Synthesis of Imidazolium Oligomers with Planar and Stereo Cores and Their Antimicrobial Applications

Article abstract of DOI:10.1002/cmdc.201700167

A series of imidazolium oligomers with novel planar and stereo core structures were designed and synthesized. These compounds have symmetric structures with different cores, tails, and linkers. These new imidazolium oligomers demonstrated a desirable set

Full text of DOI:10.1002/cmdc.201700167

Accepted Article
Title: The Synthesis of Imidazolium Oligomers with Planar and Stereo
Cores and Their Antimicrobial Applications
Authors: Yugen Zhang and Yuan Yuan
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The Synthesis of Imidazolium Oligomers with Planar and Stereo
Cores and Their Antimicrobial Applications
Yuan Yuan,[a] and Yugen Zhang*[a]
[a]
Dr. Y. Yuan and Dr. Y. Zhang
Institute of Bioengineering and Nanotechnology,
31 Biopolis Way, The Nanos, Singapore 138669, Singapore.
E-mail: ygzhang@ibn.a-star.edu.sg
Supporting information for this article is given via a link at the end of the document.
Abstract: A series of imidazolium oligomers with novel planar and
stereo core structures were designed and synthesized. These
compounds have symmetric structures with different cores, tails and
oligomers possess linear chain structures.13-14 The novel
imidazolium oligomers with planar and stereo cores would help
us to gain more insights into the bacteria killing mechanism of
synthetic polymers/oligomers.19
linkers. These novel imidazolium oligomers demonstrated
a
desirable set of bioactivities against four types of clinically relevant
microbes including E. coli, S.aureus, P. aeruginosa and C. albicans.
The planar oligomers with three di-imidazolium arms and n-octyl tails
showed good antimicrobial activity and biocompatibility. Oligomers
with ortho-xylylene linker exhibited higher antimicrobial activity and
higher hemolytic ability compared to those oligomers with para-
xylylene linker. These results shed light on structure-property-
relationship of synthetic polymeric antimicrobials.
Imidazolium salt based materials have been widely used in
various applications, such as catalysis (precursor of N-
heterocyclic carbene ligand),1 absorbent for CO2 capture,2
organo catalyst,3 ionic liquids (ILs),4 electrolytes,5 anticancer and
antimicrobial materials.6
Both monomeric and polymeric
imidazolium salts, as well as their derivatives, have been well
studied.1,7 Dimeric, trimeric or tetrameric imidazoliums have also
been investigated as ligands for catalysis1,8 or for the
construction of porous metal organic frameworks (MOFs).9
Dimeric imidazolium showed high antimicrobial activity and low
toxicity to mammalian cells. 10-12 Relatively, there are very limited
studies on imidazolium oligomers with five to fifteen imidazolium
units in their chain structures.13 In fact, imidazolium oligomers
could have potential in various applications as they have definite
molecular weight and versatile molecular structure. Recently, a
series of linear imidazolium oligomers has been developed as a
new generation of antimicrobials and anti-fungal agents which
has broad spectrum antimicrobial property, excellent selectivity
and no resistance.13-14 Herein, new structural motifs of
imidazolium oligomers with planar and stereo cores were
designed and synthesized. These new imidazolium oligomers
also exhibit high antimicrobial activity and selectivity.
Infectious diseases and the increasing threat of superbugs
have alerted the importance of hygiene and the usage of
antibiotics.15 Currently, small molecular antimicrobial agents,
such as triclosan and guanidine derivatives, are extensively
used in consumer care products to inhibit microbial growth for
preventing infections. However, triclosan and guanidine
derivatives have caused many concerns such as drug resistance
and toxicity to the environment.16 Synthetic polymeric materials
that act via a membrane-lytic antimicrobial mechanism generally
have broad spectrum antimicrobial activities against bacteria,
fungi and biofilms, and are capable of preventing drug
resistance.17-18 All previously reported antimicrobial imidazolium
Scheme 1. Imidazolium oligomers with planar core structures.
The new imidazolium oligomers were synthesized by
assembling pre-synthesized imidazolium arms with planar or
stereo cores, as shown in Scheme 1 and 2. For the synthesis of
1
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planar imidazolium oligomers, di-imidazolium arms (A1 to A3)
were prepared based on a reported method.20 Di-imidazolium
arms were then condensed with a planar core (PC1 to PC4) to
give planar imidazolium oligomers AmPCn. These imidazolium
oligomers have similar benzene cores with three or six di-
imidazolium arms. The di-imidazolium arms have o- or p-
xylylene linkages and n-hexyl or n-octyl ending groups.
Their antimicrobial activities were then evaluated against four
different and clinically relevant microbes: S. aureus, E. coli, P.
aeruginosa, and C. albicans.
The MICs of all 9 oligomers against the four microbes were
presented in Table 1. All the planar and stereo compounds
exhibited antimicrobial activity against the tested microbes.
A2PC1 showed higher antimicrobial activity than A1PC1 due to
the more hydrophobic n-octyl chain at the terminal end
compared to the n-hexyl chain. The long aliphatic ending group
facilitates stronger interaction between the compound and the
cell membrane, therefore enhancing antimicrobial activity.14,18
The MICs against E.coli for [p-C8im] based di-imidazolium salts
reported by D’anna et. al 11 and another series of di-imidazolium
To synthesize stereo imidazolium oligomers, two types of
stereo cores
of tetrakisimidazolylborate (TIB)21 and
tetra(imidazolylmethyl)carbon (TIMC) were prepared. The stereo
cores were condensed with imidazolium intermediate (IM1 or A4)
to form final stereo oligomers (A2SCB, A2SCC and A4SCC) that
have a pyramid core of borate or carbon and four di-imidazolium
arms (A2 or A4). The successful synthesis of these novel
structural motifs of imidazolium oligomers would lead to wide
potential applications. In this paper, we will focus on their
biological application as antimicrobials.
12
salts reported by Al-Mohammed et al. are about 25-50 µg/ml,
both of which are higher than A2PC1-3. It implied that the planar
oligomers are more active than di-imidazolium salts. The MICs
of A3PC1 and A3PC3 against P. aeruginosa are lower than that of
A2PC1 and A2PC2, respectively. The ortho-xylylene linker is
probably more suitable for the formation of amphiphilic
topography, which facilitates the polymers to bind to the lipid
membrane, leading to membrane rupture and eventually cell
death. A2PC4 showed relatively weak activity against bacteria,
which may be due to its low solubility in water and rigid structure.
As compared to linear imidazolium oligomers, the planar and
stereo compounds have bulkier cores and higher positive charge
density. The positive charges are confined in the core part and
the hydrophobic alkyl chains are located in the outer layer,
especially for A3PCx and A2PC4. It forms a positively-charged
hydrophilic core and neutral hydrophobic shell structure. The
result showed that this core-shell type structure is less efficient
than the linear structure. Similarly, imidazolium oligomers with
stereo core structures are also active against gram-positive and
gram-negative bacteria, as well as fungi. A2SCB, with a more
centralized core, displayed slightly lower antimicrobial activity
(against P. aeruginosa) as compared to A2SCC. As
a
comparison, we also tested the MICs of conventional
antimicrobial agents that are currently used in clinical treatment,
such as chlorhexidine for E. coli, vancomycin for S. aureus,
amphotericin B and Fluconzaole for C. albicans (SI, STable 1).
Table 1. Antimicrobial (MIC) and hemolytic activities of the synthesized
compounds.a
S.A.
E.C.
P.A.
C.A.
HC (10%)c
>2000
A1PC1
32
250
2000
63
A2PC1
A2PC2
4
4
16
16
500
63
63
>2000
>2000
1000
A2PC3
4
16
250
63
>2000
A3PC1
A3PC3
A2PC4
A2SCB
A2SCC
A4SCC
4
4
8
16
63
16
16
63
8
250
250
63
63
63
500
250
32
16
8
125
63
125
63
500
125
500
>2000
8
63
Scheme 2. Imidazolium oligomers with stereo core structures.
4
250
16
125
16
These new imidazolium oligomers have different geometric
structures compared to previously-reported linear oligomers.
b
IBNC8
4
2
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a
Minimum inhibitory concentration (MIC) against 3  108 colony forming unit
For biomedical applications, the biocompatibility of the
compounds with blood is important. Hemolysis assay examines
the hemoglobin release by rupturing of red blood cells (RBCs). It
is a commonly used method to evaluate the toxicity of
antimicrobial compounds.21 As shown in Table 1, the best non-
hemolytic properties were observed for A1-2PC1-3. No significant
hemolysis was observed even at 2000 µg/ml, the highest
concentration we tested. They are primarily qualified as active
and non-toxic compounds. In contrast, A2PC4 caused 10%
hemoglobin leakage from RBCs at 32 µg/ml. It has 6 arms and 6
octyl ending groups, resulting in the highest hydrophobicity as
compared to planar compounds with 3 arms and 3 ending
groups. A2PC4 exhibited less potency against various microbes
but higher toxicity against RBCs, which may be due to its highly
centralized core structure. Similarly, A3PC1 and A3PC3, with
ortho-xylylene linkers, showed remarkably higher hemolytic
activity as compared to oligomers with para-xylylene linkers. In
the structures of A3PC1 and A3PC3, with ortho-xylylene linkers,
all six imidazolium units tend to localize into the core part,
whereas for compounds with para-xylylene linkers, three outside
imidazolium units are stretched out and the positive charges on
these molecules are more delocalized. Oligomers with stereo
cores (A2SCB, A2SCC and A4SCC) have relatively high hemolytic
activity.
(CFU) mL-1 of bacteria 106 CFU mL-1 of fungus, values are in gmL-1. b Linear
imidazolium oligomer with similar components.11 S.A. (S. aureus), E.C. (E.
coli), P.A. (P. aeruginosa), C.A. (C. albicans). cHC10 was taken as oligomer
concentration at which the oligomers cause 10% hemolysis.
The morphological changes of bacteria after being treated
with these oligomers were observed with SEM. As shown in
Figure 1, the cell wall of E. coli was disrupted and subsequently
dissolved after 3 h exposure to these novel imidazolium
oligomers.
Figure 1. SEM images of E. coli treated with planar and stereo compounds
(62.5 g/ml) at 37 oC for 3 h ((a) control, (b) A2PC1, (c) A2PC2, (d) A2PC3, (e)
A2SCB, (f) A2SCC). The cell wall was disrupted after exposure. Bacteria treated
with TSB were used as controls. Scale bars represent 1 µm.
We have designed and synthesized a series of imidazolium
oligomers with novel planar and stereo core structures. These
compounds have symmetric structures with different cores, tails
and linkers. The structural motifs developed here enriched the
contents of imidazolium chemistry and have great potential
applications. In vitro assays demonstrated a desirable set of
bioactivities against four types of clinically relevant microbes and
shed light on structure-property-relationship of antimicrobials.
The killing kinetics of the planar and stereo compounds were
studied against E coli. The colony formation units of E. coli after
being treated with the compounds at 62.5 µg/ml for various
periods were shown in Figure 2. Although AmPCn and A2SCx
have the same MIC against E. coli, the speeds that they kill
bacteria are different. A2SCB showed the fastest killing speed
compared to the other oligomers. Total loss of cell viability was
observed within 6 h after exposure. Among the rest of the
compounds, A2SCC and A2PC1 are more efficient than others. In
general, imidazolium oligomers with stereo cores kill bacteria
faster than the planar ones but slower than the linear oligomer
IBN-C8.13
Experimental Section
Materials and Methods: For polymer synthesis, all solvents and
chemicals were used as obtained from commercial suppliers, unless
otherwise indicated. Triton-X was obtained from Aldrich. PBS buffer was
used in all experiments. Nuclear magnetic resonance (NMR) spectra
were obtained using a Bruker AV-400 (400 MHz) spectrometer. Chemical
shifts were reported in ppm from tetramethylsilane with the solvent
resonance as the internal standard. ESI-TOF-MS spectra were obtained
from a Bruker MicroTOF-Q system. The samples were directly injected
into the chamber at 20 μL·min-1. Typical instrument parameters: capillary
voltage, 4 kV; nebulizer, 0.4 bars; dry gas, 2 L∙min-1 at 120 °C; m/z range,
40 – 3000.
Minimum Inhibitory Concentration: Staphylococcus aureus (ATCC
6538, Gram-positive), Escherichia coli (ATCC 8739, Gram-negative),
Pseudomonas aeruginosa (Gram-negative), and Candida albicans
(ATCC 10231, fungus) were used as representative microorganisms to
challenge the antimicrobial functions of the imidazolium salts. All bacteria
and fungus were stored frozen at -80 °C. Bacteria were grown overnight
at 37 °C in Tryptic Soy broth (TSB) prior to experiments. Fungus was
grown overnight at 22 °C in Yeast Mold (YM) broth. Subsamples of these
cultures were grown for a further 3 h and diluted to give an optical density
value of 0.07 at 600 nm, corresponding to 3 108 CFU mL-1 for bacteria
and 106 CFU mL-1 for fungus (McFarland’ Standard 1; confirmed by plate
counts). The oligomers were dissolved in TSB at a concentration of 4 mg
mL-1 and the minimal inhibitory concentrations (MICs) were determined
by microdilution assay. Typically, 100 μL of microbial solution (containing
3 108 cells mL-1for bacteria and 106 cells mL-1 for fungus) was added to
100 μL of TSB or YM broth containing the test imidazolium compounds
(normally ranging from 2 µg mL-1 to 2 mg mL-1 in serial two-fold dilutions)
Figure 2. Colony formation units of E. coli after being treated with planar and
stereo compounds at 62.5 µg/ml for various periods. TSB media without tested
compounds was used as a control. * indicates that no colony was observed.
The data are expressed as mean ± S.D. of triplicates.
3
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in each well of the 96-well microtiter plate. The plates were incubated at
37 °C for 24 h with shaking at 300 rpm. For C. albicans, the incubation
was at room temperature for 48 h. The MICs were taken as the
concentration of the antimicrobial oligomer at which no microbial growth
was observed with the microplate reader. Broth solution containing
microbial cells alone was used as negative control. Experiments were run
in quadruplicates.
Time-kill studies: E. coli were grown overnight in TSB at 37 ºC. Cells
were diluted to 2 ~ 5 x 108 CFU/mL, and a 100 μL of this suspension was
then added to TSB broth or broth containing 125 ppm of polymer,
respectively. Sampling aliquots were withdrawn from cultures at 1, 3, 6
and 24 h after the addition of imidazolium compounds. The aliquots were
plated on solid LB plates and incubated at 37 ºC overnight before the
colony number was counted. Data from duplicate plate counts were
averaged, and the resulting values were plotted on a log scale against
time. Experiments were run in triplicates.
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This work was supported by the Institute of Bioengineering and
Nanotechnology, Biomedical Research Council, SERC Personal
Care Programme, Agency for Science, Technology and
Research.
Keywords: imidazolium oligomer • structural design •
antimicrobial
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Entry for the Table of Contents
Planar and Stereo Imidazolium Antimicrobials: A series of novel imidazolium oligomers with planar and stereo core were
designed and synthesized. They showed good antimicrobial/antifungal activity and biocompatibility. The structure-property
relationship study herein shed light on the function-oriented design of synthetic polymeric antimicrobials.
5
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