The functionalization of magnetite nanoparticles by hydroxyl substituted diazacrown ether, able to mimic natural siderophores, and investigation of their antimicrobial activity

Hasanova, Ulviyya; Рамазанов, М. А.; Maharramov, Abel M.; Gakhramanova, Zarema; Hajiyeva, S.R.; Vezirova, Leyla; Eyvazova, Goncha M.; Hajiyeva, F. V.; Huseynova, Parvana; Agamaliyev, Zohrab Adalet

doi:10.1007/s10847-016-0636-x

Cited by 12 publications

(16 citation statements)

References 19 publications

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“…NMR, mass-, FTIR spectroscopy methods, scanning electron microscopy (SEM), XRD analysis methods were used to investigate synthesized MC and to analyze the morphology of prepared nano-ensembles. Results of experiments carried by prepared nanostructures tested on gram-negative Escherichia Coli and gram-positive Staphylococcus aureus showed that nanostructures significantly increase the antimicrobial effect of cephalosporins and decrease their MIC [92].…”

Section: Iron-containing Nanoparticlesmentioning

confidence: 99%

The engineered nanoparticles in food chain: potential toxicity and effects

et al. 2019

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Nanomaterials include dispersing materials containing structural elements (grains, crystallites, blocks, clusters, etc.), due to their nano dimensions acquire qualitatively new functional and operational characteristics, offering several biomedical and technical advances over their bulk analogues. Taking into the consideration the fact that the impact of nanoparticles (NPs) to a living organism through the food chain is extremely important and have not been studied in detail yet, in this review we aimed to show the effect of different NPs towards terrestrial food chain, aquatic ecosystem, microorganisms and etc. Understanding and managing the potential risks associated with the use of nanoscale objects serves as a guide for developing new methods, tools, and concepts in order to determine how new engineering nanoparticles will interact with living organisms in the food chain and environmental systems. It is assumed that these methods will fundamentally differ and challenge the existing research and testing methodologies. Keywords Food chain • Engineered nanoparticles • Toxicity • Environment • Ecosystem Abreviation AI Anxious index BALF Bronchoalveolar lavage fluid ChlF Chlorophyll fluorescence CNTs Carbon nanotubes 2D Two-dimensional DAPI 4′,6-diamidino-2-phenylindole 2DG 2-Deoxy-d-Glucose DNA Deoxyribonucleic acid ESR Erythrocyte sedimentation rate FE Field emission FitcDx

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Section: Iron-containing Nanoparticlesmentioning

confidence: 99%

The engineered nanoparticles in food chain: potential toxicity and effects

et al. 2019

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“…[142] Ty pische Beispiele sind synthetische Kronenether oder Azakronen und natürliche Polyether-Antibiotika, wie Lasalocid A(79). [146] Ramazanov berichtete, dass der Azamakrocyclus 80 das Wachstum von Staphylococcus aureus hemmte (MIC 1 mgmL À1 ;Abbildung 24), nicht aber E. coli oder Klebsiella sp.b eeinträchtigte. [144,145] Außerdem kçnnen Kronenetherderivate als Siderophormimetika dienen und dadurch mit den bakteriellen Eisenaufnahmesystemen konkurrieren.…”

Section: Angewandte Chemieunclassified

“…[143] Es ist gut bekannt, dass Kronenether und verwandte Makrocyclen antimikrobiell wirken, da sie Poren fürK ationen in der bakteriellen Zellmembran bilden und dadurch den Ionengradienten irreversibel stçren. [146] Wenn jedoch Magnetit-Nanopartikel mit 80 über nichtkovalente Bindungen funktionalisiert wurden, inhibierte das resultierende Hybridmaterial auch E. coli (MIC 0.5 mgmL À1 )u nd Klebsiella sp. [146] Ramazanov berichtete, dass der Azamakrocyclus 80 das Wachstum von Staphylococcus aureus hemmte (MIC 1 mgmL À1 ;Abbildung 24), nicht aber E. coli oder Klebsiella sp.b eeinträchtigte.…”

Section: Angewandte Chemieunclassified

“…[144,145] Außerdem kçnnen Kronenetherderivate als Siderophormimetika dienen und dadurch mit den bakteriellen Eisenaufnahmesystemen konkurrieren. [146] Ramazanov berichtete, dass der Azamakrocyclus 80 das Wachstum von Staphylococcus aureus hemmte (MIC 1 mgmL À1 ;Abbildung 24), nicht aber E. coli oder Klebsiella sp.b eeinträchtigte. [146] Wenn jedoch Magnetit-Nanopartikel mit 80 über nichtkovalente Bindungen funktionalisiert wurden, inhibierte das resultierende Hybridmaterial auch E. coli (MIC 0.5 mgmL À1 )u nd Klebsiella sp.…”

Section: Angewandte Chemieunclassified

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Chemische und biologische Aspekte von “Nutritional Immunity” – Perspektiven für neue Antiinfektiva mit Fokus auf bakterielle Eisenaufnahmesysteme

et al. 2017

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Eine der Verteidigungsstrategien eines Wirtes gegen bakterielle Infektionen ist der Entzug essentieller Metallionen, insbesondere von Eisenionen, durch Komplexierung. Dies wird als Nährstoffimmunität (“nutritional immunity”) bezeichnet. Bakterien haben jedoch Strategien zur Anpassung an den Eisenmangel entwickelt. Sie “stehlen” zum Beispiel Eisen vom Wirt oder von anderen Bakterien durch spezifische Chelatoren mit einer hohen Affinität für Eisen. Die komplexen Wechselwirkungen zwischen Wirt und Pathogen zur Homöostase von Metallionen bieten zahlreiche Angriffspunkte für die Entwicklung neuer antibakterieller Wirkstoffe. Dieser Aufsatz ist auf Prozesse mit Eisenbeteiligung fokussiert. Es werden die neuesten Entwicklungen und mögliche Perspektiven für die Entwicklung von Antibiotikaresistenzen diskutiert.

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“…В частности, комплексы диаза-18-краун-6 с солями арилхалькогенуксусных кислот, а также глицилпроизводные диаза-18-краун-6 проявляют антипролиферативную активность, [4,5] N-гидроксикарбонилметил-и N-гидроксикарбонилпропилпроизводные бензодиаза-15-краун-5 -антимутагенное действие. [6] Комплексы диазакраун-эфиров с Fe 3 O 4 проявляют активность в отношении грамположительных и грамотрицательных микроорганизмов, [7] бензильные производные диаза-18-краун-6 -кардиотроп-ную активность, [8] нафтилпроизводные диазакраунэфиров -гемопоэтическую и колониестимулирующую активностость, [9] адамантилпроизводные диаза-18краун-6 -противоопухолевую активность. [10,11] Лариатные краун-эфиры на основе диаза-18-краун-6 обладают биологической активностью относительно бактерий E. coli, B. subtilis и S. cerevisiae, а также существенно повышают эффективность таких противомикробных препаратов, как рифампицин и тетрациклин.…”

Section: Introductionunclassified

Synthesis and Antiviral Activity of Diaza-18-crown-6 Derivatives with the Fragments of 4-Aminomethylbenzoic and 6-Aminocaproic Acids

Basok¹,

Lutsyuk²,

Gridina³

et al. 2018

MHC

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Among the most important properties governing wide spectrum of biological activities of crown ethers are their high lipophilicity, selectivity of the complex formation as well as ability of transporting ions and some neutral molecules across the biological membranes, similarly to the natural ionophores. Modification of diazacrown ethers by introducing fragments of known antiviral agents into their structure can be assumed to yield new products with high antiviral activity. The compounds of a class of protease inhibitors, 4-aminomethylbenzoic and 6-aminocaproic acids are of interest in respect of this. We have synthesized derivatives with free amino and carboxyl groups containing fragments of known antiviral drugs, 4-aminomethylbenzoic and 6-aminocaproic acids, based on the macrocyclic diaza-18-crown-6 platform. The cytotoxicity and antiviral activity of synthesized compounds against of human influenza strains А/Hong Kong/1/68 (H3N2) and А/Puerto Rico/8/34 (H1N1) have been studied. Synthesis of compounds with free amino group (1,10-bis(6-aminohexanoyl)-diaza-18-crown-6 and 1,10-bis(4-aminomethylbenzoyl)-diaza-18-crown-6) have been carried out by interaction of diaza-18-crown-6 with Boc-protected derivatives of 6-aminocaproic and 4-aminomethylbenzoic acids in the presence of DCC and HOBT followed by removal of the Boc-protective group in the intermediate compounds by the action of trifluoroacetic acid. It should be noted that using HOBT allowed us to avoid the formation of collateral bis-N-acylureas, simplify the purification, and increase the total yields of final products to 90-92 %. Acylation of benzyl esters of studied N,N'-dicarboxymethyldiaza-18-crown-6 amino acids was investigated to obtain the compounds with the free carboxyl group, 6,6'-{(7,16-diaza-18-crown-6)-7,16-diylbis[(1-oxoethane-2,1-diyl)imino]} dihexanoic acid and 4,4'-{(7,16-diaza-18-crown-6)-7,16-diylbis[(1-oxoethane-2,1-diyl)iminomethylene]} dibenzoic acid. In this case, using DCC as a condensing agent has resulted the main reaction product to be macrocyclic bis-N-acylureas, and the desired compounds have not been obtained. Therefore, another method of peptide chemistry was used for the acylation of esters of the studied acids-mixed anhydride method with ethyl chloroformate. By this method the benzyl esters of dipeptides with yields of 85-87 % were obtained. Subsequent removal of the benzyl protecting group in these compounds by catalytic hydrogenolysis resulted in desired products with yields of 92-94 %. The toxicity level for all the synthesized compounds was studied on a model using Colpoda steinii infusoria culture and the chorionallantoic membrane cells of chick embryos, and antiviral activity against human influenza strains A/ Hong Kong/1/68 (H3N2) and А/Puerto Rico/8/34 (H1N1) in culture of the chorionallantoic membrane cells of chick embryos. Synthesized compounds showed significantly higher level of antiviral activity compared to that of 4-aminomethylbenzoic and 6-aminocaproic acids on both strains of the influenza virus with no cytoto...

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The functionalization of magnetite nanoparticles by hydroxyl substituted diazacrown ether, able to mimic natural siderophores, and investigation of their antimicrobial activity

Cited by 12 publications

References 19 publications

The engineered nanoparticles in food chain: potential toxicity and effects

The engineered nanoparticles in food chain: potential toxicity and effects

Chemische und biologische Aspekte von “Nutritional Immunity” – Perspektiven für neue Antiinfektiva mit Fokus auf bakterielle Eisenaufnahmesysteme

Synthesis and Antiviral Activity of Diaza-18-crown-6 Derivatives with the Fragments of 4-Aminomethylbenzoic and 6-Aminocaproic Acids

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