Antimicrobial and antifungal activities of bifunctional cooper(ii) complexes with non-steroidal anti-inflammatory drugs, flufenamic, mefenamic and tolfenamic acids and 1,10-phenanthroline

2020 ◽  
Vol 18 (1) ◽  
pp. 1444-1451
Author(s):  
Lenka Hudecova ◽  
Klaudia Jomova ◽  
Peter Lauro ◽  
Miriama Simunkova ◽  
Saleh H. Alwasel ◽  
...  
Keyword(s):  
Growth Inhibition ◽  
Antibacterial Activities ◽  
Redox Cycling ◽  
Yeast Cells ◽  
Model Organisms ◽  
Flufenamic Acid ◽  
Antifungal Activities ◽  
E Coli ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

AbstractCooper(ii) complexes represent a promising group of compounds with antimicrobial and antifungal properties. In the present work, a series of Cu(ii) complexes containing the non-steroidal anti-inflammatory drugs, tolfenamic acid, mefenamic acid and flufenamic acid as their redox-cycling functionalities, and 1,10-phenanthroline as an intercalating component, has been studied. The antibacterial activities of all three complexes, [Cu(tolf-O,O′)2(phen)] (1), [Cu(mef-O,O′)2(phen)] (2) and [Cu(fluf-O,O′)2(phen)] (3), were tested against the prokaryotic model organisms Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) and their antifungal activities were evaluated towards the yeast, Saccharomyces cerevisiae (S. cerevisiae). The antibacterial activity of both strains has been compared with the antibiotic Neomycin. The calculated IC50 values revealed slight differences in the antibacterial activities of the complexes in the order 1 ∼ 3 > 2. The most profound growth inhibition of E. coli was observed, at its highest concentration, for the complex 1, which contains chlorine atoms in the ligand environment. The trend obtained from IC50 values is generally in agreement with the determined MIC values. Similarly, the complex 1 showed the greatest growth inhibition of the yeast S. cerevisiae and the overall antifungal activities of the Cu(ii) complexes were found to follow the order 1 > 3 ≫ 2. However, for complex 2, even at the highest concentration tested (150 μM), a 50% decrease in yeast growth was not achieved. It appears that the most potent antimicrobial and antifungal Cu(ii) complexes are those containing halogenated NSAIDs. The mechanisms by which Cu(ii) complexes cause antibacterial and antifungal activities can be understood on the basis of redox-cycling reactions between cupric and cuprous species which lead to the formation of free radicals. The higher efficacy of the Cu(ii) complexes against bacterial cells may be due to an absence of membrane-protected nuclear DNA, meaning that on entering a cell, they can interact directly with its DNA. Contrastingly, for the complexes to interact with the DNA in yeast cells, they must first penetrate through the nuclear membrane.

scholarly journals Crystal Structures of Prostaglandin D2 11-Ketoreductase (AKR1C3) in Complex with the Nonsteroidal Anti-Inflammatory Drugs Flufenamic Acid and Indomethacin

2004 ◽  
Vol 64 (5) ◽  
pp. 1802-1810 ◽  
Author(s):  
Andrew L. Lovering ◽  
Jon P. Ride ◽  
Christopher M. Bunce ◽  
Julian C. Desmond ◽  
Stephen M. Cummings ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Flufenamic Acid ◽  
Prostaglandin D2 ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

scholarly journals Synthesis of quinoline attached-furan-2(3H)-ones having anti-inflammatory and antibacterial properties with reduced gastro-intestinal toxicity and lipid peroxidation

2011 ◽  
Vol 76 (12) ◽  
pp. 1617-1626 ◽  
Author(s):  
Mohammad Alam ◽  
Priya Sarkar ◽  
Asif Husain ◽  
Akranth Marella ◽  
M.S. Zaman ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Phosphorus Oxychloride ◽  
Antibacterial Properties ◽  
Antibacterial Activities ◽  
Dimethyl Formamide ◽  
Significant Activity ◽  
Acylation Reaction ◽  
Reaction Conditions ◽  
E Coli ◽  
Anti Inflammatory

A series of 3-[2-chloroquinolin-3-yl)methylene]-5-aryl-furan-2(3H)-ones {3(a-p)} were synthesized. The required 3-(substitutedbenzoyl) propionic acids {2(a-d)} were prepared under Friedal Craft acylation reaction conditions. The substituted 2-chloroquinoline-3-carbaldehydes {1(a-d)} were synthesized by reaction of substitutedphenylethanone-oxime with phosphorus oxychloride in presence of dimethyl formamide using the Vilsmeir Haack reaction method. These compounds were screened for their anti-inflammatory and antibacterial activities along with their ulcerogenic and lipid peroxidation potentials. The compounds that showed significant anti-inflammatory activity were further screened for their analgesic activity. The compounds were less toxic in terms of ulcerogenicity as compared to a standard, which was also supported by lipid peroxidation studies. The antibacterial activities were performed against Staphylococcus aureus and Escherichia coli. Compounds 3f, 3n and 3o showed significant activity against both S. aureus and E. coli having an MIC value of 6.25?g mL-1.

Synthesis of Some New Hydroxytriazenes and their Antimicrobial and Anti-inflammatory Activities

2020 ◽  
Vol 19 (1) ◽  
pp. 50-60
Author(s):  
Shilpa Jain ◽  
Varsha Dayma ◽  
Poonam Sharma ◽  
Amit Bhargava ◽  
Prabhat K. Baroliya ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
Antiinflammatory Effect ◽  
Zone Of Inhibition ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
E Coli ◽  
The Past ◽  
Anti Inflammatory ◽  
Good Agreement

Background: Hydroxytriazenes and their derivatives have been studied for the biological and pharmacological applications in the past few years. These compounds possess antibacterial, antifungal, anti-inflammatory, analgesic and wound healing activities. In this study, we report the synthesis of ten hydroxytriazenes in two series derived from disubstituted aniline and studied for antimicrobial and anti-inflammatory activities. Methods: For this purpose, 2-methyl-5-chloroaniline and 2-trifluoromethyl-5-chloroaniline were used to synthesize compounds A1-5 and B1-5 series, respectively. All compounds were synthesized by the reported method which involves three steps of the method (i) Reduction, (ii) Diazotization, (iii) Coupling. All synthesized compounds were characterized by various techniques CHN elemental analysis, FTIR, 1H NMR, and MASS spectral analysis. The antibacterial activities of the compounds were screened against S. aureus, S. pyogenes, E. coli, P. aeruginosa, and antifungal activities were against C. albicans, A. clavatus by the zone of inhibition method. In addition, anti-inflammatory activity was also evaluated by carrageenan-induced paw edema method and results were reported as % inhibition. Results: All the synthesized compounds were obtained in pure form and their spectral data are in good agreement with their structure. The synthesized compounds have shown good antimicrobial activity and zone of inhibition was ranging 21 to 24 mm. Further antiinflammatory effect of the compounds was 96.58 to 98.71 % inhibition. Conclusion: The results of the present study indicate that chloro and trifluoromethyl substitution at hydroxytriazenes skeleton could improve anti-inflammatory and antimicrobial activities.

Flufenamic Acid and Placebo Compared in Rheumatoid Arthritis and Osteoarthritis

1981 ◽  
Vol 9 (4) ◽  
pp. 253-256 ◽  
Author(s):  
G Kagan ◽  
L Huddlestone ◽  
P Wolstencroft
Keyword(s):  
Rheumatoid Arthritis ◽  
General Practice ◽  
Side Effects ◽  
Crossover Study ◽  
Morning Stiffness ◽  
Flufenamic Acid ◽  
Moderate Pain ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

Forty patients in general practice with rheumatoid arthritis or osteoarthritis were identified as suffering from moderate pain and tenderness and moderate stiffness in excess of 30 minutes. After discontinuation of non-steroidal anti-inflammatory drugs for 2 weeks, a crossover study was conducted comparing the benefits of flufenamic acid, 100 mg, four times daily with placebo. At the same time, paracetamol at a dose up to 8 × 500 mg daily, could be used for pain which the patient judged to be unrelieved. Thirty-four patients completed the two 3-week test periods and twenty-one patients were improved in relation to morning stiffness and pain by flufenamic acid and twelve patients by placebo – a difference greater than would have occurred by chance (p = 0.05). At the same time, paracetamol consumption was reduced significantly from a mean of 91.29 tablets to 60.68 tablets for each 3-week period. Side-effects occurred in ten patients on placebo and fifteen patients on flufenamic acid. One patient on each medication had to discontinue for multiple side-effects. Diarrhoea occurred in two patients on flufenamic acid and in one patient on placebo. Flufenamic acid is clearly effective and side-effects do not occur more often than would be expected by chance when compared with placebo.

scholarly journals The Proapoptotic Effect of Traditional and Novel Nonsteroidal Anti-Inflammatory Drugs in Mammalian and Yeast Cells

2013 ◽  
Vol 2013 ◽  
pp. 1-17 ◽  
Author(s):  
Gianluca Farrugia ◽  
Rena Balzan
Keyword(s):  
Nitric Oxide ◽  
Hydrogen Sulfide ◽  
Cancer Prevention ◽  
Mammalian Cell ◽  
Yeast Cells ◽  
Mammalian Cell Lines ◽  
Inflammatory Drugs ◽  
Anti Inflammatory ◽  
Nitric Oxide Releasing

Nonsteroidal anti-inflammatory drugs (NSAIDs) have long been used to treat pain, fever, and inflammation. However, mounting evidence shows that NSAIDs, such as aspirin, have very promising antineoplastic properties. The chemopreventive, antiproliferative behaviour of NSAIDs has been associated with both their inactivation of cyclooxygenases (COX) and their ability to induce apoptosisviapathways that are largely COX-independent. In this review, the various proapoptotic pathways induced by traditional and novel NSAIDs such as phospho-NSAIDs, hydrogen sulfide-releasing NSAIDs and nitric oxide-releasing NSAIDs in mammalian cell lines are discussed, as well as the proapoptotic effects of NSAIDs on budding yeast which retains the hallmarks of mammalian apoptosis. The significance of these mechanisms in terms of the role of NSAIDs in effective cancer prevention is considered.

Effects of Anti-inflammatory Drugs in Shock Caused by Injection of Living E. coli Cells

1971 ◽  
Vol 137 (1) ◽  
pp. 219-223 ◽  
Author(s):  
J. R. Culp ◽  
E. G. Erdos ◽  
L. B. Hinshaw ◽  
D. D. Holmes
Keyword(s):  
E Coli ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

scholarly journals New Potential Nonsteroidal Anti-Inflammatory Drugs with Antileukotrienic Effects: Influence on Model Proteins with Catalytic Activity

2002 ◽  
Vol 45 (1) ◽  
pp. 7-12 ◽  
Author(s):  
Miloslava Netopilová ◽  
Jaroslav Dršata ◽  
Martin Beránek ◽  
Vladimír Palička
Keyword(s):  
E Coli ◽  
Catalytic Activities ◽  
Benzoic Acid Derivatives ◽  
Inflammatory Drugs ◽  
Common Problems ◽  
Anti Inflammatory ◽  
The Stability ◽  
And Function ◽  
Gad Activity

Unspecific and side effects caused by interaction with proteins belong to common problems of many structures synthesized as potential medicaments. Possible in vitro interactions with proteins of a group of phenylsulfonyl benzoic acid derivatives (VÚFB 19363, 19369, 19370, 19371, and 19760) as new potential anti-inflammatory compounds with antileukotrienic activities were studied in the present work. Three purified enzymes were used as model proteins with catalytic activities: Pig heart aspartate aminotransferase (AST, EC 2.6.1.1), alanine aminotransferase (ALT, EC 2.6.1.2), and glutamate decarboxylase (GAD, EC 4.1.1.15) from E. coli. Catalytic activities during incubation of individual compounds (6 x 10-5 M solution to 5 x 10-2 M suspension) at 37 °C with enzymes served as criteria of stability and function of the proteins. No immediate influence of any compound studied on enzyme activities was found. Aminotransferase activities were not affected even during incubation up to 20 d. In the case of GAD, the compounds VÚFB 19369, 19370, 19371, and 19760 had stabilizing influence on GAD activity during incubation at enzyme concentrations of 11.25 and 5.62 mg prot/l. The lack of an immediate effect of compounds and the stability of enzymes during incubation them are favorable and support the prospective of the compounds as potential drugs.

scholarly journals NMR-Guided Repositioning of Non-Steroidal Anti-Inflammatory Drugs into Tight Junction Modulators

2021 ◽  
Vol 22 (5) ◽  
pp. 2583
Author(s):  
Takeshi Tenno ◽  
Kohki Kataoka ◽  
Natsuko Goda ◽  
Hidekazu Hiroaki
Keyword(s):  
Tight Junction ◽  
Pdz Domain ◽  
Cell Monolayer ◽  
Fluorescein Isothiocyanate ◽  
Flufenamic Acid ◽  
Peptide Drugs ◽  
Absorption Enhancers ◽  
Epithelial Barrier Function ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

Bioavailability is a major bottleneck in the clinical application of medium molecular weight therapeutics, including protein and peptide drugs. Paracellular transport of these molecules is hampered by intercellular tight junction (TJ) complexes. Therefore, safe chemical regulators for TJ loosening are desired. Here, we showed a potential application of select non-steroidal anti-inflammatory drugs (NSAIDs) as TJ modulators. Based on our previous observation that diclofenac and flufenamic acid directly bound various PDZ domains with a broad specificity, we applied solution nuclear magnetic resonance techniques to examine the interaction of other NSAIDs and the first PDZ domain (PDZ1) of zonula occludens (ZO)-1, ZO-1(PDZ1). Inhibition of ZO-1(PDZ1) is expected to provide loosening of the epithelial barrier function because the domain plays a crucial role in maintaining TJ integrity. Accordingly, diclofenac and indomethacin were found to decrease the subcellular localization of claudin (CLD)-2 but not occludin and ZO-1 at the apicolateral intercellular compartment of Madin–Darby canine kidney (MDCK) II cells. These NSAIDs exhibited 125–155% improved paracellular efflux of fluorescein isothiocyanate insulin for the Caco-2 cell monolayer. We propose that these NSAIDs can be repurposed as drug absorption enhancers for peptide drugs.

scholarly journals Optimizing the synthesis of SnO2/TiO2/RGO nanocomposites with excellent visible light photocatalytic and antibacterial activities

2019 ◽  
Vol 18 (12) ◽  
pp. 2989-2999 ◽  
Author(s):  
Shujuan Yao ◽  
Shanshan Zhou ◽  
Jie Wang ◽  
Wenzhi Li ◽  
Zhihui Li
Keyword(s):  
Visible Light ◽  
Growth Inhibition ◽  
Synergistic Effects ◽  
Light Response ◽  
Antibacterial Activities ◽  
E Coli ◽  
Visible Light Response ◽  
Visible Light Photocatalytic

The as-prepared SnO2/TiO2/RGO hybrids exhibit enhanced visible-light-response photocatalytic efficiencies of RhB degradation and growth inhibition of E. coli due to the combined merits of SnO2, TiO2 and RGO to achieve maximum synergistic effects.

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