Startseite Encapsulation of Vitamin C in Sesame Liposomes: Computational and Experimental Studies
Artikel Open Access

Encapsulation of Vitamin C in Sesame Liposomes: Computational and Experimental Studies

  • Dwi Hudiyanti EMAIL logo , Noor Ichsan Hamidi , Daru Seto Bagus Anugrah , Siti Nur Milatus Salimah und Parsaoran Siahaan
Veröffentlicht/Copyright: 24. August 2019

Abstract

An experimental and computational study was carried out for encapsulation of vitamin C in sesame, Sesamum indicum L., liposomes. Based on computational studies, the packing parameter (P) of sesame phospholipids was found to be 0.64 ± 0.09. This indicates that the molecular shape of sesame phospholipids is in the form of truncated cone and, in aqueous solution, it self-assembles to form liposomes. In the liposomes, no chemical interaction was observed between phospholipid molecules and vitamin C. However, medium-strength hydrogen bonds (Ei) from -87.6 kJ/mol to -82.02 kJ/mol with bond lengths ranging from 1.746 Å to 1.827 Å were formed between vitamin C and phospholipid molecules. Because of this weak interaction, vitamin C gets released easily from the inner regions of liposome. Empirical experiments were performed to confirm the computation outcomes, where sesame liposomes were found to encapsulate almost 80% of vitamin C in their interior cavities. During the 8 days storage, release of vitamin C occurred gradually from the liposome system, which signifies week interactions in the liposome membranes amongst phospholipid molecules and vitamin C.

1 Introduction

Hudiyanti et al. are currently investigating natural liposomes as drug delivery systems [1, 2, 3]. Liposomes are made up of phospholipid molecules [4], which are amphiphilic in nature and, in aqueous solution, these instantly form bilayer membranes. Self-assembly of the membrane into liposomes occurs, which are then employed in drug delivery systems [5]. Hudiyanti et al. employed liposomes from sesame phospholipid for encapsulating vitamin C [6]. Vitamin C is a vital nutrient used in many human functions. Unfortunately, vitamin C cannot be synthesised by human, and needs to be taken as supplement from other sources. Also, human systems are not designed to store vitamin C. When the metabolism ends, it is immediately excreted. Vitamin C also gets oxidised easily [7,8]. Previous studies have reported 88% encapsulation of vitamin C in sesame liposomes [2]. Thus, employing liposomes for encapsulation will give ideal solution for vitamin C.

Liposomes are made up of phospholipid molecules. The success of sesame liposomes as a carrier for vitamin C is based on the interaction between vitamin C and phospholipid molecules. The energy interaction profile pertaining to phospholipids self-assembly in the production of liposomes was revealed with the study of dynamic interaction amongst different phospholipid species. Assembly of liposomes occurs at energy levels of −25.900 to 26.900 kcal/mol based on the acyl chains and the head group types [9].

This research study is aimed at evaluating self-assembled sesame, Sesamum indicum L., phospholipid species as well as the interaction occurring between vitamin C and phospholipid molecules. Studies were performed based on computation and wet experiments. The parameter packing concept of molecules [10] was applied to predict self-assembled shape, which revealed that aggregation of sesame phospholipids occurs to assemble into liposomes. Based on the interaction energy calculation, a weak interaction between sesame phospholipids and vitamin C was found. These were an intermolecular interaction and not chemical interaction. The encapsulation data showed that vitamin C was encapsulated by sesame liposomes with a high efficiency. Moreover, during storage, some vitamin C is released by the liposomes into the liposomes medium. Based on this data, no bond formation was found to exist between phospholipid molecules and vitamin C in liposomes. Vitamin C gets released from liposomes due to weak interaction between sesame phospholipids and vitamin C. For encapsulation of vitamin C, sesame liposomes were found to be optimum.

2 Research Methods

In this research work, in-house isolation of sesame phospholipids was done with the head groups consisting of serine, choline and ethanolamine; the acyl chain were C12:0, C16:0, C18:0, C18:1, and C18:2 [2,3].

2.1 Prediction of phospholipids self-assembled

As mentioned above, combining of the head and tail groups of sesame phospholipids was done to forecast self-assembly by the Marvin Sketch program. Through the packing parameter concept, prediction study of self-assembled shape was done [11]. Packing parameters (Figure 1) would describe amphiphilic molecules’ aggregate structure in aqueous solution in terms of molecular geometry, i.e. the head group’s cross-sectional area (a), optimum chain length (Iopt) and hydrocarbon chain volume (V). Packing parameter (P) defines the relation between these geometry parameters, given as:

Figure 1 Packing parameters of phospholipid molecules.
Figure 1

Packing parameters of phospholipid molecules.

(1)P=Va.Iopt.........

2.2 Intermolecular interaction between vitamin C and phospholipids

The computation method was employed to analyse the interactions between sesame phospholipids and vitamin C [12]. Calculation of interaction energy was done for vitamin C and phospholipid molecule C4:0 (vitC∙∙∙phospho4) and phospholipid molecule C20:0 (vitC∙∙∙phospho20). An energy difference could be seen between the molecular association energy for each molecule, phospholipids and vitamin C. This formed the energy pertaining to the most stable interaction amongst stable structures. The interaction energy (Ei) comprises the molecular energy of vitamin C (EvitC), the energy of association molecules (EvitC∙∙∙phospho) and the molecular energy of phospholipid (Ephospho).

(2)Ei=EvitcphosphoEvitc+Ephospho.......

As presented in equation 2, phospholipid’s (Ephopsho) molecular energy was regarded the molecular energy of phospholipid C20:0 (Ephospho20) or phospholipid C4:0 (Ephospho4).

2.3 Preparation of sesame liposomes

The method of Hudiyanti et al. was employed to isolate sesame phospholipid from sesame seeds [13]. The liposomes preparation followed the method of Hudiyanti et al. [2], which included thin layer formation, ultrasonication and hydration in PBS buffer solution. Into chloroform, phospholipid was dissolved in the thin layer formation stage. The solution was kept inside a reaction tube with nitrogen passing above it, which helped in the formation of a thin layer. In the hydration stage, addition of vitamin C to the PBS buffer solution in the tube was done (Cinitial), which had the thin layer. Post this, the freeze thawing sequence was performed, involving cooling (at −5°C), heating (at 50°C) and employing a vortex mixer for stirring. In each sequence, these steps were performed for 5 minutes. Repetition of freeze thawing was done until dissolution of the thin layer completely. During the sonication stage, the solution was placed in an ultrasonic bath for almost 1.5 hours.

The encapsulation efficiency (EE) was employed to determine the ability of liposomes to encapsulate vitamin C. In the liposome medium, the free vitamin C concentration was measured to determine EE pertaining to sesame liposomes. Centrifugation of the liposomes solution was done at 6,000 rpm for 30 minutes to segregate the liposomes from the medium viz. supernatants. A UV-Visible spectrophotometer at 265 nm wavelength was employed to analyse supernatant for determining un-encapsulated vitamin C concentration (Cfree). Then, EE was calculated by the following equation 3:

(3)%EE=CinitialCfreeCinitialx100..........

The solution was stored for 8 days in low temperatures (5˚C) to determine if there is leakage of sesame liposomes. Centrifugation was carried out for the dispersion, and then analysis of the supernatant is performed for each day. The increment in vitamin C concentration signified the leakage in the liposomes medium.

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

3 Result and Discussion

This research was aimed at studying encapsulation of vitamin C in sesame liposomes. Computational and empirical experiments were performed for the studies. The computation allowed calculating possibilities that may occur during encapsulation when mixing sesame phospholipids and vitamin C, while empirical data was provided via the experiment.

3.1 Prediction of sesame phospholipid self-assembled

The packing parameters (P) employing the Marvin Sketch program were computed for predictions of self-assembled sesame phospholipid. A description regarding the molecule shape of phospholipid and self-assembled stable bilayer is provided by packing parameters [10]. Volume of the hydrocarbon chain (V), cross-sectional area of the head group (a) as well as the optimum chain length (Iopt) pertaining to every head and tail groups for each of sesame phospholipid molecular types were calculated for packing parameters. For each combination of tail and head groups, these parameters were integrated in equation 1.

Based on the results (Table 1), the highest value of 0.85 was achieved for packing parameters pertaining to (C18:1/C18:1) the phosphatidyletanolamine molecule, while the lowest value of 0.50 was achieved on (C16:0/C16:0) the phosphatidylcholine molecule. On average, packing parameter (P) of 0.64 ± 0.09 was associated with sesame phospholipids, which was in the range ½ < P <1. Theoretically, this value indicates truncated cone shape of sesame phospholipids [14]. Therefore, when sesame phospholipids were kept in solution, they self-assembled into liposomes (Figure 2).

Figure 2 Self-assembled prediction of phospholipid molecules.
Figure 2

Self-assembled prediction of phospholipid molecules.

Table 1

Packing parameter (P) determination of sesame phospholipids.

1st tail group2nd tail groupPhospholipid molecular typelR1 (Å)lR2 (Å)VR13)VR23)V3)lopt (Å)a2)P
1palmitic acidoleic acidphosphatidyl-23.2119.84292.93320.17613.1023.2137.880.70
(C16:0)linoleic acidethanolamine23.2121.11292.93311.63604.5623.2137.880.69
palmitic acid23.2123.21292.93292.93585.8623.2137.880.67
oleic acidphosphatidyl-23.2119.84292.93320.17613.1023.2149.700.53
linoleic acidcholine23.2121.11292.93311.63604.5623.2149.700.52
palmitic acid23.2123.21292.93292.93585.8623.2149.700.50
oleic acidphosphatidyl-23.2119.84292.93320.17613.1023.2144.850.59
linoleic acidserine23.2121.11292.93311.63604.5623.2144.850.58
palmitic acid23.2123.21292.93292.93585.8623.2144.850.56
2oleic acidpalmitic acidphosphatidyl-19.8423.21320.17292.93613.1023.2137.880.70
(C18:1)linoleic acidethanolamine19.8421.11320.17311.63631.8021.1137.880.79
oleic acid19.8419.84320.17320.17640.3419.8437.880.85
palmitic acidphosphatidyl-19.8423.21320.17292.93613.1023.2149.700.53
linoleic acidcholine19.8421.11320.17311.63631.8021.1149.700.60
oleic acid19.8419.84320.17320.17640.3419.8449.700.65
palmitic acidphosphatidyl-19.8423.21320.17292.93613.1023.2144.850.59
linoleic acidserine19.8421.11320.17311.63631.8021.1144.850.67
oleic acid19.8419.84320.17320.17640.3419.8444.850.72
3linoleic acidpalmitic acidphosphatidyl-21.1123.21311.63292.93604.5623.2137.880.69
(C18:2)oleic acidethanolamine21.1119.84311.63320.17631.8021.1137.880.79
linoleic acid21.1121.11311.63311.63623.2621.1137.880.78
palmitic acidphosphatidyl-21.1123.21311.63292.93604.5623.2149.700.52
oleic acidcholine21.1119.84311.63320.17631.8021.1149.700.60
linoleic acid21.1121.11311.63311.63623.2621.1149.700.59
palmitic acidphosphatidyl-21.1123.21311.63292.93604.5623.2144.850.58
oleic acidserine21.1119.84311.63320.17631.8021.1144.850.67
linoleic acid21.1121.11311.63311.63623.2621.1144.850.66

3.2 Intermolecular interaction between vitamin C and phospholipids

NWChem programs were employed to analyse the interactions between phospholipids and vitamin C. The program allows optimising the geometry position as well as calculating the interaction energy [15]. Calculation of interactions was done between vitamin C (vitC) along with two different types of phospholipids: C20:0/C20:0 phosphatidylcholine (phospo20) and C4:0/C4:0 phosphatidylcholine (phospo4). Different lengths of the tail groups were considered to determine its effect on interaction.

The formation of hydrogen bonds between vitamin C and the head groups shows two interactions between phospholipid molecules and vitamin C as demonstrated in figure 3a (vitC∙∙∙phospho4) and figure 3b (vitC∙∙∙phosp20). For vitC∙∙∙phospho4 O60∙∙∙H24 and H73∙∙∙O23, the interactions occur with Ei= -87.6 kJ/mol. In vitC∙∙∙phospho20 O156∙∙∙H24 and H169∙∙∙O23, the interactions occur with Ei= -82.02 kJ/mol. In both vitC∙∙∙phospho4 and vitC∙∙∙phospho20, the lengths of hydrogen bonds (R) were changed. In vitC∙∙∙phospho4, 1.746 Å (RO60∙∙∙H24) and 1.819 Å (RH73∙∙∙O23) were the bond lengths; whereas 1.753 Å (RO156∙∙∙H24) and 1.827 Å (RH169∙∙∙O23) were the bond lengths in vitC∙∙∙phospho20.

Figure 3 Intermolecular interaction between vitamin C and phospholipid molecules.
Figure 3

Intermolecular interaction between vitamin C and phospholipid molecules.

Based on energy (Ei) and bond length data, vitamin C was seen to interact stronger with short acyl chain (C4:0) than long acyl chain (C20:0) phospholipids. Based on the data, both interactions were found to occur with medium strength of hydrogen bond [16]. Also, information was provided confirming that in the self-assembled process, no chemical interaction occurred between vitamin C and phospholipid molecules. These conditions favour easy release of vitamin C from liposomes cavity.

Based on the following discussion, the empirical experiments were seen to support the computation results or vice versa. The computation data were confirmed based on the leakage data and encapsulation efficiency. The encapsulation ability of sesame liposomes is determined by encapsulation efficiency to entrap vitamin C, while the ease of vitamin C release from liposomes cavity is confirmed with the leakage data on storing for 8 days.

3.3 Encapsulation efficiency (EE) of vitamin C

Vitamin C concentration was analysed by constructing a standard vitamin C curve (Figure 4).

Figure 4 Standard curve for vitamin C.
Figure 4

Standard curve for vitamin C.

Encapsulation parameters associated with sesame liposomes are presented in Table 2. The data were found to be in line with the computation results that showed sesame phospholipids formed liposomes when immersed in solution. 80% of vitamin C was found to be encapsulated by the liposome of the total added vitamin C. Based on the EE value and the computation results, sesame liposomes have demonstrated valuable potency as encapsulation materials, particularly for hydrophilic substances like vitamin C versus EE values for soybean and coconut [6].

Table 2

Encapsulation parameter in sesame liposomes.

ParameterValue
Cinitial94.67 ppm
Cfree18.93 ppm
EE80%

3.4 Leakage of sesame liposomes

On spontaneous exiting of encapsulated vitamin C via the liposome membrane because of membrane permeability, a leakage occurs [3]. With the leakage, in the liposome medium (Cfree), the concentration of vitamin C was seen to escalate as observed in 8 days storage period. Figure 4 displays leakage occurring for vitamin C to the liposome medium during 8 days. A concentration gradient is formed in the outer region should vitamin C get encapsulated inside liposomes. Moreover, the bilayer membrane formed by sesame phospholipids appears to be tenuous, since oleic and linoleic fatty acids dominate the sesame phospholipid acyl groups [2,13]. These long fatty acid chains include an unsaturated bond that aids in the formation of a mobile bilayer [17]. To adjust the concentration differences, the spontaneous stream pertaining to vitamin C is driven by both conditions from the inner portion of liposomes to the medium [18,19]. This process induces increasing of vitamin C concentration in the medium as presented in figure 5. The vitamin C leakage to the liposome medium was in line with the computation results. Based on the computational results, only intermolecular interactions were found to exist between sesame phospholipids and vitamin C in the form of hydrogen bonds. Based on the concentration gradient, intermolecular interaction and a mobile bilayer, it was concluded that the release of vitamin C from the liposomes occurred with ease. Also, there was a possibility that the cavities formed in the liposome membrane because of the double bond could have a role in facilitating the release of vitamin C from the liposome system.

Figure 5 Leakage of vitamin C to the liposome medium in 8 days.
Figure 5

Leakage of vitamin C to the liposome medium in 8 days.

4 Conclusion

Based on the computation study, sesame phospholipids were found to be in a truncated cone shape, which in an aqueous solution would form liposomes. The molecules in the liposome system experienced interactions due to cooperative hydrogen bonds that had energy (Ei) ranging from −87.6 kJ/mol to −82.02 kJ/mol, and bond length ranging from 1.746 Å–1.827 Å. Based on the experimental studies, sesame liposomes were found to encapsulate vitamin C with 80% encapsulation efficiency (EE). During 8 days storage, an easy release of vitamin C from sesame liposomes occurred, as confirmed with the increase in vitamin C concentration in the liposome medium. Based on experimental and computational studies, the presence of intermolecular interaction between vitamin C as well as phospholipid molecules in liposomes was confirmed, signifying that vitamin C could be easily released from liposomes.

Acknowledgement

This research was supported (in part) by the Diponegoro University PNBP Fundamental Research scheme 2014.

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

References

[1] Hudiyanti D., Raharjo T.J., Narsito, Noegrohati S., Investigation on the morphology and properties of aggregate structures of natural phospholipids in aqueous system using cryo-tem, Indones J Chem., 2012, 12, 54–61.10.22146/ijc.21372Suche in Google Scholar

[2] Hudiyanti D., Fawrin H., Siahaan P., Simultant encapsulation of vitamin C and beta-carotene in sesame (Sesamum indicum L.) liposomes, IOP Conf. Ser. Mater. Sci. Eng., 2018, 349, 012014.10.1088/1757-899X/349/1/012014Suche in Google Scholar

[3] Hudiyanti D., Raharjo T., Narsito N., Noegrohati S., Study on Leakage of Sesame (Sesamum indicum L.) and Coconut (Cocos nucifera L.) Liposomes, Orient J Chem, 2015, 31, 435–9.10.13005/ojc/310152Suche in Google Scholar

[4] Pattni B.S., Chupin V.V., Torchilin V.P., New Developments in Liposomal Drug Delivery, Chem Rev, 2015, 115, 10938–66.10.1021/acs.chemrev.5b00046Suche in Google Scholar PubMed

[5] Bulbake U., Doppalapudi S., Kommineni N., Khan W., Liposomal Formulations in Clinical Use: An Updated Review, Pharmaceutics, 2017, 9, 12.10.3390/pharmaceutics9020012Suche in Google Scholar PubMed PubMed Central

[6] Hudiyanti D., Triana D., Siahaan P., Studi Pendahuluan tentang Enkapsulasi Vitamin C dalam Liposom Kelapa (Cocos nucifera L.), J Kim Sains Dan Apl, 2017, 20, 5, (in Bahasa Indonesia).10.14710/jksa.20.1.5-8Suche in Google Scholar

[7] Tu Y-J., Njus D., Schlegel H.B., A theoretical study of ascorbic acid oxidation and HOO ˙/ O 2 ˙ radical scavenging, Org Biomol Chem, 2017, 15, 4417–31.10.1039/C7OB00791DSuche in Google Scholar PubMed

[8] Abbas S., Da Wei C., Hayat K., Xiaoming Z., Ascorbic Acid: Microencapsulation Techniques and Trends—A Review, Food Rev Int, 2012, 28, 343–74.10.1080/87559129.2011.635390Suche in Google Scholar

[9] Hudiyanti D., Radifar M., Raharjo T.J., Narsito N., Noegrohati S., A coarse-grained molecular dynamics simulation using NAMD package to reveal aggregation profile of phospholipids self-assembly in water, J Chem, 2014, 2014, 1-6.10.1155/2014/273084Suche in Google Scholar

[10] Tresset G., The multiple faces of self-assembled lipidic systems, PMC Biophys, 2009, 2, 3.10.1186/1757-5036-2-3Suche in Google Scholar PubMed PubMed Central

[11] Frolov V.A., Shnyrova A.V., Zimmerberg J., Lipid polymorphisms and membrane shape, Cold Spring Harb Perspect Biol, 2011, 3, a004747.10.1101/cshperspect.a004747Suche in Google Scholar PubMed PubMed Central

[12] Siahaan P., Wuning S., Manna A., Prasasty V.D., Hudiyanti D., Probing the Interaction between Cyclic ADTC1 Ac-CADTPPVC-NH<inf>2</inf>) Peptide with EC1-EC2 domain of E-cadherin using Molecular Docking Approach, IOP Conf. Ser. Mater. Sci. Eng., 2018, 349, 012050.10.1088/1757-899X/349/1/012050Suche in Google Scholar

[13] Hudiyanti D., Raharjo T.J., Narsito N., Noegrohati S., Isolasi Dan Karakterisasi Lesitin Kelapa Dan Wijen, J Agritech Fak Teknol Pertan UGM, 2012, 32, 23–6 (in Bahasa Indonesia).10.22146/agritech.9652Suche in Google Scholar

[14] Israelachvili J.N., Interactions of Biological Membranes and Structures, In: Intermolecular Surface Forces, 3rd ed., Academic Press, San Diego, 2011.10.1016/B978-0-12-391927-4.10021-0Suche in Google Scholar

[15] Valiev M., Bylaska E.J., Govind N., Kowalski K., Straatsma T.P., Van Dam H.J.J., et al NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations, Comput Phys Commun., 2010, 181, 1477–89.10.1016/j.cpc.2010.04.018Suche in Google Scholar

[16] Nocker M., Handschuh S., Tautermann C., Liedl K.R., Theoretical Prediction of Hydrogen Bond Strength for Use in Molecular Modeling, J Chem Inf Model, 2009, 49, 2067–76.10.1021/ci9001469Suche in Google Scholar PubMed

[17] Israelachvili J., Wennerström H., Role of hydration and water structure in biological and colloidal interactions, Nature, 1996, 379, 219–25.10.1038/379219a0Suche in Google Scholar PubMed

[18] Torchilin V.P., Recent advances with liposomes as pharmaceutical carriers, Nat Rev Drug Discov, 2005, 4, 145–60.10.1038/nrd1632Suche in Google Scholar PubMed

[19] Bozzuto G., Molinari A., Liposomes as nanomedical devices, Int J Nanomedicine, 2015, 10, 975–99.10.2147/IJN.S68861Suche in Google Scholar PubMed PubMed Central

Received: 2018-09-08
Accepted: 2019-02-05
Published Online: 2019-08-24

© 2019 Dwi Hudiyanti et al., published by De Gruyter

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

Artikel in diesem Heft

  1. Regular Articles
  2. Research on correlation of compositions with oestrogenic activity of Cistanche based on LC/Q-TOF-MS/MS technology
  3. Efficacy of Pyrus elaeagnifolia subsp. elaeagnifolia in acetic acid–induced colitis model
  4. Anti-inflammatory and antinociceptive features of Bryonia alba L.: As a possible alternative in treating rheumatism
  5. High efficiency liposome fusion induced by reducing undesired membrane peptides interaction
  6. Prediction of the Blood-Brain Barrier Permeability Using RP-18 Thin Layer Chromatography
  7. Phytic Acid Extracted from Rice Bran as a Growth Promoter for Euglena gracilis
  8. Development of a validated spectrofluorimetric method for assay of sotalol hydrochloride in tablets and human plasma: application for stability-indicating studies
  9. Topological Indices of Hyaluronic Acid-Paclitaxel Conjugates’ Molecular Structure in Cancer Treatment
  10. Thermodynamic properties of the bubble growth process in a pool boiling of water-ethanol mixture two-component system
  11. Critical Roles of the PI3K-Akt-mTOR Signaling Pathway in Apoptosis and Autophagy of Astrocytes Induced by Methamphetamine
  12. Characteristics of Stable Hydrogen and Oxygen Isotopes of Soil Moisture under Different Land Use in Dry Hot Valley of Yuanmou
  13. Specific, highly sensitive and simple spectrofluorimetric method for quantification of daclatasvir in HCV human plasma patients and in tablets dosage form
  14. Chromium-modified cobalt molybdenum nitrides as catalysts for ammonia synthesis
  15. Langerhans cell-like dendritic cells treated with ginsenoside Rh2 regulate the differentiation of Th1 and Th2 cells in vivo
  16. Identification of Powdery Mildew Blumeria graminis f. sp. tritici Resistance Genes in Selected Wheat Varieties and Development of Multiplex PCR
  17. Computational Analysis of new Degree-based descriptors of oxide networks
  18. The Use Of Chemical Composition And Additives To Classify Petrol And Diesel Using Gas Chromatography–Mass Spectrometry And Chemometric Analysis: A Uk Study
  19. Minimal Energy Tree with 4 Branched Vertices
  20. Jatropha seed oil derived poly(esteramide-urethane)/ fumed silica nanocomposite coatings for corrosion protection
  21. Calculating topological indices of certain OTIS interconnection networks
  22. Energy storage analysis of R125 in UIO-66 and MOF-5 nanoparticles: A molecular simulation study
  23. Velvet Antler compounds targeting major cell signaling pathways in osteosarcoma - a new insight into mediating the process of invasion and metastasis in OS
  24. Effects of Azadirachta Indica Leaf Extract, Capping Agents, on the Synthesis of Pure And Cu Doped ZnO-Nanoparticles: A Green Approach and Microbial Activity
  25. Aqueous Micro-hydration of Na+(H2O)n=1-7 Clusters: DFT Study
  26. A proposed image-based detection of methamidophos pesticide using peroxyoxalate chemiluminescence system
  27. Phytochemical screening and estrogenic activity of total glycosides of Cistanche deserticola
  28. Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents
  29. Chemical pretreatments of Trapa bispinosa's peel (TBP) biosorbent to enhance adsorption capacity for Pb(ll)
  30. Dynamic Changes in MMP1 and TIMP1 in the Antifibrotic Process of Dahuang Zhechong Pill in Rats with Liver Fibrosis
  31. The Optimization and Production of Ginkgolide B Lipid Microemulsion
  32. Photodynamic Therapy Enhanced the Antitumor Effects of Berberine on HeLa Cells
  33. Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
  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 5.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2019-0061/html
Button zum nach oben scrollen