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Search results for: BIOSYTHESIS OF ANTIFUNGAL ANTIBIOTICS
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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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Aromatic heptaene antibiotics as an alternative for synthetic triazole fungicides in plant protection
PublicationAn in vitro antifungal activity of candicidin and ascosin antibiotics (0,01-10 μg/mL) towards representative strains of phytopathogenic fungi was detd. Both compds. exhibited similar half max. effective concns. inhibiting growth of the fungi as that of tebuconazole used for comparison.
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Molecular Umbrellas Modulate the Selective Toxicity of Polyene Macrolide Antifungals
PublicationAntifungal polyene macrolide antibiotics Amphotericin B (AmB) and Nystatin (NYS) were conjugated through the ω-amino acid linkers with diwalled “molecular umbrellas” composed of spermidine-linked deoxycholic or cholic acids. The presence of “umbrella” substituents modulated biological properties of the antibiotics, especially their selective toxicity. Some of the AmB-umbrella conjugates demonstrated antifungal in vitro activity...
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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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Heptaene macrolides biosynthesis by Streptomyces species
PublicationPolyene macrolides are one of the groups of secondary metabolites, generated by microorganisms belonging to the Streptomyces genus. These compounds, containing 3 - 7 conjugated double bonds systems in their molecules exhibit high antifungal activity against a broad spectrum of fungal pathogens with heptaenes demonstrating the highest antifungal potential. At the large extent, efficiency of biosynthesis of these natural products...
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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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Chemical and biological stability of polyene macrolides
PublicationThe polyene macrolide antibiotics have been used in an-tifungal therapy since first o f them were discovered in 1950's. Up to now, four polyene macrolides are being used in medical practice, namely amphotericin B, nystatin, candi-cidin and pimaricin.The antifungal activity and mode of ac-tion of polyene macrolides is determined by their structure, chemical and physical properties.The main fragment of polyene...
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Does the chemical modification of Nystatin A1 affect the drug's ability to overcome the multidrug resistance of fungi?
PublicationAlthough the contemporary medicine keeps moving forward, disseminated infections caused by fungal pathogens are an emerging challenge. The dramatic rise of fungal diseases, especially the most life-threatening systemic mycoses is associated with a permanently growing number of immunodeficient patients. Undoubted difficulties in the treatment of fungal infections are caused by lack of highly effective and selective antifungal drugs,...
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Antibiotics-Basel
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Antibiotic-sterol interactions provide insight into the selectivity of natural aromatic analogues of amphotericin B and their photoisomers
PublicationAromatic heptaene macrolides (AHMs) belong to the group of polyene macrolide antifungal antibiotics. Members of this group were the first to be used in the treatment of systemic fungal infections. Amphotericin B (AmB), a non-aromatic representative of heptaene macrolides, is of significant clinical importance in the treatment of internal mycoses. It includes the all-trans heptaene chromophore, whereas the native AHMs contain two...
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Evaluation of antimicrobial activities of powdered cuttlebone against Klebsiella oxytoca, Staphylococcus aureus, and Aspergillus flavus
PublicationBackground: The presence of medicines in the environment is considered as a serious threat to the human health. The entrance of these substances into the water sources causes soil pollution, which eventually leads to the environmental pollution and it creates some problems for the public health. Also, increasing antibiotic resistant bacteria has attracted the attention of researchers to the use of natural resources such as marine...
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Membrane Sterols Modulate the Binding Mode of Amphotericin B without Affecting Its Affinity for a Lipid Bilayer
PublicationMembrane-active antibiotics are known to selectively target certain pathogens based on cell membrane properties, such as fluidity, lipid ordering, and phase behavior. These are in turn modulated by the composition of a lipid bilayer and in particular by the presence and type of membrane sterols. Amphotericin B (AmB), the golden standard of antifungal treatment, exhibits higher activity toward ergosterol-rich fungal membranes, which...
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‘Acridines’ as New Horizons in Antifungal Treatment
PublicationFrequent fungal infections in immunocompromised patients and mortality due to invasive mycosis are important clinical problems. Opportunistic pathogenic Candida species remain one of the leading causes of systemic mycosis worldwide. The repertoire of antifungal chemotherapeutic agents is very limited. Although new antifungal drugs such as lanosterol 14α-demethylase and β-glucan synthase inhibitors have been introduced into clinical...
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JOURNAL OF ANTIBIOTICS
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Antifungal Activity of Homoaconitate and Homoisocitrate Analogs
PublicationThirteen structural analogs of two initial intermediates of the L-alpha-aminoadipate pathway of L-lysine biosynthesis in fungi have been designed and synthesized, including fluoro- and epoxy-derivatives of homoaconitate and homoisocitrate. Some of the obtainedcompounds exhibited at milimolar range moderate enzyme inhibitory properties against homoaconitase and/or homoisocitrate dehydrogenase of Candida albicans. The structural...
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Antifungal dipeptides incorporating an inhibitor of homoserine dehydrogenase
PublicationThe antifungal activity of 5‐hydroxy‐4‐oxo‐L‐norvaline (HONV), exhibited under conditions mimicking human serum, may be improved upon incorporation of this amino acid into a dipeptide structure. Several HONV‐containing dipeptides inhibited growth of human pathogenic yeasts of the Candida genus in the RPMI‐1640 medium, with minimal inhibitory concentration values in the 32 to 64 μg mL−1 range. This activity was not affected by multidrug...
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Presence of antibiotics in the aquatic environment in Europe and their analytical monitoring: Recent trends and perspectives
PublicationThe presence of antibiotics and their metabolites in the aquatic environment exerts a negative impact on all organisms. Moreover, the easy migration of these substances to drinking water may also have serious consequences for public health, such as drug resistance. Although antibiotics and their metabolites are detected in surface waters and wastewater, there are still no systemic solutions preventing environmental pollution with...
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Inhibitors of amino acids biosynthesis as antifungal agents
PublicationFungal microorganisms, including the human pathogenic yeast and filamentous fungi, are able to synthesize all proteinogenic amino acids, including nine that are essential for humans. A number of enzymes catalyzing particular steps of human-essential amino acid biosynthesis are fungi specific. Numerous studies have shown that auxotrophic mutants of human pathogenic fungi impaired in biosynthesis of particular amino acids exhibit...
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Antibacterial evaluation of bioactive modifiers of bone cements: antibiotics, nanometals and chitosan
PublicationModern biomaterials in addition to their basic tasks, can serve as carriers of active substance. The release of a bioactive particles allows to locally fight infection or its prevent it. Bone cements additionally to their basic applications in orthopedic surgery can also serve to deliver locally active substances. Currently, only antibiotics are routinely used as modifiers for bone cements. Bioactive bone cements constitute...
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Peptide dendrimers as antifungal agents and carriers for potential antifungal agent—N3‐(4‐methoxyfumaroyl)‐(S)‐2,3‐ diaminopropanoic acid—synthesis and antimicrobial activity
PublicationA series of peptide dendrimers and their conjugates with antimicrobial agent FMDP (N3‐(4‐methoxyfumaroyl)‐(S)‐2,3‐diamino‐propanoic acid) were synthesized. The obtained compounds were tested for the antibacterial and antifungal activity. All novel dendrimers displayed much better activity against the tested strains than FMDP itself. Moreover, their conjugates with FMDP also exhibited antimicrobial activity. The most promising molecules...
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Efficient synthesis and antifungal investigation of nucleosides’ quaternary ammonium salt derivatives
PublicationQuaternary ammonium salts are a group of compounds with diverse biological properties, the most important of which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-O-tosyl derivatives of uridine and thymidine with triethylamine, trimethylamine, 4-(N ,N -dimethylamino)pyridine, 2-methylpyridine, and pyridine are described in this article. Two of the synthesized compounds are exceptional...
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Determination of aminoglycoside antibiotics: current status and future trends
PublicationThe use of aminoglycoside antibiotics is prevalent in medicine and agriculture. Their overuse increases their mobility in the environment, resulting in a need for reliable methods for their determination in a variety of matrices. However, the properties of aminoglycosides, in particular their high polarity, make the development of such methods a non-trivial task, inciting researchers to tackle this complex issue from different...
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Activated persulfate and peroxymonosulfate based advanced oxidation processes (AOPs) for antibiotics degradation – A review
PublicationSulfate radical AOPs (SR-AOP) were successfully utilized in degradation of antibiotics in water and wastewater treatment. The review discusses details on SR-AOPs mechanisms and applications for antibiotics degradation. The progress in this field was discussed, highlighting the most promising developments and remaining challenges. The applicability of SR-AOPs was summarized revealing the most susceptible and persistent to oxidation...
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Biomechanical testing of bioactive bone cements – a comparison of the impact of modifiers: antibiotics and nanometals
PublicationApart from its bone filler and fracture stabilizing function, bone cement can be used as a carrier of bioactive substances, and such modified bone cement can protect the implant against microorganisms, treat local infections and combat bacteria introduced during the surgical procedure. In this paper, the effects of modifying antibiotics and nanosilver on the biomechanical properties of bone cement were examined. The following tests...
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Antifungal Activity and Synergism with Azoles of Polish Propolis
PublicationThe aim of our work was to check if one of the products of natural origin, namely honey 19 bee propolis may be an alternative or supplement to currently used antifungal agents. The activity 20 of 50 ethanolic extracts of propolis (EEPs), harvested in Polish apiaries, was tested on a group of 69 21 clinical isolates of C. albicans. Most of the EEPs showed satisfactory activity, with minimum 22 fungicidal concentrations (MFC) mainly...
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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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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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Potential Saving of Antibiotics for Respiratory Infections in Several European Countries: Insights from Market Research Data
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MXene-based materials for removal of antibiotics and heavy metals from wastewater– a review
PublicationAs a novel family of 2D materials, MXenes provide an extensive variety of applications in water and effluent treatment due to their distinctive properties and attractive applicability, including superior electrical conductivity, higher thermal stability, hydrophilicity, and high sorption-reduction capacity. Their excellent sorption selectivity makes them perfect for removing hazardous contaminants. Currently, MXene-based materials...
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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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Targeting yeast topoisomerase II by imidazo and triazoloacridinone derivatives resulting in their antifungal activity
PublicationFungal pathogens are considered as serious factors for deadly diseases and are a case of medical concern. Invasive fungal infections also complicate the clinical course of COVID-19, leading to a significant increase in mortality. Furthermore, fungal strains' multidrug resistance has increased the demand for antifungals with a different mechanism of action. The present study aimed to identify antifungal compounds targeting yeast...
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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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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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Untargeted Lipidomics Reveals Differences in the Lipid Pattern among Clinical Isolates of Staphylococcus aureus Resistant and Sensitive to Antibiotics
PublicationStaphylococcus aureus resistance to antibiotics is a significant clinical problem worldwide. In this study, an untargeted lipidomics approach was used to compare the lipid fingerprints of S. aureus clinical isolates that are resistant and sensitive to antibiotics. High-performance liquid chromatography coupled with time-of-flight mass spectrometry was employed to rapidly and comprehensively analyze bacterial lipids. Chemometric...
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The influence of antibiotics on the anammox process — a review
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Antifungal Effect of Penicillamine Due to the Selective Targeting of L-Homoserine O-Acetyltransferase
PublicationDue to the apparent similarity of fungal and mammalian metabolic pathways, the number of established antifungal targets is low, and the identification of novel ones is highly desirable. The results of our studies, presented in this work, indicate that the fungal biosynthetic pathway of L-methionine, an amino acid essential for humans, seems to be an attractive perspective. The MET2 gene from Candida albicans encoding L-homoserine...
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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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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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Novel dendrimeric lipopeptides with antifungal activity
PublicationZaprojektowano, zsyntezowano i scharakteryzowano serię nowych kationowych lipopeptydów zawierających rozgałęziony, amfifilowy polarny rdzeń strukturalny pochodzący od dendronu (Lys)(Lys)(Lys) oraz łańcuchy C8 i C12 na C-końcu. Otrzymane zwiazki wykazywały aktywność przeciwdrobnoustrojową, w tym szczególnie przeciwgrzybową wobec drożdżaków z rodzaju Candida. Najwyższą aktywność, selektywną wobec drobnoustrojów grzybowych, wykazywały...
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Evaluation of Antifungal Properties of Titania P25
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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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Determination of amikacin and ciprofloxacin by liquid chromatography with pre-column derivatization to evaluate sustained delivery of antibiotics from Drug-Eluting Biopsy Needle
PublicationDetermination of chosen antibacterial antibiotics: amikacin and ciprofloxacin was carried out by HPLC-UV after derivatization with 9-fluorenylmethyl chloroformate and in their native form by HPLC-MS/MS. Developed methods have been applied to control the kinetics of antibiotic release from polymer-based controlled drug delivery system.
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Determination of aminoglycoside antibiotics: Current status and future trends
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Rapid determination of multiple aminoglycoside antibiotics in veterinary formulations by ion-pair chromatography coupled with evaporative light scattering detection
PublicationA fast and simple method for simultaneous determination of eight aminoglycoside antibiotics using ion-pairing liquid chromatography (IPLC) coupled with evaporative light scattering detection (ELSD) has been developed and validated. Separation of amikacin, apramycin, gentamicin (as a sum of gentamicin C1, C2 and C1A), kanamycin A, neomycin B, paromomycin, streptomycin and tobramycin was achieved using C18 column with H2O and MeOH/acetone,...
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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 action of the oxathiolone-fused chalcone derivative
PublicationAMG-148, pochodna chalkonu z pierścieniem oksatiolonowym, wykazuje aktywność przeciwgrzybową in vitro wobec szczepów grzybowych patogennych dla człowieka, z wartościami minimalnych stężeń hamujących wzrost mieszczących się w zakresie 1-16 mikrogramów na mililitr, natomiast w wyższych stężeniach związek ten działa grzybobójczo. Obecność głównych białek oporności wielolekowej, Cdr1p, Cgr2p lub Mdr1p nie wpływa znacząco na aktywność...
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Targeting DNA Topoisomerase II in Antifungal Chemotherapy.
PublicationTopoisomerase inhibitors have been in use clinically for the treatment of several diseases for decades. Although those enzymes are significant molecular targets in antibacterial and anticancer chemotherapy very little is known about the possibilities to target fungal topoisomerase II (topo II). Raising concern for the fungal infections, lack of effective drugs and a phenomenon of multidrug resistance underlie a strong need to expand...
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Evaluation of Langmuir and Freundlich Isotherms for Removal of Cephalexin and Tetracycline Antibiotics By Sistan Sand from Water and Wastewater Samples
PublicationIn this research, Sistan sand was used as a natural and inexpensive sorbent for removal of cephalexin and tetracycline antibiotics from water and wastewater samples. For a concentration 60.0 mg L-1 of cephalexin, optimum removal conditions were: pH of the sample 3.0, adsorbent amount 1.0 g, contact time 20.0 min, added amount of sodium chloride to adjust the ionic strength of the solution 7.0 g L-1. Langmuir isotherm was the best...
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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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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,...