Unsymmetrically substituted imidazolium salts: synthesis, characterization and antimicrobial activity

ABSTRACT Unsymmetrically substituted imidazolium salts were synthesized and characterized using 1H-NMR and 13C-NMR. The antimicrobial activities of the salts were evaluated using the agar-well diffusion method against 14 bacteria and five yeasts. The minimal inhibitory concentrations (MIC) against seven bacteria and one yeast were also determined. Among the test compounds applied, 1, 2, 3, 6 and 11 showed activities against Micrococcus luteus ATCC 9341, Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228, Bacilllus cereus ATCC 11778, Bacillus subtilis ATCC 6633, Bacillus thuringiensis, Listeria monocytogenes ATCC 19112 and Candida trophicalis. However, compounds 1, 2 and 3 showed the highest antimicrobial activities against Micrococcus luteus ATCC 9341, Stapylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228, Bacilllus cereus ATCC 11778 and Bacillus subtilis ATCC 6633 with inhibition zones of 14-20 mm. In addition, compound 6 have only demonstrated activities against Candida trophicalis while compounds 4, 5, 7, 8, 9, 10, 12, 13 and 14 had no effect on test microorganisms.

Synthesis, Characterization, and Biological Activity of N (')-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes.

Reaction of 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one and benzoyl hydrazide in refluxing ethanol gave N (')-[(Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide (HL(1)), which was characterized by NMR spectroscopy and single-crystal X-ray structure study. X-ray diffraction analyses of the crystals revealed a nonplanar molecule, existing in the keto-amine form, with intermolecular hydrogen bonding forming a seven-membered ring system. The reaction of HL(1) with Co(II), Ni(II), and Cu(II) halides gave the corresponding complexes, which were characterized by elemental analysis, molar conductance, magnetic measurements, and infrared and electronic spectral studies. The compounds were screened for their in vitro cytotoxic activity against HL-60 human promyelocytic leukemia cells and antimicrobial activity against some bacteria and yeasts. Results showed that the compounds are potent against HL-60 cells with the IC50 value ≤5 µM, while some of the compounds were active against few studied Gram-positive bacteria.

Spectroscopic and biological approach of Ni(II), Cu(II) and Co(II) complexes of 4-methoxy/ethoxybenzaldehyde thiosemicarbazone glyoxime.

Two novel vicinal dioxime ligands containing (4-methoxybenzaldehyde thiosemicarbazone glyoxime (L(1)H2) or 4-ethoxybenzaldehyde thiosemicarbazone glyoxime (L(2)H2)) thiosemicarbazone units were synthesized and characterized using (1)H NMR, (13)C NMR, HMQC, MS, infrared and, UV-VIS. spectroscopy, elemental analysis, and magnetic susceptibility measurements. Mononuclear nickel(II), copper(II) and cobalt(II) complexes with a metal:ligand ratio of 1:2 for L(1)H2 and L(2)H2 were also synthesized. The effect of pH and solvent on the absorption spectra of both ligands and complexes was determined. IR spectra show that the ligands act in a bidentate manner and coordinates N4 donor groups of the ligands to Ni(II), Cu(II) and Co(II) ions. The detection of H-bonding (O-H⋯O) in the [M(LH)2] metal complexes by IR spectra supported the square-planar MN4 coordination of mononuclear complexes. The antimicrobial activities of compounds L(1)H2, L(2)H2, and their Ni(II), Cu(II) and Co(II) complexes were evaluated using the disc diffusion method against 12 bacteria and 4 yeasts. The minimal inhibitory concentrations (MICs) against 7 bacteria and 3 yeasts were also determined. Among the test compounds attempted, L(1)H2, [Ni(L1H)2], [Cu(L1H)2], L2H2, [Ni(L2H)2] and [Cu(L2H)2] showed some activities against certain Gram-positive bacteria and some of the yeasts tested.

Reversible immobilization of urease by using bacterial cellulose nanofibers.

In this work, bacterial cellulose nanofibers were produced by using the Gluconacetobacter hansenii HE1 strain. These nanofibers were derivatized with dye affinity ligand Reactive Green 5, and these newly synthesized dye-attached nanofibers were used for affinity adsorption of urease. Reactive Green 5-attached nanofibers were characterized by Fourier transform infrared spectroscopy, SEM, and energy-dispersive x-ray spectroscopy analysis. Some adsorption conditions which significantly affect the adsorption efficiency were investigated. The maximum urease adsorption capacity was found to be 240 mg/g nanofiber in pH 6.0 and at room temperature. Dye-free plain nanofibers also used for studying nonspecific urease adsorption onto plain nanofibers and nonspecific adsorption were found to be negligible (3.5 mg/g nanofiber). Prepared dye-attached nanofibers can be used in five successive adsorption/desorption steps without any decrease in their urease adsorption capacity. The desorption rate of the adsorbed urease was found to be 98.9 %. The activity of the urease was also investigated, and it was found that free and desorbed urease from the dye-attached nanofibers showed similar specific activity.

Biological decolorization of textile dyes from isolated microfungi.

In this study, biological decolorization of two textile dyestuff (Benazol black ZN and Cibacron black W-NN) was comparatively studied using 22 microfungi strains isolated from polluted industrial soil areas. The initial dye concentrations in the medium were 250 and 500 mg l(-1). Benazol black ZN was the best decolorized by Haematonectria haematococca (HH1) (36.0%) and Cibacron black W-NN was the best decolorized by Aspergillus niger (AN1) (33.0%) at 250 mg l(-1) dye concentration. At 500 mg l(-1) dye concentration for two different dyes all microfungi strains used showed weak decolorization rates, maximum 13.0% for Benazol black ZN and 6.0% for Cibacron Black W-NN.

The short-term effects of different doses of dexamethasone on the numbers of some bacteria in the ileum.

Glucocorticoids are known to affect intestinal biota both directly or indirectly. The aim of the study reported here was to determine the short-term effects of different doses of dexamethasone on the numbers of various ileal bacteria populations. Rats were randomly put into groups, and each group was administered a single-dose injection of dexamethasone at either 0.1, 0.5, 1, 2.5, 5, or 10 mg/kg body weight. At 48-h post-injection, the numbers of total aerobe, anaerobe, lactobacilli and coliform bacteria in the ileum were determined. The numbers of total aerobes and lactobacilli were higher in the groups receiving 5 and 10 mg/kg dexamethasone than in the control and other dose groups (P < 0.01 and P < 0.001, respectively). The number of ileal anaerobic bacteria was higher in group receiving 5 mg/kg than in the other groups (P < 0.01). There were more coliform bacteria in the group receiving 0.1 mg/kg than in the groups receiving 0.5, 1 and 10 mg/kg (P < 0.05). In light of these results, the effects of dose-dependent increases in the number of different bacterial groups affecting gut functions have still to be determined in future studies.