Rhodol-based fluorescent probes for the detection of fluoride ion and its application in water, tea and live animal imaging

Article abstract of DOI:10.1016/j.saa.2019.117467

Herein, we presented two novel turn-on colorimetric and fluorescent probes based on a F^? triggered Si[sbnd]O bond cleavage reaction, which displayed several desired properties for the quantitative detection for F^?, such as high specificity, rapid response time (within 3 min) and naked-eye visualization. The fluorescence intensity at 574 nm (absorbance at 544 nm) of the solution was found to increase linearly with the concentration of F^? (0.00–30.0 μM) with the detection limit was estimated to be 0.47 μM/0.48 μM. Based on these excellent optical properties, the probes were employed to monitor F^? in real water samples and tea samples with satisfactory. Furthermore, it was successfully applied for fluorescent imaging of F^? in living nude mice, suggesting that it could be used as a powerful tool to predict and explore the biological functions of F^? in physiological and pathological processes.

Full text of DOI:10.1016/j.saa.2019.117467

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 224 (2020) 117467
Contents lists available at ScienceDirect
Spectrochimica Acta Part A: Molecular and Biomolecular
Spectroscopy
journal homepage: www.elsevier.com/locate/saa
Rhodol-based fluorescent probes for the detection of fluoride ion and its
application in water, tea and live animal imaging
Xilang Jin a,1, Jingkai Gao , Ting Wang , Wan Feng , Rong Li , Pu Xie , Lele Si ,
b,1
a
a
c
a
a
a,
b,
Hongwei Zhou ⁎, Xianghan Zhang ⁎⁎
School of Materials and Chemical Engineering, Xi'an Technological University, Xi'an 710032, Shaanxi, China
School of Life Sciences and Technology, Xidian University, Xi'an 710071, Shaanxi, China
Hancheng Hongda Sichuan Pepper Flavor Co., Ltd, Hancheng 715400, Shaanxi, China
a
b
c
a r t i c l e i n f o
a b s t r a c t
Herein, we presented two novel turn-on colorimetric and fluorescent probes based on a F− triggered S i\\ O bond
cleavage reaction, which displayed several desired properties for the quantitative detection for F , such as high
Article history:
Received 21 February 2019
Received in revised form 23 July 2019
Accepted 10 August 2019
Available online 11 August 2019
−
specificity, rapid response time (within 3 min) and naked-eye visualization. The fluorescence intensity at 574 nm
−
(
absorbance at 544 nm) of the solution was found to increase linearly with the concentration of F (0.00–30.0
μM) with the detection limit was estimated to be 0.47 μM/0.48 μM. Based on these excellent optical properties,
the probes were employed to monitor F− in real water samples and tea samples with satisfactory. Furthermore,
Keywords:
Fluoride ion
Fluorescent
Seminaphthorhodafluor dye
Tea samples
−
it was successfully applied for fluorescent imaging of F in living nude mice, suggesting that it could be used as a
powerful tool to predict and explore the biological functions of F− in physiological and pathological processes.
© 2019 Elsevier B.V. All rights reserved.
Bioimaging
1
. Introduction
As the smallest anion distributed in nature, inorganic fluoride ion
[18–26]. Accordingly, numerous turn-on fluorescent molecular probes
for monitoring F containing common fluorophores including rhoda-
−
mine, coumarin, tetrahydroxanthenone, calix[4]crown and
naphthalimide have been rapidly constructed in recent years [27–37].
Moreover, reports on rhodol-based (a special combination structure of
−
(
F ) which mainly derived from foodstuffs and groundwater exerts a
great influence on human health particularly in preventing dental caries
1–3]. Nevertheless, excessive ingestion of fluoride ion may result in
−
[
rhodamine and fluorescein) fluorescent probes for the detecting of F
fluorosis, urolithiasis, skeletal disease and even lead to cancers [4–6].
For these reasons, the controlled consumption of fluoride in the
human body is a serious concern throughout the world [7,8]. Therefore,
it is very meaningful to develop a convenient and efficient technique for
the detection and quantification of fluoride ions in real samples and
complicated biological systems.
are scarce. Rhodol dyes are excellent candidates for fluorescent probes
which have the advantages, such as excellent optical features, high ex-
tinction coefficients, high photo-stability, long wavelength absorption
and emission [38–41]. Therefore, the suitable design of a novel rhodol-
based fluorescent probe that could selectively responds to F− in real
samples and in vivo is still a challenge for the analytical chemists.
Herein, we constructed an unprecedented example (Scheme 1) of a
Compared with the traditional sophisticated analytical techniques
−
(
ion chromatography, reversed-phase high-performance liquid chro-
highly sensitive, F -selective colorimetric and fluorometric rhodol-
based probe which consisted seminaphthorhodafluor dye (chromo-
1
9
matography, F NMR, fluoride ion selective electrode), molecular
probe-based fluorometric and colorimetric methodology [9–17] has
been employed as a powerful technology to track cations, anions and bi-
ological molecules in vitro and in vivo for its high specificity, high sensi-
tivity, real-time imaging and noninvasive monitoring capability
phore) and tert-butyl dimethyl chlorosilane/tert-butyl diphenyl
−
chlorosilane (recognition site of F ). Furthermore, probe 1 exhibits
ideal fluorometric and colorimetric properties and exhibited desirable
−
selectivity to F in real samples and in vivo.
2
. Experimental
⁎
⁎
Corresponding author.
Correspondence to: X. Zhang, School of Materials and Chemical Engineering, Xi'an
⁎
2.1. Materials and methods
Technological University, Xi'an 710032, Shaanxi, China.
E-mail addresses: xatuzhou@163.com (H. Zhou), jinxilang_911@163.com,
xhzhang@xidian.edu.cn (X. Zhang).
All chemicals were purchased from commercial suppliers and used
1
Xilang Jin and Jingkai Gao contributed equally to this work.
without further purification. UV–Vis absorption and fluorescence
https://doi.org/10.1016/j.saa.2019.117467
1386-1425/© 2019 Elsevier B.V. All rights reserved.

2
X. Jin et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 224 (2020) 117467
Scheme 1. Synthesis route of probe 1.
spectra were performed on Shimadzu UV-1700 spectrophotometer and
Hitachi F-4500 fluorescence spectrophotometer (excitation and emis-
sion slits set at 5.0 nm), respectively. High-resolution mass spectra
A solution of tert-butyl dimethyl chlorosilane/tert-butyl diphenyl
chlorosilane (11.0 mmol) and imidazole (1.50 g, 22.0 mmol) in anhy-
drous CH
2 (4.38 g, 10.0 mmol) in CH
was warmed to room temperature and stirred for 3 h. Then the resultant
residue was washed with H O (50 mL) and dried over anhydrous
Na SO . The residue was concentrated and purified by column chroma-
tography (CH OH/CH Cl = 1/250).
Probe 1a: light pink powder, 3.12 g, yield: 56.52%. H NMR(DMSO d
Cl
2 2
(10 mL) was added dropwise to a solution of compound
(
HR-MS) were measured by a Brukermicro TOF-QII ESI-Q-TOF LC/MS/
2
Cl (30 mL) at 0 °C for 30 min. The solution
2
1
MS Spectrometer. H NMR spectra were recorded on a Varian INOVA-
00 MHz spectrometer using tetramethylsilane as internal standard. In
4
2
vivo fluorescence imaging analysis was carried out in an IVIS Kinetic im-
aging system.
2
4
3
2
2
1
6
,
4
3
00 MHz): δ (ppm) 0.31 (s, 6H), 1.04 (s, 9H), 1.17 (t, J = 7.0 Hz, 6H),
.45(q, J = 6.8 Hz, 4H), 6.58 (m, 2H), 6.70 (d, J = 8.8 Hz, 1H), 6.78 (d,
2
.2. General procedure
J = 2.3 Hz, 1H), 7.33 (m, 2H), 7.38 (d, J = 2.4 Hz, 1H), 7.53 (d, J =
The stock solution of probe 1 (1 mM) was prepared in DMSO. The so-
8
1
.7 Hz, 1H), 7.81 (m, 2H), 8.08 (d, J = 7.5 Hz, 1H), 8.54 (d, J = 9.0 Hz,
H). MS (ESI) m/z = 552.2547 [M], calc. for C34 38NO Si = 552.2565.
Probe 1b: light pink powder, 3.03 g, yield: 44.82%. H NMR
lutions of biologically relevant analytes stock solutions (1 mM) were
prepared in deionized water. For all measurements, the absorbance
was recorded at 544 nm and the fluorescence intensity was recorded
at 574 nm (λex = 500 nm).
H
4
1
(
(
Chloroform d, 400 MHz): δ (ppm) 1.24 (m, 6H), 1.27 (m, 9H), 3.75
q, J = 7.0 Hz, 4H), 6.63 (d, J = 8.8 Hz, 3H), 7.05 (d, J = 2.4 Hz, 1H),
7
.10 (d, J = 8.8 Hz, 1H), 7.15 (dd, J = 6.6, 1.8 Hz, 2H), 7.39 (td, J =
7.1, 6.6, 1.7 Hz, 5H), 7.44 (m, 2H), 7.55 (dd, J = 5.7, 3.3 Hz, 1H), 7.63
m, 2H), 7.77 (dt, J = 8.0, 1.2 Hz, 4H), 8.05 (m, 1H), 8.39 (d, J =
2
.3. Synthesis of probes 1a and 1b
(
Seminaphthorhodafluor dye (compound 2) was synthesized accord-
4
9.1 Hz, 1H). MS (ESI) m/z = 676.2967 [M], calc. for C44H42NO Si =
ing to the reported procedures [40].
676.2878.
1
H NMR(Chloroform d, 400 MHz): δ (ppm) 1.16 (t, J = 7.0 Hz, 6H),
3
6
1
9
1
C
.33 (q, J = 7.2 Hz, 4H), 5.32 (s, 1H), 6.44 (dd, J = 9.3, 2.5 Hz, 1H),
.58 (d, J = 2.6 Hz, 1H), 6.72 (d, J = 8.8 Hz, 1H), 6.87 (d, J = 9.0 Hz,
H), 6.95 (d, J = 2.4 Hz, 1H), 7.01 (d, J = 8.8 Hz, 1H), 7.09 (dd, J =
.1, 2.4 Hz, 1H), 7.15 (m, 1H), 7.62 (tt, J = 7.3, 5.8 Hz, 2H), 8.15 (m,
3. Results and discussion
3.1. Optical properties of probe 1a
+
−
H), 8.25 (d, J = 9.0 Hz, 1H). MS (ESI) m/z = 438.1715 [M] , calc. for
With probe 1a and 1b in hands, F -mediated fluorescence and ab-
sorption responses were initially investigated in DMSO-PBS (5/95, v/v,
+
28
H
24NO
4
= 438.1700.
Fig. 1. Fluorescence responses (574 nm)/absorption responses (544 nm) of probe 1a (10.0 μM) to various interfering species. The pillars in the front row: probe 1a treated with the
interfering species (1000 μM). The pillars in the back row: probe 1a treated with the interfering species (1000 μM) followed by F− (20.0 μM). (λex = 500 nm, silt = 5 nm/5 nm).

X. Jin et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 224 (2020) 117467
3
−
Table 1
F , the reaction mixture was purified and the corresponding product
Application of the probe 1a in determination of F− in tea samples.
1
was characterized by HRMS and H NMR. A new peak was observed at
−
Sample
Filtrate I
F−
spiked
F− recovered
mean ± SDb
(μmol/L)
Recovery
(%)
m/z 438.1614 (Fig. S23), which was assigned to compound 1a + F
a
[M] (m/z, calcd: 438.1700). Meanwhile, the 1H NMR spectral
+
(μmol/L)
(μmol/L)
−
(
Figs. S8, S20) strongly support the supposition that the F -triggered
Black Tea
9.88
5.00
10.00
15.11 ± 0.32
101.5
100.8
99.3
98.7
100.7
101.2
cleavage reaction causes the release of seminaphthorhodafluor dye.
(Puer Tea)
20.03 ± 0.32
25.55 ± 0.26
9.01 ± 0.18
14.22 ± 0.29
19.35 ± 0.31
1
5.00
-
Green Tea
4.12
5.00
10.00
15.00
3.3. Fluorescence detection of F in real sample
(Jintan
Queshe)
The adequate intake for F− from all sources was determined to be
0.05 mg/day/kg body weight and the concentration of in tea infusions
a
Mean of three determination.
SD: standard deviation.
b
of different type of teas were 0.29–6.01 mg/L [3]. To further study the
−
practicality of the present probe, it was applied to detect F in potable
water sample (Xi'an Technological University) and different type of
tea samples (Black Tea and Red Tea) qualitatively and quantitatively.
All of the samples were analyzed by probe 1a with or without additional
pH 7.4) solution. The results suggested that the R moiety (tert-butyl
dimethyl-, tert-butyl diphenyl-) had no significant impact on the spec-
tral properties. Hence, only probe 1a was discussed in this article and
the spectral properties of probe 1b was shown in the supporting
information.
−
F
at concentration levels of 5.0 μM, 10.0 μM and 15.0 μM based the re-
2
gression equation (y = 22.995x + 201.26 (R = 0.9865), Fig. 2). The
analysis results were represented in Table S1 and 1. The results indi-
cated that probe 1a effectively measured and recovered the concentra-
tions of spiked F . Therefore, the experimental results suggested that
our probe could suitably and quantitatively detected F in real samples
As shown in Fig. 1, the optical responses of probe 1a towards a vari-
ety of biologically relevant species were examined. Upon the addition of
−
−
−
−
−
−
−
3
3−
2−
2−
various analytes (HCO
3
, Cl , Br , I , CN , NO
, PO
4
, CO
3
, HPO
4
,
−
−
−
2−
−
2−
2−
−
−
4
−
2−
SCN , N
3
, SO
3
, HSO
3
, S
2
O
3
, SO
4
, NO
2
, ClO
, OAc , S , GSH, Cys,
without interference from other environmentally relevant analytes.
−
Lys, 1.00 mM), only F induced a noticeable change in the fluorescence
and absorption signals, no other interfering species had this effect.
Moreover, the spectral response of probe 1a towards F was not af-
−
3.4. Visualization of F− in vivo
fected in the presence of other interfering relevant analytes (Table 1).
In the subsequent titration experiment (Fig. S1), the solution exhib-
ited a prominent red fluorescence (Φ = 0.15) and the fluorescence in-
tensity at 574 nm (absorbance at 544 nm) of the solution was found
Inspired by these desired fluorescence properties, the applicability of
the probe for visualizing F in vivo was subsequently explored. The
−
Athymic nude mice which were selected as our model was given skin-
−
−
pop injections of probe 1a (20.0 μM) and finally by the injection of F
to increase linearly with the concentration of F (0.00–30.0 μM, Fig. 2)
(
50.0 μM) at the same region after 30 min. In virtue of the small animal
with the detection limit was estimated to be 0.50 μM. The regression
2
imaging system with a 540 nm excitation laser and a 570 nm emission
filter, we gained the real-time recording of fluorescence signal that gen-
erated from the Athymic nude mice (Fig. 3). The mouse injected with
equation was y = 22.995x + 201.26 (R = 0.9865) / y = 0.0133x +
2
0
.036 (R = 0.9981). These results showed that probe 1a could be
−
used to measure F quantitatively and qualitatively. Time-based fluo-
−
−
probe 1a and F displayed a strong fluorescence with time indicating
rescence of probe 1a with F reached its plateau within 3 min, indicat-
−
ing a rapid response of probe 1a towards F− (Figs. S3–4). Taking all
these results together, probe 1a displayed a great potential tool for the
that probe 1a could respond to F . The results further demonstrated
−
that our probe could be capable of specifically imaging exogenous F
−
in vivo.
detection of F by the colorimetric and fluorometric dual mode.
3
.2. Sensing mechanism studies
4. Conclusions
Taking consideration from previous literature [42,43], the proposed
In conclusion, we had designed and synthesized two novel probes
for the detection of F based on a F triggered S i\ \O bond cleavage re-
−
−
−
reaction mechanism was inferred as Scheme 2. Once attacked by F ,
probe 1a underwent the deprotection mechanism by the cleavage of
the S i\ \O bond (tert-butyl dimethyl- group). In order to further demon-
strate the reaction mechanism, our probe was treated with 20 equiv. of
action. The probes exhibited high sensitivity, high selectivity, rapid re-
−
−
sponse for F , and could be successfully applied for F detection in
potable water and tea samples. Moreover, the probes had been further
Fig. 2. The linear plots of fluorescence responses (574 nm)/absorption responses (544 nm) of probe 1a (10.0 μM) upon addition of varied concentration of F− (0.00–4.00 equvi.).

4
X. Jin et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 224 (2020) 117467
Scheme 2. Proposed mechanism for the detection of F−
.
Fig. 3. Fluorescence images of exogenous NaF in Athymic nude mice.
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Acknowledgements
The work was supported by the National Natural Science Foundation
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