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Search results for: AZOLE ANTIFUNGALS
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The Effect of Conjugation with Octaarginine, a Cell-Penetrating Peptide on Antifungal Activity of Imidazoacridinone Derivative
PublicationAcridine cell-penetrating peptide conjugates are an extremely important family of compounds in antitumor chemotherapy. These conjugates are not so widely analysed in antimicrobial therapy, although bioactive peptides could be used as nanocarriers to smuggle antimicrobial compounds. An octaarginine conjugate of an imidazoacridinone derivative (Compound 1-R8) synthetized by us exhibited high antifungal activity against reference...
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Characterization of PVDF/Graphene Nanocomposite Membranes for Water Desalination with Enhanced Antifungal Activity
PublicationSeawater desalination is a worldwide concern for the sustainable production of drinking water. In this regard, membrane distillation (MD) has shown the potential for effective brine treatment. However, the lack of appropriate MD membranes limits its industrial expansion since they experience fouling and wetting issues. Therefore, hydrophobic membranes are promising candidates to successfully deal with such phenomena that are typical...
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Molecular modelling of membrane activity of amphotericin B, a polyene macrolide antifungal antibiotic
PublicationPraca dotyczy różnego typu modelowań molekularnych cząsteczki przeciwgrzybowego antybiotyku (amfoterycyny B). Praca przeglądowa obejmuje opis badań nad właściwościami molekularnymi samej cząsteczki antybiotyku, jej oddziaływań z powierzchnią błony oraz struktur kanałowych jakie tworzą cząsteczki amfoterycyny wewnątrz błony lipidowej.
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Preliminary antifungal activity assay of selected chlorine-containing derivatives of xanthone and phenoxyethyl amines
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Composition of the Essential Oil of Bidens tripartita L. Roots and Its Antibacterial and Antifungal Activities
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Enhanced susceptibility to antifungal oligopeptides in yeast strains overexpressing ABC multidrug efflux pumps
PublicationPorównano podatność na działanie związków przeciwgrzybowych o strukturze oligopeptydowej oraz aminokwasowej szczepów Saccharomyces cerevisiae z usuniętymi genami kodującymi białka oporności wielolekowej oraz transformantów tych szczepów, zawierających geny CDR1, CDR2 lub MDR1, kodujące główne pompy wielolekowe Candida albicans. Rekombinowane szczepy nadprodukujące białka Cdr1p i Cdr2p wykazywały zwiększoną wrażliwość na wszystkie...
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Synthesis of phosphono and phosphate derivatives of hydroxyimino-D-alditols as new potential antifungal agents
PublicationIn search for new effective we antyfungals we focus on two enzymes involved in biosynthesis of the fungal cell wall. The first enzyme is glucosamine-6-phosphate (GlmS), which catalyzes transformation of D-fructose-6-phosphate (Fru-6P) to D-glucosamine-6-phodphate (GlcN-6P) in the chitin biosynthesis pathway. The second enzyme is phosphomannose isomerase (PMI) repored to play a crucial role in biosynthesis of many mannosylated structures,...
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Homoisocitrate dehydrogenase from Candida albicans: properties, inhibition, and targeting by an antifungal pro-drug
PublicationThe LYS12 gene from Candida albicans, coding for homoisocitrate dehydrogenase was cloned and expressed as a His-tagged protein in Escherichia coli. The purified gene product catalyzes the Mg2+- and K+-dependent oxidative decarboxylation of homoisocitrate to alpha-ketoadipate. The recombinant enzyme demonstrates strict specificity for homoisocitrate. SDS-PAGE of CaHIcDH revealed its molecular mass of 42.6±1 kDa, while in size-exclusion...
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The Antibacterial and Antifungal Textile Properties Functionalized by Bimetallic Nanoparticles of Ag/Cu with Different Structures
PublicationWe reported a preparation and characterization of five kinds of impregnation solutions, containing Ag/Cu in the formof bimetallic nanoparticles (alloy and core-shell) as well as ionic species. The cotton-polyester textiles were successfully impregnated during the washing and ironing process by as-prepared solutions to have antibacterial and antifungal properties against to Escherichia coli, Staphylococcus aureus, and Candida albicans....
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Conjugates of Ciprofloxacin and Levofloxacin with Cell-Penetrating Peptide Exhibit Antifungal Activity and Mammalian Cytotoxicity
PublicationSeven conjugates composed of well-known fluoroquinolone antibacterial agents, ciprofloxacin (CIP) or levofloxacin (LVX), and a cell-penetrating peptide transportan 10 (TP10-NH2) were synthesised. The drugs were covalently bound to the peptide via an amide bond, methylenecarbonyl moiety, or a disulfide bridge. Conjugation of fluoroquinolones to TP10-NH2 resulted in congeners demonstrating antifungal in vitro activity against human...
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A novel in vitro assay for assessing efficacy and toxicity of antifungals using human leukaemic cells infected with Candida albicans
PublicationAims: This study describes a novel in vitro assay that simultaneously determines antifungal efficiency and host cell toxicity using suspensions of human leukaemic cells (HL-60) infected with Candida albicans. Methods and Results: The effect of Candida infection on host cell viability was evaluated by the microscopy of trypan blue-stained cells and lactate dehydrogenase (LDH) activity. The in vitro ‘drug potency assay’ utilized...
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Sławomir Milewski prof. dr hab. inż.
PeopleSławomir Milewski, born in 1955 in Puck, Poland, graduated in 1979 in Chemistry from the Faculty of Chemistry, Gdańsk University of Technology (GUT). In 1984 was employed at the Department of Pharmaceutical Technology and Biochemistry. In 1985 he got his PhD, in 1994 became a DSc (habilitation) and in 2002 got the professorship in chemical sciences. Currently he is a full professor and Head of the Department of Pharmaceutical Technology...
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Synthesis and Characterization of Monometallic (Ag, Cu) and Bimetallic Ag-Cu Particles for Antibacterial and Antifungal Applications
PublicationIn this paper, the experimental studies are concerned with the effect of the synthesis parameters on the formation of monometallic Ag and Cu nanoparticles (NPs). We consider the synthesis strategies verification for the bimetallic core-shell and alloy particles preparation. It was successfully obtained by chemical reduction method. The obtained colloidal solution is characterized by the transmission electron microscopy (TEM) with...
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Analytical studies on ascosin, candicidin and levorin multicomponent antifungal antibiotic complexes. The stereostructure of ascosin A2
PublicationIn the class of polyene macrolides, there is a subgroup of aromatic heptaenes, which exhibit the highest antifungal activity within this type of antibiotics. Yet, due to their complex nature, aromatic heptaenes were not extensively studied and their potential as drugs is currently underexploited. Moreover, there are many inconsistencies in the literature regarding the composition and the structures of the individual components...
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Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent
PublicationCarbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multi-experimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder,1H and13C NMR), electrochemical (cyclic voltammetry), and...
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Inhibitory Effect of Eugenol and trans‐Anethole Alone and in Combination with Antifungal Medicines on Candida albicans Clinical Isolates
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A Central Composite Design in increasing the quercetin content in the aqueous onion waste isolates with antifungal and antioxidant properties
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Antifungal Activity of Capridine β as a Consequence of Its Biotransformation into Metabolite Affecting Yeast Topoisomerase II Activity
PublicationIn the last few years,increasing importance is attached to problems caused by fungal pathogens. Current methods of preventing fungal infections remain unsatisfactory. There are several antifungal compounds whichare highly effective in some cases, however, they have limitations in usage: Nephrotoxicity and other adverse effects. In addition, the frequent use of available fungistatic drugs promotes drug resistance....
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Eucalyptol/ β-cyclodextrin inclusion complex loaded gellan/PVA nanofibers as antifungal drug delivery system
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Sporothrix schenckii: purification and partial biochemical characterisation of glucosamine-6-phosphate synthase, a potential antifungal target
PublicationW artykule opisano izolację i charakterystykę właściwości natywnego enzymu, syntazy GlcN-6-P z komórek dimorficznego grzyba patogennego Sporothrix schenckii. Masę cząsteczkową enzymu natywnego określono na 350 kDa, a enzymu zdenaturowanego na około 79 kDa, co sugeruje homotetrameryczną strukturę białka. Wartość punktu izoelektrycznego wyniosła 6,26; wyznaczono także parametry kinetyczne katalizowanej reakcji. Aktywność enzymu była...
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Synthesis of 2-amino-2,6-dideoxy-D-glucitol-6-sulfonic acid as a potential antifungal agent.
PublicationGlucosamine-6P (GlcN-6P) synthase catalyzes the first committed step in the biosynthetic pathway leading to the formation of UDP-GlcNAc, a sugar nucleotide precursor providing D-glucosamine for the formation of chitin and manoproteins. 2-Amino-2,6-dideoxy-D-glucitol-6-sulfonic acid is an analog of 2-amino-2-deoxy-D-glucitol 6-phosphate (GlcN-ol-6-P), a known inhibitor of GlcN-6-P synthase, in which the phosphate group of the latter...
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Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer
PublicationIllumination of the aromatic heptaene macrolide antifungal antibiotic candicicin D with UV light results in an isomerization of the molecule. The product formed after irradiation of the candicidin complex with UV light (λ=365nm), namely, iso-candicidin D, was isolated and subjected to 2D NMR studies, consisting of DQF-COSY, ROESY, TOCSY, HSQC, and HMBC experiments. The obtained spectral data unambiguously evidenced that iso-candicidin...
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New Peptide Based Fluconazole Conjugates with Expanded Molecular Targets
PublicationInfections of Candida spp. etiology are frequently treated with azole drugs. Among azoles, the most widely used in the clinical scenario remains fluconazole (FLC). Promising results in treatment of dangerous, systemic Candida infections demonstrate the advantages of combined therapies carried out with combinations of at least two different antifungal agents. Here, we report five conjugates composed of covalently linked FLC and...
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Antifungal activity of propolis extracts, screening and kinetic data
Open Research DataThis folder contains results of our studies aiming in determination of antifungal potential of ethanolic extracts of propolis and components of this product. In details, MIC, MFC values were determined and kill time assays were performed.
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Molecular organization of antifungal antibiotic amphotericin B in lipid monolayers studied by means of Fluorescence Lifetime Imaging Microscopy
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Chemical composition and antifungal activity of Chelidonium majus extracts – antagonistic action of chelerythrine and sanguinarine against Botrytis cinerea
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Virulence, antifungal susceptibility and molecular mechanisms of echinocandin resistance among Candida isolates recovered from clinical specimens
PublicationFungi of the genus Candida belong to the natural microflora of healthy individuals. However, they can also be a cause of opportunistic infections especially among patients with an impaired immune system. The first line therapy of Candida infections is based on triazoles. However, in recent years there an increase of azole resistant Candida spp., in particular C. glabrata and C. krusei, has been observed. For this reason, echinocandin...
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Quest for the Molecular Basis of Improved Selective Toxicity of All-Trans Isomers of Aromatic Heptaene Macrolide Antifungal Antibiotics
PublicationThree aromatic heptaene macrolide antifungal antibiotics, Candicidin D, Partricin A (Gedamycin) and Partricin B (Vacidin) were subjected to controlled cis-trans to all trans photochemical isomerization. The obtained all-trans isomers demonstrated substantially improved in vitro selective toxicity in the Candida albicans cells: human erythrocytes model. This effect was mainly due to the diminished hemotoxicity. The molecular modeling...
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Xanthone synthetic derivatives with high anticandidal activity and positive mycostatic selectivity index values
PublicationWith the current massive increases in drug-resistant microbial infection as well as the significant role of fungal infections in the death toll of COVID-19, discovering new antifungals is extremely important. Natural and synthetic xanthones are promising derivatives, although only few reports have demonstrated their antifungal mechanism of action in detail. Newly synthetized by us xanthone derivative 44 exhibited strong antifungal...
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Genome Mining Revealed a High Biosynthetic Potential for Antifungal Streptomyces sp. S-2 Isolated from Black Soot
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Novel Nystatin A1 derivatives exhibiting low host cell toxicity and antifungal activity in an in vitro model of oral candidosis
PublicationOpportunistic oral infections caused by Candida albicans are frequent problems in immunocompromised patients. Management of such infections is limited due to the low number of antifungal drugs available, their relatively high toxicity and the emergence of antifungal resistance. Given these issues, our investigations have focused on novel derivatives of the antifungal antibiotic Nystatin A1, generated by modifications at the amino...
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Intramolecular transformation of an antifungal antibiotic nystatin A1 into its isomer, iso-nystatin A1 - structural and molecular modeling studies
PublicationNystatin A1, a polyene macrolide antifungal antibiotic, in a slightly basic or acidic solution undergoes an intramolecular transformation, yielding a structural isomer, the translactonization product, iso-nystatin A1 with lactone ring diminished by two carbon atoms. Structural evidence is provided by advanced NMR and Mass Spectrometry (MS) studies. Molecular dynamics simulations and quantum mechanics calculations gave the insight...
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Antifungal activity of propolis extracts produced with deep eutectic solvents.
Open Research DataThis dataset contains results of our investigation aiming in determination of antimicrobial potential of the propolis extracts produced with deep eutectic solvents. The activity was determined against C. albicans and C. glabarat strains. On the basis of these results MIC values can be calculated. Three samples of propolis were tested.
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Antifungal activity of L-homoserine O-acetyltransferase (CaMet2p) inhibitors.
Open Research DataThe dataset contains a set of optical densities at 600 nm measured at microplate reader to determine the rate of fungal growth in the presence of Candida albicans homoserine O-acetyltransferase inhibitors. Antifungal activities were determined against several strains from Candida spp. and others by the modified M27-A3 method specified by the CLSI. We...
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Lipophilicity Determination of Antifungal Isoxazolo[3,4-b]pyridin-3(1H)-ones and Their N1-Substituted Derivatives with Chromatographic and Computational Methods
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Amphotericin B derivatives: novel strategy for the development of non-toxic, broad spectrum, fungicidal and overcoming multidrug resistance antifungal agents.
PublicationZaprezentowano porównawczą charakterystykę działania amfoterycyny B (AmB) oraz jej pochodnych o różnym stopniu selektywnej toksyczności na szczepy grzybów reperezentujących różne mechanizmy oporności. Były to mutanty C. albicans posiadające defekt w szlaku biosyntezy ergosterolu oraz wielolekooporne szczepy S. cerevisiae wyposażone w pompy eksportujące typu ABC i MFS. Badania obejmowały: 1)porównanie aktywności przeciwgrzybowej...
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Antibacterial, Antifungal and Anticancer Activities of Compounds Produced by Newly Isolated Streptomyces Strains from the Szczelina Chochołowska Cave (Tatra Mountains, Poland)
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Mechanism of Binding of Antifungal Antibiotic Amphotericin B to Lipid Membranes: An Insight from Combined Single-Membrane Imaging, Microspectroscopy, and Molecular Dynamics
PublicationAmphotericin B is a lifesaving polyene antibiotic used in the treatment of systemic mycoses. Unfortunately, the pharmacological applicability of this drug is limited because of its severe toxic side effects. At the same time, the lack of a well-defined mechanism of selectivity hampers the efforts to rationally design safer derivatives. As the drug primarily targets the biomembranes of both fungi and humans, new insights into the...
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Solvent influence on the crystal structures of new cadmium tri-tert -butoxysilanethiolate complexes with 1,4-bis(3-aminopropyl)piperazine: luminescence and antifungal activity
PublicationMonocrystals of dinuclear -1,4-bis(3-aminopropyl)piperazine-4N1,N10:N4,N40-bis[bis(tri-tert-butoxysilanethiolato-S)cadmium(II)], [Cd2(C12H27O3SSi)4(C10-H24N4)] or [Cd2{SSi(OtBu)3}4(-BAPP)], 1, and polynuclear catena-poly[[bis-(tri-tert-butoxysilanethiolato-S)cadmium(II)]--1,4-bis(3-aminopropyl)piperazine-2N10:N40], [Cd(C12H27O3SSi)2(C10H24N4)]n or [Cd{SSi(OtBu)3}2(-BAPP)]n,2, with 1,4-bis(3-aminopropyl)piperazine (BAPP)...
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Solvent influence on the crystal structures of new cadmium tri-tert -butoxysilanethiolate complexes with 1,4-bis(3-aminopropyl)piperazine: luminescence and antifungal activity
PublicationMonocrystals of dinuclear 1,4-bis(3-aminopropyl)piperazine-�4N1,N10:N4,N40-bis[bis(tri-tert-butoxysilanethiolato-�S)cadmium(II)], [Cd2(C12H27O3SSi)4(C10-H24N4)] or [Cd2{SSi(OtBu)3}4(�-BAPP)], 1, and polynuclear catena-poly[[bis- (tri-tert-butoxysilanethiolato-�S)cadmium(II)]-�-1,4-bis(3-aminopropyl)piperazine-�2N10:N40], [Cd(C12H27O3SSi)2(C10H24N4)]n or [Cd{SSi(OtBu)3}2(�-BAPP)]n, 2, with 1,4-bis(3-aminopropyl)piperazine (BAPP)...
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N-(1-Piperidinepropionyl)amphotericin B methyl ester (PAME) - a new derivative of the antifungal antibiotic amphotericin B: Searching for the mechanism of its reduced
PublicationZ zastosowaniem techniki monowarstw Langmuira zbadano naturę oddziaływań pochodnej antybiotyku przeciwgrzybowego amfoterycyny B o obniżonej toksyczności tj. estru metylowego N-(1-piperydynopropionylo)amfoterycyny B (PAME) z komponentami błon biologicznych takich jak: ergosterol, cholesterol i modelowy fosfolipid DPPC i stwierdzono, że zróżnicowanie tych oddziaływań jest podstawą obniżonej toksyczności związku.
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Octanoic Acid—An Insecticidal Metabolite of Conidiobolus coronatus (Entomopthorales) That Affects Two Majors Antifungal Protection Systems in Galleria mellonella (Lepidoptera): Cuticular Lipids and Hemocytes
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Hydrophobic derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate: a newtype of D-glucosamine-6-phosphate synthase inhibitors with antifungal action.
PublicationDokonano syntezy szeregu N-acylowych i estrowych pochodnych 2-amino-2-deok-sy-glucitolo-6-fosforanu (ADGP) i zbadano ich aktywność przeciwgrzybową oraz wobec enzymów zaangażowanych we wczesne etapy biosyntezy chityny w komórkach grzybów. Wszystkie badane pochodne okazały się słabszymi inhibitorami enzymu syntezy GlcN-6-P aniżeli ADGP, ale niektóre z nich wykazywały znacznie wyższą aktywność przeciwgrzybową niż związek macierzysty....
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Investigation of the Antifungal Activity and Mode of Action of Thymus vulgaris, Citrus limonum, Pelargonium graveolens, Cinnamomum cassia, Ocimum basilicum, and Eugenia caryophyllus Essential Oils
PublicationThe antimicrobial activity of plant oils and extracts has been recognized for many years. In this study the activity of Thymus vulgaris, Citrus limonum, Pelargonium graveolens, Cinnamomum cassia, Ocimumbasilicum, and Eugenia caryophyllus essential oils (EOs) distributed by Pollena Aroma (Nowy Dwór Mazowiecki, Poland) was investigated against a group of 183 clinical isolates of C. albicans and 76 isolates of C. glabrata. All of...
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The absorption and fluorescence spectra of C-1305 derivatives (IKE1-IKE8), potential antifungal agents
Open Research DataOptical measurements of C-1305 derivatives (IKE1-IKE8). The absorption spectra were recorded at 300 - 800 nm for solutions with 16 μg / mL derivative concentration. The fluorescence emission spectra were determined at 420-800 nm with the excitation wavelengths 360 or 415 nm for solutions with 1 μg / mL derivative concentration. All measurements were...
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How do sterols determine the antufungal activitiy of amphotericin B? Free energy of binding between the drug and its membrane targets.
PublicationAmphotericin B (AmB) is a well-known polyene antibiotic used to treat systemic fungal infections. It is commonly accepted that the presence of sterols in the membrane is essential for the AmB biological activity, that is, for the formation of transmembrane ion channels. The selective toxicity of AmB for fungal cells is attributed to the fact that it is more potent against fungal cell membranes containing ergosterol than against...
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The absorption and fluorescence spectra of novel bisacridines (IKE15-19, IKE21) and IE10, potential antifungal agents
Open Research DataOptical measurements of novel bisacridines (IKE15-19, IKE21) and IE10 were conducted. The absorption spectra were recorded from 300 to 800 nm. The fluorescence emission spectra were determined with excitation and emission wavelengths described in the file. All measurements were recorded using a multiplate reader, Tecan Spark 10M.
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The Substantial Improvement of Amphotericin B Selective Toxicity Upon Modification of Mycosamine with Bulky Substituents
PublicationAbstract: Background: It is assumed that the unfavorable selective toxicity of an antifungal drug Amphotericin B (AmB) can be improved upon chemical modification of the antibiotic molecule. Objective: The aim of this study was verification of the hypothesis that introduction of bulky substituents at the amino sugar moiety of the antibiotic may result in diminishment of mammalian vitro toxicity of thus prepared AmB derivatives. Methods:...
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The Effect of Posaconazole, Itraconazole and Voriconazole in the Culture Medium on Aspergillus fumigatus Triazole Resistance
PublicationTriazoles are the only compounds used as antibiotics in both medicine and agriculture. The presence of triazoles in the environment can contribute to the acquisition of azole resistance among isolates of Aspergillus fumigatus. The objective of this study was to investigate the effect of A. fumigatus exposure to triazoles on susceptibility to these compounds. Seventeen triazole-resistant and 21 triazole-sensitive A. fumigatus isolates...
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A new 1-nitro-9-aminoacridine derivative targeting yeast topoisomerase II able to overcome fluconazole-resistance
PublicationFungal resistance remains a significant threat and a leading cause of death worldwide. Thus, overcoming microbial infections have again become a serious clinical problem. Although acridine derivatives are widely analyzed as anticancer agents, only a few reports have demonstrated their antifungal activity. In an effort to develop biologically active antifungals, twelve novel C-857 (9-(2′ -hydroxyethylamino)-1-nitroacridine) and...