Selective Complexation of Hydrazone Based Ketimine with 3d, 4d, and 5d Metals: Synthesis, Characterization, and Biological Activity

Article abstract of DOI:10.1134/S1070363219010250

The hydrazone derived ketimine of dehydroacetic acid and its metal {Cu(II), Ni(II), Zn(II), Fe(III), Cd(II), Pd(II), La(III), Nd(III), Ce(III)} complexes are synthesized and characterized by IR, ¹H and ¹³C NMR, and UV-Vis spectroscopy. DNA studies have been carried out for metal complexes by electronic absorption spectroscopy. It is determined that metal complexes bind to DNA through intercalation. The complexes of Cu(II), Zn(II) and Pd(II) demonstrate significant activity against HeLa cells (cervical cancer).

Full text of DOI:10.1134/S1070363219010250

ISSN 1070-3632, Russian Journal of General Chemistry, 2019, Vol. 89, No. 1, pp. 142–147. © Pleiades Publishing, Ltd., 2019.
Selective Complexation of Hydrazone Based Ketimine
with 3d, 4d, and 5d Metals: Synthesis, Characterization,
and Biological Activity
F. Ahmada, M. B. Tajb*, S. A. Tirmizia*, W. Alelwanic, D. Hajjarc, A. A. Makkic,
S. Shaha, U. Alia, U. Hassana, M. Tahira, and S. Siddiqd
a Department of Chemistry, Quaid-e-Azam University Islamabad, 44000 Pakistan
*e-mail: drbabartaj@gmail.com
b Department of Chemistry, Islamia University Bahawalpur, 63100 Pakistan
c Department of Biochemistry, Faculty of Science, University of Jeddah, 80203 Saudi Arabia
d HEJ Research Institute Karachi, 75270 Pakistan
Received November 11, 2018; revised Janyary 15, 2019; accepted Janyary 24, 2019
Abstract—The hydrazone derived ketimine of dehydroacetic acid and its metal {Cu(II), Ni(II), Zn(II), Fe(III),
1
Cd(II), Pd(II), La(III), Nd(III), Ce(III)} complexes are synthesized and characterized by IR, H and 13C NMR,
and UV-Vis spectroscopy. DNA studies have been carried out for metal complexes by electronic absorption
spectroscopy. It is determined that metal complexes bind to DNA through intercalation. The complexes of
Cu(II), Zn(II) and Pd(II) demonstrate significant activity against HeLa cells (cervical cancer).
Keywords: ketimine complexes, electronic spectroscopy, enzymatic inhibition, anti-cancer activity, DNA
interaction
DOI: 10.1134/S1070363219010250
INTRODUCTION
according to standard protocols. Metal salts were
purchased from Merck. Dehydroacetic acid and
4-nitrobenzoic acid were obtained from Aldrich.
Ethanol, methanol, THF, DMSO were purchased from
Sigma Aldrich. Melting points were determined on a
Gallon Kamp melting point apparatus using open
capillary tubes and were uncorrected. Solutions
conductivity measurements were performed by dis-
solving the complexes in DMSO, concentration 10–3 M,
and their molar conductivities were measured at room
temperature. IR spectra were recorded on a Jasco FT-
Hydrazone derived Schiff bases of dehydroacetic
acid act as active chelating agents via N and O atoms
[1, 2]. Due to specific nature of two isomeric keto and
enol forms of DHA based hydrazones, limited
attention is devoted to their metal complexes. Metal
complexes of Schiff bases derived from DHA have
been reported with no structural verification [3]. Their
metal complexes with Ni(II), Cu(II), Zn(II), Cd(II),
and Co(II) were involved in pharmaceutical studies
[4, 5]. Metal complexes of first transition series with
DHA based hydrazone [6,7], their photocleavage and
antibacterial activity were studied for 4-hydroxy-N'-[1-
(4-hydroxy-5-methyl-2-oxo-2H-pyran-3-yl)ethylidene]-
benzohydrazide [8]. In continuation of our earlier
research [9,10], herein we present the study of
complexation of hydrazone based ketimine with 3d,
4d, and 5d metals and biological activity of the
synthesized complexes.
1
IR-420 spectrophotometer. H and 13C NMR spectra
were measured on a Bruker AM-250 spectrometer
using DMSO-d6 as a solvent and TMS as an internal
standard. UV-Vis spectra were recorded on a
Shimadzu UV-1700 spectrophotometer.
Synthesis of the ligand (E)-N'-[1-(2-hydroxy-6-
methyl-4-oxo-4H-pyran-3-yl)ethylidene]-4-nitro-
benzohydrazide (Scheme 1). To 4-nitrobenzoic acid (5 g,
0.03 mol) dissolved in 50 mL of methanol was added
H2SO4 (conc.) (3 mL) as a catalyst. The mixture was
refluxed upon stirring for 12 h. Upon completion of
the process, a solution of NaHCO3 was added until
EXPERIMENTAL
All chemicals used were of high purity. Analytical
grade solvents were further purified and dried
142

143
SELECTIVE COMPLEXATION OF HYDRAZONE BASED KETIMINE
Scheme 1.
H
O
N
H2N
C
COOCH3
COOH
H6N2O
C2H5OH (20 mL )
50 mL CH3OH
H2SO4 (3 mL )
Ethanol
CH3COOH
O2N
O2N
4-Nitrobenzoic acid
NO2
Methyl 4-nitrobenzoate
4-Nitrobenzohydrazide
O
O
O
C
NO2
NO2
CH3
H
N
H
N
H3C
OH
OH
N
C
C
O
O
O
N
C
C
O
Dehydroacetic acid
CH3
CH3
H3C
O
O
H3C
OH
HL
A
B
(E)-N'-[1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene]-4-nitrobenzohydrazide
M2+ = Cu2+, Zn2+, Cd2+, Pd2+, Ni2+
EtOH
+
NH3
M3+ = La3+, Ce3+, Fe3+, Nd3+
M2+/ M3+
NO2
NO2
H
N
N
O
O
N
C
C
O
O
N
C
C
O
M
OH
CH3
CH3
M
H3C
O
H3C
O
2
2
M(L)2
evolution of CO2 was over. The oily product was
washed and extracted with ethyl acetate, purified by
column chromatography, then treated further with
10 mL of hydrazine hydrate using ethanol (20 mL) as a
solvent, and refluxed for 6 h. The reaction was
quenched by pouring the mixture on ice to produce
fluffy hydrazide, which was washed with large volume
of water to remove the excess of hydrazine hydrate.
The product obtained was recrystallized from ethanol
to give pale yellow fluffy solid, yield 85%. To a
solution of DHA (2.184 g, 0.013 mol) in 15mL of
ethanol, 4 drops of glacial acetic acid were added and
the mixture was stirred till all components were
solubilized. 4-Nitrobenzocarboxyhydrazide (2 g,
0.013 mol) was dissolved in C2H5OH (20 mL) and
added to the reaction mixture dropwise. Fluffy shiny
yellow precipitate was formed upon refluxing the
mixture for 4 h. Yield 94%, mp 185–187°C. FT-IR
spectrum, ν, cm–1 (J, Hz): 3645 (OH), 3077 (N–H),
1696 (C=O), 1638 (C=N). 1H NMR spectrum, δ, ppm:
2.14 s (3H, CH3), 2.50 s (3H, CH3), 5.8 s (1H,
olefinic), 8.15 d (2H, J = 8.157, Ph), 8.3 d (2H, J =
13
8.38), 11.95 s (1H, NH), 16.06 s (1H, OH). C NMR
spectrum, δ, ppm: 17.54, 19.75, 95.44 (C=C), 106.27
(C=C), 124.18, 129.94, 137.70, 150.08 (Ph), 162.76
(C=N), 163.64 (C=O), 163.83(C=O), 171.45, 182.30.
Found, %: C 54.57; H 3.86; N 12.67. C17H13NOS.
Calculated, %: C 54.38; H 3.96; N 12.68.
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AHMAD et al.
1
Synthesis of metal complexes. To an ethanolic
(C=N), 1489 (C=C), 687 (Pd–O), 667 (Pd–N). H
NMR spectrum, δ, ppm: 2.07 s (3H, CH3), 2.84 s
(3H,CH3), 3.3 s (4H, H2O), 5.78 s (1H, olefinic), 8.24
m ( 4H, J = 8.243 Ph), 11.04 s (1H, NH). 13C NMR
spectrum, δC, ppm: 17.39, 19.54, 94.18 (C=C), 107.90
(C=C), 123.41, 129.01, 145.02, 148.26 (Ph), 160.63
(C=N), 163.97 (C=O), 181.59 (C=O). Found, %: C
47.41; H 3.53; N 10.62. C30H24N6O12Pd. Calculated,
%: C 46.98; H 3.15; N 10.96.
solution of ligand, HL (10 mL, 2.0 mmol), an ethanolic
solution of metal chloride (5 mL, 1.0 mmol) was added
dropwise upon constant stirring. pH Of the reaction
mixture was maintained at ca 7.5 by adding ammonia
solution dropwise and stirred at room temperature for
about 6h. The precipitated solid metal complex was
filtered off, washed with hot ethanol, petroleum ether,
and finally air-dried.
Cu(L)2. Brown solid, 69%, mp 340°C (decomp.).
IR spectrum, ν, cm–1: 3370 (NH), 3335 (CH), 1687
(C=O), 1558 (C=N), 1556 (C=C), 542 (Cu–O), 444
(Cu–N). Diamagnetic. Found, %: C 47.89; H 4.49; N
10.92. C30H24N6O12Cu. Calculated, %: C 47.76; H
3.34; N 11.61. Ni(L)2. Orange red precipitate, 71%, mp
337°C (decomp.). IR spectrum, ν, cm–1: 3205 (NH),
3053 (CH), 1690 (C=O), 1558 (C=N), 1513 (C=C),
575 (Ni–O), 485 (Ni–N). Diamagnetic. Found, %: C
49.37; H 3.49; N 10.98. C30H24N6O12Ni. Calculated,
%: C 50.10; H 3.36; N 11.68.
La(L)2Cl2. Yellow solid, 75%. mp 340°C (decomp.).
IR spectrum, ν, cm–1: 3363 (OH), 1698 (C=O), 1530
(C=N), 1487 (C=C), 530 (La–O), 411 (La–N). H
1
NMR spectrum, δ, ppm: 2.10 s (3H, CH3), 2.50 s
(3H,CH3), 3.3 s (4H, H2O), 5.66 s (1H, olefinic), 8.20
d (4H, J = 8.20 Ph), 15.65 s (1H, OH). 13C NMR
spectrum, δC, ppm: 17.32 (CH3), 94.18 (C=C), 107.90
(C=C), 123.32, 128.92, 145.10, 148.13 (Ph), 158.92,
160.59 (C=N), 163.97 (C=O), 164.02 (C=O). Found,
%: C 41.86; H 2.75; N 8.74. C30H24N6O12Cl2La.
Calculated, %: C 41.40; H 2.78; N 9.66.
Cd(L)2. Yellow solid, 59%, mp 328°C (decomp.).
IR spectrum, ν, cm–1: 3423 (OH), 1694 (C=O), 1536
(C=N), 715 (Cd–O), 518 (Cd–N). H NMR spectrum,
Nd(L)2Cl2. Yellow solid, 67%, mp 343°C (decomp.).
IR spectrum, ν, cm–1: 3430 (OH), 1657 (C=O), 1549
(C=N), 1463 (C=C), 716 (Nd–N), 533 (Nd–O). H
1
1
δ, ppm: 2.05 s (3H, CH3), 2.5 s (3H,CH3), 3.3 s (4H,
H2O), 5.65 s (1H, olefinic), 8.20 m (4H, J = 8.243 Ph),
15.64 s (2H, OH.). 13C NMR spectrum, δC, ppm: 17.39,
19.54, 94.18 (C=C), 107.90 (C=C), 123.41, 129.01,
145.02, 148.26 (Ph), 160.63 (C=N), 163.97 (C=O),
181.59 (C=O). Found, %: C 45.91; H 3.36; N 10.38.
C30H24N6O12Cd. Calculated, %: C 46.62; H 3.13; N
10.87.
NMR spectrum, δ, ppm (J, Hz): 2.02 s (3H, CH3), 2.51
s (3H, CH3), 3.3 s (4H, H2O), 5.51 s (1H, olefinic),
8.24 t (4H, J = 8.243, Ph), 10.64 s (1H, NH), 15.49 s
13
(1H, OH). C NMR spectrum, δC, ppm: 17.39 (CH3),
107.90 (C=C), 123.41, 129.01, 145.02, 148.26 (Ph),
160.63 (C=N), 163.97 (C=O). Found, %: C 41.35; H
2.54; N 10.03. C30H24N6O12Cl2Nd. Calculated, %: C
41.15; H 2.76; N 9.60.
Zn(L)2. Yellow solid, 85%, mp 319°C (decomp.).
IR spectrum, ν, cm–1: 3345 (OH), 1696 (C=O), 1545
(C=N), 554 (Zn–O), 438 (Zn–N). H NMR spectrum,
Ce(L)2Cl2. Yellow solid, 69%, mp 333°C (decomp.).
IR spectrum, ν, cm–1: 3419 (OH), 1657 (C=O), 1532
(C=N), 1488 (C=C), 531 (Ce–O), 302 (Ce–N). H
1
1
δ, ppm: 2.50 s (3H, CH3), 2.59 s (3H,CH3), 3.3 s (4H,
H2O), 5.78 s (1H, olefinic), 8.27 s (4H, Ph), 15.89 s
(2H, OH); 13C NMR spectrum (75 MHz, DMSO-d6),
δC, ppm: 17.35, 19.60, 95.18 (C=C), 105.90 (C=C),
125.41, 130.01, 144.02, 147.26 (Ph), 162.63 (C=N),
164.97 (C=O), 182.59 (C=O). Found, %: C 48.21; H
4.06; N 10.88. C30H24N6O12Zn. Calculated, %: C 49.64;
H 3.33; N 11.47.
NMR spectrum, δ, ppm (J, Hz): 1.99 s (3H, CH3), 2.51
s (3H, CH3), 3.3 s (4H, H2O), 5.43 s (1H, olefinic),
8.23 d (2H, J = 8.22 Ph), 8.35 d (2H, J = 8.35), 15.23 s
13
(1H, OH). C NMR spectrum, δC, ppm: 17.32 (CH3),
107.56 (C=C), 123.43, 129.11, 145.00, 148.32 (Ph),
163.81 (C=O), 164.02 (C=O), 181.34. Found, %: C
41.91; H 2.93; N 8.93. C30H24N6O12CeCl2. Calculated,
%: C 41.34; H 2.78; N 9.64.
Fe(L)2Cl2. Black solid, 55%, mp 350°C (decomp.).
IR spectrum, ν, cm–1: 3343 (OH), 1700 (C=O), 1549
(C=N), 1464 (C=C), 452 (Fe–O), 375 (Fe–N). Dia-
magnetic. Found, %: C 45.03; H 3.47; N 10.93.
C30H24N6O12Cl2Fe. Calculated, %: C 45.77; H 3.07; N 10.67.
UV-Vis spectra. Bands in the range between 400
and 800 nm were assigned to d–d transitions and in the
range of 220 to 400 nm to π→π*, n→π* and ligand to
metal charge transfer.
Pd(L)2. Yellow solid, 85%, mp 319°C (decomp.).
IR spectrum, ν, cm–1: 3345 (OH), 1682 (C=O), 1537
DNA binding. The binding interactions between
metal complexes and DNA were studied by electronic
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SELECTIVE COMPLEXATION OF HYDRAZONE BASED KETIMINE
absorption in the wavelength range of 258–780 nm.
DNA interactions of the free ligand and metal
complexes were studied individually by using SS-
DNA 0.66 µM solution. The solution of SS–DNA was
stirred for ca 24 h at 4°C. Purity of SS–DNA free from
protein was confirmed by a band at 259 nm and the
ratio of absorbance at λmax 260 and 280 nm which was
1.84. Concentrated stock solutions of the ligand and
complexes were prepared in DMSO. On addition of
0.1mL of DNA to the compound, the time interval
between observations was 60 s.
between 1620 and 1545 cm–1 in ketimine ligand was
assigned to C=N stretching vibrations. This band was
shifted downfield for ca 50 cm–1 in the spectra of
complexes, which indicated the participation of the
azomethine nitrogen in coordination with the metals.
In the spectrum of Cu(L)2 the azomethine C=N
band was recorded at 1558 cm–1 with a downfield shift
of 80 cm–1 as compared with that of the free ligand.
The main difference between Cd(L)2 spectrum and the
spectra of Cu(L)2 and Ni(L)2 was disappearance of the
N–H band and the band of O–H recorded at 3423 cm–1.
In the spectrum of Zn(L)2 the similar band of O–H was
recorded at 3384 cm–1. In the spectra of the other
complexes the O–H bands were also recorded in the
same region.
1H NMR spectra of the complexes were in good
agreement with the proposed structures. Moderate
shifts of O–H signals in the spectra of complexes in
comparison with the spectrum of the ligand was
attributed to its shielding upon complexation. Signal of
the N–H at 11.95 ppm characteristic for the ligand was
not observed in the spectra of the complexes indicating
the complexation site. MS spectra of the synthesized
complexes supported their composition.
Antibacterial activity assay. All synthetic com-
pounds were screened in vitro for their antibacterial
activity against four bacterial strains including three
Gram-positive (Staphylococcus aureus, Micrococcus
luteus and Bacillus subtilus) and one Gram-negative
strain (Escherichia coli) using the agar disc diffusion
method. Kanamycin drug was used as a positive
control. The synthesized compounds were dissolved in
200 µg /mL of DMSO. DMSO was used as a negative
control.
Alpha-amylase inhibition assay. Alpha amylase
inhibition assay was performed on all synthetic com-
pounds at concentration of 400 µg/mL by using the test
compounds, PC, amylase; NC, negative control (DMSO).
In UV-Vis spectra shifts of λmax recorded for the
ligand indicated formation of its complexes with the
metals (Fig. 1).
Acetylcholinesterase inhibition assay. Acetyl-
choline esterase inhibition assay was performed for all
compounds at concentration of 400 µg/mL. The
activity was tested against acetylcholine esterase
enzyme by using DMSO as a negative control.
The interaction of DNA with the ligand and its
metal complexes was studied by UV-Vis spectroscopy.
All the metal complexes demonstrated the intercalative
mode of DNA binding indicated by blue shift with the
addition of 0.1mL of DNA. The max and min shift
differences of 19.5 nm and 5.5 nm were recorded for
La(L)2 and Pd(L)2. The capability of binding strength
of compound to DNA can be shown in the term of
binding constant. Gibb’s free energy value was
observed to be maximum for Zn(L)2. In its spectrum
the intense band at 370 nm was attributed to the ligand
to metal charge transfer absorption, and another at 265 nm
was assigned to the π–π* transition of the aromatic
chromophore. Polarity of the ligand, coordination
geometry, ligand donor atom type and metal ion type
dictate the chelating ability of the complex. Strong
stacking interaction between an aromatic chromophore
and the base pairs of DNA results in the red shift while
the cause of hypochromism is the intercalative mode of
DNA binding. Similarly, the hyperchromism is the
result of the electrostatic mode of DNA binding.
Strong π–π* stacking interaction between the aromatic
Alpha-glucosidase inhibition assay. Alpha-
glucosidase inhibition assay was performed at con-
centration of 400 µg/mL by addition of alpha gluco-
sidase enzyme in test compounds and using DMSO as
a negative control.
Brine shrimp cytotoxicity assay. Shrimp’s larvae
were subjected to the compounds at concentration of
400 µg/mL. The percent mortality was determined
after 24 h.
Anti-cancer activity assay. Cytotoxic activity of
compounds was evaluated in 96-well flat-bottomed
microplates by using the standard MTT colourimetric
assay culturing HeLa cells, cervical cancer.
RESULTS AND DISCUSSION
The comparative analysis of IR spectra of the
ligand and the metal complexes indicated their
differences including the new bands assigned to M–O
and M–N in the spectra of complexes. The band
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AHMAD et al.
Hypochromic shift
K = 1.14×104 M–1
ΔG = –23.14 kJ/mol
Fig. 2. The sample absorption spectrum of the complex
Zn(L)2 at various concentrations of DNA, and determina-
tion of Gibb’s free energy (ΔG) and binding constant (K).
Fig. 1. UV-Vis spectra of the ligand and its metal complexes.
chromophore ligand of the metal complex and base
pairs of DNA exhibit significant hypochromism and
redshift. Intercalative binding between DNA and metal
complex is responsible in hypochromism with slight
bathochromic shift (Fig. 2).
The synthesized compounds were screened in vitro
for their antibacterial activity against four bacterial
strains including three Gram-positive (Staphylococcus
aureus, Micrococcus luteus, and Bacillus subtilus) and
one Gram-negative strain (Escherichia coli) using agar
disc diffusion method (Table 2). Kanamycin drug was
used as a positive control. DMSO solutions of
concentration 200 µg/mL DMSO were used. DMSO
was used as a negative control. The results presented in
Table 2 indicated that this type of activity was deter-
mined by the nature of metals. Lanthanum complex
activity similar to that of the ligand was due to its very
low solubility.
Biological activities of the compounds. Alpha-
amylase enzyme inhibition assay was performed for all
synthesized compounds at concentration of 400 µg/mL.
The accumulated data indicated all compounds to be
appreciably active. The cerium and nickel complexes
demonstrated excellent activity which was different
from other activities presented herein (Table 1).
Acetylcholine esterase inhibition assay performed
for all synthesized compounds demonstrated no
activity of the complexes against acetylcholinesterase
enzyme.
Table 2. Antibacterial activity of ligand and its synthesized
complexes (zone of inhibition at 400 µg/mL)
E.
Compound E. coli M. leuteus
S. aureus
Table 1. Results of alpha amylase inhibition assay
aerogenes
Compound
HL
% Age scavenging 400 µg/mL
Control
HL
33.2
–
26.8
–
22.5
–
23.7
–
51.5
55.5
53.7
59.9
–
Cu(L)2
Cu(L)2
9.9
17.8
16.5
18.8
7.8
10.3
–
6.7
15.5
8.9
–
7.6
13.7
–
6.3
1.9
15.8
–
Zn(L)2
Fe(L)2Cl2
Pd(L)2
Ni(L)2
Cd(L)2
Ni(L)2
17.1
–
Fe(L)2Cl2
Pd(L)2
52.3
27.4
53.1
56.3
60.1
Ce(L)2Cl2
Cd(L)2
–
–
5.7
–
7.4
11.2
4.5
–
6.4
3.3
-
Nd(L)2Cl2
La(L)2Cl2
Ce(L)2Cl2
Zn(L)2
Nd(L)2Cl2
La(L)2Cl2
2.4
–
–
–
–
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SELECTIVE COMPLEXATION OF HYDRAZONE BASED KETIMINE
Among screened compounds the complexes Cu(L)2
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demonstrated high brine shrimp cytotoxicity at
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CONFLICT OF INTEREST
No conflict of interest was declared by the authors
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 1 2019