Special Issue "Research of Organic Molecules and Materials for Biological Application"

A special issue of Materials (ISSN 1996-1944). This special issue belongs to the section "Materials Chemistry".

Deadline for manuscript submissions: 30 September 2021.

Special Issue Editors

Prof. Jacek Ścianowski
E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland
Interests: organic synthesis; terpenes; chalcogenides; antioxidants; anticancer agents
Prof. Marek Krzeminski
E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland
Interests: asymmetric synthesis; organoboranes; terpenes; catalytic reactions; enantioselective reductions

Special Issue Information

Dear Colleagues,

Stress, modern lifestyle, diet, and prolonged survival of people are just a few reasons contributing to modern civilization diseases. Atherosclerosis, diabetes, obesity, oxidative stress, and cancer are contemporary challenges for medicine and, thus, modern organic chemistry. The search for new chemotherapeutics and biologically active materials based on organic components is one of the current research trends. New therapeutics based on small organic molecules, compounds, and materials of natural origin, and reagents containing heteroatoms such as sulfur, selenium, phosphorus, boron, and others are just a few of the challenges facing modern organic synthesis. The search for biologically active reagents also includes new synthetic methodologies such as organocatalysis, stereocontrolled reactions, as well as new solutions in the field of so-called “green chemistry” and “flow chemistry”, e.g., solvent-free reactions, high pressure, ultrasound, and microwaves.

The announced Special Issue is open for research related to the current studies performed in chemical laboratories involving synthesis of organic molecules and materials possessing any kind of biological applications. The works resulting from this research, aimed either at the solution of basic and mechanistic problems or of practical importance, are welcome.

This Special Issue is also announced at the 2nd International Conference "Chemistry For Beauty and Health", which will be held on 12-15 May 2021 in Poznan, Poland (https://beauty-torun.umk.pl/pages/main_page/). We invite conference participants to publish the results of research related to biomaterials, pharmaceuticals and cosmetic materials.

Prof. Jacek Ścianowski
Prof. Marek Krzeminski
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Materials is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • organic compounds and materials
  • biological activity
  • antioxidants
  • anticancer activity

Published Papers (15 papers)

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Research

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Open AccessArticle
Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives
Materials 2021, 14(9), 2138; https://doi.org/10.3390/ma14092138 - 22 Apr 2021
Viewed by 279
Abstract
N-Heterocycles are considered as desirable scaffolds for the development of novel lead compounds for anticancer drug research. Among them, phosphorus-containing amino-derivatives play a crucial role. A series of imines and products of their further reactions with P-nucleophiles were obtained starting from [...] Read more.
N-Heterocycles are considered as desirable scaffolds for the development of novel lead compounds for anticancer drug research. Among them, phosphorus-containing amino-derivatives play a crucial role. A series of imines and products of their further reactions with P-nucleophiles were obtained starting from vicinal bisamines. Reaction of ethylenediamine and α-carbonyl esters yielded in novel unexpected products, which structures were confirmed by crystallographic measurements. The cytotoxic activity evaluation was done on a variety of cell lines including HUH7, AKH12, DAOY, UW228-2, D283, D425, and U251. Human umbilical vein endothelial cells (HUVECs) were used as control. Two of the tested compounds, bearing TADDOL-derived, and trifluoromethyl substituents showed a significant effect on cell viability, though comparable to nonmalignant cells. Full article
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Open AccessArticle
Intramolecular C-N Bond Formation via Thermal Arene C-H Bond Activation Supported by Au(III) Complexes
Materials 2021, 14(7), 1676; https://doi.org/10.3390/ma14071676 - 29 Mar 2021
Viewed by 295
Abstract
One of the main tactics to access C-N bonds from inactivated C-H functionalities is direct transition metal-supported aminations. Due to the often harsh reaction conditions, the current goal in the field is the search for more mild and sustainable transformations. Herein, we present [...] Read more.
One of the main tactics to access C-N bonds from inactivated C-H functionalities is direct transition metal-supported aminations. Due to the often harsh reaction conditions, the current goal in the field is the search for more mild and sustainable transformations. Herein, we present the first solvent-free thermally induced C-N bond formation driven by Au(III) salts. The general structure of the products was confirmed by 1H, 13C, 15N NMR, TGA-DTA and ATR/FT-IR analysis. Additionally, all derivatives were tested as catalysts in a three-component coupling reaction between phenylacetylene, benzaldehyde and piperidine and as anticancer agents on HL-60 and MCF-7 cell lines. Full article
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Open AccessArticle
Platinum(II) Complexes with Bulky Disubstitute Triazolopyrimidines as Promising Materials for Anticancer Agents
Materials 2020, 13(23), 5312; https://doi.org/10.3390/ma13235312 - 24 Nov 2020
Viewed by 448
Abstract
Herein, we present dicarboxylate platinum(II) complexes of the general formula [Pt(mal)(DMSO)(L)] and [Pt(CBDC)(DMSO)(L)], where L is dbtp 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine) or ibmtp (7-isobutyl-5-methyl-1,2,4- triazolo[1,5-a]pyrimidine), as prospective prodrugs. The platinum(II) complexes were synthesized in a one-pot reaction between cis-[PtCl [...] Read more.
Herein, we present dicarboxylate platinum(II) complexes of the general formula [Pt(mal)(DMSO)(L)] and [Pt(CBDC)(DMSO)(L)], where L is dbtp 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine) or ibmtp (7-isobutyl-5-methyl-1,2,4- triazolo[1,5-a]pyrimidine), as prospective prodrugs. The platinum(II) complexes were synthesized in a one-pot reaction between cis-[PtCl2(DMSO)2], silver malonate or silver cyclobutane-1,1-dicarboxylate and triazolopyrimidines. All platinum(II) compounds were characterized by FT-IR, and 1H, 13C, 15N and 195Pt NMR; and their square planar geometries with one monodentate N(3)-bonded 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine, one S-bonded molecule of dimethyl sulfoxide and one O,O-chelating malonato (1, 2) or O,O-chelating cyclobutane-1,1-dicarboxylato (3, 4) was determined. Additionally, [Pt(CBDC)(dbtp)(DMSO)] (3) exhibited (i) substantial in vitro cytotoxicity against the lung adenocarcinoma epithelial cell line (A549) (IC50 = 5.00 µM) and the cisplatin-resistant human ductal breast epithelial tumor cell line (T47D) (IC50 = 6.60 µM); and (ii) definitely exhibited low toxicity against normal murine embryonic fibroblast cells (BALB/3T3). Full article
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Open AccessEditor’s ChoiceArticle
New Polyphenol-Containing LDL Nano-Preparations in Oxidative Stress and DNA Damage: A Potential Route for Cell-Targeted PP Delivery
Materials 2020, 13(22), 5106; https://doi.org/10.3390/ma13225106 - 12 Nov 2020
Viewed by 458
Abstract
Low-density lipoprotein (LDL) preparations of the chosen polyphenols (PPs) were prepared for the first time in the literature. The solubility of the PPs in the lipidic core of the LDL increased with the increase of their lipophilicity. The anti-/pro-oxidative properties and toxicity of [...] Read more.
Low-density lipoprotein (LDL) preparations of the chosen polyphenols (PPs) were prepared for the first time in the literature. The solubility of the PPs in the lipidic core of the LDL increased with the increase of their lipophilicity. The anti-/pro-oxidative properties and toxicity of LDL-entrapped PPs toward A 2780 human ovarian cancer cells were examined. The obtained preparations were found to be stable in PBS, and characterized by low toxicity. A binding affinity study revealed that the uptake of PP-loaded LDL particles is non-receptor-specific under experimental conditions. The antioxidative potential of the obtained PPs-doped LDL preparations was shown to be higher than for the PPs themselves, probably due to facilitating transport of LDL preparations into the cellular milieu, where they can interact with the cellular systems and change the redox status of the cell. The PPs-loaded LDL displayed the highest protective effect against Fenton-type reaction induced oxidative DNA damage. Full article
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Open AccessArticle
Synthesis of Steryl Hydroxycinnamates to Enhance Antioxidant Activity of Rapeseed Oil and Emulsions
Materials 2020, 13(20), 4536; https://doi.org/10.3390/ma13204536 - 13 Oct 2020
Viewed by 386
Abstract
In recent years, steryl esters have found potential applications in food, pharmaceutical and cosmetic industries. Therefore, three hydroxycinnamate steryl esters (HSEs): β-sitosteryl sinapate (β-SSA), β-sitosteryl caffeate (β-SCA), and β-sitosteryl ferulate (β-SFA) were synthesized by chemical approach and their antioxidant activity (AA) were analyzed [...] Read more.
In recent years, steryl esters have found potential applications in food, pharmaceutical and cosmetic industries. Therefore, three hydroxycinnamate steryl esters (HSEs): β-sitosteryl sinapate (β-SSA), β-sitosteryl caffeate (β-SCA), and β-sitosteryl ferulate (β-SFA) were synthesized by chemical approach and their antioxidant activity (AA) were analyzed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays. The values of inhibitory concentration (IC50) of each ester needed to inhibit 50% of the DPPH radical (IC50(DPPH) = 238.9, 78.3, 290.0 µmol/L for β-SSA, β-SCA, and β-SFA, respectively) and ABTS radical cation (IC50(ABTS) = 174.6, 106.7, 206.0 µmol/L for β-SSA, β-SCA, and β-SFA, respectively) were estimated and compared with antioxidant potential of phenolic acids. Moreover, the effect of HSEs addition in the concentrations range between 0.01% and 0.5% on the AA of refined rapeseed oil, mayonnaise and margarine was evaluated. Chemical structures of the synthesized HSEs and their concentrations strongly affect the AA of fat products. Oil and emulsions supplemented with higher concentrations of HSEs had significantly higher AA than control samples. Unfortunately, lower concentrations of HSEs (0.01% and 0.02%) did not increase the AA of fat products. However, steryl phenolates added in higher amounts can be considered as potential antioxidants delaying the oxidation processes of studied fats. Full article
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Open AccessArticle
Synthesis of Magnetic Molecularly Imprinted Polymer Sorbents for Isolation of Parabens from Breast Milk
Materials 2020, 13(19), 4328; https://doi.org/10.3390/ma13194328 - 29 Sep 2020
Viewed by 605
Abstract
Magnetic molecularly imprinted polymers (MMIPs) are an invaluable asset in the development of many methods in analytical chemistry, particularly sample preparation. Novel adsorbents based on MMIPs are characterized by high selectivity towards a specific analyte due to the presence of a specific cavity [...] Read more.
Magnetic molecularly imprinted polymers (MMIPs) are an invaluable asset in the development of many methods in analytical chemistry, particularly sample preparation. Novel adsorbents based on MMIPs are characterized by high selectivity towards a specific analyte due to the presence of a specific cavity on their polymer surface, enabling the lock–key model interactions to occur. In addition, the magnetic core provides superparamagnetic properties that allow rapid separation of the sorbent from the sample solution. Such a combination of imprinted polymers with a magnetic core has an innovative influence on the development of separation techniques. Hence, the present study describes the synthesis of MMIPs with 17β-estradiol used as a template molecule in the production of imprinted polymers. The as-prepared sorbent was used for a sorption/desorption study of five parabens from breast milk samples. The obtained results were characterized by sorption efficiency exceeding 92%, which shows the high affinity of the analytes to the functional groups on the sorbent. The final determination of the selected analytes was done with high-performance liquid chromatography using a fluorometric detector. The determined linearity ranges for selected parabens were characterized by high determination coefficients (r2 from 0.9992 to 0.9999), and the calculated limit of detection (LOD) and limit of quantification (LOQ) for the identified compounds were low (LOD from 1.1–2.7 ng mL−1; LOQ from 3.6–8.1 ng mL−1), which makes their quantitative analysis in real samples feasible. Full article
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Open AccessArticle
Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C
Materials 2020, 13(18), 4190; https://doi.org/10.3390/ma13184190 - 21 Sep 2020
Cited by 1 | Viewed by 677
Abstract
Condensation of diacetyl monooxime with formaldimines derived from alkoxyamines in glacial acetic acid at room temperature leads to corresponding 2-unsubstituted imidazole N-oxides bearing an alkoxy substituent at the N(1) atom of the imidazole ring. Subsequent O-benzylation afforded, depending on the type [...] Read more.
Condensation of diacetyl monooxime with formaldimines derived from alkoxyamines in glacial acetic acid at room temperature leads to corresponding 2-unsubstituted imidazole N-oxides bearing an alkoxy substituent at the N(1) atom of the imidazole ring. Subsequent O-benzylation afforded, depending on the type of alkylating agent, either symmetric or nonsymmetric alkoxyimidazolium salts considered as structural analogues of naturally occurring imidazole alkaloids, lepidilines A and C. Some of the obtained salts were tested as precursors of nucleophilic heterocyclic carbenes (NHCs), which in situ reacted with elemental sulfur to give the corresponding N-alkoxyimidazole-2-thiones. The cytotoxic activity of selected 4,5-dimethylimidazolium salts bearing either two benzyloxy or benzyloxy and 1-adamantyloxy groups at N(1) and N(3) atoms was evaluated against HL-60 and MCF-7 cell lines using the MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay. Notably, in two cases of alkoxyimidazolium salts, no effect of the counterion exchange (Br → PF6) on the biological activity was observed. Full article
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Open AccessArticle
Synthesis, Absolute Configuration, Antibacterial, and Antifungal Activities of Novel Benzofuryl β-Amino Alcohols
Materials 2020, 13(18), 4080; https://doi.org/10.3390/ma13184080 - 14 Sep 2020
Viewed by 531
Abstract
A series of new benzofuryl α-azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl β-amino alcohols bearing an imidazolyl and triazolyl substituents were obtained with excellent enantioselectivity (96–99%). The absolute configuration (R) of the products [...] Read more.
A series of new benzofuryl α-azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl β-amino alcohols bearing an imidazolyl and triazolyl substituents were obtained with excellent enantioselectivity (96–99%). The absolute configuration (R) of the products was confirmed by means of electronic circular dichroism (ECD) spectroscopy supported by theoretical calculations. Selected benzofuryl α-azole ketones were also successfully asymmetrically bioreduced by fungi of Saccharomyces cerevisiae and Aureobasidium pullulans species. Racemic and chiral β-amino alcohols, as well as benzofuryl α-amino and α-bromo ketones were evaluated for their antibacterial and antifungal activities. From among the synthesized β-amino alcohols, the highest antimicrobial activity was found for (R)-1-(3,5-dimethylbenzofuran-2-yl)-2-(1H-imidazol-1-yl)ethan-1-ol against S. aureus ATCC 25923 (MIC = 64, MBC = 96 μg mL−1) and (R)-1-(3,5-dimethylbenzofuran-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol against yeasts of M. furfur DSM 6170 (MIC = MBC = 64 μg mL−1). In turn, from among the tested ketones, 1-(benzofuran-2-yl)-2-bromoethanones (1–4) were found to be the most active against M. furfur DSM 6170 (MIC = MBC = 1.5 μg mL−1) (MIC—minimal inhibitory concentration, MBC—minimal biocidal concentration). Full article
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Open AccessArticle
Silk Fibroin/Collagen/Chitosan Scaffolds Cross-Linked by a Glyoxal Solution as Biomaterials toward Bone Tissue Regeneration
Materials 2020, 13(15), 3433; https://doi.org/10.3390/ma13153433 - 04 Aug 2020
Cited by 4 | Viewed by 1025
Abstract
In this study, three-dimensional materials based on blends of silk fibroin (SF), collagen (Coll), and chitosan (CTS) cross-linked by glyoxal solution were prepared and the properties of the new materials were studied. The structure of the composites and the interactions between scaffold components [...] Read more.
In this study, three-dimensional materials based on blends of silk fibroin (SF), collagen (Coll), and chitosan (CTS) cross-linked by glyoxal solution were prepared and the properties of the new materials were studied. The structure of the composites and the interactions between scaffold components were studied using FTIR spectroscopy. The microstructure was observed using a scanning electron microscope. The following properties of the materials were measured: density and porosity, moisture content, and swelling degree. Mechanical properties of the 3D materials under compression were studied. Additionally, the metabolic activity of MG-63 osteoblast-like cells on materials was examined. It was found that the materials were characterized by a high swelling degree (up to 3000% after 1 h of immersion) and good porosity (in the range of 80–90%), which can be suitable for tissue engineering applications. None of the materials showed cytotoxicity toward MG-63 cells. Full article
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Open AccessArticle
Modification of Collagen Properties with Ferulic Acid
Materials 2020, 13(15), 3419; https://doi.org/10.3390/ma13153419 - 03 Aug 2020
Cited by 1 | Viewed by 768
Abstract
Collagen materials are widely used in biomedicine and in cosmetics. However, their properties require improvement for several reasons. In this work, collagen solution as well as collagen films were modified by the addition of ferulic acid (FA). Thin collagen films containing FA were [...] Read more.
Collagen materials are widely used in biomedicine and in cosmetics. However, their properties require improvement for several reasons. In this work, collagen solution as well as collagen films were modified by the addition of ferulic acid (FA). Thin collagen films containing FA were obtained by solvent evaporation. The properties of collagen solution have been studied by steady shear tests. The structure and surface properties of collagen thin films were studied. It was found that for collagen solution with 5% addition of FA, the apparent viscosity was the highest, whereas the collagen solutions with other additions of FA (1%, 2%, and 10%), no significant difference in the apparent viscosity was observed. Thin films prepared from collagen with 1 and 2% FA addition were homogeneous, whereas films with 5% and 10% FA showed irregularity in the surface properties. Mechanical properties, such as maximum tensile strength and elongation at break, were significantly higher for films with 10% FA than for films with smaller amount of FA. Young modulus was similar for films with 1% and 10% FA addition, but bigger than for 2% and 5% of FA in collagen films. The cross-linking of collagen with ferulic acid meant that prepared thin films were elastic with better mechanical properties than collagen films. Full article
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Open AccessArticle
Crosslinking of Chitosan with Dialdehyde Chitosan as a New Approach for Biomedical Applications
Materials 2020, 13(15), 3413; https://doi.org/10.3390/ma13153413 - 03 Aug 2020
Cited by 7 | Viewed by 963
Abstract
Materials based on natural high molecular compounds are particularly interesting for biomedical applications. It is known that the cross-linking agent used for preparation of biomacromolecule-based materials is as important as used biopolymer. Therefore, natural cross-linkers containing reactive carbonyl groups are of great interest [...] Read more.
Materials based on natural high molecular compounds are particularly interesting for biomedical applications. It is known that the cross-linking agent used for preparation of biomacromolecule-based materials is as important as used biopolymer. Therefore, natural cross-linkers containing reactive carbonyl groups are of great interest especially for modifying properties of natural polysaccharides. One of the most popular cross-linking agents is glutaraldehyde. Nevertheless, the unreacted particles can be released from the cross-linked material and cause cytotoxic effects. This can be eliminated when using a cross-linker based e.g., on polysaccharides. This article describes quick and efficient synthesis of dialdehyde chitosan (DACS) and its application for the preparation of chitosan films. Materials obtained with different amount of DACS were fully characterized in terms of structure and surface morphology. Thermal and mechanical properties as well as hydrophilic character were also examined. The results obtained were compared with the materials obtained by cross-linking chitosan with low molecular weight glutaraldehyde and high molecular weight cross-linking agent based on polysaccharide–dialdehyde starch. Toxicity of all obtained materials was tested using the Microtox® test. It has been shown that due to better mechanical, thermal and surface properties as well as lower toxicity, dialdehyde chitosan is a very promising crosslinking agent. Full article
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Open AccessArticle
The Influence of Different Forms of Silver on Selected Pathogenic Bacteria
Materials 2020, 13(10), 2403; https://doi.org/10.3390/ma13102403 - 23 May 2020
Viewed by 776
Abstract
The application of silver nanoparticles as an antibacterial agent is becoming more common. Unfortunately, their effect on microorganisms is still not fully understood. Therefore, this paper attempts to investigate the influence of silver ions, biologically synthesized silver nanoparticles and nanoparticles functionalized with antibiotics [...] Read more.
The application of silver nanoparticles as an antibacterial agent is becoming more common. Unfortunately, their effect on microorganisms is still not fully understood. Therefore, this paper attempts to investigate the influence of silver ions, biologically synthesized silver nanoparticles and nanoparticles functionalized with antibiotics on molecular bacteria profiles. The initial stage of research was aimed at the mechanism determination involved in antibiotics sorption onto nanoparticles’ surface. For this purpose, the kinetics study was performed. Next, the functionalized formulations were characterized by Fourier transform infrared spectroscopy (FT-IR), dynamic light scattering (DLS) and a zeta potential study. The results reveal that functionalization is a complex process, but does not significantly affect the stability of biocolloids. Furthermore, the antimicrobial assays, in most cases, have shown no increases in antibacterial activity after nanoparticle functionalization, which suggests that the functionalization process does not always generate the improved antimicrobial effect. Finally, the matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) technique was employed to characterize the changes in the molecular profile of bacteria treated with various antibacterial agents. The recorded spectra proved many differences in bacterial lipids and proteins profiles compared to untreated cells. In addition, the statistical analysis of recorded spectra revealed the strain-dependent nature of stress factors on the molecular profile of microorganisms. Full article
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Open AccessArticle
Octahydroquinoxalin-2(1H)-One-Based Aminophosphonic Acids and Their Derivatives—Biological Activity towards Cancer Cells
Materials 2020, 13(10), 2393; https://doi.org/10.3390/ma13102393 - 22 May 2020
Cited by 1 | Viewed by 669
Abstract
In the search for new antitumor agents, aminophosphonic acids and their derivatives based on octahydroquinoxalin-2(1H)-one scaffold were obtained and their cytotoxic properties and a mechanism of action were evaluated. Phosphonic acid and phosphonate moieties increased the antiproliferative activity in comparison to [...] Read more.
In the search for new antitumor agents, aminophosphonic acids and their derivatives based on octahydroquinoxalin-2(1H)-one scaffold were obtained and their cytotoxic properties and a mechanism of action were evaluated. Phosphonic acid and phosphonate moieties increased the antiproliferative activity in comparison to phenolic Mannich bases previously reported. Most of the obtained compounds revealed a strong antiproliferative effect against leukemia cell line (MV-4-11) with simultaneous low cytotoxicity against normal cell line (mouse fibroblasts-BALB/3T3). The most active compound was diphenyl-[(1R,6R)-3-oxo-2,5-diazabicyclo[4.4.0]dec-4-yl]phosphonate. Preliminary evaluation of the mechanism of action showed the proapoptotic effect associated with caspase 3/7 induction. Full article
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Open AccessArticle
Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability
Materials 2020, 13(3), 661; https://doi.org/10.3390/ma13030661 - 02 Feb 2020
Cited by 3 | Viewed by 1011
Abstract
Organoselenium compounds are well-known glutathione peroxidase (GPx) mimetics that possess antioxidants/prooxidant properties and are able to modulate the concentration of reactive oxygen species (ROS), preventing oxidative stress in normal cells or inducing ROS formation in cancer cells leading to apoptosis. The purpose of [...] Read more.
Organoselenium compounds are well-known glutathione peroxidase (GPx) mimetics that possess antioxidants/prooxidant properties and are able to modulate the concentration of reactive oxygen species (ROS), preventing oxidative stress in normal cells or inducing ROS formation in cancer cells leading to apoptosis. The purpose of this study was the synthesis of potent GPx mimics with antioxidant and anticancer activity along with improved bioavailability, as a result of good solubility in protic solvents. As a result of our research, glutathione peroxidase (GPx) mimetics in the form of water-soluble benzeneseleninic acid salts were obtained. The procedure was based on the synthesis of 2-(N-alkylcarboxyamido)benzeneselenenic acids, through the oxidation of benzisoselenazol-3(2H)-ones or analogous arenediselenides with an amido group, which were further converted to corresponding potassium salts by the treatment with potassium tert-butanolate. All derivatives were tested as potential antioxidants and anticancer agents. The areneseleninic acid salts were significantly better peroxide scavengers than analogous acids and the well-known organoselenium antioxidant ebselen. The highest activity was observed for the 2-(N-ethylcarboxyamido)benzeneselenenic acid potassium salt. The strongest cytotoxic effect against breast cancer (MCF-7) and human promyelocytic leukemia (HL-60) cell lines was found for 2-(N-cyclohexylcarboxyamido)benzeneselenenic acid potassium salt and the 2-(N-ethylcarboxyamido)benzeneselenenic acid, respectively. The structure–activity correlations, including the differences in reactivity of benzeneseleninic acids and corresponding salts were evaluated. Full article
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Review

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Open AccessFeature PaperReview
Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids
Materials 2020, 13(19), 4454; https://doi.org/10.3390/ma13194454 - 08 Oct 2020
Cited by 2 | Viewed by 771
Abstract
Natural carboxylic acids are plant-derived compounds that are known to possess biological activity. The aim of this review was to compare the effect of structural differences of the selected carboxylic acids (benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic [...] Read more.
Natural carboxylic acids are plant-derived compounds that are known to possess biological activity. The aim of this review was to compare the effect of structural differences of the selected carboxylic acids (benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic acid (CFA), rosmarinic acid (RA), and chicoric acid (ChA)) on the antioxidant, antimicrobial, and cytotoxic activity. The studied compounds were arranged in a logic sequence of increasing number of hydroxyl groups and conjugated bonds in order to investigate the correlations between the structure and bioactivity. A review of the literature revealed that RA exhibited the highest antioxidant activity and this property decreased in the following order: RA > CFA ~ ChA > p-CA > CinA > BA. In the case of antimicrobial properties, structure-activity relationships were not easy to observe as they depended on the microbial strain and the experimental conditions. The highest antimicrobial activity was found for CFA and CinA, while the lowest for RA. Taking into account anti-cancer properties of studied NCA, it seems that the presence of hydroxyl groups had an influence on intermolecular interactions and the cytotoxic potential of the molecules, whereas the carboxyl group participated in the chelation of endogenous transition metal ions. Full article
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

1. Authors: Dr. Agnieszka Tafelska-Kaczmarek

2. Authors: Dr. Renata Gadzała-Kopciuch

3. Authors: M.Sc.Eng. Dobrochna Rabiej, Prof. Marek Krzemiński, Prof. Aleksandra Szydłowska-Czerniak
   Affiliations: Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland

 

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