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Fajkusova D.,University of Veterinary And Pharmaceutical Sciences Brno | Pesko M.,Comenius University | Keltosova S.,University of Veterinary And Pharmaceutical Sciences Brno | Guo J.,Cork Institute of Technology | And 9 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

In this study, a series of N-substituted 2-aminobenzothiazoles was prepared according to a recently developed method. Twelve compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the discussed compounds was also performed against fungal, bacterial and mycobacterial species. The biological activities of some compounds were comparable or higher than the standards phenoxymethylpenicillin or pyrazinamide. The most effective compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. For all compounds, the structure-activity relationships are discussed. © 2012 Elsevier Ltd. All rights reserved.


Krompiec S.,University of Silesia | Malarz J.,University of Silesia | Pietraszuk C.,Adam Mickiewicz University | Powala B.,Adam Mickiewicz University | And 14 more authors.
Current Organic Chemistry | Year: 2014

A new strategy for the synthesis of trans- and cis + trans-3,4,5-trisubstituted isoxazolines from allyl compounds of QCH2CH=CH2 type (Q = PhO, 2,2’-bithiophen-5-yl, BuO, Me3CS, PhN(COMe) and others) has been developed. The dipolarophiles are prepared via: a) Ru-carbene catalysed metathesis of Qallyl; b) catalytic isomerization followed by Ru-carbene mediated metathesis; c) Ru-carbene catalysed metathesis followed by isomerization. 1,3-dipolar cycloaddition of nitrile oxide to dipolarophiles obtained via route a), b) or c), including high pressure activated reactions leads to 3,4,5-trisubstituted isoxazolines. Quantitative E-stereoselective homometathesis of some QCH2CH=CH2 to (E)-QCH2CH=CHCH2Q and new highly effective ruthenium and basic catalytic systems for the isomerization of allyl compounds have also been presented. Moreover, easily available (Z)-XCH2CH=CHCH2X allyl compounds were used for the synthesis of cis-3,4,5-trisubstituted isoxazolines. It has been proved by in vitro tests that some of the isoxazolines show interesting antifungal activity comparable to that of fluconazole. © 2014 Bentham Science Publishers.


Serda M.,University of Silesia | Anna M.-W.,University of Silesia | Jampilek J.,University of Veterinary And Pharmaceutical Sciences Brno | Jampilek J.,Research Institute for Pharmacy and Biochemistry | And 6 more authors.
Molecules | Year: 2012

Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds. © 2012 by the authors.


Cieslik W.,University of Silesia | Musiol R.,University of Silesia | Nycz J.E.,University of Silesia | Jampilek J.,University of Veterinary And Pharmaceutical Sciences Brno | And 5 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

Series of new ring-substituted styrylquinolines and two oxorhenium complexes were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against fungal and bacterial strains. Some compounds were active against bacteria at micromolar level and against fungi at submicromolar level. Compounds 5,7-dichloro-2-[2-(2-ethoxyphenyl)vinyl]quinolin- 8-ol expressed excellent antifungal activity comparable with or higher than the standard fluconazole as well as antibacterial activity against Staphylococcus strains comparable with or higher than the standards bacitracin, penicillin and ciprofloxacin. The structure-activity relationships are discussed. © 2012 Elsevier Ltd. All rights reserved.


Coufalova L.,University of Veterinary And Pharmaceutical Sciences Brno | Mrozek L.,R.Ø.S.A. | Rarova L.,Palacky University | Placek L.,R.Ø.S.A. | And 9 more authors.
Steroids | Year: 2013

A series of final twelve propanoyloxy derivatives of 5β-cholan-24-oic acid (O-propanoyl derivatives of cholic acid) as potential drug absorption modifiers (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by 1H NMR, 13C NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (RM) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukemia cell line and breast adenocarcinoma cell line. One compound showed selective cytotoxicity against human skin fibroblast cells and another compound possessed the highest cytotoxicity against all the tested cell lines. Only one compound expressed anti-proliferative effect on leukemia cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 μM), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effect are discussed in this article.© 2013 Elsevier Inc. All rights reserved.


Vaculikova E.,University of Veterinary And Pharmaceutical Sciences Brno | Vaculikova E.,VSB - Technical University of Ostrava | Grunwaldova V.,Institute of Chemical Technology Prague | Grunwaldova V.,Academy of Sciences of the Czech Republic | And 5 more authors.
Molecules | Year: 2012

The solubility, absorption and distribution of a drug are involved in the basic aspects of oral bioavailability Solubility is an essential characteristic and influences the efficiency of the drug. Over the last ten years, the number of poorly soluble drugs has steadily increased. One of the progressive ways for increasing oral bioavaibility is the technique of nanoparticle preparation, which allows many drugs to thus reach the intended site of action. Candesartan cilexetil and atorvastatin, belonging to class II of the biopharmaceutical classification system, were chosen as model active pharmaceutical ingredients in this study. Forty samples were prepared either by antisolvent precipitation/solvent evaporation method or by the emulsion/solvent evaporation technique with various commonly used surface-active excipients as nanoparticle stabilizers. All samples were analyzed by means of dynamic light scattering. The particle size of the determined 36 nanoparticle samples was to 574 nm, whereas 32 samples contained nanoparticles of less than 200 nm. Relationships between solvents and excipients used and their amount are discussed. Based on the results the investigated solvent evaporation methods can be used as an effective and an affordable technique for the preparation of nanoparticles. © 2012 by the authors.


Vaculikova E.,University of Veterinary And Pharmaceutical Sciences Brno | Vaculikova E.,VSB - Technical University of Ostrava | Grunwaldova V.,Institute of Chemical Technology Prague | Grunwaldova V.,Academy of Sciences of the Czech Republic | And 5 more authors.
Molecules | Year: 2012

The absorption, distribution, biotransformation and excretion of a drug involve its transport across cell membranes. This process is essential and influenced by the characteristics of the drug, especially its molecular size and shape, solubility at the site of its absorption, relative lipid solubility, etc. One of the progressive ways for increasing bioavaibility is a nanoparticle preparation technique. Cholesterol, cholestenolone and pregnenolone acetate as model active pharmaceutical ingredients and some of the commonly used excipients as nanoparticle stabilizers were used in the investigated precipitation method that was modified and simplified and can be used as an effective and an affordable technique for the preparation of nanoparticles. All 120 prepared samples were analyzed by means of dynamic light scattering (Nanophox). The range of the particle size of the determined 100 nanoparticle samples was from 1 nm to 773 nm, whereas 82 samples contained nanoparticles of less than 200 nm. Relationships between solvents and used excipients and their amount are discussed. © 2012 by the authors.


Kral'ova K.,Comenius University | Jampilek J.,University of Veterinary And Pharmaceutical Sciences Brno | Jampilek J.,Research Institute for Pharmacy and Biochemistry | Ostrovsky I.,Comenius University
Ecological Chemistry and Engineering S | Year: 2012

Abiotic stresses are produced by inappropriate levels of physical components of the environment and cause plant injury through unique mechanisms that result in specific responses. Metabolomics is a relatively new approach aimed at improved understanding of metabolic networks and the subsequent biochemical composition of plants and other biological organisms. The paper is focused on the use of metabolomics, metabolic profiling and metabolic fingerprinting to study plant responses to some environmental stresses (eg elevated temperature, chilling and freezing, drought, high salinity, UV radiation, high ozone levels, nutrient deficiency, oxidative stress, herbicides and heavy metals). Attention is also devoted to the effects of some environmental factors on plants such as high or low levels of CO2 or different levels of irradiance. Alterations of plants metabolites due to multiple abiotic stresses (drought-heat, drought-salinity, elevated CO 2-salinity) are analysed as well. In addition, metabolomic approach to study plant responses to some artificial abiotic stresses, mechanical stress or pulsed electric field-induced stress is discussed. The most important analytical methods applied in metabolomics are presented and perspectives of metabolomics exploitation in the future are outlined, too.

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