Co (II), Cu (II), Mn (II), Ni (II), Pd (II), and Pt (II) complexes of bidentate Schiff base ligand: Synthesis, crystal structure, and acute toxicity evaluation
Abstract:5‐methoxy‐2‐(((2chloro‐5‐(trifluoromethyl)phenyl)imino)methyl)phenol) (HL) and its cobalt (II), copper (II), manganese (II), nickel (II), palladium (II), and platinum (II) complexes, [Co(L)2]·4H2O (1), [Cu(L)2] (2), [Mn(L)2(H2O)2]·H2O (3), [Ni(L)2] (4), [Pd(L)2] (5), [Pt(L)2] (6), were synthesized and characterized. The compounds were investigated by different physico‐chemical techniques including IR, 1H‐NMR, 13C‐NMR, UV‐Vis, mass spectroscopies, elemental and thermal analysis, magnetic susceptibility measurem… Show more
“…In metal complexes, this band is shifted to lower wavenumber by 10–11 cm −1 indicating the participation of the azomethine nitrogen in coordination. [ 30 ] In the free ligand spectrum, a broad band located at 3438 cm −1 due to the phenolic ν (OH) group is disappeared in all complexes suggesting the phenolic‐OH group participation in coordination. Involvement of the deprotonated phenolic‐OH group in chelation is confirmed by the blueshift of the ν (C–O) band (shift from 1173 cm −1 to lower frequency ranging 1157–1159 cm −1 ) in the complexes.…”
Novel binary metal complexes, 1 [Cu(FMIMBMOP)2], 2 [Ni(FMIMBMOP)2] and 3 [Co(FMIMBMOP)3], where FMIMBMOP (2‐((E)‐((furan‐2‐yl)methylimino)methyl)‐4‐bromo‐6‐methoxyphenol), were synthesized and characterized using different analytical techniques. Result of spectral studies reveals that square planar geometry is assigned for Cu (II) and Ni (II) complexes, whereas octahedral geometry is assigned for Co (III) complex. The thermodynamic and kinetic parameters for the degradation of the complexes were ascertained by Coats–Redfern method for thermogravimetric data attained from thermogravimetric analysis (TGA). The stability of the complexes has been calculated from quantum chemical parameters using highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energies. The DNA binding of complexes was studied by using ultraviolet–visible (UV–Vis) spectroscopic technique; screening their ability to bind to calf thymus DNA (CT‐DNA) showed that the complexes can interact with CT‐DNA through intercalation mood, where the Kb values are 2.59 ± 0.01 × 104, 7.43 ± 0.03 × 103, and 6.73 ± 0.02 × 104 M−1 for 1, 2, and 3, respectively. Stern–Volmer quenching constant (Ksv) values ranged from 2.32 ± 0.03 × 103 to 1.66 ± 0.02 × 104 M−1 were calculated for complexes from fluorescence studies. The oxidative and photolytic cleavage of supercoiled pBR322 DNA was studied and found that the complexes have cleaved this DNA effectively. The novel metal complexes have shown significant antioxidant activity against DPPH radical. The antibacterial activity of Schiff base and its metal complexes screened against Bacillus thuringiensis, Streptococcus pneumoniae, Escherichia coli, and Pseudomonas putida was investigated, and the results indicated that the metal complexes have better results than Schiff base ligand. The catalytic ability of metal complexes 1, 2, and 3 was found to be 3 > 1 > 2.
“…In metal complexes, this band is shifted to lower wavenumber by 10–11 cm −1 indicating the participation of the azomethine nitrogen in coordination. [ 30 ] In the free ligand spectrum, a broad band located at 3438 cm −1 due to the phenolic ν (OH) group is disappeared in all complexes suggesting the phenolic‐OH group participation in coordination. Involvement of the deprotonated phenolic‐OH group in chelation is confirmed by the blueshift of the ν (C–O) band (shift from 1173 cm −1 to lower frequency ranging 1157–1159 cm −1 ) in the complexes.…”
Novel binary metal complexes, 1 [Cu(FMIMBMOP)2], 2 [Ni(FMIMBMOP)2] and 3 [Co(FMIMBMOP)3], where FMIMBMOP (2‐((E)‐((furan‐2‐yl)methylimino)methyl)‐4‐bromo‐6‐methoxyphenol), were synthesized and characterized using different analytical techniques. Result of spectral studies reveals that square planar geometry is assigned for Cu (II) and Ni (II) complexes, whereas octahedral geometry is assigned for Co (III) complex. The thermodynamic and kinetic parameters for the degradation of the complexes were ascertained by Coats–Redfern method for thermogravimetric data attained from thermogravimetric analysis (TGA). The stability of the complexes has been calculated from quantum chemical parameters using highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energies. The DNA binding of complexes was studied by using ultraviolet–visible (UV–Vis) spectroscopic technique; screening their ability to bind to calf thymus DNA (CT‐DNA) showed that the complexes can interact with CT‐DNA through intercalation mood, where the Kb values are 2.59 ± 0.01 × 104, 7.43 ± 0.03 × 103, and 6.73 ± 0.02 × 104 M−1 for 1, 2, and 3, respectively. Stern–Volmer quenching constant (Ksv) values ranged from 2.32 ± 0.03 × 103 to 1.66 ± 0.02 × 104 M−1 were calculated for complexes from fluorescence studies. The oxidative and photolytic cleavage of supercoiled pBR322 DNA was studied and found that the complexes have cleaved this DNA effectively. The novel metal complexes have shown significant antioxidant activity against DPPH radical. The antibacterial activity of Schiff base and its metal complexes screened against Bacillus thuringiensis, Streptococcus pneumoniae, Escherichia coli, and Pseudomonas putida was investigated, and the results indicated that the metal complexes have better results than Schiff base ligand. The catalytic ability of metal complexes 1, 2, and 3 was found to be 3 > 1 > 2.
“…nauplii gut has noticeable changes as observed by a phase-contrast microscope, as shown in Figure . The results suggested that complex 1 accumulation does not induce mortality after 24 h of exposure. − …”
A cobalt(III) complex,
[Co(L)]Cl (complex
1
, where
L = 1,8-[
N
,
N
-bis{(3-formyl-2-hydroxy-5-methyl)benzyl}]-1,4,8,11-tetraaza-5,5,7,12,12,14-hexamethylcyclotetradecane)
with distorted octahedral geometry has been synthesized and characterized
using various spectroscopic techniques. The structure of the ligand
has remarkably rich hydrogen intermolecular interactions such as H···H,
H···C/C···H, and H···O/O···H
that vary with the presence of the metal ion, and the structure of
complex
1
has Cl···H interactions; this
result has been proved by Hirshfeld surface and two-dimensional (2D)
fingerprint maps analyses. The complex exhibits a quasi-reversible
Co(III)/Co(II) redox couple with
E
1/2
=
−0.76 V. Calf thymus DNA (CT DNA) binding abilities of the
ligand and complex
1
were confirmed by spectroscopic
and electrochemical analyses. According to absorption studies, the
ligand and complex
1
bind to CT DNA via intercalative
binding mode, with intrinsic binding strengths of 1.41 × 10
3
and 8.64 × 10
3
M
–1
, respectively.
A gel electrophoresis assay shows that complex
1
promotes
the pUC19 DNA cleavage under dark and light irradiation conditions.
Complex
1
has superior antimicrobial activity than the
ligand. The cytotoxicity of complex
1
was tested against
MDA-MB-231 breast cancer cells with values of IC
50
of 1.369
μg mL
–1
in the dark and 0.9034 μg mL
–1
after light irradiation. Besides, cell morphological
studies confirmed the morphological changes with AO/EB dual staining,
reactive oxygen species (ROS) staining, mitochondria staining, and
Hoechst staining on MDA-MB-231 cancer cells by fluorescence microscopy.
Complex
1
was found to be a potent antiproliferative
agent against MDA-MB-231 cells, and it can induce mitochondrial-mediated
and caspase-dependent apoptosis with activation of downregulated caspases.
The biotoxicity assay of complex
1
on the development
of
Artemia nauplii
was evaluated at
an IC
50
value of 200 μg mL
–1
and
with excellent biocompatibility.
“…Crustaceans of the species Artemia franciscana Kellogg were used to determine the toxicity of the new pyrrole derivatives on the animal cell. The test assesses how many of the crustacean nauplii die in 24 h and 48 h intervals from the contact with the solutions of the tested compounds [53][54][55][56][57].…”
A series of new pyrrole derivatives were designed as chemical analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles was based on IR, NMR spectroscopy as well as on single crystal X-ray analysis. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. Our research indicates that the newly synthetized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.
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