Biosensitive and biologically active morpholine-based transition metal(ii) complexes (1-5) were constructed as M
(L) AcO·
H
O {where M = Cu (1)
= 1; Co (2), Mn (3), Ni (4),
= 4 and Zn (5)
= 2}, which ...were synthesized from 2-(-(2-morpholinoethylimino) methyl)-4-bromophenol ligand (HL) and structurally characterized by various analytical and spectroscopic techniques, which proposed a square planar and tetrahedral geometry around the central metal ion with lattice water molecules. The gel electrophoresis results revealed that complexes 1 and 5 had more potent DNA cleavage efficacy in the presence of an oxidizing agent (H
O
) as compared to the others. The observed DNA binding results for all the compounds as determined by spectro-electrochemical and hydrodynamic techniques were in the order 3.36 (1) > 3.06 (2) > 2.73 (4) > 2.61 (5) > 1.84 (3) > 1.00 (HL) × 10
M
. The obtained bovine serum albumin (BSA) protein binding constant (
) results put forward the following order 2.38 (1) > 2.21 (2) > 2.18 (5) > 1.76 (4) > 1.40 (3) > 1.26 (HL) × 10
M
. Also, the biothermodynamic parameters (, , Δ
° and Δ
°) and binding results divulged that all the complexes (1-5) could bind to DNA
intercalation in a spontaneous manner. Density functional theory calculations were employed to optimize the structure of ligand (HL) and its complexes (1-5) to gain insights into their electronic structures. Molecular docking analysis was carried out to identify the preferential binding modes of these complexes toward DNA and BSA protein. The theoretical observations of all cases were found to be very close to the experimental observations. Among the radical scavenging activity results for all the cases toward DPPH, hydroxyl radical, superoxide, nitric oxide and ferric reducing agents, complex (1) revealed a superior scavenging potency over the other compounds. In the screened antimicrobial reports against 10 different selected pathogenic species, although all the complexes (1-5) exhibited a greater significant inhibitory effect than the free ligand, complexes 4 and 5 achieved the best potency over standard drugs. The observed percentage of growth inhibition for all the compounds against the A549, HepG2, MCF-7 and NHDF cell lines suggested that complex 1 had enhanced growth-inhibitory potency over the other compounds and slightly affected normal cells as compared to the standard drug cisplatin, which may lead to its investigation as a promising anticancer agent in future research.
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IJS, KILJ, NUK, UL, UM, UPUK
A new pyrimidine derivative Schiff base ligand (
HL
)
HL =
2-(4,6-dimethylpyrimidin-2-ylimino)methyl)-4-nitrophenol and its metal(II) complexes CuL
2
(
1)
, CoL
2
(
2)
, NiL
2
(
3)
and ZnL
2
(
...4)
have been synthesized and characterized by several spectral techniques. The square planar geometry of the complexes
1–4
confirmed by UV-Visible, ESR and EI-mass spectral techniques. DNA binding study of the complexes
1–4
with Calf Thymus (CT) DNA using absorption spectral titration at different pH (4.0, 7.0 & 10.0) have been scrutinized that the complexes
1–4
bound by groove binding mode with significant binding constant values (
K
b
= 5.61 × 10
5
M
−1
(
1
), 2.60 × 10
5
M
−1
(
2
), 2.48 × 10
5
M
−1
(
3
) and 6.98 × 10
4
M
−1
(
4
) at pH = 10.0. Binding nature of the complexes
1–4
with CT DNA has further confirmed by emission, viscometry and cyclic voltammetry which also recommended that complexes
1–4
bound with CT DNA. The complexes
1–4
possessed effective scavenging effect during the DPPH and SOD radical scavenging method. The antibacterial activity of the complexes
1–4
was vetted against several bacterial strains and the results shows that the ligand (
HL
) and complexes
1–4
are more active in
Bascillus subtilis.
The anticancer activity of the complexes
1–4
was evaluated against Human Breast Cancer Cells (MCF-7), Human Cervical Cancer Cells (HeLa), Human Laryngeal Epithelial Carcinoma (HEp2) and Normal Human Dermal Fibroblast (NHDF) by MTT assay, which revealed that complexes
1
&
2
have modest activity against the cancer cell lines than ligand (
HL
) and complexes
3
&
4
.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OBVAL, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
Biochemically active Cu(II) and Zn(II) complexes CuL(ClO
4
)
2
(
1
) and ZnL(ClO
4
)
2
(
2
) have been synthesized from N,N donor Schiff base ligand
L
derived ...from4,6-dichloropyrimdine-5-carboxaldehyde with 4-(2-aminoethyl)morpholine. The
L
, complexes
1
and
2
have been structurally characterized by elemental analysis,
1
H-NMR, FTIR, MS, UV-Visible and ESR techniques. The results obtained from the spectral studies supports the complexes
1
and
2
are coordinated with
L
through square planar geometry. DFT calculations results supports, the ligand to metal charge transfer mechanism can occur between
L
and metal(II) ions. The antimicrobial efficacy results have been recommended that, complexes
1
and
2
are good anti-pathogenic agents than ligand
L
. The interaction of complexes
1
and
2
with calf thymus (CT) DNA has been studied by electronic absorption, viscometric, fluorometric and cyclic voltammetric measurements. The calculated
K
b
values for
L
, complexes
1
and 2 found from absorption titrations was 4.45 × 10
4
,
L
; 1.92 × 10
5
,
1
and 1.65 × 10
5
,
2
. The
Ksv
values were found to be 3.0 × 10
3
, 3.68 × 10
3
and 3.52 × 10
3
for
L
, complexes
1
and
2
by using competitive binding with ethidium bromide (EB). These results suggest that, the compounds are interacted with DNA may be electrostatic binding. The molecular docking studies have been carried out to confirm the interaction of compounds with DNA. Consequently, in vitro anticancer activities of
L
, complexes
1
and
2
against selected cancer (lung cancer A549, liver cancer HepG2 and cervical carcinoma HeLa) and normal (NHDF) cell lines were assessed by MTT assay.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OBVAL, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
A new series of bio active Cu(II) and Zn(II) complexes CuL(phen)(OOCCH
3
) (1), ZnL(phen)(OOCCH
3
) (2), CuL(bpy)(OOCCH
3
) (3), ZnL(bpy)(OOCCH
3
) (4) have been synthesized using the pyrimidine ...derivative Schiff base (HL) HL = 2-(4,6-dimethylpyrimidin-2-ylimino)methyl)-4-nitrophenol, 1,10-phenanthroline (phen), 2,2'-bipyridine (bpy) and acetate salts of Cu(II) and Zn(II). UV-Visible, FT-IR,
1
H-NMR, ESR, elemental analysis, molar conductance and EI-MS spectral techniques have been used to endorse the square planar geometry for the complexes 1-4. The optimized molecular structure and the harmonic vibrational frequencies have been scrutinized by DFT methods. The antibacterial and antifungal activity of Schiff base (HL) and complexes 1-4 indicates that complex 1 acts as good antimicrobial agent against microbial strains than HL, complexes 2-4 and standard drugs streptomycin and nystatin. DNA cleavage study of the complexes 1-4 exposes that complexes 1 and 3 spectacle good cleaving agent than complexes 2 and 4. The interaction of complexes 1-4 with CT DNA using absorption, emission and viscometric measurements signifies that complexes 1-4 bind via an intercalation mode. The highest binding constants (K
b
) for the complex 1 is confirmed as 7.83 × 10
3
M
−1
and 2.98 × 10
4
M
−1
by absorption and emission spectrum respectively. These experimental observations were found to be close to the theoretical observations investigated by the molecular docking technique. Antioxidant property of the complexes 1-4 using DPPH assay clinches that complex 1 produces significant scavenging effect than other compounds. The result of in vitro cytotoxicity of the Schiff base (HL) and complexes 1-4 shows that complex 1 shows better ability to inhibit the growth of cancer cells.
Communicated by Ramaswamy H. Sarma
Highlights
All synthesized complexes are good inhibitive nature.
DFT are compassionate to reconnoitre the enhanced structure and chemical reactivity of the complexes.
Complex 1 has strong DNA binding/cleaving efficacy through intercalation binding mode.
DNA binding effect has also been proved by molecular docking studies.
Complex 1 may be an appreciated material in cancer chemotherapy mediators in imminent years.
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BFBNIB, GIS, IJS, KISLJ, NUK, PNG, UL, UM, UPUK
A novel series of bioactive water soluble mixed ligand complexes (1-5) M
II
(L)(phen)AcO. nH
2
O {where M = Cu (1) n = 2; Co (2), Mn (3), Ni (4), n = 4 and Zn (5) n = 2} were synthesized from ...2-(2-Morpholinoethylimino) methyl)phenol Schiff base ligand (LH), 1, 10-phenanthroline and metal(II) acetate salt in a 1:1:1 stoichiometric ratio and characterized by several spectral techniques. The obtained analytical and spectral data suggest the octahedral geometry around the central metal ion. Density functional theory calculations have been further supportive to explore the optimized structure and chemical reactivity of these complexes from their frontier molecular orbitals. Gel electrophoresis result indicates that complex (1) manifested an excellent DNA cleavage property than others. The observed binding constants with free energy changes by electronic absorption technique and DNA binding affinity values by viscosity measurements for all compounds were found in the following order (1) > (2) > (4) > (5) > (3) > (LH). The binding results and thermodynamic parameters are described the intercalation mode. In vitro antioxidant properties disclose that complex (1) divulges high scavenging activity against DPPH
*
,
*
OH, O
2
−*
NO
*
, and Fe
3+
. The antimicrobial reports illustrate that the complexes (1-5) were exhibited well defined inhibitory effect than ligand (LH) against the selected different pathogenic species. The observed percentage growth inhibition against A549, HepG2, MCF-7, and NHDF cell lines suggest that complex (1) has exhibited superior anticancer potency than others. Thus, the complex (1) may contribute as potential anticancer agent due to its unique interaction mode with DNA.GRAPHICAL ABSTRACT
Communicated by Ramaswamy H. Sarma
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•Au(III) and Pt(IV) complexes were synthesized from pyrimidine scaffold ligand.•Molecular structure of ligand was confirmed by single crystal X-ray analysis.•Antimicrobial and ...antioxidant activities have been carried out.•DNA binding and DNA/BSA docking analysis have been studied.•The anticancer activities have been studied by MTT assay.
Novel gold and platinum complexes AuL2·Cl, 1 and PtL2·2Cl, 2 with ligand, 2-methoxy-6-((2-(4-(trifluoromethyl)pyrimidin-2-yl)hydrazono)methyl)phenol (HL) have been synthesized and screened for their antimicrobial, antioxidant, DNA binding and anticancer (in vitro) activities. The single crystal of ligand HL was obtained by slow evaporation technique. The molecular structure of HL was confirmed from single crystal X-ray technique. Density functional theory calculations have been performed to gain insights into the electronic structure of these metal complexes. Antimicrobial result shows that, HL and complexes (1 and 2) have good antimicrobial agents against E. coli (bacteria) and C. albicans (fungi) than others bacterial and fungal strains. Antioxidant assay results suggest that, HL and complexes (1 and 2) possess good radical scavenging activity against diverse free radicals (DPPH, SOD, NO and H2O2). The intercalative interactions of HL and complexes (1 and 2) with CT-DNA were confirmed from spectroscopic titrations and viscometric measurements. Furthermore, the interactions of prepared compounds with DNA were confirmed by molecular docking analysis. In order to understand the nature of interactions between these metal complexes and BSA protein results clearly shows that complex 1 binds better than that of complex 2. The antitumor activities of prepared products were tested against single normal and different tumor cell lines by MTT assay. These results reveal that prepared complexes (1 and 2) have significant cytotoxic effect against tumor cell lines.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UL, UM, UPUK, ZRSKP
Effective interaction of natural alkaloid Luotonin A (L) and its affixed acceptor molecules 1 and 2 with donor molecule as Bovine serum albumin (BSA) at various pH (4.0, 7.4 and 10.0) medium have ...been demonstrated using various conventional spectroscopic techniques. These analyses provide some valuable features on the interaction between BSA and acceptor molecules (L, 1 and 2). From the absorption and fluorescence spectral titration studies, the formation of ground-state complexes between the acceptor molecules (L, 1 and 2) and the BSA have been confirmed. The results of the afore titrations analysis reveal that, the strong binding of receptor 1 with BSA (Kapp 5.68×104M−1; KSV 1.86×106Lmol−1; Ka 6.42×105Lmol−1; Kass 8.09×106M−1; ΔG −33.35kJ/mol) at physiological pH medium (7.4) than other receptor molecules 2 and L. The Förster resonance energy transfer (FRET) efficiency between the tryptophan (Trp) residues of BSA and acceptor molecules L, 1 and 2 during the interaction, are 28.85, 85.24 and 53.25 % respectively. The superior binding efficacy of acceptor 1 at physiological pH condition has been further confirmed by FT-IR and Raman spectral analysis methods. Moreover, theoretical docking studies of acceptors L, 1 and 2 towards HSA have been demonstrated to differentiate their binding behaviours. It reveals that, acceptor 1 has the strongest binding ability with HSA through two hydrogen bonding and the Atomic contact energy (ACE) value of −483.96kcal/mol.
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•The natural alkaloid L and its affixed acceptor molecules 1 and 2•Their interaction with the BSA are investigated at various pH medium.•Acceptor 1 has superior BSA binding efficacy at physiological pH condition.•Docking studies of acceptors towards HSA have been demonstrated.•Acceptor 1 has strongest binding ability with HSA via two hydrogen bonding.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UL, UM, UPUK, ZRSKP
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Biologically active Cu(II) complex was synthesized from pyrimidine based Schiff base ligand 4-choloro-2-(((4,6-dimethoxypyrimidin-2-yl)imino)methyl)phenol. The prepared ligand and its ...Cu(II) complex were characterized by analytical and spectroscopic techniques. Molar conductance result suggests that prepared Cu(II) complex has non-electrolytic nature. Elemental and ESI-MS spectroscopic result shows that stoichiometry of ligand and Cu(II) complex are 1:1 ratio. Spectroscopic results reveal that proposed structure of Cu(II) complex possess square planar geometry. The molecular geometry of ligand and its complex were studied by DFT calculation. Antimicrobial activity of prepared compounds was screened against Bacillus subtilis (B. subtilis), Escherichia coli (E. coli) and Staphylococcus aureus (Stap. aureus), Aspergillus niger (A. niger), Candida albicans (C. albicans) and Mucor indicus (M. indicus). These results suggest that Cu(II) complex has better antimicrobial activity than ligand. Moreover, the prepared compounds are highly active in B. subtilis bacteria and C. albicans fungi than other microorganisms. Antioxidant activity of prepared compounds were studied by DPPH assay results recommends that Cu(II) complex has better antioxidant activity than ligand. DNA binding nature of prepared compounds with calf thymus (CT) DNA was performed by electronic absorption and viscometric measurements. The result exposed that prepared compounds can interact with CT-DNA through an intercalation mode. BSA binding ability of prepared compounds were studied by electronic absorption technique and the results shows that prepared compounds posses quenching ability with BSA molecules. Furthermore, molecular docking of prepared compounds were investigated with DNA and BSA, and the result suggests the Cu(II) complex has better binding nature than ligand.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPUK, ZAGLJ, ZRSKP
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