor to detect Al3+ selectively and its application in live cells imaging

Article abstract of DOI:10.1080/00397911.2019.1631345

A turn-on photochromic sensor based on coumarin was designed and synthesized for selective and sensitive detection of Aluminium(III) (Al³⁺) in ethanol (C₂H₅OH)/water (H₂O; 1:1, v/v) with the detection limit of 0.126 μM. The mechanism was proposed to form a kind of 1:1-type complex between probe C1 and Al³⁺ in which the binding constant was 3.11 × 10⁷ M^?1. In addition, the sensor was effectively used for the detection of Al³⁺ in living HEK293T cells.

Full text of DOI:10.1080/00397911.2019.1631345

Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic
Chemistry
ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: https://www.tandfonline.com/loi/lsyc20
Isonicotinoylhydrazide modified 3-acetylcoumarin
scaffold as an efficient chemical reversible sensor
3+
to detect Al selectively and its application in live
cells imaging
Wenling Wang, Lei Jin, Yang Kuang, Zhongzhong Yuan & Qingming Wang
To cite this article: Wenling Wang, Lei Jin, Yang Kuang, Zhongzhong Yuan & Qingming Wang
(
2019): Isonicotinoylhydrazide modified 3-acetylcoumarin scaffold as an efficient chemical
3+
reversible sensor to detect Al selectively and its application in live cells imaging , Synthetic
Communications, DOI: 10.1080/00397911.2019.1631345
To link to this article: https://doi.org/10.1080/00397911.2019.1631345
Published online: 16 Jul 2019.
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https://doi.org/10.1080/00397911.2019.1631345
Isonicotinoylhydrazide modified 3-acetylcoumarin scaffold
3
þ
as an efficient chemical reversible sensor to detect Al
selectively and its application in live cells imaging
Wenling Wang, Lei Jin, Yang Kuang, Zhongzhong Yuan, and Qingming Wang
Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection,
School of Pharmacy, Yancheng Teachers’ University, Yancheng, Jiangsu, People’s Republic of China
ABSTRACT
ARTICLE HISTORY
A turn-on photochromic sensor based on coumarin was designed
and synthesized3 for selective and sensitive detection of
Received 12 March 2019
þ
KEYWORDS
Aluminium(III) (Al ) in ethanol (C H OH)/water (H O; 1:1, v/v) with
2
5
2
Fluorescent probe; limit of
detection; mechanism;
cell imaging
the detection limit of 0.126 lM. The mechanism was proposed to
3
þ
form a kind of 1:1-type complex between probe C1 and Al
in
7
ꢁ1
which the binding constant was 3.11ꢀ 10 M . In addition, the sen-
3þ
sor was effectively used for the detection of Al in living HEK293T
cells.
GRAPHICAL ABSTRACT
A new “turn-on” chemodosimeter exhibited instant / reversible and
3þ
excellent specificity towards Al in aqueous media and living cells.
Introduction
Aluminium serves as a dispensable element for living systems and is hazardous towards
[
1,2]
aquatic life and for retarding agricultural production in acidic soil.
Aluminium is
prevalently used in daily life, such as manufacturing cars, aluminium cookware, food
[
3–6]
additives, aluminium-based medicine and utensils for storage or cooking.
Because of
2þ
2þ
3þ [7,8]
the similar atomic radius and valence to Mg , Ca and Fe
,
aluminium is used as
CONTACT Qingming Wang
wangqm@yctu.edu.cn
School of Pharmacy, Jiangsu Provincial Key Laboratory of
Coastal Wetland Bioresources and Environmental Protection, Yancheng Teachers’ University, Yancheng, Jiangsu 224051,
People’s Republic of China.
Supplemental data for this article can be accessed on the publisher’s website.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
ß 2019 Taylor & Francis Group, LLC

2
W. WANG ET AL.
a competitive inhibitor for many ions in many kinds of biological processes. When excess
of aluminium is accumulated in human body, a series of adverse physiological effects and
diseases would be triggered and catalysis, such as glucose intolerance, anemia, cardiac
arrest, gastrointestinal diseases, encephalopathy, cardiotoxicity, dementia, Parkinson’s dis-
[
9,10]
ease and Alzheimer’s disease.
The World Health Organization (WHO) suggested that
ꢁ
1
[11,12]
the maximum intake of aluminium in human is 7 mg.kg per week
sible amount of aluminium (III) (Al ) in drinking water is below 7.4 lM.
Special attention was given to the development of Al detection to monitor the con-
centration level in the environment and human body. Compared with the traditional
methods such as inductively coupled plasma atomic emission spectroscopy,
absorption spectroscopy and inductively coupled plasma mass spectrometry , col-
orimetric and fluorescence ways stand out as a better choice due to the advantage of
simplicity, cost effectiveness and high sensitivity.
and the permis-
3þ
[11,13]
3
þ
[
14]
atomic
[
15]
[16]
[
17–20]
Although there are numerous
[
21,22]
[3,23]
[24,25]
fluorescent chemosensors such as triazoles,
schiff bases
calixarene,
tri-
were reported,
sensor often possess inherent disadvantages including require
ultraviolet excitation, laborious multistep organic synthesis and be vulnerable to the dis-
[
26,27]
[17,28]
[29–31]
azole-pyridyl
and secondary/tertiary amines
and others
3þ
most published Al
[
32–35]
turbance of other metal ions.
Therefore, it is valuable to design new fluorescent
3
þ
sensors for Al with long emission wavelengths, large stokes shifts, simple and inex-
pensive methodology. Coumarin derivates fluorescent probes are widely used in the last
decade. A serious of coumarin (2 H-1-benzopyran-2-one) derivatives were synthesized
[
36]
and had some unique photophysical and photochemical properties,
such as large
stokes shifts, high quantum yields and superior photostability, which make it being
[
37,38]
devoting to a variety of applications in fluorescent chemosensors.
0
Here, a novel probe ((N ;-(1-(2-oxo-2H-chromen-3-yl)ethylidene)isonicotinohydra-
zide) C1) was designed, synthesized and applied for the detection of aluminium ion in
1
13
aqueous. H-NMR, C-NMR, and ESI-MS spectroscopy were used to confirm the struc-
ture of C1 (Scheme S1 in Supplementary Material).
Results and discussion
31
Fluorescence spectra of C1 and Al
The unshared electron pairs of the nitrogen and the oxygen atom in C1 could provide a
special binding affinity to metal ions, so a fluorescence titration of aluminium chloride
(
AlCl ) was investigated by a 1.0 lM solution of C1 in ethanol (C H OH)/ water
3 2 5
3
þ
(H O;1:1, v/v). As showed in Figure 1, with the absence of Al , C1 showed almost no
2
3
þ
fluorescence emission intensity when excited at 393 nm. However, the addition of Al
(0.25–3.5 lM) induced significantly fluorescence intensity at 490 nm by PET(photo-
induced electron transfer). The visual fluorescence color was changed from colorless to
light green under a 365 nm UV light.
From the fluorescence titration spectra, the limit of detection (LOD) was 0.126 lM,
which was obtained by the formula: LOD ¼ 3d/Slope, where d was the standard deviation
of blank experiment and slope was the calibration curve (Figure S5). The LOD value was
far below the threshold value (46 mM) raised by the World Health Organization. Besides,

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3
3þ
Figure 1. Fluorescence spectra of C1 (1.0 lM) on addition of different amounts of Al in C H OH/
2
5
H2O (1:1, v/v). Inset: the visible fluorescence changes upon UV irradiation (kex ¼ 393 nm).
3þ
Figure 2. Plot of (I -I )/(I -I ) versus [Al ] for chemosensor C1.
a
f
b f
3
þ
7
ꢁ1
the binding constant between C1 and Al was estimated to be 3.11 ꢀ 10 M , indicating
3þ
that chemosensor C1 showed high affinity toward Al (Figure 2).
31
UV-Vis titration spectra of C1 and Al
The absorption spectroscopic properties of C1 were conducted in C H OH/H O (1:1,
2
5
2
v/v) solution by UV-1800 at room temperature. As showed in Figure 3, the UV-Vis
spectrum showed that there were bands centering at 287 and 375 nm for free C1,
which corresponded to p–p
spectrum of C1 and Al showed a distinct concentration-dependent with a red shift
from 275 to 295 nm. A complex between C1 and Al was formed followed by an
ꢂ pyridine and coumarin ring, respectively. The UV-Vis
3
þ
3
þ
isosbestic point at 338 nm.

4
W. WANG ET AL.
3þ
Figure 3. Absorbance spectra of chemosensor C1 (5.0 lM) in the presence of Al (0 to 85 lM) in
CH CH OH/H O (1:1, v/v).
3
2
2
Figure 4. Fluorescence (kex ¼ 393 nm) response of chemosensor C1 upon the addition of several cati-
3þ
ons in C H OH/H O (1:1, v/v) at an emission slit of 5 nm. Inset: a color change photograph for Al
2
5
2
and the other cations under illumination with a 365 nm UV lamp and visible color changes.
Fluorescence study of C1 with various cations and anions
2
þ
2þ
3þ
3þ
The recognition behavior of C1 with various cations, including Cu , Zn , Al , Cr ,
2
þ
Co , and so on were also investigated by fluorescence spectroscopy in C H OH/H O
2
5
2
(1:1, v/v) at room temperature. In the absence of cations, C1 (1.0 lM) displayed no
fluorescence emission in the range of 400–650 nm. Significant change in intensity of the
absorption peak at 490 nm was obtained in the fluorescence spectroscopy of C1 upon
3
þ
addition of Al while the other tested cations caused negligible changes as depicted in
2
þ
2þ
3þ
3þ
2þ
Figure 4. Figure 5 showed that the coexisting cations (Cu , Zn , Al , Cr , Co ,
2
þ
Mn and so on) did not interfere with the fluorescence emission intensity of Al-C1
system. Al induced about 100-fold fluorescence enhancement.
3
þ

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5
þ
þ
2þ
Figure 5. Histogram of F nm of C1 in the presence of different cations: (a) C1, (b)Na , (c) K ,
4
90
2þ
2þ
2þ
3þ
2þ
2þ
3þ
2þ
2þ
(
d) Mg , (e) Ca , (f) Ba , (g) Cr , (h) Co , (i) Mn , (j) Fe , (k) Ni , (l) Cu , (m) Cd
,
2þ
2þ
3þ
þ
2þ
2þ
þ
2þ
þ
3þ
(
n) Zn , (o) Pb , (p) Bi , (q) Ag , (r) Sn , (s) Sr , (t) NH4 , (u) Fe , (v) Cu and (w) Al
.
3þ
Figure 6. Job’s plot for determining the stoichiometry of Chemosensor C1 and Al
.
4
ꢁ
ꢁ
2ꢁ
ꢁ
ꢁ
2ꢁ
2ꢁ
Similarly, the binding ability of C1 with various anions (P O , Cl , Br , I , SO
,
2
ꢁ
7
4
ꢁ
3ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
2ꢁ
ꢁ
H PO , PO , OH , HCO , NO , HSO , C O , F , HPO4 , S O3 , NO ,
Ac , B O , HSO and SO ) were also investigated. The results showed that there
2
ꢁ
4
4
3
2ꢁ
3
4
2
4
2
2
2ꢁ
ꢁ
4
7
3
3
was no obvious fluorescence enhancement by adding 20 equiv. anions in C1 (Figures S6
and S7). An intuitionistic conclusion could be summarized that C1 could be applied to
3
þ
distinguish Al from other metal ions and anions in C H OH/H O (1:1, v/v).
2
3
2
Job’s plot
We took a meticulous investigation to understand the binding behavior of C1 towards
3
þ
Al . The Job’s plot was used to exam the stoichiometry of the binding species, the stoi-
chiometry was found to be 1:1 (Figure 6).

6
W. WANG ET AL.
3þ
Figure 7. ESI mass spectra of C1 upon addition of excess Al
.
Response time
3
þ
The time-dependent of C1 in the presence of different amounts of Al was studied by
fluorescence spectra (Figure S8). The results showed that the fluorescence emission at
4
90 nm quickly enhanced within 15 s and reached to the maximum within 1 min. The
3
þ
interaction between C1 and Al was rapidly reached equilibrium. Therefore, C1 could
be used as an effective probe for the real-time and quantitative detection of Al with-
out any pretreatment (Figure S5).
3þ
Proposed mechanism
Mass spectrometry is usually used to analyze the product in detail. In Figure 7, a peak
3
þ
3þ
at m/z ¼ 163.0257, corresponding to [C1 þ Al þ 2CH OH þ 5 H O] was clearly
3
2
3
þ
obtained, which suggested that the complex formed between Al and C1 was consist-
ent with a 1:1 stoichiometry, as showed in Scheme S2. This result was in good accord-
ance with the Job’s plot results.
Cell imaging
3þ
Due to the selective turn-on fluorescence response of C1 to Al , the cell imaging per-
formance was demonstrated by using the live HEK293T cells line. As showed in Figure 8,
ꢃ
HEK293T cells were incubated with C1 (10 lM) for 30min at 37 C almost exposed no
3þ
ꢃ
fluorescence. After Al (40 lM) was added into the C1 loaded cells for 30min at 37 C,
a very good fluorescence enhancement in the HEK293T cells were found. From Figure 8
we could find that the quantification of fluorescence intensity collected from the fluores-
cence images were 0.42 and 25.22, respectively (Figures 8c and 8f). The fluorescence emis-
3þ
sion might be due to the complex formation between Al and the C1. These results

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Figure 8. (a) bright field of HEK293T cells with C1; (b) dark field image of HEK293T cells incubated
3þ
with C1; (d) bright field of HEK293T cells with C1 and Al ; (e) dark field image of HEK293T cells with
3þ
C1 and Al . Quantification of fluorescence intensity collected from the fluorescence images (c) C1
3þ
and (f) C1 treated with Al
.
3þ
revealed that C1 could be used as a suitable cell permeable sensor to recognize Al in
living cells.
Compared with other probes
3
þ
7
ꢁ1
C1 could recognize Al with the binding constant and LOD were 3.11 ꢀ 10 M and
.126 lM, respectively. As showed in Table S1, our method had higher affinity toward
0
3
þ
Al and swift reaction time compared with these reported methods. It is a pity that
the LOD of C1 to recognize the Al was not remarkable to some reported. On the
3
þ

8
W. WANG ET AL.
whole, the proposed probe possessed higher affinity character, lower detection limit and
fast reaction time, and could be utilized in practical samples.
Experiment
Materials
The anions and metal ions were purchased from Shanghai Experiment Reagent Co., Ltd
(Shanghai, China). Deionized water was used to prepare all aqueous solutions. All other
chemicals used were of analytical grade. The detail information is given in the
Supplementary material.
Instruments
1
13
H-NMR and C-NMR spectra were recorded on a Bruker DRX 400 spectrometer with
tetramethylsilane as the internal standard. Fourier-transform infrared spectroscopy (FT-
ꢁ
1
IR) spectra (4000–400 cm ) were obtained on NICOLET380 FT-IR spectrometer in
potassium bromide disks. Elemental analyses (EAs) were carried out with a VARI-EL
elemental analyzer. Electrospray ionization mass spectra (ESI-MS) were measured on a
þ
Triple TOF TM 5600 system. Fluorescence spectral data were obtained by means of a
RF-5301 fluorescence spectrophotometer. Ultraviolet spectrum was performed on
UV-1800 ENG 240 V.
Cell incubation and imaging
[
39,40]
ꢃ
HEK293T cells were cultured at 37 C in a 5%
Followed as our reported method,
carbon dioxide (CO ) atmosphere and incubated in Dulbecco’s modified eagle medium
2
supplemented with 10% fetal bovine serum (FBS) and 0.1% antibiotic-antimycoticmix
antibiotic supplement. Afterwards, the cells were washed with 1X phosphate buffer
saline (PBS) and was incubated in the medium containing chemosensor C1 (final con-
ꢃ
centration: 10 lM) at 37 C under 5% CO for 30 min, and then treated with AlCl
2
3
(final concentration: 40 lM) for another 30 min. Subsequently, the cells were washed
with 1X PBS to remove the excessive dye. Next, the culture medium was removed, and
the cells were washed with 1X PBS for three times. Finally, the cells were imaged on a
Leica-LCS-SP8-STED laser confocal fluorescence microscope.
Study on the binding constant
[
41,42]
3þ
The Eqs. (1) and (2)
was used to indicate the affinity of C1 toward Al .
ꢀ
ꢁ
2
2
3þꢄ
1=2
½
bðb ꢁ2K C Al =sÞ
e e
b
t
a f
¼
(1)
(2)
eb ꢁ ef
2K Ct
b
3þꢄ=2s
½
b ¼ 1 þ K C þ K Al
b
t
b

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Scheme 1. Synthesis of the probe C1.
Synthesis of the chemosensor C1
The synthesis of chemosensor C1 is exhibited in Scheme 1. Following the early reported
[
41,43]
methods
mmol) in ethanolic solution, refluxed for about 6 h, white 3-acetylcoumarin was
achieved and washed with ethanol for three times. Then 3-acetylcoumarin (0.56 g,
mmol) was added to a solution of isonicotinoylhydrazide (0.42 g, 3 mmol) in methanol
30 mL) and stirred for another 6 h. The pale yellowish solid was filtered, washed repeat-
coumarin (0.73 g, 5 mmol) was added to ethyl acetoacetate (0.182 g,
2
3
(
edly with methanol, dried in air and recrystallized from ethanol. The purity of the com-
pound was checked by thin-layer chromatography analysis (Yield: 76%). Melting point:
ꢃ
1
86 C. EAs: found C: 66.43; H: 4.19; N, 13.67%. Molecular formula C H N O
17
13
3
3
1
requires: C, 66.42; H, 4.26; N, 13.67%. H-NMR (400 MHz, MeOD) d 8.64 (s, 16 H),
7
.71 (dd, J ¼ 20.7, 13.9 Hz, 34 H), 7.35 (dd, J ¼ 19.3, 7.9 Hz, 33 H), 4.86 (s, 7 H), 4.36 (q,
13
J ¼ 7.1 Hz, 32 H), 3.61 (q, J ¼ 7.0 Hz, 2 H), 3.32 (t, J ¼ 2.5 Hz, 4 H). C-NMR (101 MHz,
MeOD) d 162.90 (s), 157.12 (s), 154.91 (s), 149.21 (s), 148.88 (s), 134.35 (s), 129.84 (s),
1
24.79 (s), 117.97 (s), 117.48 (s), 116.07 (s), 61.47 (s), 13.12 (s). Exact mass for
þ
C1(C H N O , Mr ¼ 307.0957), ESI-MS (positive mode) found [C1 þ H] (m/z,
1
7
13 3 3
þ
3
08.1023), [C1 þ Na] (m/z, 330.0851).
Conclusion
In summary, a new sensor (C1) based on coumarin was developed for aluminium ion
estimation in CH CH OH/H O (1:1, v/v). C1 displayed a 1:1 binding stoichiometry and
3
2
2
3
þ
exhibited a reversible type fluorescence response toward EDTA and Al . The detection
limit (0.126 lM) was far below the limit of Al (7.4 lM) in drinking water. Besides,
the cell imaging of C1 and Al in living cells was also successfully obtained. Above all,
C1 is an effective sensor for Al .
3
þ
3
þ
3
þ
Funding
We acknowledge the National Natural Science Foundation of China [21301150], the Six Talent
Peak Project in Jiangsu Province [SWYY-063] and Qing Lan Project.
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