Synthesis and characterization of new water soluble 9,10-anthraquinonе and evaluation of its antimicrobial activity

Article abstract of DOI:10.1016/j.molstruc.2018.05.007

The synthesis and characterization of a new cationic anthraquinone derivative (S3) soluble in water has been described. Its absorption characteristics in aqueous and N,N-dimethylformamide solutions have been determined. Аntimicrobial activity of the compound S3 was tested in vitro towards eight pathogenic bacteria and two yeasts strains. The results obtained suggest that the newly synthesized compound is effective in treating the relevant pathogens and is suitable in designing new effective antimicrobial preparations. Antimicrobial activity and release of S3 after its deposition on cotton fabric and incorporation into thin polylactid film have also been investigated.

Full text of DOI:10.1016/j.molstruc.2018.05.007

Accepted Manuscript
Synthesis and characterization of new water soluble 9,10-anthraquinonе and
evaluation of its antimicrobial activity
Stanislava Yordanova, Evgenia Vasileva-Tonkova, Desislava Staneva, Stanimir
Stoyanov, Ivo Grabchev
PII:
S0022-2860(18)30563-5
10.1016/j.molstruc.2018.05.007
MOLSTR 25179
DOI:
Reference:
To appear in:
Journal of Molecular Structure
Received Date:
Revised Date:
Accepted Date:
04 April 2018
02 May 2018
03 May 2018
Please cite this article as: Stanislava Yordanova, Evgenia Vasileva-Tonkova, Desislava Staneva,
Stanimir Stoyanov, Ivo Grabchev, Synthesis and characterization of new water soluble 9,10-
anthraquinonе and evaluation of its antimicrobial activity, Journal of Molecular Structure (2018),
doi: 10.1016/j.molstruc.2018.05.007
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ACCEPTED MANUSCRIPT

ACCEPTED MANUSCRIPT
Synthesis and characterization of new water soluble 9,10-anthraquinonе
and evaluation of its antimicrobial activity
Stanislava Yordanova1, Evgenia Vasileva-Tonkova2,*, Desislava Staneva3,
Stanimir Stoyanov1, Ivo Grabchev4,*
1Sofia University “St. Kliment Ohridski”, Faculty of Chemistry and Pharmacy, 1407 Sofia,
Bulgaria
2The Stephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, 1113
Sofia, Bulgaria
3University of Chemical Technology and Metallurgy, 1756 Sofia, Bulgaria
4Sofia University “St. Kliment Ohridski”, Faculty of Medicine, 1407 Sofia, Bulgaria
Abstract
The synthesis and characterization of a new cationic anthraquinone derivative (S3) soluble in
water has been described. Its absorption characteristics in aqueous and N,N-
dimethylformamide solutions have been determined. Аntimicrobial activity of the compound
S3 was tested in vitro towards eight pathogenic bacteria and two yeasts strains. The results
obtained suggest that the newly synthesized compound is effective in treating the relevant
pathogens and is suitable in designing new effective antimicrobial preparations. Antimicrobial
activity and release of S3 after its deposition on cotton fabric and incorporation into thin
polylactid film have also been investigated.
Keywords: 9,10-anthraquinone, microbiological, antibacterial textile, polylactid,
Corresponding author: Ivo Grabchev: e-mail i.grabchev@chem.uni-sofia.bg
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1. Introduction
The cationic compounds and especially the quaternary ammonium salts (QAS) exhibit
excellent antimicrobial activity against Gram-positive and Gram-negative bacteria, fungi and
certain types of viruses, therefore they can be used as antiseptics, bactericides and fungicides,
and as therapeutic agents, as well [1]. These microbial agents damage the cell wall or alter
cell membrane permeability, denature proteins, inhibit enzyme activity or inhibit lipid
synthesis and all of those factors that are essential for cell survival. Therefore, the
introduction of such quaternary groups into certain organic compounds can be a strategy in
the design of biologically active compounds with antibacterial and antifungal activity.
Recently, we have shown that the introduction of QAS in the structure of benzanthrone leads
to the occurrence of antimicrobial activity, which is maintained after deposition into a
polylactide thin film. In this way, the effect of dyeing was combined with the antibacterial
activity [2, 3].
The derivatives of 9,10-anthraquinone belong to the group of natural quinones which
are isolated from different fungi, lichens and some plants [4]. They are the second most
important class of dyes which have been used as colorants in textiles industry, cosmetics as
hair dyes [5]. Quinones especially anthraquinones, present numerous biological activities such
as antiprotozoa, antituberculous, fungicidal, antioxidant, cytotoxic and antitumor activities [6-
11].
Polylactide (PLA) is one of the most important commercially available and common
biodegradable and biocompatible polymer produced from renewable resources such as corn,
potatoes, sugar, etc. Due to transparently and low toxicity it is one of the most promising
biopolymers able to replace the petroleum-derived polymers for different practical
applications, especially for food packaging when the antibacterial resistance is of particular
importance [12,13]. The treatment of textile materials with substances which exhibit
antimicrobial activity makes it possible to obtain textile materials with antibacterial or
antifungal properties [14, 15]. Such materials could be used as effective wound dressings in
the clinical practise.
In this work we describe the synthesis and characterisation of water soluble cationic
anthraquinone derivative, comprising quaternary ammonium group. Its antimicrobial activity
against gram-positive and gram-negative bacteria and yeasts was investigated. The minimum
inhibitory concentration and antimicrobial activity against the tested bacteria and yeasts was
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discussed. The antibacterial efficiency in aqueous solution of the thin PLA film and cotton
fabric treated with the new compound has also been evaluated.
2. Experimental part
2.1.
Materials and methods
Initial 2-aminoanthraquinon has been used as obtained from Sigma Aldrich. UV-Vis
spectrophotometric investigations were performed using “Thermo Spectronic Unicam UV
500” spectrophotometer, using 1 cm path length synthetic quartz glass cells. Absorption
1
measurements of the compound were carried out at 105 mol l1 concentration. H (600.13
MHz) and 13C (150.92 MHz) spectra were acquired on an AVANCE AV600 II+NMR
spectrometer. The measurements were carried out in DMSOd6 solution at ambient
temperature. The chemical shifts were referenced to a tetramethylsilane (TMS) standard.
Electrospray mass spectroscopic measurements were carried out using a Hewlett–Packard
Series 110 0 MSD. Thin layer chromatographic (TLC) analysis was followed on silica gel
(Fluka F60 254 20x20; 0.2 mm) using the solvent system hexane/acetone (1:1) as an eluent.
PLA was obtained from Sigma Aldrich (Mw 18,000, Tg 46-50 °C). The thickness of the
composite material has been determinate by AirBlast DFT-441 Dry Film Thickness Gauge.
2.2.
Synthesis of compound S2
2-aminoanthraqinone (2.23 g, 0.01 mol) was dissolved in 30 ml of dioxan and chloroacetyl
chloride (0.81 ml, 1.1 mol) were added. The mixture was stirred vigorously at 50 0C for 2h.
After that liquor was added to 100 ml of ice water. The precipitate was filtered off, washed
with water, and dried in vacuum at 400C. The crude product was purified by recrystallisation
from ethanol to give S2 as a yellow solid (2.76g, 96 %)
FT-IR cm-1: 3344, 3066, 2943, 1723, 1668, 1588, 1538, 1422, 1298, 1235, 1172, 926, 723,
712, 662,
1H NMR (DMSO-d6, ppm): d 11.45 (br s, 1H, NH), 8.81-8.78 (d, J = 5.34 Hz, 2H), 8.70-8.68
(d, J = 6.46 Hz, 1H), 8.59-8.42 (d, J = 8.40 Hz, 1H), 8.35-832 (d. J = 6.6 Hz, 2H), 8.09-8.06
(d, J = 8.17 Hz, 1H,), 7.79 (t, J = 7.68, Hz, 1H), 8.87 (t, J = 6.92, Hz, 1H), 7.63 (t, J =7.65 Hz,
1H), 4.57 s, 2H), 3.64-3.55 (2, J =-7.15 Hz, 6H), 1.30 (t, J =7.06 Hz, 9H,).
13C NMR: 182.7, 182.8, 166.0, 144.3, 135.0, 134.7, 134.6, 133.5, 129.0, 128.8, 127.2, 127.1,
124.4, 116.5, 43.9.
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Elemental analysis: C15H10N1O3Cl (287.6) : Calcd. C 62.58, H 3.47, N 4.86; Found C 62.68,
H 3.29, N 4.79.
2.3.
Synthesis of compound S3
Compound S2 (0.287 g, 0. 1 mol) was dissolved in 10 ml dioxin, then 1.5 ml of pyridine was
added and the solution was stirred for 6 h at 600C. After cooling to room temperature, the
precipitate was filtered off, washed with acetone and dried in vacuum at 400C. Yield: 0.30g
(84 %). The product S3 was obtained as light yelow solid and it has been used without any
purification.
FT-IR cm-1: 3416, 3054, 2940, 1714, 1673, 1624, 1593, 1553, 1492, 1331, 1293, 1198, 1000.
928, 789, 713, 679, 538,
1H NMR (DMSO-d6, ppm): d 11.45 (br s, 1H, NH), 8.81-8.78 (d, J = 5.34 Hz, 2H), 8.70-8.68
(d, J = 6.46 Hz, 1H), 8.59-8.42 (d, J = 8.40 Hz, 1H), 8.35-832 (d. J = 6.6 Hz, 2H), 8.09-8.06
(d, J = 8.17 Hz, 1H,), 7.79 (t, J = 7.68, Hz, 1H), 8.87 (t, J = 6.92, Hz, 1H), 7.63 (t, J =7.65 Hz,
1H), 4.57 s, 2H), 3.64-3.55 (2, J =-7.15 Hz, 6H), 1.30 (t, J =7.06 Hz, 9H,).
13C NMR: 182.8, 181.8, 164.9, 146.9, 144.2, 135.1, 134.8, 134.7, 133.5, 134.4, 129.1, 129.0,
128.0, 127.2, 127.1, 124.5, 62.8
Elemental analysis: C20H15N2O3Cl (362.6) : Calcd. C 66.18, H 4.14, N 7.72; Found C 66.58,
H 4.29, N 7.69.
2.4.
Preparation of PLA film
Pure PLA and antimicrobial PLA films were prepared by solvent casting method.
0.5 g polylactic acid was dissolved in 10 ml chloroform and 0.05mg compound S3 was added.
After 30 minutes stirring, the homogeneous mixture was poured into a Petri dish and the
solvent was evaporated slowly. Thus was obtained a stable polymer film having a thickness of
50 m (±1 m). The same method has been used to produce pure PLA film.
2.5. Treatment of cotton fabrics with S3
0. 5mg of compound S3 was dissolved in 5 ml water. Cotton fabric sample (1g) (weight 140
g/m2) was immersed in the solution at 25°C for 30 min, and dried at ambient temperature.
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2.6.
Antimicrobial activity test
The newly synthesized S3 compound was screened for antimicrobial activity against selected
pathogenic bacteria and yeasts by using the agar well diffusion method [16]. The following
test cultures were used: Gram-positive bacteria Bacillus subtilis, Bacillus cereus, Sarcina
lutea and Micrococcus luteus, Gram-negative bacteria Pseudomonas aeruginosa, Escherichia
coli, Acinetobacter johnsonii and Xanthomonas oryzae, and the yeasts Candida lipolytica and
Saccharomyces cerevisiae. A lawn of each test organism was prepared by spreading aliquots
(0.1 ml) of overnight cell suspensions on Mueller-Hinton agar plates. Tests were performed
using 0.1% and 0.5% water solutions of the investigated AN compound, of which equal
amount (30 µl) was added into 8 mm wells punched aseptically in the agar. Commercial discs
with gentamicin (10 µg) and nystatin (Ns, 100 units/disc) were used as a standard
antibacterial and antifungal agent, respectively. After incubation of the plates at 26°C for 24-
48 h, the diameter of growth inhibition zones (including well/disc) was measured. An
inhibition zone diameter ≥ 10 mm indicated that the tested compound is active against the
indicator cultures.
2.7.
Determination of Minimum Inhibitory Concentration (MIC)
The minimum inhibitory concentration (MIC) of the tested S3 compound was determined by
the broth-dilution method [17]. Serial dilutions of the synthesized compound were prepared in
meat-peptone broth (MPB) in the range 6-60 µg/mL. Each dilution was inoculated aseptically
with 1% of the respective overnight microbial suspension. The culture tubes were incubated at
26°C for 24 h with agitation. Three independent experiments were carried out, and averages
are given.
2.8.
Test of film antimicrobial activity
The antimicrobial effect of the obtained S3-PLA film was evaluated towards model bacteria
Gram-negative bacteria Escherichia coli and Acinetobacter johnsonii, and Gram-positive
Bacillus subtilis. For antimicrobial tests, square shape speciments (10-mm x 10-mm) were cut
from pure PLA film (control) and S3-PLA film -cotton sample under aseptic conditions. The
test tubes with 1.5 ml sterile meat-peptone broth (MPB) were inoculated with 1% overnight
bacterial cultures and left at room temperature for 15 min. Then, the specimens were inserted
into the test tubes. Test tubes without inserted film speciments were also prepared for each
bacterial culture. After 24 h incubation at 26°C under shaking, the specimens were removed
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and the bacterial growth was determined by spectrophotometric measurement of the optical
density (OD) at 600 nm.
3. Results and Discussion
3.6.
Synthesis and functional properties of new water-soluble anthraquinone
derivative
Scheme 1 illustrates the synthetic route for the synthesis of a new water-soluble
anthraquinone derivative. As a starting material, 2-aminoanthraquinone (S1) has been used.
Acylation of the primary amino group was carried out with chloracetylchloride at 50°C for 2
h in dioxan solution produces compound (S2). The activated chlorine atom from S2 can reacts
with tertiary amines to forms quaternary ammonium salt. In this case a pyridine has been used
as tertiary amine, which reacts with the chlorine atom of S2 in dioxane solution at 600С for 4
The precipitate of final product (S3) and is isolated in high yield (93%) by filtration and
several times was washed with acetone. Products S2 and S3 were characterized with
absorption, FT-IR, NMR 1Н- and 13С- spectroscopy and elemental analysis.
Scheme 1.
3.7.
Functional characteristics of compounds S1-S3.
In order to study the structural dependence, the absorption spectra of the newly synthesized
compounds S2 and S3 were examined and compared with the starting product S1 in a solution
of water and N,N-dimethylformamide (DMF). From Figure 1 it is seen that compound S1 in
both solvents absorbs in the visible spectral region with absorption maxima at A = 448 nm
(water) and A = 445 nm (DMF). After acylation with chloroacetyl chloride (S2) the
respective absorption maxima are hypochromatically shifted with A = 80 nm and A =
104 nm, respectively, due to the presence of a electron acceptor carbonyl group that
drastically alters the electron donor capability of the primary amino group and the absorption
maxima are in the ultraviolet region. The introduction of the cationic pyridine group into the
structure of S3 does not significantly affect the position of the absorption maximum in both
solvents, which are A = 362 nm (water) and A = 341 nm (DMF).
Figure 1.
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In order to use S3 in the design of antibacterial wound dressings and to make antibacterial
packages, the possibility of separating the active substance S3 from the surface and mass of
the corresponding polymeric materials (cotton cloth and PLA) was investigated. Figure 2
shows the release of compound S3 from the PLA matrix and 100% cotton fabric over the time
in aqueous solution. The process was monitored spectrophotometrically by absorption
spectroscopy at the absorption maximum A = 362 nm. The figure shows that absorption
maximum of S3 increases with time, due to the its release from the polymer matrices to an
constant quantity that is different for the different matrices. The Figure 2 shows that
compound S3 releases from the cotton surface, for around 20 minutes This indicates that at
that time a significant part of the biological active substance will be released and able to show
its microbiological activity. In the case of PLA matrix, a significantly longer release time for
S3 is required, which may be is due to the rigid polymeric structure and hence the more
difficult diffusion of S3 in the aqueous solution.
Figure 2.
Figure 3.
From Figure 3 it is seen that in pH range 7.7-9.5 compound S3 absorbs in the near UV region
with an absorption maximum at 340 nm. In alkaline media (pH = 9.5), the absorption
maximum is batochromicaly shifted by 76 nm (λ = 416 nm) and the colorless solution became
yellow. The calculated pKa value is pKa = 10.3 .
3.8.
Antimicrobial activity
3.8.1. In vitro antimicrobial activity and MIC
Compound S3 was tested in vitro for antimicrobial activity towards eight pathogenic bacteria
and two yeasts strains. The results revealed that at the used concentrations the compound
possess good antimicrobial activity against most of the test microbial cultures. As seen in
Figure 4 and 5, 0.5% S3-solution exhibited better zones of inhibition (in the range 17-28 mm)
against the test strains than those observed using 0.1% S3-solution (in the range 14-24 mm).
Figure 4.
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E. coli, P. aeruginosa and M. luteus were found to be resistant to 0.1% S3-solution while low
to moderate activity was observed using 0.5% S3-solution. The observed antibacterial activity
using 0.5% S3-solution was about 2 to 1.4-fold lower than that of the control for six test
bacteria or comparable with the control for B. subtilis and X. oryzae. The compound exhibited
good antifungal activity against the test yeasts S. cerevisiae and C. lipolytica while no growth
inhibition was observed by the control drug nystatin. MIC of S3 compound was determined
against those test cultures that showed good zones of inhibition in the preliminary screening.
Figure 5.
Table 1
As seen in Table 1, MIC values varied from 6 to 36 µg/ml. The sample was found to be most
effective (the lowest MIC) towards B. subtilis, and the highest MIC value of 36 µg/ml was
determined towards B. cereus and C. lipolytica. According to Holetz et. al. [18], MIC values
less than 100 µg/ml indicated good antimicrobial activity, from 100 to 500 µg/ml the
antimicrobial activity was considered moderate, from 500 to 1000 µg/ml – weak, and over
1000 µg/ml the compound was considered inactive. For our result to be interpreted, S3
compound possessed very good antimicrobial activity towards five of the eight test bacteria
and both yeast strains. Therefore, S3 has potential to be used as effective antimicrobial agent
in biomedical and agrochemical applications.
3.8.2. Antimicrobial activity of S3-PLA film and S3-cotton in aqueous solution
The results of in vitro antimicrobial tests of the obtained S3-PLA film and S3-cotton samples
are shown in Figure 6. After 24-h of treatment, the S3-PLA film speciment reduced the
growth of E. coli and B. subtilis by 27% and 5%, respectively, and no growth inhibition of A.
johnsonii was established. The S3-cotton speciment caused a significant decrease in the
growth of A. johnsonii and B. subtilis by 78% and 97.5%, respectively, while for E. coli this
decrease was much lower (27%). The antimicrobial effect should be due to diffusion of the
hydrophilic S3 compound from the hydrophobic PLA matrix into the medium. It has been
reported that some other factors such as the level of immobilized compound retained at film
surface and the surface area of the film may also have effect the release profile of the
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immobilized activity [19]. Preliminary tests showed good antibacterial efficiency of the
obtained S3 incorporated cotton material suggesting its suitability for application as a new
additive in wound dressings.
Figure 6.
Conclusion
A new water-soluble anthraquinone S3 with a quaternary amino group has been synthesized
and characterized and its spectral properties in water and DMF solutions have been
investigated. The new anthraquinone demonstrated very good antibacterial and antifungal
activity against different Gram-positive and Gram-negative bacteria and yeasts. The
compound has been deposited on a cotton fabric and in a PLA matrix. In view of the use of
these materials as antibacterial products, the release of the active substance in an aqueous
solution has been investigated. It was found that anthraquinone deposited on the cotton fabric
has been released significantly faster than from the PLA matrix. Antibacterial activity of
cotton fabric and PLA film treated with the new anthraquinone was investigated against the
strains A. johnsonii, B. subtilis and E. coli. The modified cotton fabric exhibited better activity
against the tested cultures than the S3-PLA film, suggesting its suitability for application as a
new additive in wound dressings.
Acknowledgements
The authors acknowledge Grant № KOCT 1/3-2016, Scientific Research Fund, Ministry of
Education and Science of Bulgaria
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0,20
0,12
0,09
0,06
0,03
0,00
S3
S2
S1
S3
S2
S1
B
A
0,15
0,10
0,05
0,00
350
400
450
500
550
600
350
400
450
500
550
Wavelength, nm
Wavelength, nm
Figure 1. Absorption spectra of compounds S1-S3 in aqueous (A) and DMF (B) solutions.

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0,04
0,14
0,12
0,10
0,08
0,06
0,04
0,02
0,00
A
B
0,03
0,02
0,01
0,00
0
50
100
150
200
250
300
350
0
10
20
30
40
50
Time / min
Time / min
Figure 2. Dependence of the releases of S3 in aqueous solution from cotton fabric (A) and
polylactide film (B)

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3,0
2,5
2,0
1,5
1,0
0,5
0,0
pH = 12.1
pH = 7.7
200 250 300 350 400 450 500 550 600
Wavelength / nm
Figure 3. Absorption spectra of compound S3 in aqueous solution at different pH values

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Figure 4. Zones of inhibition of the growth of the tested bacteria and yeasts by 0.1% and 0.5%
water solutions of S3 compound. G, Gentamicin used as a standard antibacterial agent; NS,
Nystatin used as a standard antifungal agent

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Figure 5. Zones of inhibition of the growth of some test bacteria and yeasts caused by 0.1% and
0.5% water solutions of compound S3.

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Figure 6. Effect of S3-PLA film and S3-cotton speciments on the growth of A. johnsonii, E. coli
and B. subtilis strains tested in meat-peptone broth (MPB).

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O
O
O
NH2
NHCCH2Cl
O
ClCOCH2Cl
dioxin, 96%
O
S1
S2
dioxin, 84%
N
O
O
+
NHCCH2
O
N
Cl-
S3
Scheme 1. Synthesis of new water-soluble anthraquinone S3

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1. Synthesis of a new cationic water soluble anthraqinone
2. In vitro investigation of antibacterial textile an polylactide
3. Inhibitor activity against Gram-positive and Gram-negative bacteria and yeasts
strains.

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Table 1. MIC values of compound S3 towards some test bacteria and yeasts.
Strains
MIC, µg/ml
Bacillus subtilis
6
Bacillus cereus
Acinetobacter johnsonii
Sarcina lutea
Xanthomonas oryzae
Saccharomyces cerevisiae
Candida lipolytica
36
32
12
24
12
36