World Applied Sciences Journal 33 (2): 336-342, 2015

ISSN 1818-4952
IDOSI Publications, 2015
DOI: 10.5829/idosi.wasj.2015.33.02.22206

Synthesis, Characterization and Antimicrobial Activity of Some

Mixed Trimethoprim -Sulfamethoxazole Metal Drug Complexes
1

Aderoju A. Osowole, 2Sherifah M. Wakil and 2Olaoluwa K. Alao

Inorganic Chemistry Unit, Department of Chemistry, University of Ibadan, Ibadan, Nigeria

2
Department of Microbiology, University of Ibadan, Ibadan, Nigeria

Abstract: Mixed drug metal(II) complexes of Trimethoprim (TMP, HL) and Sulfamethoxazole (SMX, HL1) were
synthesized and characterized by percentage metal, infrared and electronic spectroscopies, room temperature
magnetic moments, melting points and conductance measurements. The metal analysis revealed that the
complexes analyze as [M(HL)(HL1)X].nH2O,where M = Mn, Co, Ni, Cu, Fe, Zn and X= Cl2/SO4. Infrared spectra
data confirmed that coordination was via the SMXs sulphone oxygen and amino nitrogen atoms; and
TMPs amino and azomethine nitrogen atoms. The room temperature magnetic moment and electronic spectra
data indicated that the metal (II) complexes were all magnetically dilute and octahedral. The molar conductance
of the metal (II) complexes in DMSO confirmed that all the complexes were covalent. Interestingly, the in-vitro
antimicrobial studies on these metal (II) complexes, TMP and SMX against Bacillus spp, Escherichia
sp, Proteus mirabilis, Pseudomonas spp, Streptococcus pyogenes, Staphylococcus aureus and Candida
albicans showed that all the metal complexes, TMP and SMX had broad-spectrum antimicrobial activities
against these microbes, with the exception of the Ni (II) complex, with inhibitory zones range of 6.0-32.0 mm,
9.0- 29.0, 11.0-25.0 mm respectively.
Key words: Broad-spectrum

Covalent

Magnetically-dilute

INTRODUCTION

Octahedral Sulfamethoxazole

Trimethoprim

broad-spectrum antimicrobial agents in-vitro will be

verified as a continuation of our research in the field of
bioinorganic chemistry [18-22].

Extensive research on novel and innovative drugs is

predominantly a consequence of new emerging strains of
resistant micro-organisms [1]. The use of metal complexes
in medicine as chemotherapeutic agent, magnetic
resonance imaging contrast agent, rheumatic drugs are
well established [2 -6]. Trimethoprim is a broad-spectrum
antimicrobial agent with anti-parasitic activities [7].
Trimethoprim in combination with Sulfamethoxazole
(co-trimoxazole) is one of the most frequently prescribed
antibiotics in nephrology and Pneumocystis jirovecii
infections [8-10]. Detailed literature search revealed that
some work have been done on the metal (II) complexes
of Trimethoprim [11-13] or Sulfamethoxazole [14, 15].
Some work has been reported on co-trimoxazole and its
metal complexes [16, 17]. Thus, our aim is to investigate
the suitability of TMP and SMX in forming polymeric,
high spin and low spin complexes. In addition, the
potentials of these mixed ligand metal complexes as

MATERIALS AND METHODS

Materials and Reagents: Sulfamethoxazole and
Trimethoprim were gifts from Chemopharma Laboratories,
Lagos, Nigeria while Copper (II) sulphate pentahydrate,
Nickel (II) chloride hexahydrate, Cobalt (II) sulphate
heptahydrate, Manganese (II) chloride tetrahydrate, Iron
(II) sulphate heptahydrate and Zinc (II) sulphate
heptahydrate were obtained from Aldrich chemicals and
solvents were purified by distillation.
Preparation of [Mn (HL) (HL1) Cl2].H2O: 0.5 g
(1.72 mmole) of TMP (HL) and 0.4362 g (1.72 mmole) SMX
(HL1) were dissolved in 30 mL of methanol. To the
resulting homogenous solution, 0.3408 g (1.72 mmole) of
the Mn (II) Chloride tetrahydrate was added dry in bits

Corresponding Author: Aderoju A. Osowole, Inorganic Chemistry Unit, Department of Chemistry,

University of Ibadan, Ibadan, Nigeria. E-mail: aderoju30@gmail.com.

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World Appl. Sci. J., 33 (2): 336-342, 2015

while stirring and heating at 60C. The resulting

homogenous solution was then refluxed for 6 h, during
which the product formed. This was filtered, washed with
methanol and dried over silica gel. The same procedure
was used for the preparation of Co (II), Ni (II), Cu (II), Fe
(II) and Zn (II) complexes from their chloride and sulphate
salts respectively.
Physical Measurement: The electronic spectra of the
complexes in DMSO were recorded on a Perkin-Elmer 25
spect rophotometer and infrared spectra were recorded
as Kbr disc on a Perkin-Elmer FT-IR BX spectrometer.
The room temperature magnetic susceptibilities at 303K
were measured on Sherwood Susceptibility Balance MSB
Mark 1 and diamagnetic corrections were calculated using
Pascals constant, melting points were determined with
Mel-Temp electrothermal machine and molar conductance
of 1 x 10 3 M solutions in DMSO was obtained using
electrochemical analyzer Consort C933.

(a): M = Mn and Ni

Antimicrobial Assay: The antimicrobial activity of the

synthesized complexes as well as their metal-free ligands
was studied using the agar diffusion technique.
The bacteria and fungus used were identified laboratory
strains of Bacillus cereus, Escherichia coli, Proteus
mirabilis, Pseudomonas aeruginosa, Streptococcus
pyogenes, Staphylococcus aureus and Candida albicans.
The surface of the agar in a petri dish was uniformly
inoculated with 0.2 mL of 18 hour old test microbial
culture. Using a sterile cork borer, 5 mm wells were bored
into the agar. Then 0.06 mL of 10 mg/mL concentration of
each metal complex in DMSO was introduced into the
wells and the plates were allowed to stand on the bench
for 30 minutes before incubation at 37C for 24 hours, after
which inhibitory zones (in mm) were taken as a measure of
antimicrobial activity. The experiments were conducted in
duplicates and Streptomycin was used as the reference
drug.

(b): M = Zn, Co, Cu, Zn

Fig. 1: Proposed structures for some of the Metal (II)
complexes
(When M = Mn; a = 4, b = 1, n=3; Ni; a = 6, b = 4, n=2)
MSO4.aH2O +HL + HL1
bH2O

[M (HL) (HL1) SO4].nH2O +

(2)

(When M = Cu; a =5, b = 4, n = 1; M= Co; a = 7, b = 5,

n=2; Fe/Zn, a =7, b = 7, n = 0)
The ligands, Trimethoprim (HL) and Sulfamethoxazole
(HL1), melted at 238-240C and 169C respectively,
whereas their metal complexes all decomposed in the
range 160- 178 C, confirming coordination (Table 1).
The geometry of the metal complexes were
determined by percentage metal, room temperature
magnetic moment
measurement,
infrared
and
electronic spectroscopies since we were unable to isolate
suitable single crystal for x-ray diffraction measurement
(Figure 1).

RESULTS AND DISCUSSION

The reaction of the Trimethoprim (HL),
Sulfamethoxazole (HL1) with the metal(II) chlorides (Mn
and Ni) and metal(II) sulphate of Fe, Zn, Co and Cu gave
coloured complexes in low to moderate yields (30-50%)
according to equations 1- 2.
MCl2.aH2O + HL + HL1 [M (HL) (HL1) Cl2].nH2O + bH2O
(1)
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World Appl. Sci. J., 33 (2): 336-342, 2015

Table 1: Analytical data of the legends and complexes
Compound (Empirical formula)

F. mass

Color

M. p (co)

% yield

off (B.M)

%M (Exp)

^m

HL
HL1
[Mn(HL) (HL1) Cl2]. 3H2O
[Fe(HL)(HL1)SO4]
[Co(HL) (HL1) SO4]. 2H2O
[Ni(HL) (HL1) Cl2]. 2H2O
[Cu(HL)(HL1) SO4].H2O
[Zn(HL)(HL1) SO4]

290.32
253.28
723.60
695.47
734.57
709.34
721.13
704.97

White
White
Cream
Brown
Pink
Blue
Green
White

238-240
169
160*
172*
178*
168*
174*
166*

30
30
30
30
50
30

D
D
1.87
6.2
5.3
3.38
2.3
D

7.59 (7.51)
8.03 (7.99)
8.02 (7.98)
8.28 (8.11)
8.81 (8.86)
9.27 (9.50)

15.30
13.30
19.90
19.23
13.15
12.22

HL = Trimethoprim, HL1 = Sulfamethoxazole, D = diamagnetic, *= decomposition temperature, Molar conductance (^m) = ohm
experimental, eff = effective magnetic moments, F. mass = Formular mass, M. p = melting point.

cm2 mol 1, Exp =

Table 2: Relevant infrared and electronic spectra data of the Complexes.

Compound

(NH)

(S=O)

(C=N)

(M-N)

(M-O)

(M-Cl)

Electronic spectra (kK)

HL

3318s

1653s
1593s

25.58

HL1

3376s
3298s

1309s
1154s

32.79

[Mn(HL)(HL1)Cl2].3H2O

3382s 3237s
3298s

1309s
1161s

1622s
1598s

582s
546s

419s

395m
368m

17.24, 23.92, 31.45

[Fe(HL)(HL1)SO4]

3379s
3301s
3241m

1309s 1158s

1625s
1595s

579s
549s

422s

12.58, 16.86, 33.67

[Co(HL)(HL1)SO4].2H2O

3346s
3270s

1309s 1158s

1615s
1601s

587s
548s

473s
428s

12.36, 19.05, 23.87, 34.12

[Ni(HL)(HL1)Cl2].2H2O

3379s
3298s
3241m

1309s 1158s

1622s
1598s

576s 546m

425s

371m

14.99, 23.87, 33.98

[Cu(HL)(HL1)SO4].H2O

3376s
3298m
3237s

1312s
1158s

1619s
1598s

576s 546m

419s

13.55, 23.98, 33.01

[Zn(HL)(HL1)SO4]

3376s 3301s
3241m

1309s
1146s

1622s
1598s

576s 546m

422s

12.58, 23.92, 33.35

HL = Trimethoprim, HL1 = Sulfamethoxazole, b = broad, s = strong, m= medium, w= weak; 1kK = 1000cm

Solubility and Conductance Measurements: The molar

conductances of the complexes were measured in DMSO
because the complexes were insoluble in alcohols,
nitromethane and methylene chloride. The values
1
obtained were in the range 12.22- 19.90
cm2 mol 1
indicating their covalent nature [23].

32.79

of high spin Mn(II) complexes are expected to be in the

range 5.50-5.90 B.M while low spin octahedral Mn(II)
have moments in the range 1.73-2.20 B.M. Consequently,
a moment of 1.87 B.M. observed for this complex indicated
that, it was low spin octahedral [24].
The Fe (II) complex had a single absorption band
expectedly at 16.86 kK, typical of 6-coordinate, high spin
5
octahedral geometry and was assigned to 5T2g
Eg
transition. An observed moment of 6.2 B.M for this
complex was complimentary of high spin octahedral
geometry [25].
The Co(II) complex exhibited three bands at
12.36, 19.05 and 23.42 kK, assigned to 4T1g(F) 4T2g(F), (v1),
4
T1g(F) 4A2g(F), (v2) and 4T1g(F) 4T1g(P), (v3), transitions
of an octahedral geometry. An observed moment of
5.3 B.M was complimentary of this geometry since
moments in the range 4.7-5.3 B.M is usually observed for
octahedral Co (II) compounds [26].

Electronic Spectra and Magnetic Moments: The

ultraviolet spectra of the HL (Trimethoprim) and HL1
(Sulfamethoxazole) were characterized by strong
absorption maxima at 25.58 kK and 32.79 kK respectively
assigned to n * and
* transitions. In the metal
complexes, these bands shifted to 31.45 - 34.12 kK due to
coordination (Table 2).
The Mn (II) complex showed two absorption bands at
17.24 kK and 23.92 kK typical of low spin octahedral
geometry and was assigned to 2T2g 2A1g and 2T2g 2B1g
transitions respectively. The effective magnetic moments
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World Appl. Sci. J., 33 (2): 336-342, 2015

The Ni(II) complex displayed two absorption bands,

typical of an octahedral geometry, at 12.50 kaka and
23.26 kK and were assigned to 3A2g(F) 3T1g(F), (v2)
3
and 3A2g(F)
T1g(P), (v3), transitions respectively.
Generally, square planar Ni(II) complexes are diamagnetic
while octahedral and tetrahedral complexes are
paramagnetic with moments in the range 2.90- 3.40 B.M
and 3.50- 4.10 B.M respectively. The Ni(II) complex in this
study had a moment of 3.38 B.M. and hence octahedral
[27, 28].
The Cu(II) complex exhibited two unsymmetrical
absorption bands at 13.55 kK and 23.98 kK assigned to
2
2
2
B1g
B2g and 2B1g
E1g transitions of a tetragonal
(octahedral) geometry [29]. A moment of 1.9- 2.2 B.M. is
usually observed for mononuclear copper(II) complexes,
regardless of stereochemistry, expectedly higher than the
spin only moment due to orbital contribution and
spin-orbit coupling. The Cu((II) complex in this study, had
a moment of 2.3 B. M complimentary of octahedral
geometry [30, 31].
The Zn(II) complex showed only the CT transitions
from M ? L, as no d-d transition is expected at 12.58 and
23.92 kK. This complex was expectedly diamagnetic and
assumed a 6-coordinate octahedral geometry [32, 33].

The sulfone bands at 1309 cm 1 in SMX remains unshifted/ marginally shifted to 1312 cm-1 in the complexes
indicative of non-coordination of one of the sulphone
oxygen atoms, whereas the second sulphone band at 1154
cm 1 shifted to 1161 - 1146 cm 1 in the metal complexes
confirming coordination to the metal atom through the
second sulfone oxygen atom [14]. The bands due to (MCl), (M-O) and (M-N) were observed in the range 395 368 cm 1, 473 - 419 cm-1 and 587 - 546 cm 1 respectively.
These bands were absent in the spectra of TMP and
SMX, a further evidence of coordination [29, 30].

Infrared Spectra: The relevant infrared data are presented

in Table 2. The strong bands at 3376 cm 1, 3318cm 1 and
3298 cm 1 in TMP and SMX were assigned as NH2 band
[28]. On coordination, these bands shifted to 3382 - 3237
cm 1 in the spectra of the complexes indicating the
coordination of the amino groups nitrogen to the
metal(II) ions without deprotonation [31]. The azomethine,
(C=N), vibrations at 1635 and 1593 cm 1 in TMX shifted
to 1625 - 1615 cm 1 and 1601 - 1595 cm 1 in the metal
complexes respectively, confirming the coordination of
the imine nitrogen atom to the metal(II) ions [29, 34].

Antimicrobial Activities: The antimicrobial activities of

the drug metal complexes, Trimethoprim and
Sulfamethoxazole against different clinical, food and
environmental isolates are presented in Table 3. None of
the metal, complexes, Trimethoprim and Sulfamethoxazole
was active against E. coli (typed strain). However, the
positive standard (Streptomycin) had an activity of
9.0 mm. In contrast, all the metal complexes and their
ligands showed good activity against the clinical strain of
E. coli with inhibitory zones range of 12.0 - 31.0 mm.
Interestingly, all the metal complexes and their ligands
had activity against Bacillus cereus (food isolate)
with inhibitory zones range of 5.0-31.0 mm while
Streptomycin was not active. Its note worthy that
Streptomycin (32.0 mm, 25.0 mm, 19.0 mm, 29.0 mm and
27.0 mm) was expectedly mostly more active than the
metal complexes and their ligands against Staphylococcus
aureus, Pseudomonas aeruginosa, Bacillus sp
(environmental isolate) and E. coli (clinical strain) with
inhibitory zones range of 19.0-30.0 mm, 6.0-23.0 mm,
10.0-17.0 mm and 12.0-26.0 mm respectively. In contrast,
the metal complexes and their ligands had mostly higher
antimicrobial activities than Streptomycin (22.0 mm, 20. 0
mm, 12.0 mm and 19.0 mm) against Streptococcus sp,

Table 3.0: Antimicrobial activities of the Ligands and their metal(II) complexes
Metal Complexes

[Mn(HL)

[Fe(HL)

[Co(HL)

(HL )Cl2].3H2O

[Ni(HL)(HL1)

[Cu(HL)(HL1)

[Zn(HL)(HL1)

(HL )SO4]

(HL )SO4].2H2O

Cl2].2H2O

(SO4)].H2O

(SO4)]

HL

HL1

E. coli (Typed strain)

9.00

E. coli (Clinical strain)

26.00

27.00

31.00

12.00

23.00

29.00

17.00

27.00

27.00

Streptococcus sp (clinical/blood)

25.00

25.00

29.00

12.00

25.00

26.00

20.00

25.00

22.00

Proteus mirabilis

28.00

25.00

27.00

7.00

25.00

25.00

15.00

29.00

20.00

Candida albicans

22.00

20.00

23.00

11.00

27.00

32.00

20.00

30.00

12.00

Salmonella sp

25.00

22.00

27.00

10.00

25.00

25.00

11.00

9.00

19.00

Bacillus sp (Food)

31.00

25.00

19.00

27.00

5.00

21.00

25.00

15.00

Staphylococcus sp

30.00

32.00

29.00

29.00

23.00

25.00

19.00

22.00

32.00

+ Streptomycin

Pseudomonas sp (Clinical)

20.00

20.00

23.00

6.00

19.00

21.00

20.00

15.00

25.00

Pseudomonas sp (Environmental)

13.00

10.00

15.00

17.00

17.00

19.00

15.00

19.00

Bacillus sp (Environmental)

25.00

22.00

23.00

11.00

25.00

27.00

19.00

29.00

29.00

HL= Trimethoprim; HL1= Sulfamethoxazole; R= Resistance, + = positive control.

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World Appl. Sci. J., 33 (2): 336-342, 2015

P. mirabilis, C. albicans and Salmonella sp with inhibitory

zones range of 25.0-29.0 mm, 25.0-29.0 mm, 20.0-32.0 mm
and 22.0-27.0 mm respectively. The better activity of the
metal complexes was due to chelation, which reduces the
polarity of the metal atom and increases lipophilic
character, favouring its permeation through lipid layers of
the organism membrane while, the inactivity of some of
the metal(II) complexes in this study may be attributed to
their probable lipophobic nature and / microbe strain [35].
Conclusively, all the metal complexes and their ligands
showed good to excellent activity against all the microbes
used with the exception of the Ni(II) complex which was
inactive against Pseudomonas sp (environmental). Thus,
proving their potentials as broad-spectrum antimicrobial
agents in-vitro.

5. Adediji, J.F., E.T. Olayinka, M.A. Adebayo and

O. Babatunde, 2009. Antimalarial mixed ligand metal
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CONCLUSION
The drugs, Trimethoprim (HL) and Sulfamethoxazole
(HL1), formed only low spin, octahedral complex with the
Mn(II) ion while it formed high spin octahedral complexes
with Co, Ni, Cu, Fe, Zn ions. These complexes were all
covalent, magnetically dilute and octahedral as
corroborated by conductance measurements, room
temperature magnetic moments, infrared and electronic
spectroscopies. Interestingly, all the metal complexes
showed broad-spectrum antimicrobial activities against all
the microbes used with the exception of Ni(II) complex
proving their potentials as broad spectrum antimicrobial
agent.
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