Startseite Photophysical and antibacterial activity of light-activated quaternary eosin Y
Artikel Open Access

Photophysical and antibacterial activity of light-activated quaternary eosin Y

  • Desislava Staneva , Stanislava Yordanova EMAIL logo , Evgenia Vasileva-Tonkova , Stanimir Stoyanov und Ivo Grabchev
Veröffentlicht/Copyright: 31. Dezember 2019

Abstract

The functional characteristics of a new eosin dye with biocidal quaternary ammonium group (E) were studied in aqueous solution and in organic solvents of different polarity. The spectral properties depend on the nature and polarity of the respective solvents. The antimicrobial activity of compound E has been tested in vitro against Gram-negative bacteria (Escherichia coli, Acinetobacter johnsoni and Pseudomonas aeruginosa), Gram-positive bacteria (Sarcina lutea and Bacillus cereus) and the antifungal activity was tested against the yeasts Candida lipolytica in solution and after treated on cotton fabric. Broth dilution test has been used for quantitative evaluation of the antimicrobial activity of compound E against the model strains. The ability of compound E to inhibit the growth of model Gram-negative P. aeruginosa strain was assessed after 16 h of incubation in presence and absence of light. These experiments were conducted in planktonic format in solution and on cotton fabric. The results suggest that the new compound is effective in treating the relevant pathogens with better results being obtained by irradiation with light. In this case the quaternary ammonium group promotes the binding of eosin Y moiety to the bacterial cell wall thus accelerating bacterial photo inactivation.

1 Introduction

Fluorescent compounds are often used in medicine, pharmacy, biology and environmental protection [1,2]. Among the known fluorophore structures used in these fields, the eosin Y and its derivatives are very important. They belong to the group of xanthene fluorescent dyes with a wide range of photophysical and biological applications, due to their low toxicity in vivo, and high water solubility [3]. The utility of eosin derivatives is associated to their good spectral characteristics and the possibility to interact with different type of biomolecules [4, 5, 6, 7, 8]. Photophysical properties of eosin in solution strongly depend on the solvents polarity and possibility of hydrogen bond formations. Depending on pH eosin Y exhibit tautomeric structures with different proteolytic forms, and its colour depends on the respective forms [9,10]. In recent years, eosin Y was also successfully used as photoredox catalyst in organic synthesis [11,12].

A new scientific area of research is the combination of dyeing process with antibacterial properties in one compound [13]. This can be achieved through the introduction of specific groups into the dye chromophore systems to give antibacterial properties without changing their colour characteristics. In this case quaternary ammonium group can be bonded to the fluorophores by incorporating alkyl chain into the chromophore system through covalent bonds. The cationic dyes thus obtained show good colour characteristics and high antibacterial activity in solutions [14, 15, 16, 17, 18]. In the last years in our laboratory, fluorophores with different chemical structure having ammonium quaternary groups have been synthesized and their antibacterial and antifungal activity were investigated in solution or after their incorporation into polylactide matrix, or on the textile fabrics [19, 20, 21]. The relevance of such studies is due to the fact than in the last years the antimicrobial resistance of different pathogens has become a major problem in medicine and clinical practice. This encouraged many research laboratories to start searching for and investigating novel and more active antibacterial drugs [22, 23, 24].

Scheme 1 Chemical structure of quaternary eosin Y (E).
Scheme 1

Chemical structure of quaternary eosin Y (E).

In the last few years, photodynamic therapy has been used against the resistance of pathogens to the medicines administered in practice. In this case, the microbiological activity of the preparations used is due to the generation of reactive oxygen species upon irradiation with visible light, which kill the bacteria by oxidative burst [25]. It has been reported that eosin Y has some antibacterial photoactivity [26].

In this paper we present the results on photophysical characterization of a new ammonium quaternary eosin Y in organic solvents of different polarity and evaluation of its antimicrobial activity against different pathogens. The effect of visible light on the antimicrobial activity of the new eosin Y derivative has also been tested in solution and after its deposition on cotton fabric.

2 Experimental part

2.1 Materials and methods

The synthesis and application of a quaternary ammonium eosin Y (E) as photoinitiator of polymerization of acrylate monomers has been described recently (Scheme 1) [27]. The light source of lamp used for irradiation was with the parameters: HL 8325, 25 w, 1230 Lumen, 6400 K, Horoz. Absorption spectra were performed using “Thermo Spectronic Unicam UV 500” spectrophotometer. The fluorescence spectra were taken on a “Cary Eclipse” spectrophotometer. All spectra were recorded using 1 cm path length synthetic quartz glass cells. Absorption and fluorescence measurements of the eosin compound E were carried out at 10-6 mol.L-1 concentration. Organic solvents: acetonitrile (MeCN), methanol (MeOH), ethanol (EtOH), dimethylsulfoxide (DMSO), N,N-dimethylformamide (DMF), dichloromethane (CH2Cl2), 1,4-dioxane and ethylacetate (EtOAc) used in this study were of spectroscopic grade. Fluorescence quantum yield was determined on the basis of the absorption and fluorescence spectra, using Rhodamine 6G as reference (Φst = 0.94 in ethanol [28]).

2.2 Preliminary antimicrobial screening

The antibacterial activity of the investigated compound E was determined against Gram-positive bacteria (Sarcina lutea and Bacillus cereus), Gram-negative bacteria (Acinetobacter johnsonii, Escherichia coli and Pseudomonas aeruginosa) and the antifungal activity was tested against the yeasts Candida lipolytica. Microbial cultures were maintained at 4°C on Mueller-Hinton agar (MHA) slants and transferred monthly.

2.3 In vitro antimicrobial assay

Broth dilution test was used for quantitative evaluation of the antimicrobial activity of compound E against the model strains. Тhe concentration of compound E dissolved in water was 5 mg/ml (0.623 μM) and was further diluted in each consecutive test tube in sterile meat-peptone broth (MPB, pH 7.0) to final concentrations of 0.018, 0.038, 0.077, 0.156, 0.249 and 0.312 and 0.623 mM. After inoculation with 2% (v/v) of each standardized cell suspension, the tubes were incubated at appropriate temperature for 24 h under shaking (at 240 rpm). The microbial growth was assessed by measuring the optical density of the medium at 600 nm (OD600). The growth control, sterility control and control of the compound E were used. The % survival of the test cultures was determined on the basis of the positive control which was considered as 100%. The experiments were conducted in triplicate. The light source used for irradiation was with the parameters: HL 8325, 25 w, 1230 Lumen, 6400 K, Horoz [27].

2.4 Antimicrobial activity of cotton fabrics

The antimicrobial effectiveness of cotton fabrics treated with 0.5% solution of the compound E was investigated by the shaking flask method. C. lipolytica, B. cereus and A. johnsonii were used as model strains. Test tubes containing sterile MPB (1.0 ml) and square specimens (10 mm x 10 mm) were inoculated with each overnight grown microbial culture. Tubes with untreated cotton and without specimens were also prepared as controls. After 24 h incubation at appropriate temperature under shaking, microbial growth was determined by measuring OD600. To evaluate the antimicrobial activities of the samples, the reduction in cell density between the untreated and treated samples after incubation was compared. All antimicrobial activity tests were done in triplicate.

2.5 Treatment of cotton fabrics with E

In 5 ml of water the compound E (5 mg) was dissolved and 1g of cotton fabric (weight 140 g/m2) was added in the solution for 30 min at 25°C. Then cotton sample was dried at ambient temperature.

Ethical approval: The conducted research is not related to either human or animal use.

3 Results and Discussion

3.1 Photophysical characteristics of ammonium quaternary eosin Y (E)

Photophysical properties of the eosin Y derivatives as a part of xanthene dyes are characterized by heterocyclic system containing a dibenzo-1,4-pyran ring. Its basic spectral characteristics depend from the solvent polarity and for formation of hydrogen bonds with solvents.

All spectral measurements of the compound E were investigated at a concentration of c = 1 x 10-6 mol.L-1 and in this concentration the solution is highly coloured in red-pink colour. Table 1 presents its spectral characteristics in different organic solvents: the fluorescence (lF) and absorption (lA) maxima, Stokes shift (nA -n F), quantum yield of fluorescence (FF) and the molar absorptivity (e).

Table 1

Photophysical characteristics of compound E in solvents with different polarity.

SolventlA nmlF nmnA - nF cm-1ε l mol-1 cm-1FF
Water5155357261100000.22
MeOH5225406391100000.59
EtOH5295465891200000.54
DMF5385524711100000.36
MeCN538556602980000.71
DMSO545562555951000.68
CH2Cl2543561590951000.22
EtOAc540556533942000.40
Dioxane540555501921000.20

From the data in Table 1 it is seen than the ammonium quaternary eosin E has absorption maxima at 515-540 nm and the respective fluorescence maxima are at 540-562 nm. All absorption spectra exhibit bands with a well pronounced maximum and short-wavelength shoulder as it can be seen from Figure 1 as an example. Also Figure 1 shows that the fluorescence curve is approximately mirror images of the absorption curves which is typical for such structures with allowed transitions and similar geometries in excited and ground state.

Figure 1 Normalized absorption (black) and fluorescence (red) spectra of the compound E in N,N-dimethylformamide solution.
Figure 1

Normalized absorption (black) and fluorescence (red) spectra of the compound E in N,N-dimethylformamide solution.

The position of the absorption and fluorescence maxima depend from the polarity of solvents (Figures 2 and 3). In the case of solvents containing hydroxyl group such as alcohols and water both absorption and emission maxima are hypsochromically shifted compared to the other solvents. The difference is due to the enhancing the dipole moment of the molecule upon excitation due to the electron density distribution and from other hand the possibility for formation of hydrogen bonds.

Figure 2 Absorption (A) and fluorescence (B) spectra of compound E in solvents with different polarity.
Figure 2

Absorption (A) and fluorescence (B) spectra of compound E in solvents with different polarity.

Figure 3 Normalized excitation (black) and fluorescence (red) spectra of compound E loaded on the cotton fabric.
Figure 3

Normalized excitation (black) and fluorescence (red) spectra of compound E loaded on the cotton fabric.

Stokes shift (nA - nF) is important parameters of the fluorescent compounds which indicate the difference in properties and structure between the ground S0 and the first excited state S1 and it has been estimated according to Equation (1):

(1)(vAvF)=(1/λA1/λF)×107

From Table 1 it is seen that the Stokes shift is in a narrow range (between 501 and 726 cm-1) and it depends on the solvents. Larger values were obtained at nonpolar solvents and the results are very typical to this class of compounds [29, 30, 31, 32].

The ability of the photoactive molecules to emit the absorbed light energy is characterized quantitatively by the fluorescence quantum yield FF.. It has been calculated on the basis of the absorption and fluorescence spectra using Rhodamine 6G as a standard according to Equation (2).

(2)ΦF=ΦstSuSstAstAunDu2nDst2

The calculated FF were in the region 0.20-0.68 and its values depend on the polarity and chemical nature of the solvents. In polar solvents the obtained yields are more than three times higher compared to these in non-polar solvents.

3.2 Absorption and fluorescence investigations of coloured cotton fabric

To investigate the antimicrobial activity of compound E, it has been superficially deposited on a cotton fabric, giving it intense red colour and fluorescence. Figure 3 plots the normalized excitation spectrum and fluorescence spectrum having maxima at (l = 526 nm) and (l = 562 nm) respectively. These results show that in solid state compound E has similar absorption wavelength value to these in alcohol solution, probably due to the fact that cotton cellulose molecules are enriched with hydroxyl groups that have a similar behaviour as the alcoholic hydroxyl groups at formation of intermolecular bonds. The fluorescence maximum is bathochromically shifted compared to that in alcohol, which can be explained by the strong fixation of the fluorophore molecule to the textile matrix and hence for the lack of conformational changes in the transition from excited S1 to the ground state S0.

The release of compound E from the surface of cotton fabric has been measured in aqueous solution at pH = 7.2 by absorption and fluorescence spectroscopy in the condition of dropping method for 60 minutes.

Through the contact of coloured cotton fabric with water solvent the hydrophilic dye E is released from the surface cotton matrix to the aqueous solution, which becomes colourful. Figure 4 shows that the absorption and respective fluorescence intensity of compound E increase with time then it reaches a plateau. It is seen that in the beginning the cotton fabric releases a large amounts of E, and accordingly the absorption and fluorescence intensity increase drastically, and with time this effect disappear. This indicates that compound Е leaves the cotton fabric and passes into the aqueous solution. The respective maxima of Е in this solution are lA = 515 nm and lF = 535 nm, matching these in freshly prepared water solution. The observation that there is no change of the absorption and fluorescence maxima positions during the extraction, but only the intensity is increased, give evidence that the dye didn’t undergo any chemical change during the deposition and the release. This is a new important characteristic of coloured cotton fabric, which indicate that E release into the water solution exhibiting a prolonged antimicrobial activity.

Figure 4 Absorption (A) and fluorescence (B) release profile of E from cotton matrix in aqueous solution at pH = 7.2 at 25oC for 60 min.
Figure 4

Absorption (A) and fluorescence (B) release profile of E from cotton matrix in aqueous solution at pH = 7.2 at 25oC for 60 min.

4 Antimicrobial activity

4.1 Growth inhibitory activity in aqueous solution

A quantitative evaluation of the antimicrobial activity of the synthesized compound was carried out by the shaking flask test against two Gram-positive bacteria (B. cereus, S. lutea), three Gram-negative bacteria P. aeruginosa, A. johnsonii, E. coli) and the yeasts C. lipolytica. Figure 5 shows changes in the growth of the strains in presence of different concentrations of E ranging from 0.018 μM to 0.623 μM. As can be seen, the compound E redused the growth of all test cultures with increasingof its concentrations as compared to the negative control.. The relative order of sensitivity to the compound was found to be a function of the strain. The compound exhibited highest antimicrobial efficiency against the test Gram-positive bacterium S. lutea and the yeasts C. lipolytica (MICs at 0.156 μM) followed by Gram-negative bacterium A. johnsonii (MIC at 0.249 μM) and Gram-positive B. cereus (MIC at 0.312 μM). P. aeruginosa and E. coli exhibited highest resistance to the compound E than the other cultures and MICs were not reached up to 0.623 μM.

Figure 5 Growth of the tested model microbial strains in presence of different concentrations of compound E.
Figure 5

Growth of the tested model microbial strains in presence of different concentrations of compound E.

4.2 Antimicrobial activity of modified cotton fabric

The antimicrobial activity of cotton fabric treated with E has been evaluated by the reduction in bacterial growth. Gram-positive B. cereus, Gram-negative A. johnsonii, and the yeasts C. lipolytica were used as model strains. It was found that the treated cotton textile leads to slight reduction of the growth of B. cereus and C. lipolytica by about 14% and 22%, respectively, and no growth reduction of A. johnsonii was observed (Figure 6) In thsi case the slow release of compound E from the cotton matrix into the aqueous medium, and direct contact with matogenic cells contributed to the antimicrobial effect of the modifed cotton fabric.

Figure 6 Effect of cotton fabric treated with compound E on growth development (quantified by OD at 600 nm) of the indicated model microbial strains.
Figure 6

Effect of cotton fabric treated with compound E on growth development (quantified by OD at 600 nm) of the indicated model microbial strains.

5 Effect of light irradiation on bacterial growth

The ability of E to inhibit the growth of model Gram-negative P. aeruginosa strain was assessed after 16 h of incubation in presence and absence of light. The experiments were conducted in planktonic format in solution and applied on cotton fabric. In solution, without illumination, we observed higher density of P. aeruginosa cells compared to the illuminated sample (Figure 7). With light irradiation, the antibacterial effect was significantly higher at concentration of eosin Y 0.25 μM than observed for the 0.125 μM concentration. In the experiments with eosin-treated and non-treated cotton fabrics, about 41% reduction of cell density of P. aeruginosa was established in the absence of illumination, while almost complete growth inhibition was observed in the illuminated sample (Figure 8). Similarly to some findings reported previously [33, 34], it can be assumed that eosin Y produce large amount of singlet oxygen near the outer membrane of bacteria leading to membrane damage. Quaternary ammonium group promotes the binding of eosin Y moiety to the bacterial cell wall thus accelerating bacterial photo-inactivation.

Figure 7 Effect of visible light on planktonic cultures of P. aeruginosa in presence of compound E.
Figure 7

Effect of visible light on planktonic cultures of P. aeruginosa in presence of compound E.

Figure 8 Effect of light irradiation on the antibacterial effect of cotton fabric treated with compound E.
Figure 8

Effect of light irradiation on the antibacterial effect of cotton fabric treated with compound E.

6 Conclusions

The photophysical characteristics of a new eosin Y functionalised with quaternary ammonium biocidal group have been investigated in different media. The results demonstrated than the modified eosin Y exhibits intense fluorescence in solutions which was retained after its deposition on the surface of cotton fabric. The results showed good inhibitory activity of the novel eosin compound E towards the tested microbial cultures. Antimicrobial activity of cotton fabric treated with the new eosin derivative E was investigated against the strains A. johnsonii, B. cereus and C. lipolytica. The results showed that the compound E has released slowly into the aqueous solution and exhibits a prolonged antimicrobial activity. The modified cotton fabric exhibited higher bioactivity against B. cereus and C. lipolytica, suggesting its suitability for application as a new additive in preparation of antibacterial textile fabric. The new compound E can be use for the photodynamic bacterial inactivation.

Acknowledgements

The authors acknowledge Grant № KOST 1/3-2017, Scientific Research Fund, Ministry of Education and Science of Bulgaria

The authors are grateful to Operational programme “Science and Education for Smart Growth”, project BG05M2OP001-2.009-0028.

  1. Conflict of interest: Authors declare no conflict of interest.

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Received: 2018-12-03
Accepted: 2019-05-09
Published Online: 2019-12-31

© 2019 Desislava Staneva et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  42. Complex formation in a liquid-liquid extraction-chromogenic system for vanadium(IV)
  43. Synthesis, characterization (IR, 1H, 13C & 31P NMR), fungicidal, herbicidal and molecular docking evaluation of steroid phosphorus compounds
  44. Analysis and Biological Evaluation of Arisaema Amuremse Maxim Essential Oil
  45. A preliminary assessment of potential ecological risk and soil contamination by heavy metals around a cement factory, western Saudi Arabia
  46. Anti- inflammatory effect of Prunus tomentosa Thunb total flavones in LPS-induced RAW264.7 cells
  47. Collaborative Influence of Elevated CO2 Concentration and High Temperature on Potato Biomass Accumulation and Characteristics
  48. Methods of extraction, physicochemical properties of alginates and their applications in biomedical field – a review
  49. Characteristics of liposomes derived from egg yolk
  50. Preparation of ternary ZnO/Ag/cellulose and its enhanced photocatalytic degradation property on phenol and benzene in VOCs
  51. Influence of Human Serum Albumin Glycation on the Binding Affinities for Natural Flavonoids
  52. Synthesis and antioxidant activity of 2-methylthio-pyrido[3,2-e][1,2,4] triazolo[1,5-a]pyrimidines
  53. Comparative study on the antioxidant activities of ten common flower teas from China
  54. Molecular Properties of Symmetrical Networks Using Topological Polynomials
  55. Synthesis of Co3O4 Nano Aggregates by Co-precipitation Method and its Catalytic and Fuel Additive Applications
  56. Phytochemical analysis, Antioxidant and Antiprotoscolices potential of ethanol extracts of selected plants species against Echinococcus granulosus: In-vitro study
  57. Silver nanoparticles enhanced fluorescence for sensitive determination of fluoroquinolones in water solutions
  58. Simultaneous Quantification of the New Psychoactive Substances 3-FMC, 3-FPM, 4-CEC, and 4-BMC in Human Blood using GC-MS
  59. Biodiesel Production by Lipids From Indonesian strain of Microalgae Chlorella vulgaris
  60. Miscibility studies of polystyrene/polyvinyl chloride blend in presence of organoclay
  61. Antibacterial Activities of Transition Metal complexes of Mesocyclic Amidine 1,4-diazacycloheptane (DACH)
  62. Novel 1,8-Naphthyridine Derivatives: Design, Synthesis and in vitro screening of their cytotoxic activity against MCF7 cell line
  63. Investigation of Stress Corrosion Cracking Behaviour of Mg-Al-Zn Alloys in Different pH Environments by SSRT Method
  64. Various Combinations of Flame Retardants for Poly (vinyl chloride)
  65. Phenolic compounds and biological activities of rye (Secale cereale L.) grains
  66. Oxidative degradation of gentamicin present in water by an electro-Fenton process and biodegradability improvement
  67. Optimizing Suitable Conditions for the Removal of Ammonium Nitrogen by a Microbe Isolated from Chicken Manure
  68. Anti-inflammatory, antipyretic, analgesic, and antioxidant activities of Haloxylon salicornicum aqueous fraction
  69. The anti-corrosion behaviour of Satureja montana L. extract on iron in NaCl solution
  70. Interleukin-4, hemopexin, and lipoprotein-associated phospholipase A2 are significantly increased in patients with unstable carotid plaque
  71. A comparative study of the crystal structures of 2-(4-(2-(4-(3-chlorophenyl)pipera -zinyl)ethyl) benzyl)isoindoline-1,3-dione by synchrotron radiation X-ray powder diffraction and single-crystal X-ray diffraction
  72. Conceptual DFT as a Novel Chemoinformatics Tool for Studying the Chemical Reactivity Properties of the Amatoxin Family of Fungal Peptides
  73. Occurrence of Aflatoxin M1 in Milk-based Mithae samples from Pakistan
  74. Kinetics of Iron Removal From Ti-Extraction Blast Furnace Slag by Chlorination Calcination
  75. Increasing the activity of DNAzyme based on the telomeric sequence: 2’-OMe-RNA and LNA modifications
  76. Exploring the optoelectronic properties of a chromene-appended pyrimidone derivative for photovoltaic applications
  77. Effect of He Qi San on DNA Methylation in Type 2 Diabetes Mellitus Patients with Phlegm-blood Stasis Syndrome
  78. Cyclodextrin potentiometric sensors based on selective recognition sites for procainamide: Comparative and theoretical study
  79. Greener synthesis of dimethyl carbonate from carbon dioxide and methanol using a tunable ionic liquid catalyst
  80. Nonisothermal Cold Crystallization Kinetics of Poly(lactic acid)/Bacterial Poly(hydroxyoctanoate) (PHO)/Talc
  81. Enhanced adsorption of sulfonamide antibiotics in water by modified biochar derived from bagasse
  82. Study on the Mechanism of Shugan Xiaozhi Fang on Cells with Non-alcoholic Fatty Liver Disease
  83. Comparative Effects of Salt and Alkali Stress on Antioxidant System in Cotton (Gossypium Hirsutum L.) Leaves
  84. Optimization of chromatographic systems for analysis of selected psychotropic drugs and their metabolites in serum and saliva by HPLC in order to monitor therapeutic drugs
  85. Electrocatalytic Properties of Ni-Doped BaFe12O19 for Oxygen Evolution in Alkaline Solution
  86. Study on the removal of high contents of ammonium from piggery wastewater by clinoptilolite and the corresponding mechanisms
  87. Phytochemistry and toxicological assessment of Bryonia dioica roots used in north-African alternative medicine
  88. The essential oil composition of selected Hemerocallis cultivars and their biological activity
  89. Mechanical Properties of Carbon Fiber Reinforced Nanocrystalline Nickel Composite Electroforming Deposit
  90. Anti-c-myc efficacy block EGFL7 induced prolactinoma tumorigenesis
  91. Topical Issue on Applications of Mathematics in Chemistry
  92. Zagreb Connection Number Index of Nanotubes and Regular Hexagonal Lattice
  93. The Sanskruti index of trees and unicyclic graphs
  94. Valency-based molecular descriptors of Bakelite network BNmn
  95. Computing Topological Indices for Para-Line Graphs of Anthracene
  96. Zagreb Polynomials and redefined Zagreb indices of Dendrimers and Polyomino Chains
  97. Topological Descriptor of 2-Dimensional Silicon Carbons and Their Applications
  98. Topological invariants for the line graphs of some classes of graphs
  99. Words for maximal Subgroups of Fi24
  100. Generators of Maximal Subgroups of Harada-Norton and some Linear Groups
  101. Special Issue on POKOCHA 2018
  102. Influence of Production Parameters on the Content of Polyphenolic Compounds in Extruded Porridge Enriched with Chokeberry Fruit (Aronia melanocarpa (Michx.) Elliott)
  103. Effects of Supercritical Carbon Dioxide Extraction (SC-CO2) on the content of tiliroside in the extracts from Tilia L. flowers
  104. Impact of xanthan gum addition on phenolic acids composition and selected properties of new gluten-free maize-field bean pasta
  105. Impact of storage temperature and time on Moldavian dragonhead oil – spectroscopic and chemometric analysis
  106. The effect of selected substances on the stability of standard solutions in voltammetric analysis of ascorbic acid in fruit juices
  107. Determination of the content of Pb, Cd, Cu, Zn in dairy products from various regions of Poland
  108. Special Issue on IC3PE 2018 Conference
  109. The Photocatalytic Activity of Zns-TiO2 on a Carbon Fiber Prepared by Chemical Bath Deposition
  110. N-octyl chitosan derivatives as amphiphilic carrier agents for herbicide formulations
  111. Kinetics and Mechanistic Study of Hydrolysis of Adenosine Monophosphate Disodium Salt (AMPNa2) in Acidic and Alkaline Media
  112. Antimalarial Activity of Andrographis Paniculata Ness‘s N-hexane Extract and Its Major Compounds
  113. Special Issue on ABB2018 Conference
  114. Special Issue on ICCESEN 2017
  115. Theoretical Diagnostics of Second and Third-order Hyperpolarizabilities of Several Acid Derivatives
  116. Determination of Gamma Rays Efficiency Against Rhizoctonia solani in Potatoes
  117. Studies On Compatibilization Of Recycled Polyethylene/Thermoplastic Starch Blends By Using Different Compatibilizer
  118. Liquid−Liquid Extraction of Linalool from Methyl Eugenol with 1-Ethyl-3-methylimidazolium Hydrogen Sulfate [EMIM][HSO4] Ionic Liquid
  119. Synthesis of Graphene Oxide Through Ultrasonic Assisted Electrochemical Exfoliation
  120. Special Issue on ISCMP 2018
  121. Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells
  122. The influence of the grafted aryl groups on the solvation properties of the graphyne and graphdiyne - a MD study
  123. Electrochemical modification of platinum and glassy carbon surfaces with pyridine layers and their use as complexing agents for copper (II) ions
  124. Effect of Electrospinning Process on Total Antioxidant Activity of Electrospun Nanofibers Containing Grape Seed Extract
  125. Effect Of Thermal Treatment Of Trepel At Temperature Range 800-1200˚C
  126. Topical Issue on Agriculture
  127. The effect of Cladophora glomerata exudates on the amino acid composition of Cladophora fracta and Rhizoclonium sp.
  128. Influence of the Static Magnetic Field and Algal Extract on the Germination of Soybean Seeds
  129. The use of UV-induced fluorescence for the assessment of homogeneity of granular mixtures
  130. The use of microorganisms as bio-fertilizers in the cultivation of white lupine
  131. Lyophilized apples on flax oil and ethyl esters of flax oil - stability and antioxidant evaluation
  132. Production of phosphorus biofertilizer based on the renewable materials in large laboratory scale
  133. Human health risk assessment of potential toxic elements in paddy soil and rice (Oryza sativa) from Ugbawka fields, Enugu, Nigeria
  134. Recovery of phosphates(V) from wastewaters of different chemical composition
  135. Special Issue on the 4th Green Chemistry 2018
  136. Dead zone for hydrogenation of propylene reaction carried out on commercial catalyst pellets
  137. Improved thermally stable oligoetherols from 6-aminouracil, ethylene carbonate and boric acid
  138. The role of a chemical loop in removal of hazardous contaminants from coke oven wastewater during its treatment
  139. Combating paraben pollution in surface waters with a variety of photocatalyzed systems: Looking for the most efficient technology
  140. Special Issue on Chemistry Today for Tomorrow 2019
  141. Applying Discriminant and Cluster Analyses to Separate Allergenic from Non-allergenic Proteins
  142. Chemometric Expertise Of Clinical Monitoring Data Of Prolactinoma Patients
  143. Chemomertic Risk Assessment of Soil Pollution
  144. New composite sorbent for speciation analysis of soluble chromium in textiles
  145. Photocatalytic activity of NiFe2O4 and Zn0.5Ni0.5Fe2O4 modified by Eu(III) and Tb(III) for decomposition of Malachite Green
  146. Photophysical and antibacterial activity of light-activated quaternary eosin Y
  147. Spectral properties and biological activity of La(III) and Nd(III) Monensinates
  148. Special Issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  149. Soil organic carbon mineralization in relation to microbial dynamics in subtropical red soils dominated by differently sized aggregates
  150. A potential reusable fluorescent aptasensor based on magnetic nanoparticles for ochratoxin A analysis
  151. Special Issue on 13th JCC 2018
  152. Fluorescence study of 5-nitroisatin Schiff base immobilized on SBA-15 for sensing Fe3+
  153. Thermal and Morphology Properties of Cellulose Nanofiber from TEMPO-oxidized Lower part of Empty Fruit Bunches (LEFB)
  154. Encapsulation of Vitamin C in Sesame Liposomes: Computational and Experimental Studies
  155. A comparative study of the utilization of synthetic foaming agent and aluminum powder as pore-forming agents in lightweight geopolymer synthesis
  156. Synthesis of high surface area mesoporous silica SBA-15 by adjusting hydrothermal treatment time and the amount of polyvinyl alcohol
  157. Review of large-pore mesostructured cellular foam (MCF) silica and its applications
  158. Ion Exchange of Benzoate in Ni-Al-Benzoate Layered Double Hydroxide by Amoxicillin
  159. Synthesis And Characterization Of CoMo/Mordenite Catalyst For Hydrotreatment Of Lignin Compound Models
  160. Production of Biodiesel from Nyamplung (Calophyllum inophyllum L.) using Microwave with CaO Catalyst from Eggshell Waste: Optimization of Transesterification Process Parameters
  161. The Study of the Optical Properties of C60 Fullerene in Different Organic Solvents
  162. Composite Material Consisting of HKUST-1 and Indonesian Activated Natural Zeolite and its Application in CO2 Capture
  163. Topical Issue on Environmental Chemistry
  164. Ionic liquids modified cobalt/ZSM-5 as a highly efficient catalyst for enhancing the selectivity towards KA oil in the aerobic oxidation of cyclohexane
  165. Application of Thermal Resistant Gemini Surfactants in Highly Thixotropic Water-in-oil Drilling Fluid System
  166. Screening Study on Rheological Behavior and Phase Transition Point of Polymer-containing Fluids produced under the Oil Freezing Point Temperature
  167. The Chemical Softening Effect and Mechanism of Low Rank Coal Soaked in Alkaline Solution
  168. The Influence Of NO/O2 On The NOx Storage Properties Over A Pt-Ba-Ce/γ-Al2O3 Catalyst
  169. Special Issue on the International conference CosCI 2018
  170. Design of SiO2/TiO2 that Synergistically Increases The Hydrophobicity of Methyltrimethoxysilane Coated Glass
  171. Antidiabetes and Antioxidant agents from Clausena excavata root as medicinal plant of Myanmar
  172. Development of a Gold Immunochromatographic Assay Method Using Candida Biofilm Antigen as a Bioreceptor for Candidiasis in Rats
  173. Special Issue on Applied Biochemistry and Biotechnology 2019
  174. Adsorption of copper ions on Magnolia officinalis residues after solid-phase fermentation with Phanerochaete chrysosporium
  175. Erratum
  176. Erratum to: Sand Dune Characterization For Preparing Metallurgical Grade Silicon
Heruntergeladen am 5.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2019-0135/html?lang=de
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