In vitro cytotoxicity activity of novel Schiff base ligand-lanthanide complexes.
Ontology highlight
ABSTRACT:
SUBMITTER: Andiappan K
PROVIDER: S-EPMC5812993 | biostudies-literature |
REPOSITORIES: biostudies-literature
Similar Datasets
Project description:This work describes the syntheses, structural characterization, and biological profile of Mn(II)- and Zn(II)-based complexes 1 and 2 derived from the aroyl-hydrazone Schiff base ligand (L1). The synthesized compounds were thoroughly characterized by elemental analysis, Fourier transform infrared spectroscopy (FTIR), UV-vis, electron paramagnetic resonance (EPR), nuclear magnetic resonance (NMR), and single-crystal X-ray diffraction (s-XRD). Density functional theory (DFT) studies of complexes 1 and 2 were performed to ascertain the structural and electronic properties. Hirshfeld surface analysis was used to investigate different intermolecular interactions that define the stability of crystal lattice structures. To ascertain the therapeutic potential of complexes 1 and 2, in vitro interaction studies were carried out with ct-DNA and bovine serum albumin (BSA) using analytical and multispectroscopic techniques, and the results showed more avid binding of complex 2 than complex 1 and L1. The antioxidant potential of complexes 1 and 2 was examined against the 2,2-diphenyl picrylhydrazyl (DPPH) free radical, which revealed better antioxidant ability of the Mn(II) complex. Moreover, the antibacterial activity of synthesized complexes 1 and 2 was tested against Gram-positive and Gram-negative bacteria in which complex 2 demonstrated more effective bactericidal activity than L1 and complex 1 toward Gram-positive bacteria. Furthermore, the in vitro cytotoxicity assessment of L1 and complexes 1 and 2 was carried out against MDA-MB-231 (triple negative breast cancer) and A549 (lung) cancer cell lines. The cytotoxic results revealed that the polymeric Zn(II) complex exhibited better and selective cytotoxicity against the A549 cancer cell line as was evidenced by its low IC50 value.
| S-EPMC9878661 | biostudies-literature
Project description:Four cobalt(iii) complexes of the general formula [Co(Schiff base)(L)2]+, where L is ammonia (NH3) or 3-fluorobenzylamine (3F-BnNH2), were synthesized. The complexes were characterized by NMR spectroscopy, mass spectrometry, and X-ray crystallography. Their electrochemical properties, ligand substitution mechanisms, and ligand exchange rates in aqueous buffer were investigated. These physical properties were correlated to the cellular uptake and anticancer activities of the complexes. The complexes undergo sequential, dissociative ligand substitution, with the exchange rates depending heavily on the axial ligands. Eyring analyses revealed that the relative ligand exchange rates were largely impacted by differences in the entropy, rather than enthalpy, of activation for the complexes. Performing the substitution reactions in the presence of ascorbate led to a change in the reaction profile and kinetics, but no change in the final product. The cytotoxic activity of the complexes correlates with both the ligand exchange rate and reduction potential, with the more easily reduced and rapidly substituted complexes showing higher toxicity. These relationships may be valuable for the rational design of Co(iii) complexes as anticancer or antiviral prodrugs.
| S-EPMC6504617 | biostudies-literature
Project description:The thermal condensation of 3-(2-Furyl)acrolein with 2-Amino-6-ethoxybenzothiazole generated a new Schiff base, (1E,2E)-N-(6-ethoxybenzo[d]thiazol-2-yl)-3-(furan-2-yl)prop-2-en-1-imine (L), with general formula of C16H14N2O2S. Also, a series of lanthanide complexes of gadolinium, samarium, and neodymium (La-Lc) were synthesized utilizing acetonitrile as the solvent and triethylamine as a buffer and catalyst. Based on elemental analysis, mass spectroscopy, and FTIR analysis, all of the Bis-(1E,2E)-N-(6-ethoxybenzo[d]thiazol-2-yl)-3-(furan-2-yl)prop-2-en-1-iminetri-nitratolanthanide(III) complexes with the general formula [LnL2(NO3)3]·H2O are solids with a 2:1 molar ratio (ligand: metal). Based on conductivity estimates, they are nonelectrolytes and monoatomic paramagnetic according to the magnetic moment measurements, and one mole of lattice water was found after thermal gravimetric measurements and FTIR analysis. Therefore, the lanthanide complexes show a ten-coordination structure with a deformed bicapped square antiprismatic. The Schiff base and its complexes were screened for their antimicrobial, antifungal, antioxidant, and antitumor properties. Their antimicrobial and antifungal activities were strong, and they also produced good antioxidant and antitumor effects.
| S-EPMC9027428 | biostudies-literature
Project description:A series of fifteen silver (I) quinoline complexes Q1-Q15 have been synthesized and studied for their biological activities. Q1-Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1-L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1-Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes' moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.
| S-EPMC7956476 | biostudies-literature
Project description:Unsymmetrical tetradentate Schiff base Fe(III) and Cu(II) complexes were prepared by the coordination of some unsymmetrical tetradentate Schiff base ligands with CuCl2·2H2O or FeCl3·6H2O. The obtained complexes were characterized by ESI-MS, IR, and UV-Vis. The spectroscopic data with typical signals are in agreement with the suggested molecular formulae of the complexes. Their cyclic voltammetric studies in acetonitrile solutions showed that the Cu(II)/Cu(I) and Fe(III)/Fe(II) reduction processes are at (-)1.882-(-) 1.782 V and at (-) 1.317-(-) 1.164 V, respectively. The in vitro cytotoxicity of obtained complexes was screened for KB and Hep-G2 human cancer cell lines. The results showed that almost unsymmetrical tetradentate Schiff base complexes have good cytotoxicity. The synthetic complexes bearing the unsymmetrical tetradentate Schiff base ligands with different substituted groups in the salicyl ring indicate different cytotoxicity. The obtained Fe(III) complexes are more cytotoxic than Cu(II) complexes and relative unsymmetric Schiff base ligands.
| S-EPMC8118743 | biostudies-literature
Project description:In this study, two Ni(II) complexes, namely [Ni(HL1)₂(OAc)₂] (1) and [Ni(L2)₂] (2) (where HL1 and HL2 are (E)-1-((1-(2-hydroxyethyl)-1H-pyrazol-5-ylimino)methyl)-naphthalen-2-ol) and (E)-ethyl-5-((2-hydroxynaphthalen-1-yl)methyleneamino)-1-methyl-1H-pyrazole-4-carboxylate, respectively), were synthesized and characterized by X-ray crystallography, Electrospray Ionization Mass Spectrometry (ESI-MS), elemental analysis, and IR. Their uptake in biological macromolecules and cancer cells were preliminarily investigated through electronic absorption (UV-Vis), circular dichroism (CD) and fluorescence quenching measurements. Bovine serum albumin (BSA) interaction experiments were investigated by spectroscopy which showed that the complexes and ligands could quench the intrinsic fluorescence of BSA through an obvious static quenching process. The spectroscopic studies indicated that these complexes could bind to DNA via groove, non-covalent, and electrostatic interactions. Furthermore, in vitro methyl thiazolyl tetrazolium (MTT) assays and Annexin V/PI flow cytometry experiments were performed to assess the antitumor capacity of the complexes against eight cell lines. The results show that both of the complexes possess reasonable cytotoxicities.
| S-EPMC6151616 | biostudies-literature
Project description:Resistance to currently available antifungal drugs has quietly been on the rise but overshadowed by the alarming spread of antibacterial resistance. There is a striking lack of attention to the threat of drug-resistant fungal infections, with only a handful of new drugs currently in development. Given that metal complexes have proven to be useful new chemotypes in the fight against diseases such as cancer, malaria, and bacterial infections, it is reasonable to explore their possible utility in treating fungal infections. Herein we report a series of cobalt(III) Schiff base complexes with broad-spectrum antifungal activity. Some of these complexes show minimum inhibitory concentrations (MIC) in the low micro- to nanomolar range against a series of Candida and Cryptococcus yeasts. Additionally, we demonstrate that these compounds show no cytotoxicity against both bacterial and human cells. Finally, we report the first in vivo toxicity data on these compounds in Galleria mellonella, showing that doses as high as 266 mg kg-1 are tolerated without adverse effects, paving the way for further in vivo studies of these complexes.
| S-EPMC7855930 | biostudies-literature
Project description:Metal-based drugs, including lanthanide complexes, have been extremely effective in clinical treatments against various diseases and have raised major interest in recent decades. Hence, in this work, a series of lanthanum (III) and cerium (III) complexes, including Schiff base ligands derived from (1H-benzimidazol-2-yl)aniline, salicylaldehyde, and 2,4-dihydroxybenzaldehyde were synthesized and characterized using different spectroscopic methods. Besides their cytotoxic activities, they were examined in human U-937 cells, primate kidney non-cancerous COS-7, and six other, different human tumor cell lines: U251, PC-3, K562, HCT-15, MCF-7, and SK-LU-1. In addition, the synthesized compounds were screened for in vitro antiparasitic activity against Leishmania braziliensis, Plasmodium falciparum, and Trypanosoma cruzi. Additionally, antibacterial activities were examined against two Gram-positive strains (S. aureus ATCC® 25923, L. monocytogenes ATCC® 19115) and two Gram-negative strains (E. coli ATCC® 25922, P. aeruginosa ATCC® 27583) using the microdilution method. The lanthanide complexes generally exhibited increased biological activity compared with the free Schiff base ligands. Interactions between the tested compounds and model membranes were examined using differential scanning calorimetry (DSC), and interactions with calf thymus DNA (CT-DNA) were investigated by ultraviolet (UV) absorption. Molecular docking studies were performed using leishmanin (1LML), cruzain (4PI3), P. falciparum alpha-tubulin (GenBank sequence CAA34101 [453 aa]), and S.aureus penicillin-binding protein 2a (PBP2A; 5M18) as the protein receptors. The results lead to the conclusion that the synthesized compounds exhibited a notable effect on model membranes imitating mammalian and bacterial membranes and rolled along DNA strands through groove interactions. Interactions between the compounds and studied receptors depended primarily on ligand structures in the molecular docking study.
| S-EPMC8235109 | biostudies-literature
Project description:Two new zinc complexes, Zn(HL1)2 (1) and [Zn2(H2L2)(OAc)2]2 (2) [H2L1 = Schiff base derived from o-vanillin and (R)-(+)-2-amino-3-phenyl-1-propanol, H3L2 = Schiff base derived from o-vanillin and 2-amino-2-ethyl-1,3-propanediol], have been synthesized and characterized by single crystal X-ray diffraction, elemental analyses, TG analyses, solid fluorescence, IR, UV-Vis and circular dichroism spectra. The structural analysis shows that complex 1 has a right-handed double helical chain along the crystallographic b axis. A homochiral 3D supramolecular architecture has been further constructed by intermolecular C-H··· ?, O-H···O and C-H···O interactions. Complex 2 includes two crystallographically independent binuclear zinc molecules. The two binuclear zinc molecules are isostructural. The 2-D sheet supramolecular structure was formed by intermolecular hydrogen bonding interaction. The fluorescence of ligands and complexes in DMF at room temperature are studied. The interactions of two complexes with calf thymus DNA (CT-DNA) are investigated using UV-Vis, CD and fluorescence spectroscopy. The results show that complex 1 exhibits higher interaction with CT-DNA than complex 2. In addition, in vitro cytotoxicity of the complexes towards four kinds of cancerous cell lines (A549, HeLa, HL-60 and K562) were assayed by the MTT method. Investigations on the structures indicated that the chirality and nuclearity of zinc complexes play an important role on cytotoxic activity.
| S-EPMC4482705 | biostudies-literature
Project description:The proton dissociation processes of two tridentate salicylidene aminoguanidine Schiff bases (SISC, Pro-SISC-Me), the solution stability and electrochemical properties of their Cu(II), Fe(II) and Fe(III) complexes were characterized using pH-potentiometry, cyclic voltammetry and UV-visible, 1H NMR and electron paramagnetic resonance spectroscopic methods. The structure of the proline derivative (Pro-SISC-Me) was determined by X-ray crystallography. The conjugation of L-proline to the simplest salicylidene aminoguanidine Schiff base (SISC) increased the water solubility due to its zwitterionic structure in a wide pH range. The formation of mono complexes with both ligands was found in the case of Cu(II) and Fe(II), while bis complexes were also formed with Fe(III). In the complexes these tridentate ligands coordinate via the phenolato O, azomethine N and the amidine N, except the complex [Fe(III)L2]+ of Pro-SISC-Me in which the (O,N) donor atoms of the proline moiety are coordinated beside the phenolato O, confirmed by single crystal X-ray crystallographic analysis. This binding mode yielded a stronger Fe(III) preference for Pro-SISC-Me over Fe(II) in comparison to SISC. This finding is also reflected in the lower redox potential value of the iron-Pro-SISC-Me complexes. The ligands alone were not cytotoxic against human colon cancer cell lines, while complexation of SISC with Cu(II) resulted in moderate activity, unlike the case of its more hydrophilic counterpart.
| S-EPMC9000575 | biostudies-literature