Volume 7, Issue 2, February – 2022 International Journal of Innovative Science and Research Technology

ISSN No:-2456-2165

Synthesis, Characterization and Antimicrobial

Properties of Mixed Ligand of Sulphamethoxazole
and Trimethoprim and Their Manganese (II) and
Copper (II) Complexes
Olagboye S.A. And Ige S.E.
Chemistry Department, Ekiti State University, Ado- Ekiti.

Abstract:- Sulphamethoxazole and trimethoprim mixed health defects such as cardiovascular, nervous, kidney and
ligand and their Mn(II) and Cu(II) metal complexes have bone diseases (Araromi et al., 2020). Copper is an example
been synthesized and characterized. The characterization of transition metal, it plays a crucial role in human
of metal complexes is based on the results of the solubility, metabolism because it allows many critical enzymes to
colour, melting points and spectroscopic studies. The UV- function properly. Copper is essential for maintaining the
Visible spectra revealed characteristic wavelength strength of the skin, blood vessels, epithelial and connective
maxima at 600 nm, 700 nm, 750 nm and 800 nm assigned tissues throughout the body. It is highly important in the
to the d-d electronic transition of the metal complexes. production of hemoglobin, myelin, melanin and it also keeps
The FTIR results confirmed that the manganese and thyroid gland functioning normally. Copper can act as both
copper ions coordinated through the nitrogen atom and an antioxidant and a pro-oxidant (Osredkar & Sustar, 2011).
oxygen atom (S=O) of sulphamethoxazole and through
the nitrogen atoms in trimethoprim. The antimicrobial Cu(II) Complexes are four-coordinate which are
activities of the metal complexes synthesized indicated generally blue or green due to the maximum of four electronic
that the metal complexes were more potent against transitions; d-d transitions; charge transfer transitions and
selected organisms than the free ligands. internal ligand transitions. Electronic spectroscopy cannot be
used in isolation as a tool for structural identification due to
Keywords:- Sulphamethoxazole, Trimethoprim, Mixed the large distortion associated with this compound (Gaikwad
ligands, Metal complexes, Antimicrobial activities, Spectra & Yadav, 2016). Cu is one of the various metals commonly
studies, Characterization. used for metal based drugs because of its ability to form low
molecular weight complexes which prove to be more potent
I. INTRODUCTION against several diseases (Olagboye et al., 2018; Kozarich,
2005). Whereas, manganese is a hard but brittle metal which
The discovery of coordination compounds resulted in a is difficult to fuse but easy to oxidize. Manganese have
synthetic revolution in Inorganic Chemistry which leads to variable oxidation state from +2 to +7 but the +2 state is most
formation of new products with effective applications in wide prevalent in the biological system. Manganese (II) ions
selection of areas including fungicides, paints, pigments, function as cofactors for a large variety of enzymes with
polymers, pharmaceuticals, catalysis and photoconductors many functions (Schmidt and Husted, 2019).
(Gaikwad & Yadav, 2016). The effectiveness of a
coordination compound can be enhanced by the nature of Metal complexes formed from most transition metal
ligands coordinated. The nature of metal- ligand bonding ions is an important class of coordination compounds which
range from covalent to ionic with bond order from one to are studied extensively due to their enormous applicability in
three. Ligands are lewis bases but in rare cases occur as lewis various fields of human interests (Ejelonu et al., 2018)
acids. ranging from biological, chemical, agricultural and industrial
applications. Metal drug complexes are attracting research
Transition metals are a class of element with partially interests due to their increasing importance in the design of
filled d sub-shell distinguished by characteristics such as drugs (Lawal and Obaleye, 2007).
formation of coloured compounds, having variable oxidation
state and formation of complexes. Although, high level of Antioxidant, water softening, ion exchange resin,
heavy metals could relatively lead to increase serum liver photosynthesis in plants, removal of undesirable and harmful
enzymes, kidney function parameters and reduction in metals from living organisms, electroplating and dying are
haemoglobin level packed cell volume and Red Blood Cells some of the diverse ways in which mixed ligand complexes
(Oguntuase et al., 2019), Cu and Mn are nutrient minerals are applied in medicine, chemical and biological systems
which play major roles in metabolic processes such as (Taghreeed & Lekaa, 2016).
muscular activity, endocrine function, reproduction, skeletal
integrity and overall development (Adeyeye et al., 2021). Microbial infections are a menace worldwide which
They are essential micronutrients for plants and animals does not subside despite active research devoted to the
growth but when present in higher concentrations can cause discovery and development of novel antimicrobial agents.

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Volume 7, Issue 2, February – 2022 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
Antibiotics are used to treat bacterial infections and its A. Physical measurement
improper and unnecessary use has made antibiotic resistance The melting points of the complexes were determined
a growing problem (Miniyar & Makhija, 2009). using melting point apparatus. The solubility tests were
carried using polar and non polar solvents. The FTIR spectra
Sulphamethoxazole is an antibacterial which has been were recorded using FTIR 8300 shimadzu
utilized in combination with trimethoprim or pyrimethamine specterophotometer in the frequency range of 4000-400cm-1.
since the 1960s for the treatment of various systemic The UV-visible spectra were also recorded using shimadzu
infections in humans and other species (IARC monographs UV-VIS.16OA ultra-violet spectrophotometer in the range of
Vol. 79). Urinary tract infection is one of the most common 200-800nm.
infectious diseases caused by Escherichia coli in many
countries. E. coli have been found to be highly resistant to III. EXPERIMENTAL
trimethoprim-sulphamethoxazole (Kurutepe et al., 2005),
efforts are therefore progressively made to develop novel A. Synthesis of Sulphamethoxazole-metal complexes in
antibiotics. ratios 1:1 and 1:2
The complexes were prepared by adding aqueous
Trimethoprim (TMP) is an antibiotic drug used mainly methanol solution of 0.01mol of the cu (1.7054g) & Mn
in the treatment of bladder infections, it is also used for (1.69g) metal salts to an aqueous methanol solution of 0.01
middle ear infections and travellers’diarrhoea. It interferes (2.5328g) and 0.02 (5.0656g) moles sulphamethoxazole
with the production of tetrahydrofolic acid, a chemical that is respectively. The mixture was stirred for 2hrs 30mins on a
necessary so as for bacteria and human cells to produce magnetic stirrer. The complexes were recovered from
proteins (Akinyele et al., 2020). The pharmaceutical use of solutions by filtration followed by washing with distilled
metal complexes has excellent potentials (Zhang & Lippard, water and methanol and then dried to a constant weight in a
2003) which has gained tremendous attention overtime dessicator.
(Ejelonu et al., 2018; Allardyce et al., 2005).
B. Synthesis of the mixed ligand-metal complexes
Malaria, tuberculosis and AIDS are the three major 2.5328g (0.01mole) of sulphamethoxazole and
infectious diseases grievously damaging the world. Efforts 2.9032g(0.01mole) of trimethoprim were dissolved in 20ml
are being made to eradicate and control malaria for over a aqueous methanol. 0.01mole (1.69g MnSO4.H2O and
decade but the disease still remain a major threat to human 1.7054g CuCl2.2H2O) of the metal salts were added. The
health and economic development around the world. resulting solution was stirred for 2hrs 30mins on a magnetic
Sulfanilamides are used as antibacterial as well as stirrer. The product formed was filtered, washed with a
antimalarial drugs (Ajibade et al., 2006). The continuous mixture of methanol and water and then dried to a constant
emergence of resistant parasites to available antimalarial weight in a dessicator.
drugs has made the development of novel antimalarials and
modification of existing antimalarial drugs a necessity in C. Antimicrobial studies of the metal complexes
order to eradicate or control the disease. This research work Ten (10) different bacteria and four fungi were collected
involved the synthesis, characterization and antimicrobial from University of ife Teaching Hospital, Ile ife osun state
properties of sulphamethoxazole and trimethoprim mixed Nigeria. They were sub-cultured on nutrient agar for bacteria
ligand metal complexes. and potato dextrose agar for fungi. Both media were prepared
according to manufacturer’s specifications. True
II. MATERIALS AND METHODS representatives of each of the different organisms were sub-
cultured, their identification and taxonomic studies were
Materials and Reagents; Trimethoprim Salt, carried out to confirm each organism. The confirmed
Sulphamethoxazole Salt, Manganese(II)sulphate organisms were then prepared for use as test organisms for
monohydrate (MnSO4.H2O), Copper(II)Chloride dihydrate the antibiotic susceptibility test. Each of the test organisms
(CuCl2.2H2O), Methanol, sodium hydroxide, hydrogen was transferred to a liquid medium nutrient both for bacteria
peroxide, n-Hexane, chloroform and ethanol used were and enriched peptone both for fungi. They were inoculated
obtained in analytical grade and used without further for 18h after which they were used for the test. Mueller-
purification. Hinton agar was prepared according to manufacturer’s
specification, poured into petri dishes and allowed to set.
Sterile swab were then used to seed the set agar plates with
each test organism, then an 8mm diameter cork-borer was
used to bore wells in the plates, after which each wells was
filled with the solution of each test compound. The plates
were incubated for 24h at 370c.

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Volume 7, Issue 2, February – 2022 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
IV. RESULTS AND DISCUSSIONS

TABLE 1; PHYSICAL AND ANALYTICAL DATA OF THE COMPLEXES

COMPLEXES MOLECULAR WEIGTH COLOUR YIELD (%) MELTING POINT (°C)
SMT C10H11N3O3S 253.28 White - 165-167
TMP C14H18N4O3 290.32 White - 190-192
[Cu(SMT)Cl2]H2O 405.55 Green 51 148-150
[Cu(SMT)2Cl2]H2O 658.55 Light green 53 152-154
[Cu(SMT-TMP)Cl2]H2O 695.55 Light green 65 138-140
Mn(SMT)SO4 403.94 White 48 166-168
Mn(SMT)2SO4 656.94 White 75 166-168
Mn(SMT-TMP)SO4 693.94 693.94 90 172-174
LEGEND; SMT= SULPHAMETHOXAZOLE (C10H11N3O3S) TMP= TRIMETHOPRIM (C14H18N4O3)

The results of the physical measurements are presented which could be linked to the reactivity of the metals. Sharp
in Table 1. All the complexes were stable and obtained in melting points were observed in all the complexes with
moderate to high yield 48% - 90%. The mixed ligand- melting temperature ranging from 138°C in copper mixed
manganese complex has the highest yield of 90% while the ligand complex to 174°C in manganese mixed ligand
least yield was recorded from the 1:1 sulphamethoxazole- complex suggesting the formation of pure metal complexes.
manganese complex. The copper complexes generally have The melting point is generally higher in the manganese
less yield compared to their analogous manganese complexes complexes than their corresponding copper complexes.

TABLE 2; SOLUBILITY OF THE COMPLEXES

COMPLEXES Chloroform Ethanol n-Hexane Ethyl acetate

[Cu(SMT)Cl2]H2O Very soluble Very soluble Slightly soluble Very soluble

[Cu(SMT)2Cl2]H2O Very soluble Very soluble Slightly soluble Very soluble
[Cu(SMT-TMP)Cl2]H2O Very soluble Very soluble Slightly soluble Very soluble
Mn(SMT)SO4 Very soluble Very soluble Slightly soluble Very soluble
Mn(SMT)2SO4 Very soluble Very soluble Slightly soluble Very soluble
Mn(SMT-TMP)SO4 Very soluble Very soluble Slightly soluble Very soluble

The solubility test of the complexes were also done strongly affected by the presence of other species such as
using different solvents, they were soluble in chloroform, anions and ligands, therefore, the colour of the metal complex
ethyl acetate and ethanol but insoluble in n-hexane. solution changes as well as the wavelength of maximum
absorption. The wavelength of maximum absorption was
The result of the UV-visible analysis of the compounds observed at 700 nm for the metal complexes. Higher
prepared is presented in Table 3. The results indicated that the absorbances (23.86, 23.54 and 23.67) were observed for the
metal complexes are coloured because of the d-d electronic Copper (II) complexes as compared to the manganese (II)
transition within the metal atoms and charge transfer between complexes (23.06, 23.56 and 23.75).
the metal and the ligands. The colour of metal ion solution is

TABLE 3: UV RESULT OF THE COMPLEXES

Wavelengths (nm) 200 300 400 500 600 700 800 900
SMT 0.09 0.09 0.59 10.10 17.75 23.24 13.16 13.99
[Cu(SMT)Cl2]H2O 0.09 0.10 0.57 10.08 17.89 23.86 13.12 13.95
[Cu(SMT)2Cl2]H2O 0.09 0.10 0.59 10.07 17.75 23.54 13.11 13.93
[Cu(SMT-TMP)Cl2]H2O 0.09 0.10 0.57 10.13 17.83 23.67 13.98 14.02
Mn(SMT)SO4 0.09 0.10 0.57 10.07 17.75 23.06 13.11 13.94
Mn(SMT)2SO4 0.09 0.10 0.58 10.26 18.02 23.56 13.79 14.18
Mn(SMT-TMP)SO4 0.09 0.10 0.59 10.16 17.92 23.75 13.59 14.07

The prominent IR bands of the ligands and metal far IR region (400 - 600cm-1) while the bands due to structural
complexes are represented with table 4. The stretching modes changes of the ligands appear in the finger print region of the
of the ligands are expected to change upon complexation due spectra (1500-750cm-1) (Saha et al., 2002; Nakamoto, 1986).
to either weakening or strengthening of the bonds involved in Assignments of bands are done based on comparison with the
the bond formation (Olagboye et al., 2018) the absorption spectra data of similar compounds (Lawal and Obaleye,
bands due to metal- ligand coordination are observed in the 2007). The bonding of the ligands to metal ions was

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Volume 7, Issue 2, February – 2022 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
investigated by comparing the FTIR spectra of the complexes through the N atom of sulfonamide group and one of the
with those of the free ligands (Eugene-Osoikhia et al., 2020). oxygen atom of the sulfonyl. The absence of broad bands in
the region 3300-3500 in all the spectra of the complexes
IR spectrum of the free ligand shows two strong bands indicates that there is no coordinated H2O molecule. The
at 3465 and 3374 cm-1 equivalent to the asymmetric and metal-nitrogen and metal-oxygen stretching frequency were
symmetric stretching vibrations of the aromatic amino group observed at 682-685 and 559-562 cm-1 respectively for all the
(NH2). This band did not show any appreciable changes in all metal complexes.
the complexes which demonstrates its non participation in the
coordination (Eugene-Osoikhia et al., 2020 ; Rostamizadeh Generally, mixed ligand complexes demonstrate better
et al., 2019). The medium and strong signals at 3140 and activities because chelation reduces the polarity of the metal
3296 cm-1 are due to the presence of asymmetric and ion by partial sharing of its positive charge with the donor
symmetric frequency vibration of the sulfonamide -NH groups and also due to pi -electron delocalization on the
group. The shifting of the band in the spectra of the whole chelating ring, increased lipophilicity enhances the
complexes indicated its involvement in the coordination or penetration of the complexes into lipid membrane and
chelation with central metal ion through the N atom of this blocking off all of the metal binding sites in the enzymes of
group (Eugene-Osoikhia et al., 2020 ; Mondelli et al., 2013). microorganisms. These complexes also disturb the
The peak at 1613 is assigned to the C=N stretching vibration. respiration process and thus block the synthesis of the protein
Based on the IR result, the coordination mode of which restricts further growth of the organisms (Eugene-
sulphamethoxazole with metal ion is predicted as a bidentate Osoikhia et al., 2020 ; Raman et al., 2009).

TABLE 4; IR RESULTS OF THE LIGAND AND COMPLEXES

COMPLEXES v(NH) v(S=O) v(C=N) vNH2 v(C=C) C=N M-N M-O M-Cl
SMT 3296 1309 - 3465 1476 - - - -
3140 1147 3374
TMP 3314 - 1639 3464 1456 1456 - - -
[Cu(SMT)Cl2]H2O 3394 1311 1613 3463 1500 1395 685 562 381
3210 1148
[Cu(SMT)2Cl2]H2O 3391 1309 1613 3391 1499 1404 684 559 375
3207 1146
[Cu(SMT- 3356 1310 1613 3391 1497 1403 683 560 381
TMP)Cl2]H2O 3209 1146
Mn(SMT)SO4 3207 1145 1614 3393 1500 1405 683 559 ---
Mn(SMT)2SO4 3206 1146 1614 3393 1501 1405 682 559 ---
Mn(SMT-TMP)SO4 3209 1146 1613 3393 1500 1405 684 560 ---

TABLE 5; ANTIFUNGAL ACTIVITY OF THE COMPLEXES IN PERCENTAGE (%)

COMPLEXES Collectotrichum Rhizoctonia Fusurium Verticillium albo-
gloeosporioides solani oxysporum atrum
SMT 16.60 15.00 11.00 13.00
TMP 10.00 12.00 10.00 12.00
[Cu(SMT)Cl2]H2O 29.40 45.05 33.33 13.04
[Cu(SMT)2Cl2]H2O 62.35 59.34 36.36 43.48
[Cu(SMT-TMP)Cl2]H2O 72.34 71.87 54.24 57.39

Mn(SMT)SO4 27.05 30.77 22.73 26.09

Mn(SMT)2SO4 59.41 67.03 36.36 60.87
Mn(SMT-TMP)SO4 28.24 34.07 27.27 17.39
MANCOZEB 100.00 90.00 69.00 69.00

The antimicrobial screening of the synthesized that the activity increases with increasing concentrations of
complexes were carried out using agar well diffusion method. the sulphamethoxazole ligand. SMT complexes can also be
Table 5 presents the antifungal activity of the complexes said to have higher antifungal activity than the co- ligand
against four different fungi including Collectotrichum TMP. Also, Cu (II) complexes show higher antifungal
gloeosporioides, Rhizoctonia solani, Fusurium oxysporum activity than the corresponding Mn (II) complexes.
and Verticillium albo-atrum. All the complexes shows Rhizoctonia solani was observed to show highest
appreciable antifungal activity in the order Mn(SMT)SO4 < susceptibility to the tested compounds and Fusarium
Mn(SMT-TMP)SO4 < [Cu(SMT)Cl2]H2O < oxysporum was least. Generally, the activity of the
[Cu(SMT)2Cl2]H2O < Mn(SMT)2SO4 < [Cu(SMT- compounds against the tested organisms increases in the
TMP)Cl2]H2O. From this trend of activity, it was observed

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Volume 7, Issue 2, February – 2022 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
order ; Fusurium oxysporum < Verticillium albo-atrum < TABLE 6; ANTIBACTERIAL ACTIVITY OF THE
Collectotrichum gleosporoides < Rhizoctonia solani. COMPLEXES
DIAMETER OF ZONE OF INHIBITION (mm)
All the ligands and their metal complexes synthesized COMPLE A B C D E F G H I J
are sensitive to the selected organisms. The combined dual XES
properties of both the ligands and metal ions interacted with SMT 0 0 02 -- -- 0. 0 0 0 0
different steps of fungal life cycle (Iornumbe et al., 2018). 5 2 - - 1 1 5 6 2
There is also an evidence that the control antifungal TMP 0 0 0. 0. 1 -- 1 0. 0 0
commercial agent proved to be more active than both the 3 1 15 1 5 - 5 3 4 1
ligands and metal complexes. Cu(SMT) 1 0 10 0 0 -- 0 1 1 1
Cl2 1 5 4 3 - 3 6 7 1
The antibacterial screening of the complexes against ten Cu(SMT)2 1 0 04 0 0 -- 0 0 2 0
bacteria strains Agrobacterium tumefaciens, Xanthomonas Cl2 0 5 4 4 - 8 9 0 6
phaseoli, Pseudomonas glycinea, Erwinia carotovora, Cu(SMT- 0 0 07 0 0 -- 0 0 1 0
Clavibacter michiganensis, Pseudoman solanacearium, TMP)Cl2 8 9 3 4 - 3 7 5 6
Xanthomonas campestris, Corynebacterium sepedonicum, Mn(SMT) 0 0 05 0 0 -- 0 1 1 0
Agrobacterium rhizogenes and Corynebacterium SO4 6 9 3 2 - 5 0 6 6
flaccumfaciens was carried out and the diameter of zone of Mn(SMT) 0 0 03 0 0 2 0 2 1 1
inhibition of the antibacterial activities of the complexes
2SO4 7 8 9 3 5 3 1 7 7
against the standard bacteria strains were measured in mm as Mn(SMT- 0 0 02 0 0 3 0 2 1 2
a mean of triplicates and the results are presented in Table 6.
TMP)SO4 7 4 4 3 1 4 0 8 2
SOLVEN -- -- --- -- -- -- -- -- -- --
The activity of the metal complexes and the mixed
T - - - - - - - - -
ligand complexes increase as the concentration of ligand
STREP. 2 1 22 2 2 2 3 4 2 2
increases, the increase in activity is attributed to chelation.
(std.drug) 0 2 7 1 5 0 0 5 5
The polarity of metal atom is reduced as a result of sharing of
LEGEND; Diameter of cork-borer= 8mm, STREP=
its positive charge with donor group of the ligand and the
delocalization of the pi electrons on the aromatic rings. The streptomycin, --- = not susceptible
A= Agrobacterium tumefaciens B= Xanthomonas phaseoli
cell membrane of the bacteria is permeated due to the increase
C= Pseudomonas glycinea D= Erwiniacarotovora E=
in lipophilicity thereby resulting in the death of the bacteria
Clavibacter michiganensis F= Pseudoman solanacearium
(Khameneh et al., 2019).
G= Xanthomonas campestris H= Corynebacterium
The highest zone of inhibition was recorded in the Mn sepedonicum I= Agrobacterium rhizogenes J=
Corynebacterium flaccumfaciens.
(II) mixed ligand complex with a value of 31mm which is
higher compared to 25mm reported for the standard drug. The
compounds of Mn has shown outstanding activity against V. CONCLUSION
Pseudoman solanacearium as compared to the inactivity of
the Cu (II) complexes in inhibiting the growth of this Sulphamethoxazole and Trimethoprim mixed ligand
organism. Of all the tested bacteria strain, Agrobacterium complexes with manganese (II) and copper (II) were
rhizogenes showed high susceptibility to all the chemical synthesized and characterized. The complexes were polar
compounds screened with the complexes showing higher with sharp melting points which confirm the formation of
activity than their ligands. Also, the zones of inhibition pure complexes. The formation of the complexes was
indicated by the appearance and disappearance of bands in
observed for this organism is comparable to that of the
standard drug streptomycin. their FTIR spectra which confirmed that the complexes
coordinated through the nitrogen atoms of trimethoprim and
through S=O and –NH group in sulphamethoxazole. The
Generally, reduced activity was observed for
Xanthomonas campestris and Clavibacter michiganensis as antimicrobial activities of the metal complexes synthesized
against the high zone of inhibition observed with the standard indicated that the metal complexes were comparatively potent
against selected organisms with respect to the standard drug
drug, the reduced activity might be associated to the inability
of these compounds to permeate the membrane of these streptomycin.
organisms (Ramzan et al., 2017). The Cu (II) complexes have
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