Asian Journal of Chemistry; Vol. 30, No. 7 (2018), 1537-1545
A
SIAN
J
OURNAL OF HEMISTRY
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Synthesis, Characterization and Biological Activities of Some Metal Complexes Derived from
Azo Dye Ligand 2-[2'-(5-Methyl thiazolyl)azo]-5-dimethylamino Benzoic Acid
*
KHALID J. AL-ADILEE and SUDAD A. JABER
Department of Chemistry, College of Education, University of Al-Qadisiyah, Diwaniya 1753, Iraq
*Corresponding author: E-mail: khalidke_1962@yahoo.com; Khalid.Jawad@qu.edu.iq
Received: 11 January 2018;
Accepted: 18 April 2018;
Published online: 31 May 2018;
AJC-18927
In this paper we report the synthesis and identification of Ni(II), Cu(II) and Zn(II) complexes with new thiazole based azo dye 2-[2’-(5-
methyl thiazolyl)azo]-5-dimethyl amino benzoic acid (5-MeTAMB) by the diazotization of 2-amino-5-methyl thiazole and coupling with
3-dimethyl amino benzoic acid in alkaline alcoholic solution. The structures of the azo dye ligand and its metal complexes were confirmed
by various analytical techniques like by elemental analysis (C.H.N.S), UV-visible, FT-IR spectroscopic, mass spectroscopic, 1H NMR
spectroscopic, SEM, XRD data and thermal studies (TGA & DSC). The magnetic moment value of metal complexes [ML2] M = Ni(II)
and Cu(II) occurs in the range of high spin octahedral environment of azo ligand while Zn(II) complex show diamagnetic properties and
octahedral structure. The analytical and spectral techniques show that the ligand coordinates as tridentate (N,N,O) donor molecule. The
antibacterial and antifungal activity of the thiazolylazo ligand and its metal complexes have shown activity towards both bacterial and
fungal strains. The biological activity was also conducted by cells cytotoxicity and viability of the ligand and Cu(II)-complex was
screened for in vitro, antitumor activity against human breast cancer using MTT assay. The results shows that this type of compounds
plays an important role in the rate of inhibition of the growth of cells of cancerous and natural lines and indicate undoubtedly the
possibility of using them as antitumor drugs against breast cancer.
Keywords: Synthesis, Thiazolylazo dye, Metal complexes, Spectral studies, Biological activity, Anticancerous.
microbial activities such as antibacterial [17], antiviral [18]
and antifungal [19]. In this work describe the preparation and
characterization of new thiazolylazo ligand (5-MeTAMB) and
its complexes with Ni(II), Cu(II) and Zn(II) ions, is described
biological activities (antibacterial and antifungal). The
thiazolylazo ligand and its Cu(II) complex evaluated for in
vitro anticancer activity against human breast cancer MCF7
by MTT assay.
INTRODUCTION
Thiazolylazo dyes are an important class of organic com-
plexion compounds and very important class of chemical
constituents having a wide applications in different fields such
as leather, polymer, paint and coating industries as dyeing agent
[1-3]. The dyeing capability of dye depends on functional groups
present in the dyes, such as azo, hydroxyl, carboxylic acids,
esters and amines [4,5]. The thiazolylazo dyes and its deriva-
tives are also used for colouring consumer goods, such as clothes,
plastics, textiles, food, toys and cosmetics [6,7]. Thiazolylazo
dyes were also used in chemical operations such as spectro-
photometry, solid phase extraction, liquid chromatography,
electrochemistry and cloud point [8-10]. The application of
thiazolylazo dyes in spectrophotometry is based on coloured
compounds resulting from their reaction with metal ions,
especially transition metals [10]. Thiazolylazo derivatives are
active biological agents [11] which possess strong biological
activities such as antihistamines [12], antitumor [13], anti-
inflammatory [14], antibacterial effects [15] and production
of drugs in chemotherapy [16].
EXPERIMENTAL
All the chemicals and solvents were of the highest purity
obtained from BDH, Aldrich, sigma and Merck. Mass spectra
was obtained using a Shimadzu Agilent Technologies 5973C
at 70e and MSD energy using a direct insertion probe (Acq
method 10W energy) at temperature 90-110 °C. 1H NMR spectra
were recorded in DMSO on a Bruker 500 MHZ spectrophoto-
meter using TMS as an interior reference. IR spectra of the
ligand as well as the complexes are recorded as KBr discs
using a Shimadzu 8400 S FT-IR spectrophotometer in wave
number at range (4000-400) cm-1. The electronic spectra of
ligand and its metal complexes were recorded on a T80-PG
double beam UV-visible spectrophotometer in the range of
Thiazolylazo compounds and some of its metal complexes
also show significant effects against cancer and also exhibit