Synthesis and spectral, antimicrobial, anion sensing, and DNA binding properties of Schiff base podands and their metal complexes

Yıldız, Mustafa; Tan, Eric; Demir, Neslihan; Yıldırım, Nuray; Ünver, Hüseyin; Kiraz, Aşkın; Mestav, Burcu

doi:10.1134/s1070363215090200

Cited by 10 publications

(7 citation statements)

References 51 publications

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“…Schiff bases of substituted salicylaldehydes (2-hydroxybenzaldehydes) are well-known antimicrobial agents in “free” form or as ligands in metallic complexes [ 4 , 5 , 6 , 7 ]. Similar biological action have been reported for Schiff bases of various sulfonamides [ 4 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

et al. 2017

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The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, yeasts, moulds, Mycobacterium tuberculosis, nontuberculous mycobacteria (M. kansasii, M. avium) and their cytotoxicity was determined. Among bacteria, the genus Staphylococcus, including methicillin-resistant S. aureus, showed the highest susceptibility, with minimum inhibitory concentration values from 7.81 µM. The growth of Candida sp. and Trichophyton interdigitale was inhibited at concentrations starting from 1.95 µM. 4-[(2,5-Dihydroxybenzylidene)amino]-N-(pyrimidin-2-yl)-benzenesulfonamide was identified as the most selective Schiff base for these strains with no apparent cytotoxicity and a selectivity index higher than 16. With respect to M. tuberculosis and M. kansasii that were inhibited within the range of 8 to 250 µM, unsubstituted 4-[(2-hydroxy-benzylidene)amino]-N-(pyrimidin-2-yl)benzenesulfonamide meets the selectivity requirement. In general, dihalogenation of the salicylic moiety improved the antibacterial and antifungal activity but also increased the cytotoxicity, especially with an increasing atomic mass. Some derivatives offer more advantageous properties than the parent sulfadiazine, thus constituting promising hits for further antimicrobial drug development.

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Section: Introductionmentioning

confidence: 99%

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

et al. 2017

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“…Furthermore, the red shift of maximum absorption shows the energy decrease in energy between the HOMO and LUMO. This indicates that DNA interacts with the Schiff base (14)(15)(16)(17)(18)(19)(20). If the DNA interacts with the Schiff base, π-π* transition energy decreases, and the absorption shifts to red.…”

Section: Minimum Inhibitory Concentration (Mic)mentioning

confidence: 99%

“…Some characteristic properties of Schiff bases, such as antimicrobial, antioxidant, anticancer, anti-helmintic, anti-inflammatory, anticonvulsant, antitubercular and analgesic activities (1)(2)(3)(4)(5) as well as chemosensory and DNA binding properties (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) have been reported. The technique used in chemosensors is concerned with the quenching of the colorimetric chemosensor of fluorescence by interaction with various anions.…”

Section: Introductionmentioning

confidence: 99%

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A Schiff Base Sensor Selective to Anions, Biological Activity and Spectral Studies

Yıldırım

Yıldız

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, synthesis, characterization, anion sensor properties, and DNA binding of a benzothiazole-based Schiff base 4-bromo-2-((6-methoxybenzo[d]thiazol-2-ylimino)methyl)phenol have been investigated. The structure of the Schiff base was revealed with elemental analysis and spectroscopic methods. The colorimetric and fluorescent anion sensor properties of the Schiff base in DMSO were investigated by adding an equivalent amount of anions. In this context, the solution containing Schiff base had a color change after the addition of F-, CN-, AcO-, H2PO4and OHanions, while the color change was not observed with the addition of Br-, I-, SCN-, ClO4and HSO4anions. The anion-binding power of the compound was found to be F->OH->AcO->CN->H2PO4using UV-Vis spectrophotometry, respectively. The antimicrobial activity of the compound was investigated against some microorganisms. The compound showed activity against bacteria and yeast. Schiff base showed a similar effect against both bacteria and yeast. Interactions between the compound and CT-DNA were studied with UV-Vis spectra. The UV-Vis experiment results confirm that the Schiff base binds to CT-DNA in an intercalative mode. The compound did not show any cleavage effect on SC DNA as hydrolytic and oxidative.

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“…The intramolecular hydrogen bond and proton transfer explained above are thought to affect anion-sensory properties. [15][16][17] It could be specifically stated that the keto-amine and enol-imine tautomer balances contribute to the bonding and selection of anions. Undoubtedly, colorimetric anion sensors are of more importance, because such materials are useful as they provide visual information more readily.…”

Section: Introductionmentioning

confidence: 99%

DFT calculation, biological activity, anion sensing studies and crystal structure of (E)-4-chloro-2-((pyridin-2-ylimino)-methyl)phenol

Yıldırım

Demir

Alpaslan

et al. 2018

JSCS

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Chloro-2-[(pyridin-2-ylimino)methyl]phenol was synthesized in the reaction of 2-aminopyridine with 5-chlorosalicylaldehyde. The structure of compound was investigated by FTIR, UV-Vis, 1 H-NMR, 13 C-NMR and X-ray data. In addition, characterization of the compound was realized using theoretical quantum mechanical calculations and experimental spectroscopic methods. The molecular structure of the compound was confirmed using X-ray single-crystal data, NMR, FTIR and UV-Vis, which were in good agreement with the structure predicted by the theoretical calculations using the density functional theory (DFT). Moreover, the antimicrobial activity of the compound was investigated against some bacteria and yeast cultures by the broth microdilution test. UV-Vis spectroscopy studies of the interactions between the Schiff base and calf thymus DNA (CT-DNA) showed that the compound interacts with CT-DNA via electrostatic binding. The colorimetric response of the compound receptors was investigated before and after the addition of an equivalent amount of each anion to evaluate anion recognition properties.

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Synthesis and spectral, antimicrobial, anion sensing, and DNA binding properties of Schiff base podands and their metal complexes

Cited by 10 publications

References 51 publications

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

A Schiff Base Sensor Selective to Anions, Biological Activity and Spectral Studies

DFT calculation, biological activity, anion sensing studies and crystal structure of (E)-4-chloro-2-((pyridin-2-ylimino)-methyl)phenol

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