Metal complexes based on polyfluorosalicylic acids and their antimycotic and antimicrobial activity

Shchur, Irina V.; Shchegolkov, Evgeny V.; Burgart, Yanina V.; Козицина, А. Н.; Ivanova, Anna V.; Alyamovskaya, I. S.; Евстигнеева, Н. П.; Герасимова, Н. А.; Ганебных, И. Н.; Зильберберг, Н. В.; Кунгуров, Н. В.; Салоутин, В. И.; Чупахин, О. Н.

doi:10.1016/j.poly.2019.114279

Cited by 15 publications

(29 citation statements)

References 29 publications

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“…The treatment of compounds 5 e with Ar‐bipy 3 a , c – g at refluxing in a mixture of ethanol‐water (1 : 1) led to mixed complexes [Mn(SalF 4 −2H)( Ar‐bipy) 2 (H 2 O) n ] 10 a , c – g , in which a ratio of SalF 4 and azoligand is an equal 1 : 2, while 5‐(4‐methylphenyl)‐2,2′‐bipyridine 3 b in analogous reaction resulted in the complex [Mn(SalF 4 −2H) 2 ( Ar ‐ bipy ) 2 (H 2 O) 3 ] 10 b (Scheme 5). Note that the similar complexes [Mn(SalF 4 ‐H) 2 ( bipy ) 2 ] 10 h and [Mn(SalF 4 ‐H) 2 ( phen ) 2 ] 10 i were obtained based on manganese(II) tetrafluorosalicylate 5 e with bipy or phen [57] …”

Section: Resultsmentioning

confidence: 64%

“…When analysing an antimycotic activity of salicylic acids 4 a – c , it was noted that only tetrafluorosalicylic acid 4 b revealed a weak action against fungi T. rubrum, T. gypseum, T. tonsurans at MIC∼120 μM [57] . Trifluorosalicylic and salicylic acids 4 a , 4 c , as well as copper(II) salicylates 5 a – c were almost inactive.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have obtained heteroligand metal complexes based on polyfluorosalicylic acids [57] and their esters [58] with 2,2′‐bipyridine ( bipy ) and 1,10‐phenanthroline ( phen ). The complexes were shown to have a promising antimicrobial action [57–59] .…”

Section: Introductionmentioning

confidence: 99%

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Promising Antifungal and Antibacterial Agents Based on 5‐Aryl‐2,2′‐bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking

et al. 2021

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A series of new 5‐aryl‐2,2′‐bipyridines and their (polyfluoro)salicylate complexes of Cu(II), Co(II) and Mn(II) were synthesized. Their antimicrobial activity was evaluated in vitro against six strains of Trichophytons, E. floccosum, M. canis, C. ablicans and Gram‐negative bacteria N. gonorrhoeae. Among azo‐ligands, Ph‐bipy and Tol‐bipy showed promising antifungal activity (minimum inhibitory concentration (MIC)<0.8–27 μM). Their antifungal action was found can be realized via binding Fe(III) ions. Tol‐bipy suppressed growth of Gram‐positive bacteria S. aureus, S. aureus MRSA and their monospecies biofilms (MIC 6–16 μM). Using molecular docking, the anti‐staphylococcal action mechanism based on the inhibition of S. aureus DNA gyrase GyrB was proposed for the lead compounds. Among metal complexes, Cu(II) and Mn(II) complexes based on tetrafluorosalicylic acid and Tol‐bipy or Ph‐bipy had the high antifungal activity (MIC<0.24–32 μM). Mn(SalF4−2H)2(Tol‐bipy)2] suppressed the growth of seven Candida strains at MIC 12–24 μM. [Cu(Sal−2H)(Ph‐bipy)] and [Cu(SalF3−2H)(Ph‐bipy)2] showed the promising anti‐gonorrhoeae activity (MIC 4.2–5.2 μM). (Cu(SalFn−2H)(Tol‐bipy)2], [Cu(SalF4−2H)(Ph‐bipy)2] and [Cu(SalF3−2H)(Ph‐bipy)2]) were found active against the bacteria of S. aureus, S. aureus MRSA and their biofilms (MIC 2.4–41.4 μM). The most active compounds were tested for toxicity in vitro against human embryonic kidney (HEK‐293) cells and in vivo experiments with CD‐1 mice.

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Section: Resultsmentioning

confidence: 64%

Section: Resultsmentioning

confidence: 99%

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Promising Antifungal and Antibacterial Agents Based on 5‐Aryl‐2,2′‐bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking

et al. 2021

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“…Their effectiveness against bacterial and fungal pathogens was enhanced when coordinated with transition metal ions [20]. Moreover, heteroligand Co(II) complexes of salicylic acid with pyridine showed a pronounced antimicrobial and fungicidal effect [36]. The present study compares the antibacterial and antifungal activity of new Co(II)-PicHA-AlaSal complexes with those of PicHA alone and Co(II)-PicHA complexes [25], and examines the effect of storage for two weeks.…”

Section: Heteroligand Complex Formation Equilibriamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical Characterization and Biological Evaluation of New Cobalt(II) Complexes with Bioactive Ligands, 2-Picolinehydroxamic Acid and Reduced Schiff Base N-(2-Hydroxybenzyl)alanine, in Terms of DNA Binding and Antimicrobial Activity

et al. 2021

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Five new heteroligand cobalt(II) complexes with 2-picolinehydroxamic acid and reduced Schiff base, N-(2-hydroxybenzyl)alanine, were formed in an aqueous solution over a wide pH range. The coordination properties of ligands towards the metal ion were determined using a pH-metric method, and then the speciation model was confirmed by UV–Vis studies. A stacking interaction between the Schiff base phenol ring and the 2-picolinehydroxamic acid pyridine ring was found to improve the stability of the heteroligand species, indicating more effective coordination in mixed-ligand complexes than in their respective binary systems. The antimicrobial properties of heteroligand complexes were determined against Gram-negative and Gram-positive bacteria, as well as fungal strains. The formulation demonstrated the highest bacteriostatic and bactericidal activity (3.65 mM) against two strains of Gram-negative Helicobacter pylori bacteria and towards Candida albicans and Candida glabrata; this is important due to the potential co-existence of these microorganisms in the gastric milieu and their role in the development of gastritis. The binary complexes in the cobalt(II)—2-picolinehydroxamic acid system and 2-picolinehydroxamic acid were not cytotoxic against L929 mouse fibroblasts, neither freshly prepared solutions or after two weeks’ storage. By comparison, the heteroligand complexes within the range 0.91–3.65 mM diminished the metabolic activity of L929 cells, which was correlated with increased damage to cell nuclei. The concentration of the heteroligand species increased over time; therefore, the complexes stored for two weeks exhibited stronger anticellular toxicity than the freshly prepared samples. The complexes formed in an aqueous solution under physiological pH effectively bound to calf thymus DNA in an intercalative manner. This DNA-binding ability may underpin the antimicrobial/antifungal activity of the heteroligand complexes and their ability to downregulate the growth of eukaryotic cells.

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Salicylic Acid: Synthetic Strategies and Their Biological Activities

2023

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Phenolic acids are the phytochemicals formthe key part of the organic chemistry and are widely found in the plants, plant foods and human metabolites possessing a wide range of biological activities like anti‐oxidant, anti‐bacterial, anti‐inflammatory, anti‐carcinogenic activities. Owing to their pharmaceutical activities, they are known for their different roles in prevention of various diseases in plants and as well as humans. Although a number of biologically active compounds are known in literature but unfortunately due to their cost, non‐availability and toxicity, there is an urgent need to develop such bioactive agents which can overcome all the shortcomings of reported agents. Salicylic acid is one of the hydroxybenzoic acid that is well known for possessing antimicrobial, anti‐inflammatory, anti‐cancer,anti‐tumor, anti‐proliferative, anti‐viral and analgesic properties. This review mainly outlines the synthesis and biological activities of various salicylic acid derivatives which provides guidance to the researchers working in this field for improving their activity by modification of already reported drugs.

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Metal complexes based on polyfluorosalicylic acids and their antimycotic and antimicrobial activity

Cited by 15 publications

References 29 publications

Promising Antifungal and Antibacterial Agents Based on 5‐Aryl‐2,2′‐bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking

Promising Antifungal and Antibacterial Agents Based on 5‐Aryl‐2,2′‐bipyridines and Their Heteroligand Salicylate Metal Complexes: Synthesis, Bioevaluation, Molecular Docking

Chemical Characterization and Biological Evaluation of New Cobalt(II) Complexes with Bioactive Ligands, 2-Picolinehydroxamic Acid and Reduced Schiff Base N-(2-Hydroxybenzyl)alanine, in Terms of DNA Binding and Antimicrobial Activity

Salicylic Acid: Synthetic Strategies and Their Biological Activities

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