Molecules

Research

11 pages, 3651 KiB

Open AccessArticle

Comparison of Hydrogels Based on Commercial Chitosan and Beetosan^® Containing Nanosilver

by Bożena Tyliszczak¹

, Anna Drabczyk^2,* and Sonia Kudłacik²

¹ Department of Chemistry and Technology of Polymers, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland

² Institute of Inorganic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland

Molecules 2017, 22(1), 61; https://doi.org/10.3390/molecules22010061 - 31 Dec 2016

Cited by 24 | Viewed by 6256

Abstract

Two series of hydrogels on the basis of commercial chitosan and chitosan derived from naturally expired honeybees are presented in this article. Sorption capacity and behavior of both kind of materials in simulated body fluids such as Ringer’s liquid or artificial saliva have [...] Read more.

Two series of hydrogels on the basis of commercial chitosan and chitosan derived from naturally expired honeybees are presented in this article. Sorption capacity and behavior of both kind of materials in simulated body fluids such as Ringer’s liquid or artificial saliva have been determined and compared. Presence of functional groups in synthesized materials have been determined by means of FT-IR spectroscopy. Structure and homogeneity of their surface have been defined using Scanning Electron Microscopy. Based on the conducted research, it can be stated that both chitosan and Beetosan^® hydrogels have very similar characteristics. It is worth noting that synthesis of such materials is environmentally friendly and leads to obtaining polymers that can be used for biomedical applications. Tested materials are characterized by low sorption capacity and do not have a negative impact on simulated body fluids. Moreover, based on the cell lines studies, it can be stated that Beetosan^® hydrogels have a negative influence on cells of cancerous origin and, what is important, significantly less adverse effects on fibroblasts. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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14 pages, 8104 KiB

Open AccessArticle

Spectroscopic Studies on the Molecular Ageing of Serum Albumin

by Mariola Chudzik^*, Małgorzata Maciążek-Jurczyk

, Bartosz Pawełczak and Anna Sułkowska

School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia, Chair and Department of Physical Pharmacy, Jagiellońska 4, 41-200 Sosnowiec, Poland

Molecules 2017, 22(1), 34; https://doi.org/10.3390/molecules22010034 - 27 Dec 2016

Cited by 32 | Viewed by 7458

Abstract

Pathological states in the organism, e.g., renal or hepatic diseases, cataract, dysfunction of coronary artery, diabetes mellitus, and also intensive workout, induce the structural modification of proteins called molecular ageing or N-A isomerization. The aim of this study was to analyze the structural [...] Read more.

Pathological states in the organism, e.g., renal or hepatic diseases, cataract, dysfunction of coronary artery, diabetes mellitus, and also intensive workout, induce the structural modification of proteins called molecular ageing or N-A isomerization. The aim of this study was to analyze the structural changes of serum albumin caused by alkaline ageing using absorption, spectrofluorescence, and circular dichroism spectroscopy. The N-A isomerization generates significant changes in bovine (BSA) and human (HSA) serum albumin subdomains—the greatest changes were observed close to the tryptophanyl (Trp) and tyrosyl (Tyr) residue regions while a smaller change was observed in phenyloalanine (Phe) environment. Moreover, the changes in the polarity of the Trp neighborhood as well as the impact of the ageing process on α-helix, β-sheet content, and albumin molecule rotation degree have been analyzed. Based on the spectrofluorescence study, the alterations in metoprolol binding affinity to the specific sites that increase the toxicity of the drug were investigated. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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12 pages, 3311 KiB

Open AccessArticle

The Influence of Anionic Initiator on the Selected Properties of Poly-N-Isopropyl Acrylamide Evaluated for Controlled Drug Delivery

by Agnieszka Gola

, Tomasz Knysak and Witold Musial^*

Department of Physical Chemistry, Pharmaceutical Faculty, Wroclaw Medical University, Borowska 211, 50-556 Wroclaw, Poland

Molecules 2017, 22(1), 23; https://doi.org/10.3390/molecules22010023 - 26 Dec 2016

Cited by 8 | Viewed by 5627

Abstract

The aim of the study was to monitor the influence of increasing initiator concentrations on the properties of poly-N-isopropylacrylamide (polyNIPA) nanoparticles obtained via surfactant free precipitation polymerization (SFPP). In all studied systems P-001 to P-1, the same amount of monomer was [...] Read more.

The aim of the study was to monitor the influence of increasing initiator concentrations on the properties of poly-N-isopropylacrylamide (polyNIPA) nanoparticles obtained via surfactant free precipitation polymerization (SFPP). In all studied systems P-001 to P-1, the same amount of monomer was used, and increasing amounts of potassium persulphate (KPS). The course of each reaction was monitored by measuring the conductivity of the whole system. The resulting composition of products was confirmed by attenuated total reflectance within Fourier transformed infrared spectroscopy (ATR-FTIR) measurements. The hydrodynamic diameters with polydispersity index (PDI) and zeta potential (ZP) were measured in aqueous dispersions of the synthesized polymers in dynamic light scattering (DLS) device (λ = 678 nm), and were found to be for P-1: 20.33 nm (PDI = 0.49) and −7 mV, for P-05: 22.24 nm (PDI = 0.39) and −5 mV, for P-01: 50.14 nm (PDI = 0.49) and −3 mV, for P-005: 62.75 nm (PDI = 0.54) and −3 mV and for P-001: 509.4 nm (PDI = 0.61) and −12 mV at 18 °C, respectively. Initiator concentration affects the size and ZP of particles. The hydrodynamic diameter decreases with initiator concentration increase, whereas the time of the reaction decreases when the initiator concentration increases. This fact is reflected in the observed values of conductivity in the course of the performed reaction. Evaluated volume phase transition temperature in the range of 32 °C enables further research of the nanoparticles as thermosensitive drug carriers. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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12 pages, 2696 KiB

Open AccessArticle

Methotrexate and Cytarabine—Loaded Nanocarriers for Multidrug Cancer Therapy. Spectroscopic Study

by Danuta Pentak^1,*, Violetta Kozik^2,*, Andrzej Bąk³

, Paulina Dybał³, Aleksander Sochanik⁴ and Josef Jampilek^5,*

¹ Department of Materials Chemistry and Chemical Technology, Institute of Chemistry, University of Silesia, 40-006 Katowice, Poland

² Department of Synthesis Chemistry, Institute of Chemistry, University of Silesia, 40-006 Katowice, Poland

³ Department of Organic Chemistry, Institute of Chemistry, University of Silesia, 40-006 Katowice, Poland

⁴ Center for Translational Research and Molecular Biology of Cancer, Maria Skłodowska-Curie Memorial Cancer Center and Institute of Oncology, Gliwice Branch, 44-100 Gliwice, Poland

⁵ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, 832 32 Bratislava, Slovakia

Molecules 2016, 21(12), 1689; https://doi.org/10.3390/molecules21121689 - 8 Dec 2016

Cited by 25 | Viewed by 6545

Abstract

Determining the properties of nanoparticles obtained by novel methods and defining the scope of their application as drug carriers has important practical significance. This article presents the pioneering studies concerning high degree incorporation of cytarabine (AraC) and methotrexate (MTX) into liposome vesicles. The [...] Read more.

Determining the properties of nanoparticles obtained by novel methods and defining the scope of their application as drug carriers has important practical significance. This article presents the pioneering studies concerning high degree incorporation of cytarabine (AraC) and methotrexate (MTX) into liposome vesicles. The main focus of this study were cytarabine-methotrexate-dipalmitoylphosphatidylcholine (DPPC) interactions observed in the gel and fluid phases of DPPC bilayers. The proposed new method of use the Transmittance_2919/2850 ratio presented in our research is sensitive to subtle changes in conformational order resulting from rotations, kinks and bends of the lipid chains. The transition temperatures characterized by Fourier Transform Infrared Spectroscopy (FT-IR) were consistent with the results obtained by Differential Scanning Calorimetry (DSC). Transmission Electron Microscopy (TEM) was used in order to determine the size and shape of the liposomes obtained. The mutual interactions occurring between the drugs studied and the phospholipids were analyzed using the Nuclear Magnetic Resonance (NMR). Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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13 pages, 748 KiB

Open AccessCommunication

Synthesis and Determination of Physicochemical Properties of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Alkoxyethoxybenzoates

by Pavlina Marvanova^1,*, Tereza Padrtova¹, Klara Odehnalova¹, Ondrej Hosik¹, Michal Oravec²

and Petr Mokry^1,*

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech Republic

² Global Change Research Institute CAS, Belidla 986/4a, 60300 Brno, Czech Republic

Molecules 2016, 21(12), 1682; https://doi.org/10.3390/molecules21121682 - 7 Dec 2016

Cited by 5 | Viewed by 5724

Abstract

Nine new dihydrochloride salts of 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-alkoxyethoxybenzoates were designed and synthesized. The physicochemical properties such as lipophilicity index (log k_w) and dissociation constant (pK_a) were experimentally determined and compared to the software calculated data. The lipophilicity index was [...] Read more.

Nine new dihydrochloride salts of 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-alkoxyethoxybenzoates were designed and synthesized. The physicochemical properties such as lipophilicity index (log k_w) and dissociation constant (pK_a) were experimentally determined and compared to the software calculated data. The lipophilicity index was determined by means of reversed-phase high performance liquid chromatography (RP-HPLC). The pK_a values were determined by means of capillary zone electrophoresis. The “drug-likeness” properties according to the Lipinski Rule of Five and prediction of possible blood–brain barrier penetration were computed and discussed. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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12 pages, 701 KiB

Open AccessArticle

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

by Veronika Opletalova¹

, Jan Dolezel², Jiri Kunes³, Vladimir Buchta^4,5, Marcela Vejsova^4,5 and Marta Kucerova-Chlupacova^1,*

¹ Department of Pharmaceutical Chemistry and Pharmaceutical Analysis, Faculty of Pharmacy in Hradec Kralove, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

² GlaxoSmithKline, Hvezdova 1734/2c, 140 00 Prague, Czech Republic

³ Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

⁴ Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

⁵ Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic

Molecules 2016, 21(11), 1592; https://doi.org/10.3390/molecules21111592 - 23 Nov 2016

Cited by 9 | Viewed by 6816

Abstract

Two novel thiosemicarbazones and eight novel 2-{[1-(5-alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones were prepared and tested against a panel of eight fungal strains–Candida albicans ATCC 44859, Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I, Trichosporon asahii 1188, Aspergillus fumigatus 231, Lichtheimia corymbifera 272, and Trichophyton [...] Read more.

Two novel thiosemicarbazones and eight novel 2-{[1-(5-alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones were prepared and tested against a panel of eight fungal strains–Candida albicans ATCC 44859, Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I, Trichosporon asahii 1188, Aspergillus fumigatus 231, Lichtheimia corymbifera 272, and Trichophyton interdigitale 445. 1,3-Thiazolidin-4-ones exhibited activity against all strains, the most potent derivative was 2-{[1-(5-butylpyrazin-2-yl)ethylidene]hydrazono}e-1,3-thiazolidin-4-one. Susceptibility of C. glabrata to the studied 1,3-thiazolidin-4-ones (minimum inhibitory concentrations (MICs) were in the range 0.57 to 2.78 mg/L) is of great interest as this opportunistic pathogen is poorly susceptible to azoles and becomes resistant to echinocandins. Antifungal potency of thiosemicarbazones was slightly lower than that of 1,3-thiazolidin-4-ones. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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19 pages, 11367 KiB

Open AccessArticle

Characteristics of the Protoporphyrin IX Binding Sites on Human Serum Albumin Using Molecular Docking

by Leszek Sułkowski^1,*

, Bartosz Pawełczak², Mariola Chudzik² and Małgorzata Maciążek-Jurczyk²

¹ Department of General and Vascular Surgery, Regional Specialist Hospital, Bialska 104/118, 42-218 Częstochowa, Poland

² Department of Physical Pharmacy, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland

Molecules 2016, 21(11), 1519; https://doi.org/10.3390/molecules21111519 - 17 Nov 2016

Cited by 27 | Viewed by 7830

Abstract

Human serum albumin (HSA) is the main plasma protein responsible for a distribution of drugs in the human circulatory system. The binding to HSA is one of the factors that determines both the pharmacological actions and the side effects of drugs. The derivative [...] Read more.

Human serum albumin (HSA) is the main plasma protein responsible for a distribution of drugs in the human circulatory system. The binding to HSA is one of the factors that determines both the pharmacological actions and the side effects of drugs. The derivative of heme, protoporphyrin IX (PpIX), is a hydrophobic photosensitizer widely used in photodynamic diagnosis and therapy of various malignant disorders. Using absorption and fluorescence spectroscopy, it has been demonstrated that PpIX forms complexes with HSA. Its binding sites in the tertiary structure of HSA were found in the subdomains IB and IIA. PpIX binds to HSA in one class of binding sites with the association constant of 1.68 × 10⁵ M⁻¹ and 2.30 × 10⁵ M⁻¹ for an excitation at wavelength λ_ex = 280 nm and 295 nm, respectively. The binding interactions between HSA and PpIX have been studied by means of molecular docking simulation using the CLC Drug Discovery Workbench (CLC DDWB) computer program. PpIX creates a strong ‘sandwich-type’ complex between its highly conjugated porphine system and aromatic side chains of tryptophan and tyrosine. In summary, fluorescent studies on binding interactions between HSA and PpIX have been confirmed by the results of computer simulation. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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11 pages, 1339 KiB

Open AccessArticle

Natural Deep Eutectic Solvents (NADES) as a Tool for Bioavailability Improvement: Pharmacokinetics of Rutin Dissolved in Proline/Glycine after Oral Administration in Rats: Possible Application in Nutraceuticals

by Marta Faggian¹, Stefania Sut¹, Beatrice Perissutti²

, Valeria Baldan¹, Iztok Grabnar³ and Stefano Dall’Acqua^1,*

¹ Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Via Marzolo 5, 35131 Padova, Italy

² Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127 Trieste, Italy

³ Faculty of Pharmacy, University of Ljubljana, Askerceva cesta 7, SI-1000 Ljubljana, Slovenia

Molecules 2016, 21(11), 1531; https://doi.org/10.3390/molecules21111531 - 14 Nov 2016

Cited by 189 | Viewed by 18373

Abstract

There is a need for innovation in plant-derived pharmaceuticals, food supplements and nutraceutical products regarding the use of more eco-sustainable solvents for their extraction. Furthermore, the poor oral bioavailability of several phytochemicals with health promoting effects stimulates the research in the field of [...] Read more.

There is a need for innovation in plant-derived pharmaceuticals, food supplements and nutraceutical products regarding the use of more eco-sustainable solvents for their extraction. Furthermore, the poor oral bioavailability of several phytochemicals with health promoting effects stimulates the research in the field of pharmaceutical formulations. Natural Deep Eutectic Solvents (NADES) are formed by natural compounds, and can be considered as future solvents being especially useful for the preparation of nutraceuticals and food-grade extracts. In this paper various NADES were prepared using sugars, aminoacids and organic acids. Rutin (quercetin-3-O-α-l-rhamnopyranosyl-(1→6))-β-d-glucopyranose) was used as a model compound to study NADES. Moreover, the effect of various eutectic mixtures on rutin’s water solubility was studied. Proline/glutamic acid (2:1) and proline/choline chloride (1:1) mixtures have a solubility comparable to ethanol. The proline/glutamic acid (2:1) eutectic containing rutin was used in a pharmacokinetic study in Balb/c mice while bioavailability was compared to oral dosing of water suspension. Plasmatic levels of rutin were measured by HPLC-MS/MS showing increased levels and longer period of rutin permanence in plasma of NADES treated animals. This paper reports the possible use of non-toxic NADES for pharmaceutical and nutraceutical preparations. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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11 pages, 2288 KiB

Open AccessArticle

Feasibility of Fraction Collection in HPLC Systems with Evaporative Light Scattering Detector: Analysis of Pectinatella magnifica

by Jiří Pazourek^1,*

and Karel Šmejkal²

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tr. 1946/1, Brno 61242, Czech Republic

² Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tr. 1946/1, Brno 61242, Czech Republic

Molecules 2016, 21(11), 1495; https://doi.org/10.3390/molecules21111495 - 8 Nov 2016

Cited by 2 | Viewed by 6374

Abstract

The use of a liquid chromatography (LC) splitter inserted between an HPLC column and an evaporative light scattering detector (ELSD) is described. This paper aims to show the feasibility of using the splitter in an HPLC-ELSD system to fractionate a model mixture of [...] Read more.

The use of a liquid chromatography (LC) splitter inserted between an HPLC column and an evaporative light scattering detector (ELSD) is described. This paper aims to show the feasibility of using the splitter in an HPLC-ELSD system to fractionate a model mixture of analytes, namely salicin (2-(hydroxymethyl)-phenyl-β-d-glucopyranoside) and glucose. The retention factors and efficiency of the separation were studied under various temperatures and water contents in the mobile phase in order to clarify the mechanism of polyols separation on a diol column under the conditions of hydrophilic liquid chromatography (HILIC). Finally, the system was applied to a biological sample (a lyophilized colony gel of Pectinatella magnifica), where the presence of fructose and glucose was confirmed. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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14 pages, 587 KiB

Open AccessArticle

Assessment of Chemical Impact of Invasive Bryozoan Pectinatella magnifica on the Environment: Cytotoxicity and Antimicrobial Activity of P. magnifica Extracts

by Peter Kollar^1,*, Karel Šmejkal², Hana Salmonová³

, Eva Vlková³, Olga Lepšová-Skácelová⁴, Zuzana Balounová⁵, Josef Rajchard⁵, Josef Cvačka⁶

, Libor Jaša^7,8, Pavel Babica^7,8

and Jiří Pazourek⁹

¹ Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tř. 1946/1, Brno 61242, Czech Republic

² Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tř. 1946/1, Brno 61242, Czech Republic

³ Department of Microbiology, Nutrition and Dietetics, Faculty of Agrobiology, Food and Natural Resources, Czech University of Life Sciences Prague, Kamýcká 129, Prague 6, 16521, Czech Republic

⁴ Department of Botany, Faculty of Science, University of South Bohemia in České Budějovice, Branišovská 31, České Budějovice 37005, Czech Republic

⁵ Department of Biological Studies, Faculty of Agriculture, University of South Bohemia in České Budějovice, Studentská 13, České Budějovice 37005, Czech Republic

⁶ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, Prague 16610, Czech Republic

⁷ RECETOX—Research Centre for Toxic Compounds in the Environment, Faculty of Science, Masaryk University, Kamenice 753/5, Brno 60200, Czech Republic

⁸ Department of Experimental Phycology and Ecotoxicology, Institute of Botany, Academy of Sciences of the Czech Republic, Lidická 25/27, Brno 60200, Czech Republic

⁹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tř. 1946/1, Brno 61242, Czech Republic

Molecules 2016, 21(11), 1476; https://doi.org/10.3390/molecules21111476 - 4 Nov 2016

Cited by 7 | Viewed by 7383

Abstract

Pectinatella magnifica, an invasive bryozoan, might significantly affect ecosystem balance due to its massive occurrence in many areas in Europe and other parts of the world. Biological and chemical analyses are needed to get complete information about the impact of the animal [...] Read more.

Pectinatella magnifica, an invasive bryozoan, might significantly affect ecosystem balance due to its massive occurrence in many areas in Europe and other parts of the world. Biological and chemical analyses are needed to get complete information about the impact of the animal on the environment. In this paper, we aimed to evaluate in vitro cytotoxic effects of five extracts prepared from P. magnifica using LDH assay on THP-1 cell line. Antimicrobial activities of extracts against 22 different bacterial strains were tested by microdilution method. Our study showed that all extracts tested, except aqueous portion, demonstrated LD₅₀ values below 100 μg/mL, which indicates potential toxicity. The water extract of P. magnifica with LD₅₀ value of 250 μg/mL also shows potentially harmful effects. Also, an environmental risk resulting from the presence and increasing biomass of potentially toxic benthic cyanobacteria in old colonies should not be underestimated. Toxicity of Pectinatella extracts could be partially caused by presence of Aeromonas species in material, since we found members of these genera as most abundant bacteria associated with P. magnifica. Furthermore, P. magnifica seems to be a promising source of certain antimicrobial agents. Its methanolic extract, hexane, and chloroform fractions possessed selective inhibitory effect on some potential pathogens and food spoiling bacteria in the range of MIC 0.5–10 mg/mL. Future effort should be made to isolate and characterize the content compounds derived from P. magnifica, which could help to identify the substance(s) responsible for the toxic effects of P. magnifica extracts. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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11 pages, 1001 KiB

Open AccessArticle

Synthesis and Formulation of Thermosensitive Drug Carrier for Temperature Triggered Delivery of Naproxen Sodium

by Monika Gasztych, Agnieszka Gola

, Justyna Kobryń and Witold Musiał^*

Department of Physical Chemistry, Pharmaceutical Faculty, Wroclaw Medical University, Borowska 211, Wroclaw 50-556, Poland

Molecules 2016, 21(11), 1473; https://doi.org/10.3390/molecules21111473 - 4 Nov 2016

Cited by 11 | Viewed by 5564

Abstract

Nanospheres and microspheres are known as a multipurpose compounds and are used in various branches of science. Recent controlled delivery systems for drugs are also based on poly-micro and nanospheres. In our study we describe an investigation of the influence of thermosensitive polymer [...] Read more.

Nanospheres and microspheres are known as a multipurpose compounds and are used in various branches of science. Recent controlled delivery systems for drugs are also based on poly-micro and nanospheres. In our study we describe an investigation of the influence of thermosensitive polymer N-isopropylacrylamide (NIPA) on the release of the drug naproxen sodium (NS) with a hydrogel hydroxypropyl methylcellulose (HPMC) base. The hydrodynamic diameter (D_H) of the obtained polymer was measured by using dynamic light scattering (DLS) at a wavelength of 678 nm. Hydrogel formulations of NS were prepared in a specific way ex tempore. NS was sprinkled on the surface of a distilled water, then polymer soluted in water was added. Afterward, HPMC was affixed to the solution. Prepared samples were stored at room temperature for 24 h. Release tests showed that modification of thevcross-linker type influenced the properties of synthesized polymeric particles. The NIPA derivatives obtained via surfactant free precipitation polymerization (SFPP) may be formulated as hydrogel preparations using HPMC. The obtained formulations presented varied half-release times, depending on the type of applied NIPA derivatives in hydrogel formulations. At 18 °C, the release rates were lower comparing to the reference HPMC hydrogel, whereas at 42 °C, the release rates were significantly higher. The synthesized thermosensitive polymers enabled temperature-triggered release of NS. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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10 pages, 1816 KiB

Open AccessArticle

Developing HIV-1 Protease Inhibitors through Stereospecific Reactions in Protein Crystals

by Folasade M. Olajuyigbe^1,2,†, Nicola Demitri^1,3,†

, Rita De Zorzi¹ and Silvano Geremia^1,*

¹ Centre of Excellence in Biocrystallography, Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste 34127, Italy

² Department of Biochemistry, School of Sciences, Federal University of Technology Akure, P.M.B. 704, Akure 340252, Ondo State, Nigeria

³ Elettra-Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, Basovizza, Trieste 34149, Italy

^† These authors contributed equally to this work.

Molecules 2016, 21(11), 1458; https://doi.org/10.3390/molecules21111458 - 31 Oct 2016

Viewed by 6628

Abstract

Protease inhibitors are key components in the chemotherapy of HIV infection. However, the appearance of viral mutants routinely compromises their clinical efficacy, creating a constant need for new and more potent inhibitors. Recently, a new class of epoxide-based inhibitors of HIV-1 protease was [...] Read more.

Protease inhibitors are key components in the chemotherapy of HIV infection. However, the appearance of viral mutants routinely compromises their clinical efficacy, creating a constant need for new and more potent inhibitors. Recently, a new class of epoxide-based inhibitors of HIV-1 protease was investigated and the configuration of the epoxide carbons was demonstrated to play a crucial role in determining the binding affinity. Here we report the comparison between three crystal structures at near-atomic resolution of HIV-1 protease in complex with the epoxide-based inhibitor, revealing an in-situ epoxide ring opening triggered by a pH change in the mother solution of the crystal. Increased pH in the crystal allows a stereospecific nucleophile attack of an ammonia molecule onto an epoxide carbon, with formation of a new inhibitor containing amino-alcohol functions. The described experiments open a pathway for the development of new stereospecific protease inhibitors from a reactive lead compound. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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16 pages, 889 KiB

Open AccessArticle

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

by Marta Kucerova-Chlupacova^1,*

, Veronika Vyskovska-Tyllova¹, Lenka Richterova-Finkova¹, Jiri Kunes², Vladimir Buchta^3,4, Marcela Vejsova^3,4, Pavla Paterova^3,4, Lucia Semelkova¹, Ondrej Jandourek¹

and Veronika Opletalova¹

¹ Department of Pharmaceutical Chemistry and Pharmaceutical Analysis, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

² Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

³ Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

⁴ Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic

Molecules 2016, 21(11), 1421; https://doi.org/10.3390/molecules21111421 - 27 Oct 2016

Cited by 32 | Viewed by 8376

Abstract

Chalcones, i.e., compounds with the chemical pattern of 1,3-diphenylprop-2-en-1-ones, exert a wide range of bio-activities, e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc. Our research group has been focused on pyrazine analogues of chalcones; several series have been synthesized and tested in vitro on antifungal [...] Read more.

Chalcones, i.e., compounds with the chemical pattern of 1,3-diphenylprop-2-en-1-ones, exert a wide range of bio-activities, e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc. Our research group has been focused on pyrazine analogues of chalcones; several series have been synthesized and tested in vitro on antifungal and antimycobacterial activity. The highest potency was exhibited by derivatives with electron withdrawing groups (EWG) in positions 2 and 4 of the ring B. As halogens also have electron withdrawing properties, novel halogenated derivatives were prepared by Claisen-Schmidt condensation. All compounds were submitted for evaluation of their antifungal and antibacterial activity, including their antimycobacterial effect. In the antifungal assay against eight strains of selected fungi, growth inhibition of Candida glabrata and Trichophyton interdigitale (formerly T. mentagrophytes) was shown by non-alkylated derivatives with 2-bromo or 2-chloro substitution. In the panel of selected bacteria, 2-chloro derivatives showed the highest inhibitory effect on Staphylococcus sp. In addition, all products were also screened for their antimycobacterial activity against Mycobacterium tuberculosis H37RV My 331/88, M. kansasii My 235/80, M. avium 152/80 and M. smegmatis CCM 4622. Some of the examined compounds, inhibited growth of M. kansasii and M. smegmatis with minimum inhibitory concentrations (MICs) comparable with those of isoniazid. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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8 pages, 958 KiB

Open AccessArticle

The Determination of Food Dyes in Vitamins by RP-HPLC

by Monika Šuleková^*, Alexander Hudák and Miroslava Smrčová

Department of Chemistry, Biochemistry and Biophysics, Institute of Pharmaceutical Chemistry, The University of Veterinary Medicine and Pharmacy in Košice, Košice 04181, Slovakia

Molecules 2016, 21(10), 1368; https://doi.org/10.3390/molecules21101368 - 17 Oct 2016

Cited by 30 | Viewed by 11453

Abstract

Reversed-phase high performance liquid chromatography (RP-HPLC) for the determination of five synthetic food dyes (Quinoline Yellow E104, Sunset Yellow E110, Ponceau 4R E124, Tartrazine E102 and Carmine E120) in vitamins was used. The dyes were analyzed within 10 min using a column with [...] Read more.

Reversed-phase high performance liquid chromatography (RP-HPLC) for the determination of five synthetic food dyes (Quinoline Yellow E104, Sunset Yellow E110, Ponceau 4R E124, Tartrazine E102 and Carmine E120) in vitamins was used. The dyes were analyzed within 10 min using a column with stationary phase C 18 (250 mm × 4.6 mm, 5 μm) at 40 °C with isocratic elution, and the mobile phase contained acetonitrile and a mixture of CH₃COONa:CH₃OH (85:15, v/v) in a ratio of 10:90 (v/v) for yellow-colored capsules and 20:80 (v/v) for red-colored capsules, respectively. A diode-array detector was used to monitor the dyes between 190 and 800 nm. It was established that the analyzed samples contained synthetic dyes in a concentration range from 79.5 ± 0.01 μg/capsule of Ponceau 4R, E124 to 524 ± 0.01 μg/capsule of Tartrazine, E102. The obtained results were compared with existing acceptable daily intakes (ADIs) for individual dyes. This paper provides information about the content of dyes in samples of vitamins. This information is not generally available to consumers. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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25 pages, 1815 KiB

Open AccessArticle

The Structure–Antimicrobial Activity Relationships of a Promising Class of the Compounds Containing the N-Arylpiperazine Scaffold

by Ivan Malík^1,*, Jozef Csöllei², Josef Jampílek¹

, Lukáš Stanzel¹, Iveta Zadražilová³, Jan Hošek⁴

, Šárka Pospíšilová³, Alois Čížek³, Aidan Coffey⁵

and Jim O’Mahony⁵

¹ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, Bratislava SK-832 32, Slovak Republic

² Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences in Brno, Palackého 1946/1, Brno CZ-612 42, Czech Republic

³ Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences in Brno, Palackého 1946/1, Brno CZ-612 42, Czech Republic

⁴ Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences in Brno, Palackého 1946/1, Brno CZ-612 42, Czech Republic

⁵ Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork T12 P928, Ireland

Molecules 2016, 21(10), 1274; https://doi.org/10.3390/molecules21101274 - 26 Sep 2016

Cited by 17 | Viewed by 6291

Abstract

This research was focused on in silico characterization and in vitro biological testing of the series of the compounds carrying a N-arylpiperazine moiety. The in silico investigation was based on the prediction of electronic, steric and lipohydrophilic features. The molecules were screened [...] Read more.

This research was focused on in silico characterization and in vitro biological testing of the series of the compounds carrying a N-arylpiperazine moiety. The in silico investigation was based on the prediction of electronic, steric and lipohydrophilic features. The molecules were screened against Mycobacterium avium subsp. paratuberculosis CIT03, M. smegmatis ATCC 700084, M. kansasii DSM 44162, M. marinum CAMP 5644, Staphylococcus aureus ATCC 29213, methicillin-resistant S. aureus 63718, Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Candida albicans CCM 8261, C. parapsilosis CCM 8260 and C. krusei CCM 8271, respectively, by standardized microdilution methods. The eventual antiproliferative (cytotoxic) impact of those compounds was examined on a human monocytic leukemia THP-1 cell line, as a part of the biological study. Promising potential against M. kansasii was found for 1-[3-(3-ethoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride (MIC = 31.75 μM), which was comparable to the activity of isoniazid (INH; MIC = 29.17 μM). Moreover, 1-{2-hydroxy-3-(3-methoxyphenylcarbamoyl)oxy)propyl}-4-(4-fluorophenyl)piperazin-1-ium chloride was even more effective (MIC = 17.62 μM) against given mycobacterium. Among the tested N-arylpiperazines, 1-{2-hydroxy-3-(4-methoxyphenylcarbamoyl)oxy)propyl}-4-(3-trifluorometh-ylphenyl)piperazin-1-ium chloride was the most efficient against M. marinum (MIC = 65.32 μM). One of the common features of all investigated substances was their insignificant antiproliferative (i.e., non-cytotoxic) effect. The study discussed structure–antimicrobial activity relationships considering electronic, steric and lipophilic properties. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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15 pages, 844 KiB

Open AccessArticle

Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates

by Tomas Gonec^1,*

, Sarka Pospisilova², Lucie Holanova³, Josef Stranik¹, Aneta Cernikova¹, Valeria Pudelkova², Jiri Kos¹, Michal Oravec⁴

, Peter Kollar³, Alois Cizek² and Josef Jampilek^5,*

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic

² Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic

³ Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic

⁴ Global Change Research Institute CAS, Belidla 986/4a, Brno 60300, Czech Republic

⁵ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, Bratislava 83232, Slovakia

Molecules 2016, 21(9), 1189; https://doi.org/10.3390/molecules21091189 - 7 Sep 2016

Cited by 10 | Viewed by 5646

Abstract

Series of thirteen 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl carbamates and thirteen 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl carbamates with alkyl/cycloalkyl/arylalkyl chains were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, two methicillin-resistant S. aureus strains, Mycobacterium marinum, and M. kansasii. 1-[(2-Chlorophenyl)carbamoyl]naphthalen-2-yl ethylcarbamate [...] Read more.

Series of thirteen 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl carbamates and thirteen 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl carbamates with alkyl/cycloalkyl/arylalkyl chains were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, two methicillin-resistant S. aureus strains, Mycobacterium marinum, and M. kansasii. 1-[(2-Chlorophenyl)carbamoyl]naphthalen-2-yl ethylcarbamate and 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl ethylcarbamate showed antistaphylococcal (MICs = 42 µM against MRSA) and antimycobacterial (MICs = 21 µM) activity against the tested strains comparable with or higher than that of the standards ampicillin and isoniazid. In the case of bulkier carbamate tails (R > propyl/isopropyl), the activity was similar (MICs ca. 70 µM). Screening of the cytotoxicity of both of the most effective compounds was performed using THP-1 cells, and no significant lethal effect was observed (LD₅₀ >30 µM). The structure-activity relationships are discussed. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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17 pages, 1472 KiB

Open AccessReview

Discovery of Bioactive Compounds by the UIC-ICBG Drug Discovery Program in the 18 Years Since 1998

by Hong-Jie Zhang^1,*,†, Wan-Fei Li^1,†, Harry H. S. Fong² and Djaja Doel Soejarto²

¹ School of Chinese Medicine, Hong Kong Baptist University, Hong Kong SAR, China

² Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA

^† These authors contributed equally to this work.

Molecules 2016, 21(11), 1448; https://doi.org/10.3390/molecules21111448 - 31 Oct 2016

Cited by 7 | Viewed by 5839

Abstract

The International Cooperative Biodiversity Groups (ICBG) Program based at the University of Illinois at Chicago (UIC) is a program aimed to address the interdependent issues of inventory and conservation of biodiversity, drug discovery and sustained economic growth in both developing and developed countries. [...] Read more.

The International Cooperative Biodiversity Groups (ICBG) Program based at the University of Illinois at Chicago (UIC) is a program aimed to address the interdependent issues of inventory and conservation of biodiversity, drug discovery and sustained economic growth in both developing and developed countries. It is an interdisciplinary program involving the extensive synergies and collaborative efforts of botanists, chemists and biologists in the countries of Vietnam, Laos and the USA. The UIC-ICBG drug discovery efforts over the past 18 years have resulted in the collection of a cumulative total of more than 5500 plant samples (representing more than 2000 species), that were evaluated for their potential biological effects against cancer, HIV, bird flu, tuberculosis and malaria. The bioassay-guided fractionation and separation of the bioactive plant leads resulted in the isolation of approximately 300 compounds of varying degrees of structural complexity and/or biological activity. The present paper summarizes the significant drug discovery achievements made by the UIC-ICBG team of multidisciplinary collaborators in the project over the period of 1998–2012 and the projects carried on in the subsequent years by involving the researchers in Hong Kong. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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27 pages, 1004 KiB

Open AccessConference Report

The Eighth Central European Conference “Chemistry towards Biology”: Snapshot

by András Perczel^1,*, Atanas G. Atanasov^2,3,*

, Vladimír Sklenář⁴, Jiří Nováček⁴, Veronika Papoušková⁴, Pavel Kadeřávek⁴, Lukáš Žídek⁴, Henryk Kozłowski⁵, Joanna Wątły⁵

, Aleksandra Hecel⁵, Paulina Kołkowska⁵, Jaroslav Koča^4,6, Radka Svobodová-Vařeková^4,6, Lukáš Pravda^4,6

, David Sehnal^4,6, Vladimír Horský^4,6, Stanislav Geidl^4,6, Ricardo D. Enriz^7,8, Pavel Matějka⁹, Adéla Jeništová⁹, Marcela Dendisová⁹, Alžběta Kokaislová⁹, Volkmar Weissig¹⁰, Mark Olsen¹⁰, Aidan Coffey¹¹

, Jude Ajuebor¹¹, Ruth Keary¹¹, Marta Sanz-Gaitero¹², Mark J. Van Raaij¹²

, Olivia McAuliffe¹³, Birgit Waltenberger¹⁴, Andrei Mocan¹⁵, Karel Šmejkal¹⁶, Elke H. Heiss², Marc Diederich¹⁷

, Robert Musioł¹⁸, Janez Košmrlj¹⁹, Jarosław Polański¹⁸ and Josef Jampílek^20,*

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¹ Laboratory of Structural Chemistry and Biology and MTA-ELTE Protein Modeling Research Group at the Institute of Chemistry, Eötvös Loránd University, 1518, 112, PO Box 32, H-1053 Budapest, Hungary

² Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria

³ Institute of Genetics and Animal Breeding of the Polish Academy of Sciences, ul. Postepu 36A, 05552 Jastrzebiec, Poland

⁴ Central European Institute of Technology, Masaryk University, Kamenice 5, 62500 Brno, Czech Republic

⁵ Department of Biological Chemistry, Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland

⁶ National Centre for Biomolecular Research, Faculty of Science, Masaryk University, Kamenice 5, 62500 Brno, Czech Republic

⁷ Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco 917, 5700 San Luis, Argentina

⁸ Instituto Multidisciplinario de Investigaciones Biológicas de San Luis, Ejercito de Los Andes 950, 5700 San Luis, Argentina

⁹ Department of Physical Chemistry, Faculty of Chemical Engineering, University of Chemistry and Technology, Technická 5, 16628 Prague 6, Czech republic

¹⁰ Department of Medical Chemistry, College of Pharmacy Glendale, Midwestern University, 19555 N. 59th Avenue, Glendale, 85308 AZ, USA

¹¹ Department of Biological Sciences, Cork Institute of Technology, Bishopstown, T12 P928 Cork, Ireland

¹² Departamento de Estructura de Macromoleculas, Centro Nacional de Biotecnologia, Calle Darwin 3, 28049 Madrid, Spain

¹³ Biotechnology Department, Teagasc, Moorepark Food Research Centre, Fermoy, P61 C996 Co. Cork, Ireland

¹⁴ Department of Pharmacognosy, Institute of Pharmacy, University of Innsbruck, Innrain 80-82/IV, 6020 Innsbruck, Austria

¹⁵ Department of Pharmaceutical Botany, Iuliu Hațieganu University of Medicine and Pharmacy, 8 Victor Babes, 400012 Cluj-Napoca, Romania

¹⁶ Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého 1, 61242 Brno, Czech Republic

¹⁷ Department of Pharmacy, College of Pharmacy, Seoul National University, 1 Gwanak-ro, 08826 Seoul, Korea

¹⁸ Institute of Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland

¹⁹ Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia

²⁰ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, 83232 Bratislava, Slovakia

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Molecules 2016, 21(10), 1381; https://doi.org/10.3390/molecules21101381 - 17 Oct 2016

Cited by 5 | Viewed by 9424

Abstract

The Eighth Central European Conference “Chemistry towards Biology” was held in Brno, Czech Republic, on August 28–September 1, 2016 to bring together experts in biology, chemistry and design of bioactive compounds; promote the exchange of scientific results, methods and ideas; and encourage cooperation [...] Read more.

The Eighth Central European Conference “Chemistry towards Biology” was held in Brno, Czech Republic, on August 28–September 1, 2016 to bring together experts in biology, chemistry and design of bioactive compounds; promote the exchange of scientific results, methods and ideas; and encourage cooperation between researchers from all over the world. The topics of the conference covered “Chemistry towards Biology”, meaning that the event welcomed chemists working on biology-related problems, biologists using chemical methods, and students and other researchers of the respective areas that fall within the common scope of chemistry and biology. The authors of this manuscript are plenary speakers and other participants of the symposium and members of their research teams. The following summary highlights the major points/topics of the meeting. Full article

(This article belongs to the Special Issue Selected Papers from the 8th Central European Conference ‘Chemistry towards Biology’ (CTB-2016))

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