Synthesis, spectral characterization and eukaryotic DNA degradation of thiosemicarbazones and their platinum(IV) complexes

Article abstract of DOI:10.1016/j.saa.2007.03.010

The condensation products of acetophenone (or its derivatives), salicylaldehyde and o-hydroxy-p-methoxybenzophenone with thiosemicarbazide and ethyl- or phenyl-thiosemicarbazide are the investigated thiosemicarbazones. Their reactions with H₂Pt

Full text of DOI:10.1016/j.saa.2007.03.010

Available online at www.sciencedirect.com
Spectrochimica Acta Part A 69 (2008) 56–61
Synthesis, spectral characterization and eukaryotic DNA degradation of
thiosemicarbazones and their platinum(IV) complexes
G.A. Al-Hazmia, N.M. El-Metwallyb, O.A. El-Gammalb, A.A. El-Asmyb,∗
a Chemistry Department, Faculty of Science, Taiz University, Taiz, Yemen
b Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Received 20 December 2006; received in revised form 22 February 2007; accepted 9 March 2007
Abstract
The condensation products of acetophenone (or its derivatives), salicylaldehyde and o-hydroxy-p-methoxybenzophenone with thiosemicar-
bazide and ethyl- or phenyl-thiosemicarbazide are the investigated thiosemicarbazones. Their reactions with H2PtCl6 produced Pt(IV) complexes
characterized by elemental, thermal, mass, IR and electronic spectral studies. The coordination modes were found mononegative bidentate in
the acetophenone derivatives and binegative tridentate in the salicylaldehyde derivatives. The complexes were analyzed thermogravimetrically
and found highly stable. Some ligands and their complexes were screened against Sarcina sp. and E. coli using the cup-diffusion technique.
[Pt(oHAT)(OH)Cl] shows higher activity against E. coli than the other compounds. The degradation power of the tested compounds on the calf
thymus DNA supports their selectivity against bacteria and not against the human or related eukaryotic organisms.
© 2007 Elsevier B.V. All rights reserved.
Keywords: Pt(IV) complexes; Mass spectra; Thermal analysis; Biological activity
1. Introduction
2.1. Preparation of the ligands
Aninterestingpointforinvestigatingthiosemicarbazonesand
their complexes is the antimicrobial activity; the reported work
shows a high dependence on their substituents [1–4]. Several
of thiosemicarbazones have been used for metal ion determina-
tion. The previous studies focused on their structural elucidation
[5–9]. Recently, thiosemicarbazones were reported involving
their complexes with different metal ions [10–14].
In this work, substituted thiosemicarbazones (Scheme 1)
and their Pt(IV) complexes were prepared, characterized and
screened for their biological activity.
Theinvestigatedligandswerepreparedaspreviouslyreported
[13]. The synthesis of o-hydroxyacetophenone thiosemicar-
bazone (H2oHAT) was explained in detail as an example. 1:1
molar amounts of o-hydroxyacetophenone (20 mL, 0.1 mol) and
ethanolic solution (30 mL) of thiosemicarbazide (9.1 g, 0.1 mol)
were heated for 2 h under reflux on a water bath. Drops of glacial
acetic acid were added at the onset of the reflux. The precipi-
tate thus formed was removed by filtration, recrystallized from
absolute ethanol and dried. The purity was checked by TLC. The
yield of the prepared ligands was found in the range 65–80%.
1
Identification of the ligands was confirmed by IR spectra, H
NMR and mass spectra.
2. Experimental
2.2. Preparation of Pt(IV) complexes
Reagent grade (BDH) materials and solvents were purified
according to the reported methods [15]. Platinum metal pur-
chased from Merck was used in the preparation of H2PtCl6. All
other chemicals were used without further purification.
The complexes were prepared by heating 0.01 mol from each
ligand and [H2PtCl6] in 50 mL aqueous ethanol (v/v) solution
with the addition of 0.5 g of sodium acetate to raise the medium
pH. The reaction mixture was heated under reflux for 4 h. The
precipitate thus formed was filtered off, washed several times
with ethanol and diethylether then dried. As an example, the
preparation of [Pt(AET)Cl3][PtCl4] is described in detail. To
∗
Corresponding author. Tel.: +20 101645966.
E-mail address: aelasmy@yahoo.com (A.A. El-Asmy).
1386-1425/$ – see front matter © 2007 Elsevier B.V. All rights reserved.
doi:10.1016/j.saa.2007.03.010

G.A. Al-Hazmi et al. / Spectrochimica Acta Part A 69 (2008) 56–61
57
madzu thermogravimetric analyzer, TGA-50. The nitrogen flow
and heating rate were 20 mL/min and 10 ◦C/min, respectively,
using ␣-Al2O3 as reference. The pH-metric titrations were per-
formed using a Metrohm E536 potentiograph equipped with
a 665 DOSIMAT (Metrohm, Herisau, Switzerland). The com-
bined glass electrode was standardized using buffer solutions
produced by Fisher’s, NJ, USA. Carbon and hydrogen content
for the investigated complexes was determined at the Microan-
alytical Unit, Cairo University, Egypt. Pt(IV) and Cl contents
were determined by the well-known methods [16].
2.4. Antimicrobial activity
The ligands and complexes were screened against Sarcina sp.
as Gram-positive and E. coli as Gram-negative bacteria using the
cup-diffusion technique [17]. A 0.2 mL of each (10 ␮g/mL) was
placed in the specified cup made in the nutrient agar medium on
which a culture of the tested bacteria has been spread to produce
uniform growth. After 24 h incubation at 37 ◦C, the diameter of
inhibition zone was measured as mm.
2.5. Genotoxicity
Scheme 1. Structure of thiosemicarbazones.
A solution of 2 mg of calf thymus DNA was dissolved in
1 mL of sterile distilled water. Stock concentrations of the inves-
tigated ligands and their complexes were prepared by dissolving
2 mg/mL DMSO. An equal volume of each compound and DNA
were mixed thoroughly and kept at room temperature for 2–3 h.
The effect of the chemicals on the DNA was analyzed by agarose
gel electrophoresis. A 2 ␮L of loading dye was added to 15 ␮L of
the DNA mixture before being loaded into the well of an agarose
gel. The loaded mixtures were fractionated by electrophoresis,
visualized by UV and photographed.
50 mL reaction flask, add 0.22 g (1 mmol) of 1-acetophenone-
4-ethylthiosemicarbazone dissolved in 20 mL ethanol and 0.4 g
(1 mmol) of H2PtCl6, dissolved in 20 mL distilled H2O. 0.5 g of
sodium acetate is added to the reaction and heated under reflux
on a water bath for 2 h. The precipitate thus formed is removed
by filtration, washed with distilled water and ethanol then dried
in an oven at 90 ◦C.
2.3. Physical measurements
The infrared spectra were recorded as KBr discs on a
1
Mattson 5000 FTIR Spectrophotometer. The H NMR spectra
3. Results and discussion
in d6-DMSO were recorded on a Varian Gemini Spectrome-
ter (200 MHz) at Cairo University. The UV/vis spectra were
recorded on UV2 Unicam UV/vis Spectrophotometer using 1 cm
path length quartz cuvette with a stopper. Thermogravimetric
curves (TGA and DrTG, 20–1000 ◦C) were recorded on a Shi-
The reaction between HAT, HAET, HAPT, HApCPT,
H2oHATS, HpNATS, H2ST, H2SET, H2SPT or H2HyMBpCPT
(Scheme 1) and H2PtCl6 yields complexes that have differ-
ent formulae, are stable in air, insoluble in water and common
Table 1
Physical properties, elemental analysis and formula weights of the complexes
Complex/formula
Formula weight
Color
Yield (%) mp (◦C) Found (Calcd.) (%)
Founda
Calcd.
C
H
Pt
[Pt(AT)2(H2O)2]Cl2, C18H24PtN6O2S2Cl2
[Pt(AET)Cl3][PtCl4], C11H14Pt2N3SCl5
[Pt(APT)(H2O)(C2H5OH)Cl2]Cl, C17H22PtN3O2SCl3
[Pt(ApClPT)Cl3]H2O, C16H19PtN3O3SCl3
[Pt(pNAT)Cl3(H2O)], C9H11N4O3SPtCl3
688
–
–
–
554
689.0
789.6
634.3
599.8
556.6
Brown
Brown
Brown
Brown
Yellowish
brown
83
80
78
81
77
32.0 (31.4)
17.1 (16.7)
33.0 (32.2)
32.6 (32.0)
19.3 (19.4)
3.4 (3.5)
1.9 (1.8)
3.8 (3.5)
3.8 (3.2)
1.8 (2.0)
28.7 (28.4)
49.4 (49.5)
30.1 (30.8)
32.9 (32.6)
35.5 (35.1)
>300
>300
>300
>300
[Pt(oHAT)(OH)Cl], C9H10N3O2SPtCl
451
450
623
577
640
452.8
450.2
623.7
577.8
641.7
Brown
Brown
Brown
Brown
Brown
60
71
86
81
75
>300
>300
>300
>300
>300
24.2 (23.9)
20.1 (21.3)
18.9 (19.3)
33.2 (33.3)
39.5 (39.3)
2.0 (2.2)
1.9 (2.0)
2.0 (2.9)
3.1 (2.3)
2.7 (2.6)
43.5 (43.1)
43.2 (43.4)
31.2 (31.3)
33.7 (33.8)
30.6 (30.5)
[Pt(ST)(OH)Cl]0.5H2O, C8H9PtN3O2.5SCl
[Pt(H2SET)Cl3]Cl·3H2O, C10H18PtN3O4SCl4
[Pt(SPT)(C2H5OH)Cl2], C16H19PtN3O2SCl2
[Pt(HyMBPT)Cl2], C21H17PtN3O2SCl2
a
Values obtained from mass spectra.

58
G.A. Al-Hazmi et al. / Spectrochimica Acta Part A 69 (2008) 56–61
organic solvents, but are completely soluble in DMF and DMSO.
Their elemental analyses are presented in Table 1.
3.1. IR spectral studies
The important IR bands of the ligands and their complexes
are summarized in Table 2. The data reveal the formation of
two types of chelates. The ligands in the first type behave as
mononegative bidentate and coordinate through the azome-
thine (C N) and thiol (C–S) groups; [Pt(AT)2(H2O)2]Cl2,
[Pt(AET)Cl3][PtCl4],
[Pt(APT)(H2O)(C2H5OH)Cl2]Cl,
[Pt(pNAT)Cl3(H2O)] and [Pt(ApCPT)Cl3]H2O are the com-
plexes of this type. The bonding sites are assigned based
on the disappearance of ␯(N2H), the appearance of a new
band due to ␯(C N)* at the same position for the ␯(C N)thio
,
the shift of ␯(C N) to lower frequency [18] by 9–54 cm−1
(coordination of the azomethine nitrogen is also consistent
with the presence of a new band at 402–462 cm−1, assignable
to ␯(M–N) [19] vibration) and finally the thioamide band (IV)
is absent with the appearance of new bands at 606–656 and
346–370 cm−1 due to ␯(C–S) [20] and ␯(M–S) vibrations,
respectively. The reduction of thioamide band (III) observed at
970 cm−1 is possible if the coordination occurs both through
N and S atoms. The bands observed at 485 and 506 cm−1 in
the spectra of [Pt(AT)2(H2O)2]Cl2, [Pt(pNAT)Cl3(H2O)] and
[Pt(APT)(H2O)(C2H5OH)Cl2]Cl are assigned to ␯(M–O) of
the coordinated water or the ethanol OH. The band observed
at 260–330 cm−1 in the chloro complexes is due to ␯(M–Cl)
[21]. Furthermore, the signal observed at 12.07 ppm (s, 1H)
1
in the H NMR spectrum of [Pt(APT)(H2O)(C2H5OH)Cl2]Cl
may be due to the ethanol OH proton where the broad signal at
4.849 ppm (br) is due to the coordinated water molecule.
The second mode of chelation was found through C N,
C–S and deprotonated phenolic OH in which the ligand
acts as binegative tridentate. This behavior is found in the
complexes [Pt(ST)(OH)Cl]0.5H2O, [Pt(SPT)(C2H5OH)Cl2],
[Pt(oHAT)(OH)Cl] and [Pt(HyMBPT)Cl2]. Elucidation of this
mode is proposed by: (i) the disappearance of ␯(N2H); (ii) the
shift of ␯(C N) bands by 9–83 cm−1 to lower frequency; (iii)
the phenolic oxygen of these ligands, after deprotonation, occu-
pies the third coordination site by the disappearance of ␯(OH)
band; (iv) the band at 485–505 cm−1 in the spectra of the com-
plexes is assignable to ␯(Pt–O); (v) the disappearance of ␯(C S)
at 778–835 cm−1 in the complex spectra with the appearance
of new bands at 606–638, 345–370 and 405–453 cm−1 due to
␯(C–S), ␯(Pt–S) and ␯(Pt–N), gave an evidence for S, N and
O donors. In the spectrum of [Pt(ST)(OH)Cl]0.5H2O, the dou-
blet strong bands at 3451 and 3422 may be due to the ␯(OH)
vibrations of the two OH; the second is due to the ␯(OH) that
exists in the ligand. Strong evidence for the presence of OH
1
in [Pt(ST)(OH)Cl]0.5H2O comes from its H NMR spectrum
which shows a signal at 11.18 ppm (s, 1H).
3.2. UV and visible spectra
The solution and solid state spectra are more or less
the same indicating that the solvent has little effect on the

G.A. Al-Hazmi et al. / Spectrochimica Acta Part A 69 (2008) 56–61
59
Table 3
Electronic spectral data of Pt(IV) complexes
Compound
State
Charge transfer and intraligand bands (cm−1
)
[Pt(AT)2(H2O)2]Cl
[Pt(AET)Cl3]PtCl4
DMF
DMF
DMF
DMF
DMF
DMF
DMF
20,780
–
–
–
–
–
–
28,735; 30,675
27,855
27,780; 31,745
28,090
26,455
26,810; 30,865
27,030
24,096
23,474
24,095
[Pt(APT)(H2O)(C2H5OH)Cl3]
[Pt(ST)(OH)Cl]0.5H2O
[Pt(H2SET)Cl3]Cl·3H2O
[Pt(SPT)(C2H5OH)Cl2]
[Pt(HyMBPT)Cl2]
–
21,210
24,210
Pt(IV) complexes. The electronic spectra of the ligands in
plex and removed with the OH in the first step leaving a peak at
425. The strongest peak (base beak) at m/e = 169 represents the
stable species C7H5NO2S after which multipeaks are observed
ending with 4C at m/e = 50 with 22% abundance.
The second example is the ms of [Pt(HyMBPT)Cl] (Fig. 1)
which exhibits triplet peak at 638 (8.92%), 639 (14.48%)
and 640 (10.84%) representing the molecular ion peak,
C21H17PtN3O3SCl2. The second peak at m/e 416 represents the
removal of C7H5N2SCl2 after which Pt metal is removed. The
base peak at m/e 78 represents C6H5 moiety.
*
*
DMF show ␲ → ␲ band at 32,790–40,820 cm−1 and n → ␲
band at 28,570–30,960 cm−1; little change is observed on
*
the spectra of their complexes with a new n → ␲ band at
27,000–28,250 cm−1. The band at 22,680–24,040 cm−1 in the
spectra of the complexes may be due to LMCT. Previous stud-
ies on thiosemicarbazone complexes proved that the band in the
region 25,000–26,040 cm−1 is assignable to S(␴) → Cu(II) tran-
sition, the 20,600 cm−1 band is due to S(ꢀ) → Cu(II) transition
[22,23] whereas the band at 21,790–24,750 is due to O → M(II).
Table 3 shows the spectral bands of the investigated complexes.
The spectra displayed charge transfer and spin allowed transi-
tions correlated with an octahedral geometry [24].
3.4. Thermal studies
The TG thermograms of some complexes were studied in
the temperature range 30–800 ◦C. The data of all decomposi-
tion steps are collected in Table 4. As shown the complexes
are not decomposed completely. It is observed that the com-
plexes are stable except [Pt(H2SET)Cl3]Cl·3H2O in which its
first decomposition step at 23–91 ◦C represents the removal of
one of the water molecule. As a representative example for the
decompositionof thesecomplexes, theTGof[Pt(HyMBPT)Cl2]
shown in Fig. 2 is described. The complex is stable till 194 ◦C
and its thermogram reveals two main decomposition stages. The
C13H11N2Cl2 moiety may be eliminated in the first step which is
major (Found 40.7, Calcd. 41.6%). The second step suggests the
3.3. Mass spectra
The mass spectra of some complexes are recorded and the
obtained molecular ion peaks confirm the proposed formulae.
The found and calculated molecular weights are presented in
Table 1. The mass spectrum of [Pt(ST)(OH)Cl]0.5H2O shows
quartet peak at 449, 450, 451 and 452 with 2.39, 7.49, 4.21
and 3.85% abundances, respectively. The one at 450 may rep-
resent the molecular ion peak of the complex; the others are
isotopic species. The formula of the complex contains half water
molecule which may exist in hydrogen bonding with the com-
Table 4
Thermogravimetric data of some investigated complexes
Complex
Temperature (◦C)
Species removed
Found (Calcd.) (%)
[Pt(APT)(H2O)(C2H5OH)Cl2]Cl, C17H22PtN3O2SCl3
194–329
330–412
413–541
542–800
–(C2H5OH + H2O + Cl2)
–Cl
–(CH3 + C7H6N2)
[Pt(C7H5NS)]
21.1 (21.3)
4.6 (5.6)
21.4 (21.0)
53.8 (52.0)
[Pt(ST)(OH)Cl]0.5H2O, C8H9PtN3O2.5SCl
174–244
245–342
343–517
518–800
–(0.5H2O + Cl + OH + NH2)
–CN
–C7H5
[PtNOS]
16.2 (17.2)
7.4 (6.0)
17.1 (20.0)
59.3 (57.2)
[Pt(H2SET)Cl3]Cl·3H2O, C10H18PtN3O4SCl4
23–91
92–203
204–416
417–629
630–800
–H2O
Stable
–(2H2O + 3Cl)
–(Cl + C2H5)
[Pt(C8H7N3SO)]
2.5 (2.9)
–
21.7 (22.8)
9.8 (10.4)
62.6 (62.5)
[Pt(SPT)(C2H5OH)Cl2], C16H17PtN3O2SCl2
210–300
301–408
409–555
556–800
–(C2H5OH + C6H6N)
–Cl2
–C8H5N
25.4 (23.9)
12.9 (12.3)
22.0 (19.9)
44.1 (44.6)
[PtNOS]

60
G.A. Al-Hazmi et al. / Spectrochimica Acta Part A 69 (2008) 56–61
Table 5
Antimicrobial activity of the tested compounds
Compound
Diameter of growth zone of inhibition (mm)
E. coli
Sarcina
[Pt(H2SET)Cl3]Cl·3H2O (1)
[Pt(SPT)(C2H5OH)Cl2] (2)
H2HyMBPT (3)
[Pt(HyMBPT)Cl2] (4)
[Pt(ST)(OH)Cl]0.5H2O (5)
H2ST (6)
[Pt(pNAT)(H2O)Cl3] (7)
[Pt(oHAT)(OH)Cl] (8)
H2oHAT (9)
0
0
0
0
0
0
8
21
7
0
0
10
32
34
25
8
12
18
0
HpNAT (10)
0
than the Gram-positive bacterium (Sarcina). Compounds
number 3, 7, 8 and 9 are more potent in killing Sarcina sp.
than the others because of their relatively large zones of growth
inhibition. Also, compounds 7 and 8 exhibited low to moderate
inhibition on the growth of E. coli which can be classified to
wide host range because of their activity against Gram-positive
and Gram-negative bacteria. On the other hand, compounds 2, 3,
6 and 9 are only active against Gram-positive bacteria, i.e. have
narrow host range. The compounds may be arranged accord-
ing to their activity against Sarcina as: [Pt(oHAT)(OH)Cl]
> [Pt(NAT)(H2O)Cl3] > H2oHAT > H2HyMBpCPT > H2ST
> [Pt(SPT)(C2H5OH)Cl2] > HpNAT > [Pt(ST)(OH)Cl]0.5H2O
(5). It is observed also that o-hydroxyacetophenone thiosemi-
carbazone and its complex (Scheme 2) have higher activity
against E. coli than the other compounds. The sixth coordination
position is vacant and may be occupied and the complex may
act as a co-enzyme.
Fig. 1. The mass spectrum of [Pt(HyMBPT)Cl2].
expulsion of C8H6NO2S (Found 28.3, Calcd. 29.1%). A contin-
uous decomposition is taking place until 800 ◦C. The residue is
Pt (Found 30.9, Calcd. 30.4%).
3.5. Antimicrobial activity bioassay
The antimicrobial activity of some investigated ligands
and complexes against Sarcina sp. and E. coli is summa-
rized in Table 5. The ligands are H2HyMBpCPT (3), H2ST
(6), H2oHAT (9) and HpNAT (10), where the complexes
are [Pt(H2SET)Cl3]Cl·3H2O (1), [Pt(SPT)(C2H5OH)Cl2]
(2), [Pt(HyMBPT)Cl2] (4), [Pt(ST)(OH)Cl]0.5H2O (5),
[Pt(pNAT)Cl3(H2O)] (7) and [Pt(oHAT)(OH)Cl] (8). Growth
inhibition zones are proportional to the antimicrobial activity
of the tested compound. The data suggest that Gram-negative
bacterium (E. coli) was less affected by the tested chemicals
3.6. Eukaryotic DNA degradation test
Examination of the electrophoretic mobility (Fig. 3) of all
treatments in comparison to the control sample revealed that no
change in lanes 1, 2 and 3, whereas, slight downward shifts in
mobility are observed in lanes 4–10, and this was associated with
tailing of the DNA. Electrophoretic mobility shift and tailing of
DNA in any lane are indicative of the degradation of calf thymus
DNA. It is important to note that DNA degradation and antimi-
crobial activity against Gram-positive bacteria coincided real
well. However, the degradation powers of the tested chemicals
on the calf thymus DNA were very slight. This would support
Fig. 2. The TG and DrTG thermograms of [Pt(HyMBPT)Cl2].
Scheme 2. Structure of [Pt(oHAT)(OH)Cl].

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61
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The complexation between H2PtCl6 and the investigated
thiosemicarbazones proceed by the same technique but with
different modes of coordination depending on the substitutent
group. Most complexes are thermally stable and completely
undecomposed. The antimicrobial activity shows that some
compounds are more potent in killing Sarcina sp. Elec-
trophoretic mobility of all treatments revealed slight shifts in
lanes 4–10. The data of antimicrobial activity against Gram-
positive bacteria agree well with those of DNA degradation.
[23] J.P. Jasinski, J.R. Bianchani, J. Cueva, F.A. El-Saied, A.A. El-Asmy, D.X.
West, Z. Anorg, Allg. Chem. 629 (2003) 202.
Appendix A. Supplementary data
[24] G. Ponticelli, A. Spanu, M.T. Cocco, V. Onnis, Transition Met. Chem. 24
(1999) 370.
Supplementary data associated with this article can be found,
in the online version, at doi:10.1016/j.saa.2007.03.010.