Development of antimicrobial aminoacid-modified bisphenol-A formaldehyde resin and its transition-metal complexes

A polymeric ligand (BFG), containing glycine moiety was synthesized by the polycondensation reaction of bisphenol-A and formaldehyde with amino acid (glycine) in alkaline medium. The polymer–metal complexes were synthesized with transition metal ions. The polymer and its metal complexes were characterized by elemental analysis and other spectroscopic techniques. The analytical data revealed that the coordination polymers of Cr(III), Co(II), and Ni(II) were coordinated with two water molecules, which are further supported by FTIR spectra and TGA data. The amino acid was found to act as bidentate ligand toward metal ions via the nitrogen of the NH group and carboxyl oxygen of the respective amino acid. The in-vitro preliminary antimicrobial activities of all the synthesized polymers were investigated against some bacteria and fungi. The polymer–metal complexes showed excellent antimicrobial activities against both types of microorganisms. Interestingly the polymeric ligand was found antimicrobial in nature but less effective as compared the polymer–metal complexes. On the basis of the antimicrobial behavior, these polymers hold potential in their application as antifungal and antifouling coating materials in medical devices as well as antimicrobial packaging material.     

Synthesis of the Bacteriostatic Poly(l-Lactide) by Using Zinc (II)[(acac)(L)H2O] (L = Aminoacid-Based Chelate Ligands) as an Effective ROP Initiator

The paper presents a synthesis of poly(l-lactide) with bacteriostatic properties. This polymer was obtained by ring-opening polymerization of the lactide initiated by selected low-toxic zinc complexes, Zn[(acac)(L)H₂O], where L represents N-(pyridin-4-ylmethylene) tryptophan or N-(2-pyridin-4-ylethylidene) phenylalanine. These complexes were obtained by reaction of Zn[(acac)₂ H₂O] and Schiff bases, the products of the condensation of amino acids and 4-pyridinecarboxaldehyde. The composition, structure, and geometry of the synthesized complexes were determined by NMR and FTIR spectroscopy, elemental analysis, and molecular modeling. Both complexes showed the geometry of a distorted trigonal bipyramid. The antibacterial and antifungal activities of both complexes were found to be much stronger than those of the primary Schiff bases. The present study showed a higher efficiency of polymerization when initiated by the obtained zinc complexes than when initiated by the zinc(II) acetylacetonate complex. The synthesized polylactide showed antibacterial properties, especially the product obtained by polymerization initiated by a zinc(II) complex with a ligand based on l-phenylalanine. The polylactide showed a particularly strong antimicrobial effect against Pseudomonas aeruginosa, Staphylococcus aureus, and Aspergillus brasiliensis. At the same time, this polymer does not exhibit fibroblast cytotoxicity.     

Therapeutic Effect of a Newly Isolated Lytic Bacteriophage against Multi-Drug-Resistant Cutibacterium acnes Infection in Mice

Acne vulgaris, which is mostly associated with the colonization of Cutibacterium acnes (C. acnes), is a common skin inflammatory disease in teenagers. However, over the past few years, the disease has extended beyond childhood to chronically infect approximately 40% of adults. While antibiotics have been used for several decades to treat acne lesions, antibiotic resistance is a growing crisis; thus, finding a new therapeutic target is urgently needed. Studies have shown that phage therapy may be one alternative for treating multi-drug-resistant bacterial infections. In the present study, we successfully isolated a C. acnes phage named TCUCAP1 from the skin of healthy volunteers. Morphological analysis revealed that TCUCAP1 belongs to the family Siphoviridae with an icosahedral head and a non-contractile tail. Genome analysis found that TCUCAP1 is composed of 29,547 bp with a G+C content of 53.83% and 56 predicted open reading frames (ORFs). The ORFs were associated with phage structure, packing, host lysis, DNA metabolism, and additional functions. Phage treatments applied to mice with multi-drug-resistant (MDR) C.-acnes-induced skin inflammation resulted in a significant decrease in inflammatory lesions. In addition, our attempt to formulate the phage into hydroxyethyl cellulose (HEC) cream may provide new antibacterial preparations for human infections. Our results demonstrate that TCUCAP1 displays several features that make it an ideal candidate for the control of C. acnes infections.     

Antibacterial polyamide obtained by the incorporation of glass microparticles doped with ionic zinc and by zinc oxide nanoparticle: Evaluation with Salmonella typhimurium and Staphylococcus aureus

Food security is very important in all processes executed for the manufacture of meat in meatpacking industries. Meat security can be improved by the use of accessories produced with antimicrobial materials in the manufacture lines. In this work, the antibacterial property was incorporated in the plates of polyamide 6 by the addition of two antibacterial compounds and the antimicrobial characteristics were studied. The antibacterial materials used were glass microparticles doped with ionic zinc and zinc oxide nanoparticles. The antibacterial polyamide 6 was produced containing different percentages of antibacterial compound and its microbiological characterization was realized with the bacteria Salmonella typhimurium and Staphylococcus aureus. The distribution of the antimicrobial compound in polyamide 6 matrix was evaluated by scanning electron microscopy and energy dispersive spectroscopy. Atomic absorption spectrometry was applied to study the migration capacity of the antibacterial compound in the aqueous medium. The results demonstrated that the polyamide 6 containing glass microparticles doped with ionic zinc present better antibacterial action than the polyamide 6 containing zinc oxide nanoparticles. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 45005.     

Absorption and release of zinc and copper ions by chitosan fibers

Chitosan fibers were treated with aqueous solutions of ZnCl₂ and CuSO₄·5H₂O to prepare zinc and copper containing fibers, respectively. Significant weight gains were obtained as the zinc and copper ions were absorbed onto the fibers through chelation with the primary amine groups. The fibers were then placed in contact with aqueous solutions containing NaCl and water soluble proteins, respectively, to assess the release of zinc and copper ions. Results showed that the release of zinc and copper ions were affected by the treatment temperature, time, and the composition of the contacting media. More metal ions were released when the fibers were in contact with aqueous protein solutions than in NaCl solution, indicating the binding abilities of the protein molecules for zinc and copper ions. The zinc and copper containing fibers were tested for their antimicrobial effects against several species of bacteria commonly found in wound and skin. Results showed that these metal containing chitosan fibers had much stronger antimicrobial properties than the original chitosan fiber. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007     

Determination of filtration efficiency and aerodynamic characteristics of antimicrobial filter material

This article describes tests of nonwoven antimicrobial filter materials from viscose fibre (rayon) containing the antimicrobial preparations catamin AB and desant. Wide-ranging tests of antimicrobial filter materials have been carried out to determine the aerodynamic characteristics, dust content and dust penetrability, weather tolerance, resistance to saprophytic (mold) fungi, etc. The tests and function-based classification of antimicrobial filter materials comply with GOST R 51251. Investigations were carried out at the microbiological laboratories of I. V. Michurin All-Russia Scientific Research Institute of Orcharding, Center of Hygiene and Epidemiology in the Moscow Region, and FGU “Mendeleevskii TsSM” to determine the efficiency of air purification from microorganisms by antimicrobial filter materials made of viscose fibre containing the preparations catamin AB and desant employing a specially designed equipment. Performance tests of various types of air filters having filter elements from filter materials containing desant and catamin AB have been carried out. The efficiency of air purification from the microorganisms Staphylococcus aureus, Micrococcus falvus, Bacillus subtilis, etc. that infect patients in medical institutions has been determined.     

Synthesis and characterization of polysiloxanes with pendant bicyclic fragments

Transparent poly vinyl alcohol (PVA) based coatings with antimicrobial activity against a wide range of microorganisms have been prepared. The films have been prepared by spincoating a mixture of PVA, ammonium dichromate and metal (zinc or silver) precursor from water solutions, and then rendered insoluble by crosslinking under UV illumination. Antimicrobial activity has been tested against different bacteria and fungi, such as Bacillus atrophaeus, Bacillus megaterium, Staphylococcus aureus, Enterococcus faecium, Pseudomonas aeruginosa, Salmonella enterica, Escherichia coli, Neurospora crassa, and Saccharomyces cerevisiae. It was found that combining the zinc and silver precursors resulted in films which had excellent antimicrobial activity and at the same time exhibited superior environmental stability compared to films containing prepared with single metal precursor. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Antimicrobial Catanionic Vesicular Self-Assembly with Improved Spectrum of Action

A catanionic mixture based on three components, N-dodecyldiethanolamine, decanoic acid and azelaic acid, was prepared and investigated from a physico-chemical point of view and for its antimicrobial activity. The spontaneously formed vesicles were characterized by dynamic light scattering, zeta potential and electron microscopy. These experiments showed spherical vesicles with an average diameter of 200 nm and a zeta potential of +22 mV. The antimicrobial activity of the vesicle dispersion against different strains (Staphylococcus aureus, Escherichia coli, Staphylococcus epidermidis, Propionibacterium acnes and Candida albicans), was evaluated and compared with the activity of the components separately. The synergistic effect of these bioactive self-assembled catanionic vesicles on the spectrum of activity and on the cytoplasmic membrane is discussed.     

Lipidation of Temporin-1CEb Derivatives as a Tool for Activity Improvement,Pros and Cons of the Approach

The alarming raise of multi-drug resistance among human microbial pathogens makes the development of novel therapeutics a priority task. In contrast to conventional antibiotics, antimicrobial peptides (AMPs), besides evoking a broad spectrum of activity against microorganisms, could offer additional benefits, such as the ability to neutralize toxins, modulate inflammatory response, eradicate bacterial and fungal biofilms or prevent their development. The latter properties are of special interest, as most antibiotics available on the market have limited ability to diffuse through rigid structures of biofilms. Lipidation of AMPs is considered as an effective approach for enhancement of their antimicrobial potential and in vivo stability; however, it could also have undesired impact on selectivity, solubility or the aggregation state of the modified peptides. In the present work, we describe the results of structural modifications of compounds designed based on cationic antimicrobial peptides DK5 and CAR-PEG-DK5, derivatized at their N-terminal part with fatty acids with different lengths of carbon chain. The proposed modifications substantially improved antimicrobial properties of the final compounds and their effectiveness in inhibition of biofilm development as well as eradication of pre-formed 24 h old biofilms of Candida albicans and Staphylococcus aureus. The most active compounds (C5-DK5, C12-DK5 and C12-CAR-PEG-DK5) were also potent against multi-drug resistant Staphylococcus aureus USA300 strain and clinical isolates of Pseudomonas aeruginosa. Both experimental and in silico methods revealed strong correlation between the length of fatty acid attached to the peptides and their final membranolytic properties, tendency to self-assemble and cytotoxicity.     

Chelating polymeric particles intended for the therapy of Wilson’s disease

Wilson’s disease is a genetic disorder that leads to a high accumulation of copper in multiple organs with subsequent toxic effects. In this paper, a gentle therapy to eliminate harmful copper concentrations in patients with Wilson’s disease is proposed using an oral administration of insoluble polymeric sorbents containing selective chelating groups for copper(II). The sorbents contained triethylenetetramine, N,N-di(2-pyridylmethyl)amine, 8-hydroxyquinoline or 8-hydroxyquinoline-5-sulfonic acid chelating groups bound to a methacrylate-based macroporous support. Nearly quantitative copper(II) uptake within minutes was achieved in buffers modeling the pH range present in the gastric environment (pH 2.0 and 4.0). The sorbents demonstrated chelating selectivity for copper(II) against zinc(II) with ratios of up to 1321. The sorbents demonstrated sufficient stability of the copper complexes against rechelation using studies in a model environment for the small intestine (the presence of chelating amino acids, pH 6.8).     

Peptoid Efficacy against Polymicrobial Biofilms Determined by Using Propidium Monoazide‐Modified Quantitative PCR

Biofilms containing Candida albicans are responsible for a wide variety of clinical infections. The protective effects of the biofilm matrix, the low metabolic activity of microorganisms within a biofilm and their high mutation rate, significantly enhance the resistance of biofilms to conventional antimicrobial treatments. Peptoids are peptide‐mimics that share many features of host defence antimicrobial peptides but have increased resistance to proteases and therefore have better stability in vivo. The activity of a library of peptoids was tested against monospecies and polymicrobial bacterial/fungal biofilms. Selected peptoids showed significant bactericidal and fungicidal activity against the polymicrobial biofilms. This coupled with low cytotoxicity suggests that peptoids could offer a new option for the treatment of clinically relevant polymicrobial infections.     

Comparative Antimicrobial Activity of Hp404 Peptide and Its Analogs against Acinetobacter baumannii

An amphipathic α-helical peptide, Hp1404, was isolated from the venomous gland of the scorpion Heterometrus petersii. Hp1404 exhibits antimicrobial activity against methicillin-resistant Staphylococcus aureus but is cytotoxic. In this study, we designed antimicrobial peptides by substituting amino acids at the 14 C-terminal residues of Hp1404 to reduce toxicity and improve antibacterial activity. The analog peptides, which had an amphipathic α-helical structure, were active against gram-positive and gram-negative bacteria, particularly multidrug-resistant Acinetobacter baumannii, and showed lower cytotoxicity than Hp1404. N-phenyl-1-naphthylamine uptake and DisC₃-5 assays demonstrated that the peptides kill bacteria by effectively permeating the outer and cytoplasmic membranes. Additionally, the analog peptides inhibited biofilm formation largely than Hp1404 at low concentrations. These results suggest that the analog peptides of Hp1404 can be used as therapeutic agents against A. baumannii infection.     

Aminimides: II. Antimicrobial effect of short chain fatty acid derivatives

A new family of surfactants, aminimides, has been screened forin vitro antimicrobial activity. These compounds are active against both bacteria and yeast, activity being a function of chain length. Maximum activity for acetimide and acrylimide amine derivatives was extablished with chain lengths of C₁₄–C₁₆. Homologous compounds with lower or higher chain lengths were less active. While showing low antimicrobial activity against gram negative bacteria, mixtures containing C₁₂ and C₁₆ gave good activity against gram negative strains without losing gram positive activity. Aminimides gave low acute LD₅₀’s (200–400 mg/kg) when tested in mice by intraperitoneal injection.     

Zinc(II) coordination complexes as membrane-active fluorescent probes and antibiotics

Molecular probes with zinc(II)-(2,2'-dipicolylamine) coordination complexes associate with oxyanions in aqueous solution and target biomembranes that contain anionic phospholipids. This study examines a new series of coordination complexes with 2,6-bis(zinc(II)-dipicolylamine)phenoxide as the molecular recognition unit. Two lipophilic analogues are observed to partition into the membranes of zwitterionic and anionic vesicles and induce the transport of phospholipids and hydrophilic anions (carboxyfluorescein). These lipophilic zinc complexes are moderately toxic to mammalian cells. A more hydrophilic analogue does not exhibit mammalian cell toxicity (LD(50) >50 microg mL(-1)), but it is highly active against the Gram-positive bacteria Staphylococcus aureus (MIC of 1 microg mL(-1)). Furthermore, it is active against clinically important S. aureus strains that are resistant to various antibiotics, including vancomycin and oxacillin. The antibiotic action is attributed to its ability to depolarize the bacterial cell membrane. The intense bacterial staining that was exhibited by a fluorescent conjugate suggests that this family of zinc coordination complexes can be used as molecular probes for the detection and imaging of bacteria.     

New antimicrobial agents: The synthesis of Schiff base polymers containing transition metals and their characterization and applications

A new polymeric Schiff base containing formaldehyde and 2‐thiobarbituric acid moieties was synthesized by the condensation of a monomeric Schiff base derived from 2‐hydroxyacetophenone and hydrazine. Polymer–metal complexes were also synthesized by the reaction of the polymeric Schiff base with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) acetate. The polymeric Schiff base and its polymer–metal complexes were characterized with magnetic moment measurements, elemental analyses, and spectral techniques (infrared, ¹H‐NMR, and ultraviolet–visible). The thermal behaviors of these coordination polymers were studied by thermogravimetric analysis in a nitrogen atmosphere up to 800°C. The thermal data revealed that all of the polymer–metal complexes showed higher thermal stabilities than the polymeric Schiff base and also ascribed that the Cu(II) polymer–metal complex showed better heat resistant properties than the other polymer–metal complexes. The antimicrobial activity was screened with the agar well diffusion method against various selected microorganisms, and all of the polymer–metal complexes showed good antimicrobial activity. Among all of the complexes, the antimicrobial activity of the Cu(II) polymer–metal complex showed the highest zone of inhibition because of its higher stability constant and may be used in biomedical applications. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Chirality-antimicrobial relationship of quaternary ammonium cationics

Optically active and racemic quaternary ammonium cationics containing a chiral alkyl group, such as N,N-dimethyl-N-(1-phenylethyl)alkylammonium bromides were prepared and showed excellent antimicrobial properties against Gram positive and negative bacteria, with some exceptions, and against fungi. The influence of optical isomerism on their antimicrobial properties showed that the antimicrobial properties between racemic and optically active cationics were obscure. The order of activity of substituted alkyl groups was tetradecyl > dodecyl ° hexadecyl.     

Аntimicrobial and anticancer activity of new poly(propyleneamine) metallodendrimers

The synthesis, EPR characterisation and biological evaluation of two new metallodendrimers, i.e. a poly(propyleneamine) dendrimer functionalized at the external surface with 4-bromo-1,8-naphthalimide and conjugated with Cu(II) and Zn(II), was performed with the aim to evaluate their antimicrobial and anticancer activity. The antimicrobial activity was investigated in meat-peptone broth against bacteria B. subtilis and P. aeruginosa, and the yeast C. lipolytica. The results showed that the compounds inhibited effectively the tested pathogens even after their deposition on a textile fabric. Anticancer activity was investigated against three human permanent cell lines from non-small cell lung cancer (A549), triple negative breast cancer (MDA-MB-231) and carcinoma of the uterine cervix (HeLa) in the c?=?0.01–30 μM concentration range. The results suggest that these compounds are promising for application in biomedicine as anticancer drugs in the design of new effective preparations. The antimicrobial and anticancer activity may be related to the peculiar structural and dynamical properties revealed for the Cu(II) complexes, by a computer aided analysis of the electron paramagnetic resonance (EPR) spectra. This analysis indicated the formation, at the lowest Cu(II) concentrations, of a flexible rhombic Cu-N4 coordination with the internal amino groups of the dendrimer, which transformed into a Cu2-N4 coordination already at 0.25 equiv. of Cu(II).     

Chelation and Foam Separation of Metal Ions from Solutions

Abstract

An experimental study was conducted on the chelation and foam separation of trace amounts of cadmium, zinc, and lead from their water solutions. The chelation agents ethylenediaminetetraacetate (sodium salt), sodium diethyl-dithiocarbamate, and citric acid were used with sodium dodecylsulfate (SDS) as a foam-producing agent. The chelation agents did not produce metal complexes that were very surface active. The foam-producing agent produced metal ion complexes that were surface active and resulted in appreciable separation of the metal ions. The use of 100 ppm SDS resulted in separation of 90% of the zinc ions from solution containing 2 to 20 ppm zinc. At concentrations below and above this, the removal efficiency dropped significantly     

Enhancement of antimicrobial and long-term biostability of the zinc-incorporated hydroxyapatite coated 316L stainless steel implant for biomedical application

Antimicrobial hydroxyapatite (HAp) nanoparticles with different concentrations (0, 3, and 6 mol%) of zinc were prepared by the ultrasonication process. The prepared nanoparticles and chitosan (CTS) composite were coated on 316L stainless steel implant by spin coating technique. The powder samples were characterised by particle size analyser, X-ray fluorescence, and X-ray diffraction studies. The morphology of the coating was investigated by scanning electron microscopy. The diameter of the particle size decreased with increase in the concentration of zinc in HAp structure. The structure of the coated implant was found to be uniform without any cracks and pores. Antimicrobial activity of the composites against Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia, Salmonella typhi and Pseudomonas aeruginosa was analysed. The results showed that the increase in the concentration of zinc enhances the antimicrobial properties of 316L stainless steel implant. The stability of the implant in physiological environment was characterised by electrochemical impedance spectroscopy and polarisation analysis. The higher concentration of the ZnHAp/CTS composite shows higher corrosion resistance than that of the HAp/CTS-coated implant. This study shows that the coating provides corrosion resistance to the stainless steel substrate in simulated body fluid (SBF). The in vitro bioactivity study of the coated samples immersed in SBF solution confirms the formation of bone-like apatite layer on the surface of the implant. Thus, highly biocompatible ZnHAp/CTS-coated materials could be very useful in the long-term stability of the biomedical applications.