ABSTRACT
In this study, new unsymmetrical meso-tetraaryl AB3-type porphyrins 1 and 2 were successfully synthesized by the reaction of p-bromobenzaldehyde and p-hydroxybenzaldehyde with pyrrole in propionic acid. AB3-type porphyrin building blocks with hydroxyl functionality (1 and 2) were further used to generate both covalently linked metal free and Zn(II) porphyrins 3-6 having piperidine and morpholine heterocyclic units. These novel compounds were characterized by using 1H NMR, 13C NMR, FT-IR and MALDI-TOF spectrophotometry. The photophysical and photochemical properties of compounds 1-6 were investigated by employing UV-vis absorption and fluorescence emission spectroscopy in tetrahydrofuran (THF). From the view of biological properties, the antioxidant capacities of porphyrins were determined by using DPPH radical scavenging activity and 2 was determined as the most potent porphyrin analog with a value of 98.42% at 200 mg L-1. All the targeted compounds displayed significant DNA nuclease activity. In addition, the antimicrobial potential of compounds 1-6 was also investigated by a micro-dilution process and 2 was found to be the most effective candidate against the tested microbial strains. The newly synthesized porphyrins also showed 100% microbial cell viability inhibition against E. coli at all examined concentrations. In terms of biofilm inhibition activity, the best results for the maximum photodynamic antimicrobial biofilm inhibition of S. aureus and P. aeruginosa were obtained by compound 2 with the values of 99.75% and 93.39%, respectively.
Subject(s)
Porphyrins , Porphyrins/pharmacology , Porphyrins/chemistry , Spectroscopy, Fourier Transform Infrared , Escherichia coli , Staphylococcus aureus , Piperidines , MorpholinesABSTRACT
Alzheimer's disease (AD) is known as one of the most devastating neurodegenerative disease diagnosed for the old-aged people and cholinesterase inhibitors (ChEI) can be used as an effective palliative treatment for AD. A range of novel monomeric and dimeric indole based thiosemicarbazone derivatives 17-28 was synthesized in order to target cholinesterases (ChE). Biological importance of the targeted compounds 17-28 was investigated by employing the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes along with three different antioxidant property determination assays, namely DPPH free radical scavenging, ABTS cationic radical decolarization, and CUPRAC cupric reducing antioxidant capacity. The compounds 18 and 19 displayed the best inhibitor activity against BChE with IC50 values of 7.42 and 1.95 µM, respectively. The antioxidant potentials were found to be moderate for DPPH and ABTS assays and the compounds 28 and 18 were the most potent candidates for both antioxidant assays. Cupric reducing capacity was the most promising assay and the compounds 25, 26 and 28 provided better inhibition values than all the standards. Further binding mode and affinity studies performed by molecular docking and molecular dynamics simulations. Accordingly, the compound 19 is the most plausible candidate that can compete with galantamine (GNT), a common pharmaceutics targeting both cholinesterase enzymes.
Subject(s)
Alzheimer Disease , Neurodegenerative Diseases , Thiosemicarbazones , Acetylcholinesterase/metabolism , Aged , Antioxidants/chemistry , Butyrylcholinesterase/metabolism , Cholinesterase Inhibitors/chemistry , Humans , Middle Aged , Molecular Docking Simulation , Molecular Dynamics Simulation , Thiosemicarbazones/pharmacologyABSTRACT
The synthesized and sensing capability of two novel azaindole substituted mono and distyryl BODIPY dyes against bisulfate anion were reported. Structural characterizations of the targeted compounds were conducted by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H and 13C NMR spectroscopies. Photophysical properties of the azaindole substituted BODIPY compounds were investigated employing absorption and fluorescence spectroscopies in acetonitrile solution. It was found that the final compounds 3 and 4 exhibited exclusively selective and sensitive turn-off sensor behavior on HSO4- anion. Additionally, the stoichiometry ratio of the targeted compounds to bisulfate anion was measured 0.5 by Job's method. Also, density function theory was performed to the optical response of the sensor for targeted compounds. Furthermore, the cytotoxicity of Azaindole-BODIPYs was examined against living human leukemia K562 cell lines.
