Selective detection of non-aromatic pesticides via cyclodextrin-promoted fluorescence modulation

Article abstract of DOI:10.1039/c5nj02357b

Reported herein is the detection of aliphatic pesticides using cyclodextrin-promoted fluorescence modulation. The introduction of the pesticide leads to noticeable changes in the emission of a fluorophore held in close proximity by cyclodextrin, leading to a pesticide detection system that operates with 100% successful differentiation and low limits of detection.

Full text of DOI:10.1039/c5nj02357b

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New Journal of Chemistry
ARTICLE
Selective Detection of Non‐Aromatic Pesticides via Cyclodextrin‐
Promoted Fluorescence Modulation
Dana J. DiScenzaa and Mindy Levinea
Received 00th January 20xx,
Accepted 00th January 20xx
Reported herein is the detection of aliphatic pesticides using cyclodextrin‐promoted fluorescence modulation. The
introduction of the pesticide leads to noticeable changes in the emission of a fluorophore held in close proximity by
cyclodextrin, leading to a pesticide detection system that operates with 100% successful differentiation and low limits of
detection.
DOI: 10.1039/x0xx00000x
www.rsc.org/
by the supramolecular cyclodextrin scaffold.
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Introduction
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
The widespread use of pesticides is of significant concern due
to the known and suspected toxicities of many small‐molecule
pesticides,1 as well as their long‐term environmental
persistence.2 Currently used methods for pesticide detection
overwhelmingly rely on chromatography for the purification of
the small molecule pesticides, followed by mass spectrometry
for accurate pesticide identification.3 Although such methods
are highly sensitive for individual pesticides, they tend to
suffer from tedious sample preparations, which limits the
ability to conduct high throughput assays of multiple samples
for multiple pesticide analytes.4 Newer detection methods
such as nanoparticle‐based Raman spectroscopy5 and
electrochemical assays6 have recently been developed.
The use of fluorescence‐based methods for pesticide detection
would be highly advantageous, as fluorescence spectroscopy is
sensitive to even trace amounts of a target analyte,7 can
rapidly generate response signals,8 and is amenable to the
development of high throughput assays for rapid screening of
multiple environmental samples.9 Fluorescence assays for non‐
photophysically active compounds such as organochlorine
pesticides (compounds 1‐4, Figure 1) are complicated by the
fact that the analytes themselves do not have notable
fluorescence signals, and require either derivatization10 or an
indirect method for efficient fluorescence detection.11
Cl
Cl
Cl
Cl
Cl Cl
Cl Cl
Cl
Cl
O
Cl
Cl
Cl
mirex
cis-chlordane
heptachlor
lindane
4
tetrahydrofuran
1
2
3
5
HS
C
O
O
CH3
N
S
10
N
H3
CH3
CH3
H3C
CH3
N
H3C
H3C
N
O
O
B
H3
C
F
F
H3C
N
O
N
CH3
H
H
Cl
BODIPY
6
Rhodamine 6G
Coumarin 6
7
8
Fig. 1 Pesticides (1‐4), control analyte 5, and fluorophores (6‐8) under investigation
Recently, we have developed
a new concept termed
“fluorescence modulation,” which enables the detection of
aliphatic analytes that do not participate in cyclodextrin‐
promoted energy transfer. These analytes are detectable
through quantifying proximity‐induced changes in the
fluorescence spectrum of a high quantum yield fluorophore
upon introduction of the analyte (Figure 2), with the
cyclodextrin acting as a supramolecular scaffold to ensure
productive analyte‐fluorophore interactions. Reported herein
is the use of such fluorescence modulation for the sensitive
and selective detection of aliphatic pesticides 1‐4, with
detection limits as low as 5.2 µM and 100% selectivity in array‐
based identification.
Previous research in our laboratory led to the development of
cyclodextrin‐promoted energy transfer for the detection of
aromatic toxicants and toxicant metabolites12 in multiple
complex environments.13 This system uses the aromatic
analytes as energy donors in combination with high quantum
yield fluorophore acceptors, which are held in close proximity
Fig. 2 Schematic illustration of cyclodextrin‐promoted fluorescence modulation with
several potential association complexes
a. Department of Chemistry, University of Rhode Island, 51 Lower College Road,
Kingston, RI 02881; mlevine@chm.uri.edu; tel: 401‐874‐4243; fax: 401‐874‐5072
Electronic Supplementary Information (ESI) available: Synthesis of fluorophore 6,
experimental details for fluorescence modulation experiments, limit of detection
experiments, and fluorescence array experiments, summary tables and figures for
all experiments. See DOI: 10.1039/x0xx00000x
Experimental Section
All analytes and cyclodextrins were obtained from Sigma‐
Aldrich. Fluorophore
6
was synthesized according to literature
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procedures.17 All fluorescence measurements were performed fluorescence changes observed in Me‐β‐CD systems, which we
using a Shimadzu RF 5301 spectrophotometer. All fluorescence have previously shown to be the most efficient cyclodextrin for
spectra were integrated vs. wavenumber on the X‐axis using the binding and extraction of fluorophore 6 13
.
OriginPro. All arrays were generated using SYSTAT.
Table 1. Selected fluorophore emission ratios with fluorophore 6
Fluorescence modulation experiments: The fluorescence
spectra were integrated vs. wavenumber on the X‐axis, and
fluorescence modulation was quantified using Equation 1.
Limit of detection experiments: The limit of detection (LOD) is
defined as the lowest concentration of analyte at which a
signal can be detected. The limit of quantification is defined at
the lowest concentration of analyte that can be accurately
quantified. These experiments were conducted following
literature‐reported procedures.5
Selection of cyclodextrins. A variety of cyclodextrin scaffolds
were investigated, including β‐cyclodextrin (β‐CD) and methyl‐
β‐cyclodextrin (Me‐β‐CD) that are known to bind to small
molecule fluorophores.14 Also included were 2‐hydroxypropyl‐
β‐cyclodextrin (2‐HPCD), which has been shown to promote
proximity‐induced energy transfer,15 and α‐cyclodextrin (α‐
CD), which is capable of acting as a supramolecular scaffold
despite its limited cavity size.16 All results were compared to
those obtained in a cyclodextrin‐free phosphate buffered
saline (PBS) solution, buffered at pH 7.4.
Analyte
α‐CD
1.12
1.15
1.30
1.26
β‐CD
1.15
1.15
1.24
1.15
Me‐β‐CD
1.01
0.97
0.96
0.99
2‐HPCD
1.10
1.14
1.18
1.08
PBS
1.22
1.33
1.27
1.34
1
2
3
4
Moreover, a closer examination of the absolute fluorescence
intensities in each of the cyclodextrin hosts (Figure 3) indicates
that the fluorescence emission of compound
cyclodextrin was markedly higher than its emission in any of
the other hosts. Increases in absolute fluorescence intensity
generally indicate strong binding in a supramolecular host (due
to the elimination of non‐radiative decay pathways),18 and
support the hypothesis that strong binding of the fluorophore
6 in methyl‐β‐
in the cyclodextrin (in this case fluorophore
limits its intermolecular interactions with the pesticide analyte.
6 in Me‐β‐CD)
Selection of fluorophores. The fluorophores chosen have all
been investigated previously for their ability to participate in
cyclodextrin‐promoted energy transfer.12 They are either
commercially available (
7 and 8) or were synthesized following
literature‐reported procedures.17
Quantification of fluorescence changes. The changes in the
fluorophore emission spectra of fluorophores 6‐8 with
introduction of the pesticide analyte were determined by
combining small amounts of fluorophores 6‐8 in
tetrahydrofuran with a 10 mM aqueous cyclodextrin solution.
The fluorescence emission of the fluorophores in the
cyclodextrin solution were compared to their emission after
the introduction of small amounts of pesticides 1‐4 in
tetrahydrofuran, and the results were quantified according to
Equation 1:
Fig. 3 Fluorescence changes in fluorophore 6 upon introduction of: (A) analyte 1; (B)
analyte 2; (C) analyte 3; and (D) analyte 4. (λex = 460 nm).
Fluorophore Ratio = (Flanalyte)/Flblank
(Eq. 1)
where Flanalyte is the fluorescence emission of the fluorophore
in the presence of the analyte, and Flblank is the fluorescence
emission of the fluorophore in the absence of the analyte.
Fluorophore
fluorescence emission when combined with analytes
(Table 2). Analytes and , by contrast, led to noticeable
changes in the fluorescence emission of fluorophore in the
7
showed no significant changes in its
1
and
2
3
4
7
presence of α‐CD, β‐CD, 2‐HPCD and in the absence of any CD.
In the presence of Me‐β‐CD, no significant changes in
Results and Discussion
When combined with fluorophore
compounds 1‐4 induced significant increases in the
fluorophore’s emission spectra (Table 1). In each of these
cases, the changes in fluorescence emission were even greater
in the absence of a CD host (indicated by higher fluorophore
emission ratios in PBS).
These results suggest that pesticide‐fluorophore interactions
result in increases in the fluorophore emission of compound 6,
and that cyclodextrin hosts modulate the degree of
fluorescence enhancement by partially shielding the
fluorophore from such close interactions with the pesticide
analytes. This hypothesis is supported by the limited
6 in α‐CD, β‐CD, or 2‐HPCD,
fluorophore
the results observed for fluorophore
with our previously reported results.13
Fluorophore showed an increase in fluorescence emission
7
’s emission spectrum was observed, in line with
6
and in good agreement
8
when combined with analytes 1‐4 in the presence of α‐CD;
decrease in the fluorescence emission when combined with
analytes 1‐4 in the presence of Me‐β‐CD and 2‐HPCD, and
variable, analyte‐dependent fluorescence changes when
combined with analytes 1‐4 in the presence of β‐CD (Table 3).
Uniform increases in fluorescence were observed in the
absence of any CD, which supports the notion of pesticide‐
2 | J. Name., 2012, 00, 1‐3
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mediated fluorescence increases that are being attenuated in
the presence of favorably interacting cyclodextrin hosts.
Table 2. Selected fluorophore emission ratios with fluorophore 7
Analyte
α‐CD
1.09
0.98
1.08
1.28
β‐CD
1.00
1.00
0.96
1.05
Me‐β‐CD
1.00
0.99
1.04
1.03
2‐HPCD
1.02
0.97
0.99
0.99
PBS
1.00
1.00
0.88
1.09
1
2
3
4
Fig. 4 Electrostatic potential surfaces of analytes 1‐4, calculated using Spartan 10,
version 1.1.0. The red colour represents the electron‐rich regions and the blue colour
represents electron‐deficient regions.
Table 3. Selected fluorophore emission ratios with fluorophore 8
Literature precedent shows that halogen atoms interact with
planar aromatic surfaces under a variety of conditions.22 In our
system, we observe a similar degree of intermolecular
interactions between the halogenated pesticides 1‐4 and the
aromatic surface areas of fluorophores 6‐8 in the cyclodextrin‐
free solution, which results in quantifiable enhancements in
the fluorescence emission spectra. In the presence of a variety
of cyclodextrin hosts, the fluorophores preferentially bind to
Analyte
α‐CD
1.21
1.07
1.08
1.21
β‐CD
1.01
1.03
1.24
1.08
Me‐β‐CD
0.97
0.87
0.94
0.83
2‐HPCD
0.88
PBS
1.22
1.10
1.23
1.23
1
2
3
4
0.94
0.88
0.94
Mechanism of differentiation. Each component of the system
has structural features that facilitate intermolecular
interactions: (a) Cyclodextrins bind small molecule guests using
a range of intermolecular forces, including hydrophobic
association, hydrogen bonding, and van der Waals
interactions.19 (b) Fluorophores 6‐8 can participate in
intermolecular interactions through aromatic π‐stacking,20
hydrophobic association and hydrogen bonding. (c) Pesticides
1‐4 are expected to participate in intermolecular interactions
largely through hydrophobic association and/or through
intermolecular interactions with the chlorine moieties.21
Electrostatic potential surfaces of pesticides 1‐4 are shown in
Figure 4 and quantitative data is summarized in Table 4. These
marked differences in solvent accessible surface area and in
electrostatic potential surfaces contributes to the differences
in the interactions of these analytes with fluorophores and
cyclodextrins, which gives rise to the unique fluorescence
modulation patterns. These patterns enable high levels of
selectivity in array‐based detection (vide infra), even though
the quantitative binding constants of the analytes in β‐
cyclodextrin are relatively weak (Table 4).
the cyclodextrin (Ka in β‐CD = 0.11 mM‐1 for fluorophore
7;
0.30 mM‐1 for fluorophore 8). In such cases, the introduction
of the pesticide analyte leads to attenuated interactions
between the pesticide and the fluorophore, resulting in
generally lower degrees of fluorescence enhancements.
Array‐based detection. Overall, the observed fluorescence
modulation responses are unique to each analyte‐fluorophore‐
cyclodextrin combination, with the reported modulation
providing
a snapshot of the complicated interplay of
intermolecular interactions between the three components.
These unique responses generate well‐separated signals for all
of the pesticides investigated using linear discriminant analysis
(LDA) methods (Figure 5),23 with even a single cyclodextrin
host providing sufficient differentiation for all target analytes.
Interestingly, these responses are markedly different than the
response pattern obtained using tetrahydrofuran
5 as a
control, which confirms that the fluorescence modulation is
due to pesticide‐specific interactions and is not a result of the
small amount of tetrahydrofuran used to dissolve the pesticide
analyte prior to addition.
Table 4. Quantitative information about the small molecule pesticides
Analyte
Binding in β‐
CD (mM‐1)a
0.067
Solvent‐accessible
Electrostatic potential
(min/max) (kJ/mol)c
‐50/102
surface area (Å2)c
1
2
171
148
b
‐118/100
3
4
0.067
0.017
160
139
‐75/150
‐96/174
a Calculated by 1H NMR titrations
b 1H NMR titrations indicated no measurable binding
c Calculated using Spartan 10, version 1.1.0.
Overall, the low degrees of fluorescence modulation and weak
binding affinities observed in these systems indicate the
possibility that variable binding geometries may exist,
including those in which the pesticide and fluorophore are
each bound to a different cyclodextrin molecule (Figure 2).
Fig. 5 Selected array results with hosts: (A) α‐CD; (B) β‐CD; (C) Me‐β‐CD; and (D) PBS.
J. Name., 2013, 00, 1‐3 | 3
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Control experiments in the absence of any cyclodextrin (Figure
5D) indicate well‐separated signals for the analytes; however,
the scale of the X‐axis indicates a markedly lower degree of
separation in PBS and in α‐cyclodextrin compared to the
results obtained in β‐cyclodextrin and Me‐β‐cyclodextrin,
which highlights stronger intermolecular interactions with the
larger cyclodextrin systems compared to the results obtained
with the smaller α‐cyclodextrin or without a cyclodextrin host.
The limits of detection (LODs) and limits of quantification
(LOQs) of cyclodextrin‐promoted fluorescence modulation
were assayed using literature‐reported methods,5 and some
select results are highlighted in Table 5. Detection limits as low
as 5 µM were obtained. These results are slightly higher than
literature reported values for other pesticide detection
systems; however, the system reported herein has a number
of notable operational advantages that make it attractive from
a practical detection perspective.24 The negative calculated
values occur because the limit of detection calculations use
Conclusions
In summary, measurable changes in fluorescence emission
spectra are seen upon addition of an aliphatic analyte to a high
quantum yield fluorophore. The degree of intermolecular
interactions between the two components strongly depends
on the structures of each component, as well as on the
supramolecular host. These changes, termed “fluorescence
modulation,” enable the rapid, sensitive, and selective
detection of analytes such as aliphatic organochlorine
pesticides, with 100% success in identifying unique response
patterns for each analyte‐CD‐fluorophore combination and
low limits of detection. The use of this fluorescence
modulation technique for aliphatic alcohol detection in
complex mixtures represents a significant challenge in terms of
selectivity and sensitivity, and current efforts in our laboratory
are focused on addressing these challenges and optimizing
detection in complex environments. Results of these and other
investigations will be reported in due course.
the assumption of
fluorescence emission and the analyte concentration. Because
the fluorescence emission in this case is result of
a linear relationship between the
a
Acknowledgements
This research was funded by the National Science Foundation
grant #1453483.
complicated intermolecular interactions between the analyte,
fluorophore, and cyclodextrin, there are cases where that
linear relationship does not hold.
Table 5. Limits of detection calculated for analytes 1‐4 with fluorophore 6 in β‐CD and
in PBS
References
Analyte
in β‐CD
82 µM
a
31 µM
189 µM
in PBS
a
a
1
2
3
4
a
5 µM
a
Efforts to calculate limits of detection for these analyte‐fluorophore‐
cyclodextrin combinations led to negative calculated values; current efforts are
focused on understanding these phenomena
The practicality of this system would be markedly enhanced by
its ability to detect a broader range of lipophilic compounds
with high sensitivity. Aromatic organochlorine pesticides have
already been detected by our group using cyclodextrin‐
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The introduction of pesticides to a cyclodextrin-fluorophore solution leads to highly specific fluorescence
changes that are used for pesticide detection.

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