Startseite Naturwissenschaften Influence of Human Serum Albumin Glycation on the Binding Affinities for Natural Flavonoids
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Influence of Human Serum Albumin Glycation on the Binding Affinities for Natural Flavonoids

  • Liangliang Liu , Yi Liu , Aiping Xiao , Shiyong Mei und Yixi Xie EMAIL logo
Veröffentlicht/Copyright: 2. Oktober 2019

Abstract

Increasing the degree of glycation in diabetes could affect the ability of plasma proteins in binding to small molecules and active compounds. In this study, the influence of glycation of Human serum albumin (HSA) on the binding affinities for six dietary flavonoids was investigated by fluorescence spectra. Glycated HSA was prepared through incubation with glucose and characterized by several methods to confirm the glycation. It was found that the level of glycation increased with the increasing incubation time. The glycation of HSA increased the binding affinities for flavonoids by 1.40 to 48.42 times, which indicates that modifications caused by the glycation may have different influences on the interactions of flavonoids with HSA at separate binding sites on this protein. These results are valuable for understanding the influence of diabetes on the metabolism of flavonoids and other bioactive small molecules in human body.

Graphical Abstract

1 Introduction

Diabetes, which is also known as diabetes mellitus, has become a big challenge in human health all over the world, and the prevalence rate of diabetes is rising quickly in recent years. One of the most typical symptoms of diabetesis the high concentration of glucose in blood. This kind of high level glucose could react with plasma proteins and initiate the Maillard reaction [1]. The Maillard reaction starts with the formation of Schiff base, and then

transformed into early glycation product. After a battery of complex reactions, the intermediate finally become the advanced glycation end products (AGEs) [2, 3]. AGEs are harmful to human body and could induce the crosslinking between key proteins in extracellular matrix, alter cellular structure and interact with receptors to initiate a series of signal transactions leading to inflammatory and oxidative stress [4]. The glycations of proteins and lipids play important roles in diabetic complications like nephropathy, diabetic foot, retinopathy and so on [5]. Besides, the system of AGEs and their receptors has been proven to be closely related to the vascular injury in diabetes [6]. Therefore, more research focused on the glycated proteins is helpful for the treatment of diabetes and related diseases.

Serum albumin is an albumin found in blood and is the most common protein in blood. Serum albumin maintains osmotic pressure, buffers the pH and works as a important carrier to transport many bioactive molecules such as vitamins and fatty acids to tissues and organs [7]. The interactions between serum albumin and small active compounds attracts great interests in related research area since it is closely related to the metabolism, availability and kinetic profile of drugs [8]. As reported by the references, about twenty to thrity percent of human serum albumin (HSA) in the body of diabetes patients was glycated. However, the level of glycated HSA is only six to thirteen percent in the body of healthy persons [9], which becomes one of the characteristics for diabetes patients.

As active compounds widely distributed in foods, dietary flavonoids have shown inhibitory effects on formation of AGEs [10, 11, 12]. Moreover, they are identified as inhibitors of many human digestive enzymes, which makes them drug candidates for diabetes mellitus [13]. As small molecules, the biological effects of flavonoids depend on their binding behaviors to plasma proteins [14]. The purified HSA, bovine serum albumin, hemoglobin and other commercially acquired proteins are widely used as models to investigate the interaction between proteins and flavonoids [15, 16]. However, the reports on the non-covalent interaction between flavonoids and glycated

HSA are few. The mechanism of how glucose affects the binding properties of dietary flavonoids for plasma proteins like HSA is still not clear.

Fluorescence spectroscopy is a typical and appropriate method to investigate the interaction between small molecules like dietary flavonoids and biological macromolecules [17]. HSA molecule contains tryptophan and tyrosine residues which give out intrinsic fluorescence under the excitation light at 280 nm. Through measuring the intensity of emission peak and observing its possible shift, the information about structural fluctuations and micro-environmental alterations of the molecule could be gained. In this study, the glycation of HSA was characterized and the effects of glycated HSA on the affinities for the interaction with dietary flavonoids (Figure 1) were studied by fluorescence spectra.

Figure 1 The studied chemical structures of dietary flavonoids.
Figure 1

The studied chemical structures of dietary flavonoids.

2 Materials and Methods

2.1 Chemicals and apparatus

Human serum albumin (HSA, 96-99%) and 1-deoxy-1-morpholino fructose were bought from Sigma-Aldrich (MO, USA). Nitrotetrazolium blue chloride (NBT) was obtained commercially from Sinopharm Chemical Reagent Co., Ltd (Beijing, China). Apigenin and luteolin (99.0%) were purchased from Aladdin Co. Ltd. (Shanghai, China). Galangin, kaempferol, quercetin and myricetin (99.5%) were bought from Shanghai Tauto Biotech Co., Ltd (Shanghai, China). The working solutions of flavonoids (1.0×10-3 mol/L) were prepared by dissolving each flavonoid with methanol. All other reagents and solvents were analytical grade and used without further purification.

2.2 Glycation of HSA

Glycation of HSA was carried out by incubating HSA (1.0×10-5 mol/L) with glucose (5.0×10-2 mol/L) containing 0.02% (w/v) NaN3 for 20 days at 37°C. As a control group, HSA was incubated with double-distilled water instead of glucose for 20 days at 37°C.

2.3 Analysis of HSA glycation products

The glycation products were quantified by measuring the contents of fructosamine residues as described by Johnson et al. with slight modification [18]. 1-deoxy-1-morpholino fructose at concentrations between 0 and 1.0 mmol/L containing 1.0×10-5 mol/L HSA was used for calibration. The ultraviolet (UV) spectra of HSA incubated with glucose were recorded on a Nano Drop 2000 spectrophotometer (Thermo Fisher Scientific, Wilmington, USA) from 250 nm to 800 nm and the absorbances at 330 nm, 360 nm and 400 nm were monitored. The fluorescence emission spectra of glycated HSA were recorded from 400 to 650 nm using a fluorometer (Hitachi F-7000, Tokyo, Japan) with the excitation wavelength at 375 nm.

2.4 Fluorescence spectra

3.0 mL working solution of HSA or glycated HSA were poured into a 1.0 cm quartz cell. And then, a series amounts of flavonoid solution (1.0×10-3 mol/L) was titrated by using trace syringes. When HSA or glycated HSA samples were titrated with different amounts of flavonoids, the fluorescence spectrum of mixture was recorded from 295nm to 420 nm using a fluorometer (Hitachi F-7000, Tokyo, Japan) upon excitation wavelength at 280 nm. The fluorescence quenchings of HSA and glycated HSA with samples were calculated by Stern-Volmer formula shown as follow [19]:

(1)F0/F=1+Kqτ0[Q]=1+Ksv[Q]

Where F0 represents the fluorescence intensities of protein, F represents the fluorescence intensities of protein in the presence of flavonoid. [Q] represents the concentration of flavonoid. Kq is the quenching rate constant, τ0 is the average lifetime (6.2 ns), and Ksv is the Stern-Volmer quenching constant. The binding constants were calculated according to the double-logarithm equation shown as follow [19]:

(2)Log(F0-F)/F=logKa+nlog[Q]

Where Ka is the binding constant, and n is the number of binding sites per HSA molecule. The fluorescence spectra of studied flavonoids were not observed in the same condition and the flavonoids were stable during fluorescence measurements. Each determination was repeated three times and reproducible within experimental errors.

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

3 Results and Discussion

3.1 Characterization of HSA glycation

The generated glycation products during the glycation of proteins are fluorescent and could be used as indicators for the evaluation of glycation degree [20]. As shown in in Figure 2, after the incubation with glucose, the fluorescence spectra of HSA showed a characteristic peak at 465 nm. The fluorescence intensities of glycated HSA increased with the increasing incubation time, indicating the modification process of HSA induced by

Figure 2 The fluorescence spectra of HSA incubated with glucose for different periods.
Figure 2

The fluorescence spectra of HSA incubated with glucose for different periods.

glucose. Schmitt and coworkers investigated the reaction of HSA with glucose and found that glucose modified HSA exhibited the maximum fluorescence intensity at 440 nm [21]. The colorimetric determination of frucotosamine residues was also utilized to further evaluate the glycation level of HSA considering some glycation products of HSA are non-fluorescent [22]. As shown in Table 1, no frucotosamine residues was detected in HSA solution at the beginning. However, frucotosamine residues showed up and accumulated as time went on. After 20 days incubation, the content of fructosamine residues was up to 31.3 μmol/L, which was more than three times that in 5 days incubation.

Table 1

The results of UV measurements and fructosamine contents of HSA incubated with glucose.

TimeAbsorbanceFructosamine residues *
330 nm360 nm400 nm
0 day0.0020.0080.001-
5 day0.0520.0280.0119.36
14 day0.1760.0820.03120.8
20 day0.3690.1840.06431.3
  1. * Represented by the equivalent content of 1-deoxy-1-morpholino fructose (1×10-6 mol/L)

Because the chromophores in proteins would be modified during the glycation of HSA, the influence of glycation on the UV spectra of HSA was investigated. The UV adsorptions of HSA at 330 nm, 360 nm and 400 nm spectra are summarized in Table 1. Like the increasing of fluorescence intensities, the increased incubation periods led to enhancing absorbance at specified wavelength, which indicated that more structural modifications occurred. Hence, through fluorescence spectra, UV spectra and colorimetric determination, the glycation of HSA was confirmed and increased over time.

3.2 Fluorescence quenching of HSA

The fluorescence of HSA under the excitation at 280 nm was mainly caused by tryptophan residues (Trp214) which were part of subdomain IIA. HSA can bind various ligands in Subdomain IIA in its hydrophobic cavity [23]. When small molecules such as flavonoids are bound to HSA, the microenvironment of Trp214 was affected and its fluorescence was consequently quenched. Compared with HSA, the fluorescence spectra of glycated HSA showed a loss of intensity, which might be due to that the local environment of Trp214 on HSA molecule was perturbed during glycation [24].

Glycated HSA was prepared according to the mentioned method and used after 20 days incubation with glucose. The fluorescence quenchings of six flavonoids on HSA and glycated HSA were investigated. As an example shown in Figure 3, the fluorescence quenching effect of apigenin was shown. When apigenin was continuously added into HSA and glycated HSA solution, the increasing attenuation in the fluorescence intensities could be observed in Figure 3A and 3B. In addition, similar extents of blue-shifts for the maximum emission of HSA and glycated HSA induced by addition of apigenin were observed as well. The quenching ratios of the HSA fluorescence with addition of apigenin were also shown in insets of Figure 3. The fluorescence intensities of both HSA and glycated HSA were found to decline rapidly in the presence of apigenin. It illustrates that after incubated with glucose, the fluorescence quenching properties of HSA were changed to certain degree.

Figure 3 The quenching effect of apigenin on fluorescence spectra of HSA (A) and glycated HSA (B). λex =280 nm; HSA, 1.00 × 10-5 mol/L; a-i: 0.00, 1.00, 2.00 .... 8.00 (× 10-6 mol/L) of apigenin. Inset: The Stern-Volmer plots for HSA (A) and glycated HSA (B) fluorescence quenching by apigenin.
Figure 3

The quenching effect of apigenin on fluorescence spectra of HSA (A) and glycated HSA (B). λex =280 nm; HSA, 1.00 × 10-5 mol/L; a-i: 0.00, 1.00, 2.00 .... 8.00 (× 10-6 mol/L) of apigenin. Inset: The Stern-Volmer plots for HSA (A) and glycated HSA (B) fluorescence quenching by apigenin.

3.3 The binding constants (Ka) and the number of binding sites (n)

The binding processes of six flavonoids with HSA and glycated HSA were tested, and the binding constants (logKa and n) were summarized in Table 2. As shown in the table, all the logKa values of flavonoids for HSA were in the range of 1×106 to 1×108 L/mol, which were in agreement with the reported data [25, 26]. The relationship between logKa and n for HSA and glycated HSA were calculated and shown in Figure 4. The linear regression equations for HSA and glycated HSA were shown as follow:

Figure 4 The relationship between the affinities (logKa) and the number of binding sites (n) for HSA and glycated HSA.
Figure 4

The relationship between the affinities (logKa) and the number of binding sites (n) for HSA and glycated HSA.

Table 2

The affinities (logKa), the number of binding sites (n) and corresponding fitting degrees of flavonoids for HSA and glycated HSA.

0 day5 days
FlavonoidsHSAGlycated HSAHSAGlycated HSA
logKanR2logKanR2logKanR2logKanR2
Apigenin6.7601.3000.9856.7621.3020.9817.0351.3260.9888.0661.5210.985
Luteolin6.6801.2710.9926.8001.2930.9857.1831.3480.9897.4501.3870.989
Galangin6.9481.3180.9887.3731.3890.9827.5321.4150.9957.6791.4360.992
Kaempferol7.2891.3410.9918.3131.5230.9987.5361.3220.9918.1721.4340.992
Quercetin6.6681.2910.9936.9861.3390.9926.7091.2540.9838.0571.4940.990
Myricetin6.5131.2420.9906.8461.3060.9907.1661.3390.9957.3901.3690.997
14 days20 days
FlavonoidsHSAGlycated HSAHSAGlycated HSA
logKanR2logKanR2logKanR2logKanR2
Apigenin6.6891.2890.9986.9701.330.9966.3801.210.9896.9161.3110.996
Luteolin6.5331.2430.9826.9811.3280.9956.6701.2450.9887.5141.3980.988
Galangin6.5661.2630.9886.9331.3270.9946.4341.2450.9877.2731.3760.986
Kaempferol6.8141.3170.9856.5301.2540.9946.8691.3070.9977.3441.3880.995
Quercetin6.5121.2310.9976.7971.2680.9896.5741.2570.9948.2591.5650.997
Myricetin6.4701.2650.9956.2601.2120.9885.9871.1970.9916.9091.3960.990

For HSA, n = 0.44144 + 0.12455 logKa (R2=0.91238).

For glycated HSA, n = 0.28808 + 0.14912 logKa (R2=0.95371).

The values of number of binding sites (n) are proportional to logKa. The linear relationship between these two parameters showed the equation used in this calculation is suitable. However, the linear relationships of n-logKa for HSA and glycated HSA were different.

3.4 Effect of glycation on the affinities of flavonoids for HSA

It was found that the binding constants of Glycated HSA-flavonoid interaction were clearly higher than that of normal HSA (Table 2). The magnitudes of binding constants in HSA-flavonoid interaction after incubation with glucose from 0 to 20 days were mainly in the range of 107-108 L/mol, which was significantly greater than the corresponding data in the absence of glucose (106-107 L/mol) and also higher than the in vivo tested affinities between drugs and common serum albumins (104-106 L/mol) [25]. While, the values of logKa for these flavonoids were similar to that in reports [24]. Therefore, the increase of logKa for these interactions is worth attention. These results indicate that the modifications of HSA induced by glycation might affect the interactions between flavonoids and HSA at separate binding sites.

As shown in Figure 5, in most case, the binding affinities for HSA incubated with glucose for 5 or 20 days increased by 1.40 to 48.42 times depending on their structures. The affinities (Ka values) of quercetin and apigenin for glycated HSA were apparently increased.

Figure 5 The effect of HSA glycation on the improvement of affinities for flavonoids.
Figure 5

The effect of HSA glycation on the improvement of affinities for flavonoids.

However, the affinities of other flavonoids for glycated HSA were slightly changed. The higher affinities between flavonoids and glycated HSA might be caused by the non-enzymatic process of HSA [27]. With the increasing affinity for glycated HSA, the number of hydroxy groups in structure increased as well (quercetin, 5 -OH; myricetin, 5 -OH; luteolin, 4 -OH; galangin, 3 -OH; apigenin, 3 -OH; kaempferol, 3 -OH). It could be assumed that the affinity for glycated HSA enhanced with the increasing hydroxy groups in flavonoids and the hydrogen bonding might play a crucial part in the interaction between glycated HSA and flavonoids. However, more specific and deeper research needs to be done in future.

The modifications at two binding sites and different levels of glycation of HSA were found to change the glycation pattern of HSA. It also suggested that various kinds of modified forms for HSA may be found at different stages of diabetes [28]. As Joseph et al., reported the binding constants of warfarin for glycated HSA changed little, while the binding affinities for L-tryptophan with glycated HSA increased with a 4.7-5.8 fold [29]. It was also found tolbutamide was bound to both of two Sudlow sites on the glycated HSA and the constants increased by 1.1-1.4 fold [29]. In our case, increasing of binding constants induced by glycation was even more significant (48-fold at maximum) depending on the kinds of flavonoids and the level of glycation of HSA. The results here showed the significant changes of the interactions between flavonoids and HSA induced by glycation of HSA, which might be valuable in further understanding the influence of diabetes on the metabolism of flavonoids and other bioactive small molecules in human body.

4 Conclusions

The effects of HSA and glycated HSA on the binding affinities for dietary flavonoids was investigated by fluorescence spectra. The formation of AGEs was confirmed by observing the increased fluorescence intensity of glycation products during increasing incubation time. And fructosamine residues were accumulated up to 31.3 μmol/L after 20 days’ incubation. UV spectra also revealed that the structural modifications of HSA by glucose were going up with time. The glycation was found to increase the binding affinities of HSA for flavonoids by 1.40 to 48.42 times contingent on the flavonoid’s structures and the glycation level of HSA. These findings showed the changes in interaction between glycated HSA and flavonoids might be valuable in further understanding the influence of diabetes on the metabolism of flavonoids and other bioactive small molecules in human body.

Acknowledgments

This work was financially supported by the Natural Science Foundation of Hunan Province (2017JJ3303 and 2017JJ3348) and the Central Public-interest Scientific Institution Basal Research Fund (No. Y2019PT22-02).

  1. Conflict of Interest

    Conflicts of Interest: The authors declare no conflict of interest.

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Received: 2018-10-19
Accepted: 2019-02-17
Published Online: 2019-10-02

© 2019 Liangliang Liu et al., published by De Gruyter

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

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  34. Correlation of Water Fluoride with Body Fluids, Dental Fluorosis and FT4, FT3 –TSH Disruption among Children in an Endemic Fluorosis area in Pakistan
  35. A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  36. Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol
  37. Effects of Blue and Red Light On Growth And Nitrate Metabolism In Pakchoi
  38. miRNA-199a-5p functions as a tumor suppressor in prolactinomas
  39. Solar photodegradation of carbamazepine from aqueous solutions using a compound parabolic concentrator equipped with a sun tracking system
  40. Influence of sub-inhibitory concentration of selected plant essential oils on the physical and biochemical properties of Pseudomonas orientalis
  41. Preparation and spectroscopic studies of Fe(II), Ru(II), Pd(II) and Zn(II) complexes of Schiff base containing terephthalaldehyde and their transfer hydrogenation and Suzuki-Miyaura coupling reaction
  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 4.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2019-0079/html
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