Novel enantioselective fluorescent sensors for tartrate anion based on acridinezswsxa

Article abstract of DOI:10.1002/bio.3327

Novel chiral fluorescence sensors L-1 and D-1 incorporating N-Boc-protected alanine and acridine moieties were synthesized. The recognition ability of the sensors was studied by fluorescence titration, ¹H NMR spectroscopy and density functional

Full text of DOI:10.1002/bio.3327

Received: 9 September 2016
DOI: 10.1002/bio.3327
Revised: 23 February 2017
Accepted: 24 February 2017
R E S E A R C H A R T I C L E
Novel enantioselective fluorescent sensors for tartrate anion
based on acridinezswsxa
1
1
1
1
2
1
|
|
|
|
|
Chaoyu Wang
Peng Wang
Xiaoyan Liu
Jiaxin Fu
Kun Xue
Kuoxi Xu
1
Engineering Laboratory for Flame Retardant
and Functional Materials of Henan Province,
College of Chemistry and Chemical
Abstract
Novel chiral fluorescence sensors L‐1 and D‐1 incorporating N‐Boc‐protected alanine and
Engineering, Henan University, Kaifeng, China
acridine moieties were synthesized. The recognition ability of the sensors was studied by
2
Institute of Environmental and Analytical
1
fluorescence titration, H NMR spectroscopy and density functional theory (DFT) calculations.
Sciences, College of Chemistry and Chemical
Engineering, Henan University, Kaifeng, China
The sensors exhibited good enantioselective fluorescent sensing ability toward enantiomers of
tartrate anion for the selected carboxylate anions and formed 1: 1 complexes by multiple
hydrogen bonding interactions.
Correspondence
Kuoxi Xu, Engineering Laboratory for Flame
Retardant and Functional Materials of Henan
Province, College of Chemistry and Chemical
Engineering, Henan University, Kaifeng, Henan
KEYWORDS
4
75004, China
enantioselective recognition, sensor, tartrate anion
Email: xukx@henu.edu.cn
Funding Information
National Natural Science Foundation of
China, Grant/Award Number: U1404207;
The Program for He’nan Innovative Research
Team in University, Grant/Award Number:
1
5IRTSTHN005
1
|
INTRODUCTION
interactions with hydroxyl or carboxylate anions of the guest via
[
12–15]
hydrogen bonding and electrostatic forces.
Furthermore, when
Fluorescence sensors can effectively provide a real‐time analytical tool
the sensor interacts with the guest, oxygen or nitrogen atoms adjacent
for the direct and simple chiral enantiomeric determination of chiral
to the acridine fluorophore might quench the fluorescence via photo‐
[1–3]
[16–18]
reagents, catalysts, natural products and drugs.
Because of their
induced electron transfer.
Here, we report the study of an
sensitivity, selectivity and versatility fluorescence techniques have
acridine derivative as an enantioselective fluorescent sensor for
recognition of tartrate anions.
been used to study the interaction between enantiomers and
[
4]
sensors. The principles for constructing chiral fluorescent sensors
are based on studies of biological compounds, among which carboxylic
acids are one of the most attractive targets in this field because of their
central role in many enzyme activities, DNA regulation, hormone
2
2
|
EXPERIMENTAL
Materials
[
5–7]
transport, peptide synthesis and intracellular communication.
The
.1
|
practical, rapid and accurate methods applied in enantioselective
recognition of chiral carboxylate are an important analytically in nature
The reagents used were of commercial origin and were employed with-
out further purification. Purification by column chromatography was
carried out over silica gel (230–400 mesh). Optical rotations were
undertaken on a Perkin–Elmer Model 341 polarimeter. The infrared
[8–11]
and biological processes.
Our approach to the design of a novel
chiral fluorescence sensor relies on the covalent attachment of chiral
amino acid substituents to the fluorophore acridine via a short ester
linker. Specifically, the chiral amino acid groups provide stereo centers,
whereas the oxygen or amino atoms of the sensor form non‐covalent
(
IR) spectra were performed on a Nicolet 670 FTIR spectrophotometer.
High‐resolution mass spectra were measured on an Agilent 1290LC‐
1
6
540 Accurate Mass Q‐TOF using electrospray ionization (ESI).
H
13
NMR and C NMR spectra were recorded on a Bruker AV‐400 spec-
trometer. Fluorescence spectra were obtained with an F‐7000 FL
spectrophotometer. Anions were used as their tetrabutylammonium
Abbreviations used: DFT, density functional theory; DMSO, Dimethyl sulfoxide;
ESI, Electrospray ionization; IR, Infrared; MS, Mass spectrometry; NMR, Nuclear
magnetic resonance; TDDFT, Time‐dependent DFT; UV, Ultraviolet; Vis, Visible.
Luminescence. 2017;1–6.
wileyonlinelibrary.com/journal/bio
Copyright © 2017 John Wiley & Sons, Ltd.
1

2
WANG ET AL.
salts. 4,5‐Bis(bromomethyl)acridine was prepared as described in the
with 4,5‐bis(bromomethyl)acridine at room temperature for 24 h to
introduce the fluorescence group (Scheme 1). Preparation of com-
pound D‐1, an enantiomer of L‐1, was the same as that for L‐1 by
[
19]
literature.
starting with D‐N‐Boc‐alanine and 4,5‐bis(bromomethyl)acridine. The
2
.2
|
Syntheses
1
structures of these compounds were characterized by IR, MS,
NMR spectra and elemental analysis.
H
To a solution of 4,5‐bis(bromomethyl)acridine (0.37 g, 1.0 mmol) in
dichloromethane (10 ml), 20% NaOH (10 ml), tetrabutylammonium
iodide (0.81 g, 2.2 mmol) and L‐ or D‐N‐Boc‐protected alanine
(
2.2 mmol) were added consecutively. The mixture was stirred at room
3.2
|
Fluorescence spectroscopic studies
temperature for 2 days with monitoring by thin‐layer chromatography.
After consumption of the starting material, the mixture was poured
into a separator funnel over water and extracted with dichlorometh-
ane. The combined organic extracts were rinsed with brine, dried over
There was almost no change in the UV/vis spectra of sensor L‐1 or D‐1
upon addition of carboxylate anions such as D‐ or L‐dibenzoyl tartrate,
benzene lactate, phenylalanine, alanine, mandelate, malate, tartrate (as
tetrabutylammonium salts) in acetonitrile, even when the guests were
present in excess ([guest]/[L‐1 or D‐1] = 50; Figure S1). Therefore,
enantioselective recognition was investigated using the fluorescence
spectra only. The fluorescence spectra of sensor L‐1 were studied in
the presence of the above‐mentioned enantiomers; we found that
other anions produce a slight change in fluorescence, except for tar-
trate (Fig. 1).
2 4
anhydrous Na SO , and the solvent evaporated under reduced
pressure to yield crude products, which were then purified by column
chromatography over silica gel using petroleum ether: ethyl acetate
(
10: 1) as the eluent to obtain the pure products L‐1 or D‐1 as
yellow solids.
L‐1: 0.23 g, yield, 39.7%; m.p.: 136–138°C; ½αꢀD = –52.8 (c = 0.50,
20
2
D
0
CHCl
3
); D‐1: 0.24 g, yield, 41.5%; m.p.: 137–139°C; ½αꢀ = +49.6
Figure 2 shows the different fluorescence intensity changes when
50 equiv. of L‐ or D‐tartrate anion was added to sensor L‐1. The
1
(
c = 0.50, CHCl
3
); H NMR (CDCl
3
): δ8.73 (s, 1H), 7.94 (d, J = 5.4 Hz,
2
H), 7.75 (d, J = 4.4 Hz, 2H), 7.52 (q, J = 5.1 Hz, 2H), 6.08 (d,
J = 9.2 Hz, 2H), 5.95 (d, J = 9.2 Hz, 2H), 5.31 (s, 2H) 5.23 (s, 2H),
1
3
1
1
2
.58 (s, 6H), 1.41 (s, 18H);
3
C NMR (CDCl ): 173.40, 155.25,
45.96, 136.29, 134.05, 128.50,126.31, 125.58, 79.81, 63.88, 49.45,
–1
8.37, 18.86; IR (KBr): 3357, 1741, 1689, 1531, 1220, 761 cm
.
+
39 3
ESI‐MS calcd for C31H N O
8
[M + Na] 604.26, found 604.30;
elemental analysis calcd (%) for C31
H
39
N
3
O
8
: C 64.01, H 6.76, N
.22, found: D‐1, C 63.97, H 6.73, N 7.18; L‐1: C 63.95, H 6.71, N
.17.
7
7
3
3
|
RESULTS AND DISCUSSION
Synthesis
.1
|
Enantiopure chiral L‐N‐Boc‐alanine was developed from the cheap and
commercially available chiral alanine. The product was further reacted
SCHEME 1 Synthesis of compounds L‐1 and D‐1
FIGURE 1 Fluorescent spectra changes of
−5
3
sensor L‐1 (3.0 × 10 M) measured in CH CN
upon the addition of 100 equiv. of various
anions (λex = 356 nm). Fluorescent spectra
−5
changes ((I–I
at 423 nm upon addition of different carboxylic
acid anions (as tetrabutylammonium) in CH CN
0 0
)/I ) of sensor L‐1 (3.0 × 10 M)
3
−3
at 25°C (50 equiv., 1.5 × 10 M). L‐Dibenzoyl
tartrate anion, D‐dibenzoyl tartrate anion,
L‐benzene lactate anion, D‐benzene lactate
anion, L‐phenylalanine anion, D‐phenylalanine
anion, L‐alanine anion, D‐alanine anion,
L‐mandelate anion, D‐mandelate anion,
L‐malate anion, D‐malate anion, L‐tartrate anion
and D‐tartrate anion

WANG ET AL.
3
occupied molecular orbital (SOMO) of the excited fluorophore, which
in turn prevents the excited‐state binaphthyl electron from transferring
to the lowest unoccupied molecular orbital (LUMO). Therefore, an
6
5
4
3
2
1
00
00
00
00
00
00
0
L1
[
22,23]
anion‐induced decrease in fluorescence was observed.
To further understand the host–guest interaction, fluorescent
L1+50.0 equiv. D-Tar
L1+50.0 equiv. L-Tar
–
5
titration was carried out. Titration of sensor L‐1 (3.0 × 10 M) with
0 equiv. of L‐ or D‐tartrate anion in acetonitrile was undertaken.
5
With the increase in anions, the fluorescence intensity of L‐1
gradually weakened, indicating that a host–guest interaction had
happened. The fluorescence quenching efficiency was related to the
nonlinear curve fitting (Fig. 3), which was determined by monitoring
changes in the fluorescence intensity and applying measurable values
[
24,25]
to equation (1) below.
fluorescence intensity of L‐1 in the absence and presence of L‐ or
D‐tartrate anion, and C and C are the concentrations of sensor
L‐1 and tartrate anion respectively. C is the initial concentration of
0
In equation (1) I and I represent the
4
00
450
500
550
600
Wavelength (nm)
H
G
‐5
FIGURE 2 Fluorescent spectra of L‐1 (3.0 × 10 M) with 50.0 equiv.
of L‐ or D‐tartrate anion in CH CN (λex = 356 nm)
0
3
L‐1. Satisfactory nonlinear curve fitting (the correlation coefficient
is >0.99) (Fig. 4) confirmed that a 1: 1 complex formed between
sensor L‐1 and the L‐ or D‐tartrate anion. For the1: 1 stoichiometry
complex, the association constant (Kass) was calculated from equation
quenching efficiency was ~70% when L‐tartrate was added to the
solution of L‐1, but only ~38% when D‐tartrate was added. The fluo-
L D
rescence quenching efficiencies (ΔI /ΔI = 1.90) indicated that sensor
3
–1
L‐1 shows good enantioselective recognition between L‐ and D‐tartrate
(1). The values of Kass were 1.15 × 10
M
for L‐tartrate and
2
–1
anions. The decrease in fluorescence was similar to the anion‐induced
2.29 × 10 M for D‐tartrate. This demonstrated that the interaction
of sensor L‐1 with the tartrate anion was highly enantioselective (Kass
(L)/Kass(D) = 4.83).
[20,21]
fluorescence quenching previously reported.
When the guest
binds with the host, an electron from the anion transfers to the singly
–
5
FIGURE 3 (a) Fluorescence spectra of sensor L‐1 (3.0 × 10 M) with L‐tartrate anion in CH
3
CN. Equivalents of anion: 0 ! 50.0. (b) Fluorescence
–
5
spectra of sensor L‐1 (3.0 × 10 M) with D‐tartrate anion in CH
3
CN. Equivalents of anion: 0 ! 50.0
5
50
600
500
400
300
200
100
500
450
400
350
300
0
20
40
60
80 100 120
-5
0
5
10 15 20 25 30 35 40
Equiv. of D-Tar
Equiv. of L-Tar
FIGURE 4 (a) Changes in the fluorescence intensity of L‐1 at 423 nm upon addition of L‐tartrate anion. The line shown is a non‐linear fitted curve.
The correlation coefficient (R) of the non‐linear curve fitting is 0.9949. (b) Changes in the fluorescence intensity of L‐1 at 356 nm upon addition of
D‐tartrate anion. The line shown is a non‐linear fitted curve. The correlation coefficient (R) of the non‐linear curve fitting is 0.9988

4
WANG ET AL.
ꢀ
ꢁ
h
i
1
=2
2
I ¼ I þ ðI −I Þ=2C0 CH þ C þ 1=Kass– ðCH þ C þ 1=KassÞ –4 CH C
(1)
0
lim
0
G
G
G
L-Tar
D-Tar
30
25
20
15
10
5
0
The binding characteristics of L‐1 towards D‐ or L‐tartrate anions
were further examined using Job's plot (Fig. 5). A maximum change in
fluorescence was observed when the molar fraction of sensor L‐1 vs.
[L‐1] + [tartrate anion] was 0.5, indicating1: 1 binding stoichiometry
[
26,27]
between L‐1 and D‐ or L‐tartrate anions.
To ascertain whether the change in fluorescence of L‐1 toward
the enantiomers of tartrate anion was due to enantioselective recogni-
tion, we investigated use of the enantiomeric compound D‐1. It was
found that the fluorescence intensity of D‐1 was slightly quenched
upon addition of L‐tartrate, but D‐tartrate had a much greater fluores-
cence quenching effect on D‐tartrate anions under the same conditions
(
Figures 6 and 7). Values of the association constant (Kass) and correla-
tion coefficient (R) obtained by nonlinear least squares analysis are
0.0
0.2
0.4
0.6
0.8
1.0
2
–1
[G]/[G]+[H]
listed in Table 1. The values of Kass were 2.86 × 10 M for L‐tartrate
3
–1
and 1.05 × 10
M
for D‐tartrate anions. This indicated that D‐1
FIGURE 5 Job's plot for L‐1 and L‐tartrate and D‐tartrate anion in
CH CN. The total amount of substance of L‐1 and L‐tartrate or
D‐tartrate anion is 1.0 × 10 M. I
and I = fluorescent intensity of sensor L‐1 in the presence of tartrate
anion
exhibited remarkable fluorescence enantioselectivity towards tartrate
anions (Kass(D)/Kass(L) = 0.27) (Table 1). The results of fluorescence
spectra titrations indicated that enantiomers of the guest anion
interacted with L‐1 and D‐1 in a similar fashion.
3
‐4
0
= fluorescent intensity of sensor L‐1
600
500
400
300
200
100
0
L-Tar 0
50.0 equiv.
600
500
400
300
200
100
400
450
500
550
600
-20
0
20 40 60 80 100 120 140
Equiv. of L-Tar
Wavelength (nm)
‐5
FIGURE 6 (a) Fluorescence spectra of sensor D‐1 (3.0 × 10 M) with L‐tartrate anion in CH
b) Changes in the fluorescence intensity of D‐1 at 423 nm upon addition of L‐tartrate anion. The line shown is a non‐linear fitted curve. The
correlation coefficient (R) of the non‐linear curve fitting is 0.9938
3
CN. Equivalents of anion: 0 ! 50.0. λex = 356 nm.
(
‐5
FIGURE 7 (a) Fluorescence spectra of sensor D‐1 (3.0 × 10 M) with D‐tartrate anion in CH
b) Changes in the fluorescence intensity of D‐1 at 423 nm upon addition of D‐tartrate anion. The line shown is a non‐linear fitted curve. The
correlation coefficient (R) of the non‐linear curve fitting is 0.9941
3
CN. Equivalents of anion: 0 ! 50.0. λex = 356 nm.
(

WANG ET AL.
5
TABLE 1 The association constant (K) of sensor L‐1 and D‐1
3.4
|
DFT calculations recognition properties of L‐1
–
5
(
3.0 × 10 M) with L‐tartrate anion and D‐tartrate anion in acetonitrile
and tartrate anion
at 25°C
a
‐1 b,c
The enantioselective recognition mechanism and binding energy
between chiral L‐1 and tartrate anions can be obtained by calculation.
In this study, All density functional theory (DFT)/ time‐dependent DFT
Entry
Host
Guest
K
ass [M
]
K(L)/K(D)
R
3
1
2
L‐1
L‐1
D‐1
D‐1
L‐tartrate
D‐tartrate
L‐tartrate
D‐tartrate
1.15 × 10
2.39 × 10
2.86 × 10
1.05 × 10
4.83
0.9949
0.9988
0.9938
0.9941
2
2
3
(
DFT/time dependent density functional theory (TDDFT)) calculations
3
0.27
[
29]
based on the hybrid exchange correlation functional B3LYP
with 6‐
[31]
4
[
30]
31G**basis set
were carried out using Gaussian 03 program.
For
a
Data were calculated from the results of the results of the fluorescent
titrations in acetonitrile.
all calculations, the solvent effect of acetonitrile was considered using
[32]
Cossi and Barone's conductor‐like polarizable continuum model.
To
b
All error values were obtained from nonlinear curve fitting.
investigate the electronic properties of singlet excited states, TDDFT
was performed in the ground state geometries of L‐1 and L‐1 with D‐
or L‐tartrate anion. Bond lengths were calculated and are shown in
Figure 9. There was weak interaction between L‐1 and tartrate anion,
with hydrogen bond sites between L‐1 and L‐tartrate anion and bond
lengths of 1.96 and 2.81 Å, respectively. However, the hydrogen bond
lengths between L‐1 and D‐tartrate anion were only 1.92 and 3.79 Å,
with only one bond length < 3.50 Å; this indicated that the complex of
L‐1 and L‐tartrate anion was more stable. From the binding energy, it
was possible to judge the interaction strength and enantiomer complex
ability, which could provide enantioselective recognition. The results of
the binding energy calculation for the interaction between L‐1 and tar-
trate anion enantiomers were ΔE = –12.27 and –8.44 KJ/mol, respec-
tively. It was found that the negative binding energies between L‐1
and tartrate anion enantiomers were ~3.83 kJ/mol. In other words, sta-
ble complexes between L‐1 and tartrate enantiomers could be formed
by molecular weak interactions. |ΔEL‐1—L| > |ΔEL‐1—D| showed that the
complex of L‐1 and L‐tartrate anion was more stable than that of L‐1
and D‐tartrate anion, which made the enantioselective recognition of
salbutamol enantiomers feasible. Where |ΔEL‐1—L| and |ΔEL‐1—D| repre-
sented the binding energy between L‐1 and L‐tartrate anion and L‐1
and D‐tartrate anion, respectively.
c
Tartrate anions were used as their tetrabutylammonium salts.
1
3
.3
|
H NMR studies
1
H NMR experiments were applied to investigate the stability of com-
plexes of sensor L‐1 with enantiomers of tartrate anion because this is
one of the most effective tools in studying host–guest supramolecular
[
28]
chemistry.
without (Figure 8b) and on addition of 1.0 equiv. D‐ or L‐tartrate anion
Figure 8c,d). We found that on addition of D‐ or L‐tartrate, the chiral
CH proton of L‐1 was downshifted from 5.31 p.p.m. to 4.20 or
.10 p.p.m. (Δδ = 1.11 or 1.21 p.p.m.), whereas the CH proton of tar-
trate appeared at 4.47 or 4.50 p.p.m. (Δδ = 0.80 or 0.83 p.p.m.)
Figure 8c,d). The interaction of sensor L‐1 with L‐tartrate showed that
6
Figure 8 shows the spectra of L‐1 in DMSO‐d solution
(
4
(
the CH proton had a larger downfield shift than the chiral CH proton of
the D‐enantiomer. We also found that the –OH protons of tartrate at
3
.30 p.p.m. had weakened and downshifted to 3.42 and 3.49 p.p.m.
indicating that the –OH of tartrate interacted with the sensor
Figure 8b–d). Therefore, as the proposed modes show in Figure 9,
(
the hydroxy group of tartrate may form hydrogen bonds with the
oxygen atoms of L‐1.
1
FIGURE 8
6 6
H NMR spectra (400 MHz, DMSO‐d 25°C) of L‐1 and tartrate anion complexes at ([L‐1] = [guest] = 4.0 nM in DMSO‐d at 400 MHz.
(
a) Racemic tartrate anion, (b) sensor L‐1, (c) sensor L‐1+ D‐tartrate anion, (d) sensor L‐1 + L‐tartrate anion

6
WANG ET AL.
FIGURE 9 (a) Optimized geometry of the complex: L‐1 and L‐tartrate anion. (b) Optimized geometry of the complex: L‐1 and D‐tartrate anion
The above results illustrated that the nature of the sensor, multiple
hydrogen‐bonding interactions and complementary stereogenic center
interactions may be responsible for the enantioselective recognition of
tartrate.
[15] Q. Li, K. X. Xu, P. Song, Y. P. Dai, L. Yang, X. B. Pang, Dyes Pigment
014, 109, 169.
2
[
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4
|
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We have demonstrated that upon the introduction of N‐Boc‐protected
alanine to the acridine, acridine‐based chiral fluorescence sensors L‐1
and D‐1 act as excellent enantioselective fluorescent sensors for
tartrate anions.
J. Am. Chem. Soc. 2003, 125, 12376.
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How to cite this article: Wang C, Wang P, Liu X, Fu J, Xue K,
Xu K. Novel enantioselective fluorescent sensors for tartrate
anion based on acridinezswsxa. Luminescence. 2017. https://
doi.org/10.1002/bio.3327
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