Synthesis and ultrasound mediated antibacterial activity of ferrocene-Triazole-porphyrin derivative

Article abstract of DOI:10.1142/S1088424620500431

The [3 + 2]-cycloaddition reaction of various azides with ferrocenylmethylpropargyl ester in the presence of copper (I) salt lead to the formation of ferrocenyl-containing derivatives, including porphyrin, which exhibit pronounced cytotoxicity against Esc

Full text of DOI:10.1142/S1088424620500431

Journal of Porphyrins and Phthalocyanines
J. Porphyrins Phthalocyanines 2020; A–F
DOI: 10.1142/S1088424620500431
Published at https://www.worldscinet.com/jpp/
(
pp. 6)
Synthesis and ultrasound mediated antibacterial activity
of ferrocene-triazole-porphyrin derivative
a
a
b
ElenaYu. Rogatkina *, Alexey N. Rodionov , Svetlana E. Mazina
a
and Alexander A. Simenel
a
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov st.,
1
19991 Moscow, Russia
b
Department of Chemistry, M.V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991 Moscow,
Russia
Received 5 May 2020
Accepted 14 August 2020
ABSTRACT: The [3 + 2]-cycloaddition reaction of various azides with ferrocenylmethylpropargyl ester
in the presence of copper (I) salt lead to the formation of ferrocenyl-containing derivatives, including
porphyrin, which exhibit pronounced cytotoxicity against Escherichia coli under ultrasound irradiation.
KEYWORDS: ferrocene, porphyrin, sonodynamic therapy, [3 + 2]-cycloaddition, Escherichia coli,
ultrasound.
the regions responsible for photosynthesis [14, 15]. The
INTRODUCTION
redox centers of ferrocenoporphyrins are interesting for
modeling molecular machines [16, 17] or molecular
electrical sensors [18]. The ability to reversibly accept and
give electrons in a different range of potentials can be used
in redox catalysis [19], as well as in modeling systems for
storing information [20, 21]. Heterocyclic derivatives of
ferrocene exhibit a variety of biological activity, including
antitumor, while being low toxic compounds [22–29].
Moreover, the membranotrophy of the ferrocene group and
the redox properties of ferrocene, manifested in cells, can
positively affect the porphyrin system. Ferrocene-modified
porphyrins, are hitherto, poorly studied as antitumor and
anti-inflammatory agents. Recently, we obtained original
ferrocene-containing porphyrins [30–32], which were
firstly studied for sonodynamic activity against Staphylo-
coccus aureus [33] (previously such compounds were not
studied under the conditions of sonodynamic therapy). Both
its own cytotoxic effect and its pronounced amplification
under ultrasound were revealed. It appears obvious
that further research of such complexes will lead to the
creation of new drugs. Existing methods for the synthesis
of ferrocene-modified porphyrins are multistage and
sometimes difficult to reproduce; others require expensive
reagents. In this work we studied CuAAC (copper-
catalyzed azide-alkyne cycloaddition) [34, 35] (special case
Cancer treatment is one of the leading problems in
scientific research. Sonodynamic therapy (SDT) is a
promising selective treatment method that allows targeting
of tumor cells with special drugs (sonosensitizers), the
activity of which appears through ultrasound irradiadion
[1–7]. Unlike photodynamic therapy (PDT) SDT has
the advantage of affecting tumors located deep in organs
and tissues. The method of sonodynamic therapy also
affects the foci of inflammation, and can be very effective
in the treatment of such socially significant diseases as
“diabetic foot” (currently, PDT is the only method in use
for this) [8–10]. The search for suitable sonosensitizers
is a task that must be solved. Porphyrin compounds
are now used as sonosensitizers [11, 12]; however, the
structures of porphyrin compounds are subjected to
various chemical modifications in order to identify and
select the best. Interest in ferrocene-containing porphyrins
[13] is due primarily to their physicochemical properties.
The donor–acceptor nature of such structures and their
electrochemical properties are used to study the processes
of photoinduced electron transfer in order to simulate
*
Correspondence to: Elena Yu. Rogatkina email: jdyotvet@
yandex.ru.
Copyright © World Scientific Publishing Company

B
E. YU. ROGATKINA ET AL.
1
3
of [3 + 2]-cycloaddition) of ferrocenylmethylpropargyl
ether with tetraphenylporphyrinazide. Sonodynamic eff-
ect of ferrocenyl-1,2,3-triazolylporphyrin using in vitro
experiments on Escherichia coli was studied.
CH). C NMR (100 MHz; CDCl ; Me Si): d, ppm 13.92
3
4
(CH CH ), 50.84 (-CH -), 62.36 (CH CH ), 63.13 (C H ),
68.47 (C H ), 69.57, 68.61 (-CH -), 68.68 (-CH -), 82.89
(ipso-C H ), 123.98 (Tr), 145.94 (ipso-Ctr), 166.2 (C=O).
MS (EI): m/z 457 (calc.for [M] 457).
2
3
2
2
3
5
5
5
5
2
2
5
4
+
EXPERIMENTAL
4
-((Ferrocenylmethoxy) methyl)-1-(3-(trifluoromethyl)
phenyl)-1H-1,2,3-triazole (3b)
Apparatus and analysis
(
110°C, 3h). Yield 90 %. Yellow powder. mp
1
9
4
4
2
(
(
8
(
1
2–93°C. H NMR (400 MHz; CDCl ; Me Si): d, ppm
.16 (s, 5H, C H ), 4.20 (s, 2H, C H ), 4.29 (s, 2H, C H ),
.46 (s, 2H, -CH -), 4.74 (s, 2H, -CH -), 7.66–7.72 (m,
H, C H ), 8.00 (s, 1H, Tr), 8.03 (s, 1H, C H ). C NMR
All chemicals used were reagent grade and used as
received without further purification. 5-(p-Azidophenyl)
3
4
5
5
5
4
5
4
-
10,15,20-triphenylporphyrin was synthesized accor-
2
2
13
dingly to described method [36]. The solvents purified
according to standard procedures and distilled just before
use. The mass spectra were obtained by the electron
impact method on a Finnigan Polaris Q instrument
6
5
6
5
100 MHz; CDCl ; Me Si): d, ppm 63.17 (C H ), 68.50
3
4
5
5
C H ), 68.74 (C H ), 69.16 (-CH -), 69.67 (-CH -),
5 5 5 5 2 2
2.67 (ipso-C H ), 117.42 (Ctr), 120.58 (C H ), 121.60
5 4 6 5
q, J = 269 Hz, C F), 121.97 (ipso-C H ), 124.68 (C H ),
(
2
USA), the temperature of the ionization chamber was
50°C, the energy of ionizing electrons was 70 eV, and
1
1
6
5
6
5
25.04 (C H ), 125.33 (C H ), 130.57, 132.30 (q, J = 33
6
5
6
5
2
Hz, CF), 137.38 (C H ), 146.90 (ipso-Ctr). MS (EI): m/z
the electrospray method was used on a Thermo Finnigan
instrument under standard conditions (electrospray
ionization, acetonitrile, capillary voltage 4.5 kV). The
NMR spectra recorded on an Avance spectrometer with
operating frequencies of 400 for protons, and 100 MHz
6
5
+
4
41 (calc.for [M] 441).
4
-((Ferrocenylmethoxy) methyl)-1-phenyl-1H-1,2,3-
triazole (3c)
1
3
13
for C nuclei, in CDCl at 30°C. For calibration,
C
3
(
60°C, 12h).Yield 85 %.Yellow powder. mp 98–99°C.
signals and residual protons of deuterium solvents taken.
The purity of the isolated compounds was checked by
TLC on Silufol UV 254, Sorbfil, 25 DC-Alufolien, and
Kieselgel 60 F254 plates. Preparative chromatography was
performed on neutral alumina (Brockmann activity grade
II; from Reanal), Kieselgel 60 F254 (Merck), or Kieselgel
1
H NMR (400 MHz; CDCl ; Me Si): d, ppm 4.18 (s, 5H,
C H ), 4.21 (s, 2H, C H ), 4.31 (s, 2H, C H ), 4.45 (s, 2H,
3
4
5
5
5
4
5
4
-
CH -), 4.74 (s, 2H, -CH -), 7.46 (t, 1H, C H , J = 8Hz),
2
2
6
5
7
1
6
6
.55 (t, 2H, C H , J = 8Hz), 7.74 (d, 2H, C H ), 7.96 (s,
6
5
6
5
13
H, CH). C NMR (100 MHz; CDCl ; Me Si): d, ppm
3
4
3.24 (C H ), 68.49 (C H ), 68.69 (C H ), 68.96 (-CH -),
5
4
5
5
5
4
2
(
0.035–0.070 mm, 90 Å, Acros).
9.64 (-CH -), 82.81 (ipso-C H ), 120.53 (C H ), 120.72
2
5
4
6
5
(
1
C H ), 128.73 (C H ), 129.76 (C H ), 137.08 (C H ),
46.29 (ipso-Ctr). MS (EI): m/z 373 (calc.for [M] 373).
6 5 6 5 6 5 6 5
General procedure for CuAAC reaction
of ferrocenylmethylpropargyl ether with azides
+
4
1
-((Ferrocenylmethoxy) methyl)-1-(4-methoxyphenyl)-
H-1,2,3-triazole (3d)
To a mixture of the ferrocenylmethylpropargyl ether
(
was synthesized according to the method [37]) (1 mmol)
and copper acetate hydrate (3 mg, 1.4 mol%) in toluene
5 ml) was added the corresponding azide (1 mmol) at
room temperature. The reaction mixture was stirred at
ambient temperature; the reaction progress monitored by
TLC. The reaction mixture was cooled to room temper-
ature and then poured into water (20 ml) and ethyl acetate
(20°C, 5h) Yield 95%. Yellow powder. mp 98–99°C.
(
1
H NMR (400 MHz; CDCl ; Me Si): d, ppm 3.88 (s, 3H,
3
4
CH ), 4.16 (s, 5H, C H ), 4.19 (s, 2H, C H ), 4.29 (s, 2H,
3
5
5
5
4
C H ), 4.45 (s, 2H, CH ), 4.72 (s, 2H, CH ), 7.01 (d, 2H,
C H J = 12 Hz), 7.61 (d, 2H, C H J = 12 Hz), 7.87
5
4
2
2
6
4
6
4
13
(
s, 1H, CH). C NMR (100 MHz; CDCl ; Me Si): d,
3
4
(
10 ml). The organic layer was separated and the aqueous
phase extracted with ethyl acetate (10 ml). The combined
ppm 55.64 (O-CH ), 63.27 (C H ), 68.48 (C H ), 68.69
3
5
4
5
5
(C H ), 69.93 (-CH -), 69.65 (-CH -), 82.81 (ipso-C H ),
5 4 2 2 5 4
organic fractions were dried (MgSO ) and the solvent
4
114.77 (Ctr), 120.91, 122.18, 130.6, 146.05 (ipso-Ctr),
1
was removed. The residue was chromatographed (silica
gel, methylene chloride).
+
59.93 (-C-OCH ). MS (EI): m/z 403 (calc.for [M] 403).
3
Zinc 4-((ferrocenylmethoxy) methyl)-1-(5-(p-
aminophenyl)-10,15,20-triphenylporphyrin)-1H-
1,2,3-triazole (5)
Ethyl 4-(4-((ferrocenylmethoxy) methyl-1H-1,2,3-
triazole-1-carboxylate (3a)
1
(
110°C, 24h). Yield 75%. Yellow crystals. mp
Yield 75%. Purple powder. mp >250°C. H NMR
1
6
1
(
5–66°C H NMR (400 MHz; CDCl ; Me Si): d, ppm
(400 MHz; CDCl ; Me Si): d, ppm 4.16 (s, 5H, C H ),
3
4
3
4
5
5
.31 (t, 3H, CH CH , J = 8 Hz), 4.15 (s, 5H, C H ), 4.18
4.21 (s, 2H, C H ), 4.30 (s, 2H, C H ), 4.43 (s, 2H, -CH -),
2
3
5
5
5 4 5 4 2
s, 2H, C H ), 4.27 (s, 2H, C H ), 4.28 (m, 2H, CH CH ),
4.74 (s, 2H, -CH -), 7.74–7.83 (m, 9H, Ph); 8.05–8.07
5
4
5
4
2
3
2
4
.40 (s, 2H, -CH -), 4.68 (s, 2H, -CH -), 7.67 (s, 1H,
(d, 2H, Ph, J = 8 Hz), 8.23–8.25 (d, 6H, Ph, J = 8 Hz),
2
2
Copyright © World Scientific Publishing Company
J. Porphyrins Phthalocyanines

SYNTHESIS AND ULTRASOUND MEDIATED ANTIBACTERIAL ACTIVITY OF FERROCENE-TRIAZOLE-PORPHYRIN
C
8
.43–8.45 (d, 2H, Ph, J = 8 Hz), 8.80–8.92 (m, 8H ,
of the suspension was transferred onto a sterile medium
in a Petri dish with the culture medium. The Petri dishes
were then placed in an air thermostat. The temperature in
the thermostat for culturing bacteria was 37°C. The result
of bacterial growth was evaluated after 24 h, counting
the number of colony forming units in the experimental
and control samples. The experiments were performed in
duplicate. The final result was evaluated as a percentage
of control/experience.
ab
1
3
Py). C NMR (100 MHz; CDCl ; Me Si): d, ppm 63.17
3
4
(
C H ), 68.50 (C H ), 68.74 (C H ), 69.16 (-CH -), 69.67
5 5 5 5 5 5 2
(
-CH -), 82.67 (ipso-C H ), 117.42 (Ctr), 118.97, 120.40,
2 5 4
1
1
26.81, 127.85, 128.38, 134.67, 135.82, 139.03, 139.92,
+
42.20. MS (ESI): m/z 973 (calc.for [M + H] 973).
Zinc 5-(p-azidophenyl)-10,15,20-triphenylporphyrin (4)
A solution containing 1 mol of zinc acetate in ethanol
was added to a solution of 0.001 mol of 5-(p-azido-
phenyl)-10,15,20-triphenylporphyrin porphyrin in met-
hylene chloride. The reaction mass was stirred at room
temperature for 15 minutes. Next, the organic layer was
RESULTS AND DISCUSSION
CuAAC reaction of ferrocenylmethyl propargyl
ether with azides
washed with water, dried over MgSO . The solvent was
removed in vacuo.
4
1
Yield 98%. Purple powder. mp >250°C. H NMR
In order to develop and optimize the CuAAC reaction
for the synthesis of ferrocene-containing porphyrin,
reactions of ferrocenylmethyl propargyl ether with
aromatic azides and azidoacetic ester were carried out in
toluene using copper acetate. (Scheme 1)
The fastest reaction occured with the participation of
electron-donor substituents at phenyl ring, at 20°C for
(
7
CDCl , 400d, ppm): 7.48 (d, 2H, 2CH, Ph-NH, J = 6 Hz),
3
.80–7.85 (m, 9H, 9CH, Ph), 8.28–8.33 (m, 8H, 2CH,
13
Ph-NH), 8.72 (br s, 1H, 2CH, Ph), 7.81 (m, 8H, Py). C
NMR (CDCl , 126 MHz, d, ppm): 117.53, 118.97, 120.40,
3
126.81, 127.85, 128.38, 134.67, 135.82, 139.03, 139.92,
+
142.20. MS (ESI): m/z 717 (calc.for [M + H] 717).
5
6
h. With phenylazide the reaction proceeds for 12h at
0°C, and under boiling temperature for a day with a
The bacterial model
trifluoromethyl substituent. When using aliphatic azides
the reaction time increased.
Viability and effects were evaluated on Escherichia
coli bacteria. The bacterial culture was grown on Endo
gel medium, prepared with the addition of agarose, at a
temperature of 37°C. For the experiment, a suspension of
bacterial cells was prepared in a sterile isotonic sodium
chloride solution, washing off the bacterial cells from the
gel substrate into the solution. To assess cell viability,
preparations were introduced into the culture medium at a
concentrationof0.002g/mlsuspensionofmicroorganisms,
the preparations were dissolved in DMSO.
CuAAC reaction for the synthesis of ferrocenyl-
1,2,3-triazole-porphyrin
Successful testing of the CuAAC reaction of ferrocen-
ylmethylpropargyl ether with aromatic azides allowed
the reaction with tetraphenylporphyrinazide (Scheme 2).
It should be noted that when using catalytic amounts
of copper acetate the terminal triple bond was not
activated, and only the incorporation of the copper
ion into porphyrin was observed. When an equivalent
amount of copper acetate added, the target product
formed in which copper is embedded in the porphyrin
ring. In order to avoid the incorporation of copper
into porphyrin we conducted a metallation reaction
of azidoporphyrin with zinc acetate in a mixture of
ethanol/methylene chloride solvents. Afterwards, a
similar CuAAC reaction of ferrocenylmethylpropargyl
ether with tetraphenylporphyrinazide was carried out
(Scheme 2).
Assessment of the impact of ultrasound
on bacterial suspension
Viability assessment was performed minus the effect
of exposure to DMSO. 10 ml of a suspension of bacterial
cells and the experimental substance was introduced
into a vessel with a soundproof bottom. The vessel was
placed in a thermostatic bath with water at a temperature
of 37°C above an ultrasonic emitter (0.88 MHz) and
the suspension was subjected to ultrasonic treatment for
2
5
min at ultrasound intensities of 1.5 W/cm . Then 1 ml
Scheme 1. CuAAC reaction of ferrocenylmethyl propargyl ether with azides.
Copyright © World Scientific Publishing Company
J. Porphyrins Phthalocyanines

D
E. YU. ROGATKINA ET AL.
Scheme 2. CuAAC reaction of ferrocenylmethyl propargyl ether with porphyrinazide.
Fig. 1. Sonosensitisers for SDT experiment.
Table 1. The results of SDT experiment on Escherichia coli cells.
Sonosensitiser*
DMSO mkl/10 ml**
US control, % death
20
US + sample, % death Effect % Stand. deviation
FcCO H
300
300
300
300
28
38
29
41
8
18
9
0.41
0.72
0.47
0.71
2
H TPP
2
20
20
20
Fc-Pz-NH-H TPP [33]
2
Fc-Tz-H TPP
21
2
-
5
*
*
Sonosensitiser molar concentration 10 M (0.001 g/ml).
*DMSO concentration in 10 ml of bacterial medium.
Sonodynamic experiment
to the death of Escherichia coli. Under the ultrasound
action, as expected, there was an increase in biocidal
action of all samples. It is noteworthy that, in its activity,
In vitro tests using ultrasound irradiation to study
the biocidal action of several porphyrin and ferrocene
compounds against Escherichia coli were carried
out. Effects of ferrocenylporphyrin with results for
tetraphenylporphyrin, ferrocenecarboxilic acid and the
previously synthesized ferrocene-modified porphyrin
ferrocene carboxylic acid (FcCO H) is not inferior in
2
activity to ferrocene-modified substrates. Concerning
tetraphenylporphyrin, its activity is lower than that of
ferrocenemodifiedporhyrin (Fc-Tz-ZnTPP), and higher
than that of Fc-Pz-NH-H TPP; however, the effect of
2
[
33] were first compared. In a DMSO solution, a
H TPP cannot be denied. Unfortunately, the effect of
2
pronounced cytotoxic effect of all injected samples, led
Fc-Pz-NH-H TPP under ultrasound is lower than was
2
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J. Porphyrins Phthalocyanines

SYNTHESIS AND ULTRASOUND MEDIATED ANTIBACTERIAL ACTIVITY OF FERROCENE-TRIAZOLE-PORPHYRIN
E
hoped. The most effective compound was Fc-Tz-ZnTPP
Fig. 1). Table 1 shows the number of dead cells in the
experiment on Escherichia coli.
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(
This was a screening study for the sono-activity
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Reactions of ferrocenylmethyl propargyl, both with
aliphatic and aromatic azides, were carried out in toluene
using copper acetate. The reaction rate depends on the
electronic effect of substituent. For the CuAAC reaction
new ferrocene-modified porphyrins were obtained. The
results obtained are one of the test steps being carried
out at present and will continue to be carried out in the
future with other samples from a large amount of self-
obtained ferrocenemodified porphyrins and ferrocene
derivatives. Sonodynamic effect of ferrocene-modified
porphyrin was studied on Escherichia coli cells
and compared with synthesized previously ferrocene-
porphyrin, tetraphenylporphyrin and ferrocene carboxylic
acid. The insolubility of most compounds in water makes
experiments with them difficult. Alternative use of oils or
DMSO sometimes have negative affects on the state of
experimental cell cultures which are already extremely
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2
2
This work was supported by Ministry of Science
and Higher Education of the Russian Federation using
the equipment of Center for molecular composition
studies of A. N. Nesmeyanov Institute of Organoelement
Compounds, Russian Academy of Sciences, Moscow.
We thank collaborators from The Faculty of Chemistry
of Moscow State University for carrying out the in vitro
tests.
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