Synthesis, characterization and antimicrobial activity of water-soluble silver(<scp>i</scp>) complexes of metronidazole drug and selected counter-ions

Kalinowska-Lis, Urszula; Felczak, Aleksandra; Chęcińska, Lilianna; Zawadzka, Katarzyna; Patyna, Emilia; Lisowska, Katarzyna; Ochocki, Justyn

doi:10.1039/c5dt00403a

Cited by 86 publications

(73 citation statements)

References 42 publications

(7 reference statements)

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“…Metronidazole needs to be combined with another antibiotic agent to cover mixed infections with aerobic bacteria, and silver could be the right partner for it. A series of water-soluble silver complexes with metronidazole have thus been synthesized and tested in the treatment of Gram-positive (S. aureus, S. epidermidis) and Gram-negative strains (P. aeruginosa, E. coli, P.hauseri), as well as yeast C. albicans[94]. These novel silver(I) coordination compounds of metronidazole have been synthesized in the form of monomers, [Ag(MTZ)…”

mentioning

confidence: 99%

Silver coordination compounds: A new horizon in medicine

Medici

Peana

Crisponi

et al. 2016

Coordination Chemistry Reviews

238

157

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mentioning

confidence: 99%

Silver coordination compounds: A new horizon in medicine

Medici

Peana

Crisponi

et al. 2016

Coordination Chemistry Reviews

238

157

View full text Add to dashboard Cite

“…Therefore, light stability of 2h was studied in direct light under an air atmosphere at room temperature to mimic their exposure to light under every life conditions. 26) Cotton pads were impregnated with 0.025 mol/L aqueous solutions of the compounds and exposed to air and light. The stability was monitored visually within 5 d. The photos of the samples (2h, 2a and AgNO 3 ) are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…26) The positive controls were AgNO 3 and Zn(II) complex (2a). Cotton pads were impregnated with 0.025 M aqueous solutions of the compounds and exposed to air and light.…”

Section: Procedures For the Preparation Of Benzoxazoles And Their Zinmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

et al. 2018

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Key words antibacterial activity; fluorinated benzoxazole; metal complex; trifluoroacetylBacterial infection remains a serious threat to human lives due to rapid development of resistance to the existing antibiotics. In order to prevent this major medical problem, the discovery of new types of antimicrobial agents is a very important but challenging task.1,2) Transition metal complexes have received great attention because many drugs such as antibiotics and quinolone antibiotics possess better pharmaceutical properties when they are in the form of metal complexes. 3-7)Benzoxazole heterocycle system is an important pharmacophore and privileged structure in the medicinal chemistry. 8-10)Its derivatives and particularly, 2-substituted benzoxazoles exert various biological activities such as antimicrobial, antiviral, antifungal, and anticancer. [11][12][13][14][15] In previous studies, we have identified 2-trifluoroacetonylbenzoxazole (1a) with in vitro antimicrobial activity against Helicobacter pylori and Escherichia coli (Ec) from our compound library of trifluoromethyl ketones obtained by our developed reactions. 16,17) The heteroaryl-substituted alkenol systems such as 1a are known to chelate some metal ions such as aluminum 18) and to form a stable six-membered metal complexes in a bidentate mode, where the complexes were reinforced by a positive inductive effect of the heterocyclic moiety and a negative inductive effect of the CF 3 groups. [19][20][21][22][23] In the light of these knowledge, three 2-fluoroacetonylbenzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been synthesized in order to check how the metal ion binding may influence their antibacterial activity (Chart 1). In addition, syntheses of new metal [Mg(II), Ni(II), Cu(II), Pd(II), and Ag(I)] complexes 2d-h from 1a have been also described ( Table 1). The structures of six metal complexes 2b and 2d-h were determined by single-crystal X-ray diffraction analyses. In vitro antimicrobial activities of the ligands 1a-c and their metal complexes 2a-h were investigated against six Gram-positive (G(+)) and six Gram-negative (G(−)) bacteria and the results were compared with those of silver nitrate and appropriate antibiotics such as Kanamycin, Gentamicin, Norfloxacin, and/or Linezolid. The most potent Ag(I) complex 2h is bacteriostatic, disrupts membrane integrity observed by scanning electron microscopy (SEM) and is less likely to develop resistance development against Pseudomonas aeruginosa (Pa). Results and DiscussionChemistry First, three benzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been prepared in order to investigate the relationship of the ligands and their Zn(II) complexes with their antibacterial activities.Our synthetic protocol to obtain the ligand 1a consists of a trifluoroacetylation of 2-methylbenzoxazole with trifluoroacetic anhydride (TFAA) in the presence of pyridine 24) (Chart 1). The Zn(II) complex 2a was prepared by the reaction of 1a with zinc dust in MeCN in 78% yield, consisting of 1a with zinc(...

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“…Metronidazole was also reported as a potent agent against the Gram negative bacteria Helicobacter pylori , which is the major factor in peptic ulcer disease. The antibiotic MT forms complexes with different metallic ions as silver, gold, iron, palladium and copper. The complex formed by TN and copper was characterized by the coordination of N3 imidazolic nitrogen, and its antibacterial activity was reported.…”

Section: Introductionmentioning

confidence: 99%

A SERS investigation of antimicrobial adsorption on silver nanoparticles as mediated by surface modifiers

Filgueiras

Dutra

Paschoal

et al. 2017

J Raman Spectroscopy

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In this work, the adsorptions of the antimicrobial drugs aztreonam, tinidazole and metronidazole on silver nanoparticle surfaces were investigated using surface‐enhanced Raman scattering (SERS) spectroscopy. The chemical properties of silver surface were modified by using mercaptoethanol, polyvinyl alcohol or chloride ions for changing the adsorption mechanisms, which led to distinct SERS spectral patterns. These were analyzed regarding the proximity of molecular moiety from the analyte to the silver surface. The adsorption processes were monitored by the localized surface plasmon resonance bands, which were recorded through ultraviolet‐visible spectroscopy. Theoretical models were obtained from density functional theory and used for supporting the vibrational assignments. The analyses of the SERS spectral patterns allow inferring aztreonam adsorbed through carboxylate moiety while tinidazole and metronidazole adsorbed via nitro group. The surface modifiers led to changes of the adsorption geometries of the molecules on the silver surfaces, which were rationalized based on differences in the relative intensities of the bands assigned to the out‐of‐plane modes. Copyright © 2017 John Wiley & Sons, Ltd.

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Synthesis, characterization and antimicrobial activity of water-soluble silver(i) complexes of metronidazole drug and selected counter-ions

Cited by 86 publications

References 42 publications

Silver coordination compounds: A new horizon in medicine

Silver coordination compounds: A new horizon in medicine

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

A SERS investigation of antimicrobial adsorption on silver nanoparticles as mediated by surface modifiers

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