Highly Fluorescent π-Conjugated Azomethines and Divalent Metal Complexes as Antibacterial and Antibiofilm Nominees.

π-Conjugated azomethine ligands differing in the naphthalene or phenylmethane-centered core structure and their divalent cobalt, nickel, copper, and zinc metal complexes were prepared and well-characterized by spectral analyses in solid state. Magnetic natures of the complexes were determined by magnetic susceptibility measurements in solid-state. Their remarkable photophysical characteristics were recorded by Uv-vis and Fluorescence spectroscopic techniques. At their excitation wavelenght of 265 nm, all molecules exhibited triple fluorescence emission bands with promising intensities above 673 nm in near infra-red region. Antibacterial and antibiofilm activities of the π-conjugated azomethines are promising for potential applications in medical and healthcare settings. Hence, the antibacterial/antibiofilm activity of the π-conjugated azomethine ligands and their metal complexes against some clinically important bacteria namely Staphylococcus aureus (MSSA), Methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa and Proteus mirabilis was investigated, and the obtained results have shown that the ligands and complexes had a remarkable antibacterial effect, especially on Proteus mirabilis. Metal complexes have been found to have a significant inhibitory effect on biofilm formation by MRSA, MSSA, and P. mirabilis compared to ligands. The copper (II) complex of ligand-2 showed the highest inhibition percentage, significantly reducing biofilm formation for MRSA and MSSA. Furthermore, cobalt (II) complexes of the ligands selectively inhibited the growth of the opportunistic pathogen P. mirabilis biofilms, indicating that metal complexes might be a good choice for future antibiofilm studies.

Ortho-hydroxy bioactive schiff base compounds: Design, comprehensive characterization, photophysical properties and elucidation of antimicrobial and mutagenic potentials.

Preparation and comprehensive characterization of three Schiff base ligands; with trimethoxy substitution (1E,1'E)-N,N'-(naphthalene-1,5-diyl)bis(1-(3,4,5-trimethoxyphenyl)methanimine, 1, with ortho-hydroxy substitution 6,6'-((1E,1'E)-(naphthalene-1,5-diylbis(azaneylylidene))bis(methaneylylidene))bis(2-methoxyphenol), 2 and 3,4-bis(((E)-2-hydroxy-3-methoxy benzylidene)amino)benzoicacid, 3 and their Ni(II), Cu(II), Co(II), Zn(II), Fe(II), Mn(II) complexes have been reported. Their spectral properties were studied in solution and solid-state by a combination of different analytical techniques; FT-IR spectroscopy, 1H NMR and 13C NMR spectroscopy, elemental analysis and thermal analysis. Diamagnetic and paramagnetic natures of the complexes were also determined by magnetic susceptibility measurements in solid-state. Promising photophysical properties were observed as; Amax. were recorded at 226 nm for 2; at 795 nm for 2-Ni, at 782 nm for 2-Cu, at 784 nm for 2-Co, at 702 nm for 2-Zn, at 784 nm for 2-Fe, at 702 nm for 2-Mn and at 289 nm for 3, at 786 nm for 3-Ni, at 797 nm for 3-Cu, at 746 nm for 3-Co, at 794 nm for 3-Zn, at 699 nm for 3-Fe, at 781 nm for 3-Mn ; and Imax were also recorded at; 380, 490, 725 nm for 2 and 2-Metal; 375 nm, 510 nm, 725 nm for 3 and 3-Metal when excitated at 220 nm. Antibacterial activities against different microorganisms; Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae ATCC 70603, Staphylococcus aureus ATCC 43,300 (MRSA), Salmonella enteritidis ATTC 13076, Sarcina lutea ATCC 9341, Bacillus cereus ATTC 11778, and antifungal activities against Candida albicans NRRL Y-417 of the compounds 1, 2, 3, 2-Cu, 2-Fe, 3-Zn, 3-Fe were determined. Mutagenic properties of the compounds were also studied and according to the results 2-Cu and 3 have been found non-mutagenic in Ames test but also they have strong antimicrobial potential against pathogen microorganisms. For 2-Cu MIC values were ranging between 0.39 and 0.024 mg/ml and the lowest minimum inhibitory concentration (0.024 mg/ml) was determined against E. coli. The 3 numbered compound revealed strong antimicrobial activity at doses of ranging between 0.39 and 0.097 mg/ml and E. coli was the most sensitive bacterium against this chemical.

Antibacterial activities and DNA-cleavage properties of novel fluorescent imidazo-phenanthroline derivatives.

Design and biological activities of fluorescent imidazo-phenanthroline derivatives; (E)-5-((4-((4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenoxy)methyl)benzylidene)amino)- isophthalicacid, 2 and 2-(4-(((5-chloroquinolin-8-yl)oxy)methyl)phenyl)-1H-imidazo[4,5f] [1,10]phenanthroline, 3, have been reported. Their characterizations were performed by spectroscopic techniques. Their promising photophysical behaviours were observed in absorbance and fluorescence studies. The antibacterial activities of the compounds were determined against seven different microorganisms; Bacillus subtilis ATCC 6633(G + ), Pseudomonas aeruginosa ATCC 29853(G-), Escherichia coli ATCC 35,218 (G-), Enterococcus faecalis ATCC 292,112 (G + ), Salmonella typhimurium ST-10 (G-), Streptococcus mutans NCTC 10,449 (G + ), and Staphylococcus aureus ATCC 25923(G + ). MIC values of 3 was determined as 156,25 µM on all tested bacteria. A preliminary study of the structure-activity relationship (SAR) also revealed that the antimicrobial activity depended on the substituents on the phenyl ring. The electron withdrawing Cl-substitued compound 3 most favour for antimicrobial activity even at lowest concentration compared to other compounds. DNA-cleavage activities of the compounds were also investigated. The interactions of the compounds with supercoiled pBR322 plasmid DNA were obtained by agarose gel electrophoresis. All imidazo-phenanthroline derivatives were found to be highly effective on DNA, even at the lowest concentrations because of their planar nature which provides ease of bind to the helix structure of DNA.