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Novel conformationally locked nucleosides and nucleotides based on bicyclo[3.2.1]octane scaffold as a pseudosugar moiety
Šála, Michal; Dejmek, Milan; Procházková, Eliška; Hřebabecký, Hubert; Rybáček, Jiří; Dračínský, Martin; Novák, Pavel; Rosenbergová, Šárka; Fukal, J.; Sychrovský, Vladimír; Rosenberg, Ivan; Nencka, Radim
2014 - English
A route to a series of novel carbocyclic nucleosides locked in North conformation with bicyclo[3.2.1]octane scaffold was developed. Prepared nucleosides served as a starting material for the synthesis of modified oligomers [d(GCATATCAC), r(GCAUAUCAC), and A9]. Biological effects of the prepared nucleosides as well as the hybridization properties of the appropriate duplexes were evaluated.
Keywords:
locked nucleosides; LNA
Available at various institutes of the ASCR
Novel conformationally locked nucleosides and nucleotides based on bicyclo[3.2.1]octane scaffold as a pseudosugar moiety
A route to a series of novel carbocyclic nucleosides locked in North conformation with bicyclo[3.2.1]octane scaffold was developed. Prepared nucleosides served as a starting material for the ...
Bi-substrate inhobitors of human pyrimidine 5’-nucleosidases
Šimák, Ondřej; Pachl, Petr; Jandušík, T.; Brynda, Jiří; Buděšínský, Miloš; Rosenberg, Ivan
2014 - English
The work is aimed at the synthesis of bi-substrate inhibitors of 5’-nucleosidases. The pyrimidine nucleobase of lead compound was derivatized in the 5-position with various phosphonic acids differing in conformational flexibility and in the length of alkyl side chain carrying phosphonate group. The phosphonic acid with optimal linker can reach the phosphate binding side and make strong interaction with the enzyme. Inhibition activity of such inhibitors and crystal structure of inhibitor-enzyme complex will be presented.
Keywords:
5’-nucleosidases; NPAs; bi-substrate inhibitors
Available at various institutes of the ASCR
Bi-substrate inhobitors of human pyrimidine 5’-nucleosidases
The work is aimed at the synthesis of bi-substrate inhibitors of 5’-nucleosidases. The pyrimidine nucleobase of lead compound was derivatized in the 5-position with various phosphonic acids differing ...
Synthesis and biological activity of thiophene fused 7-deazapurine ribonucleosides
Tichý, Michal; Hocek, Michal
2014 - English
A series of thieno[2’,3’:4,5]pyrrolo[2,3-d]pyrimidine ribonucleosides bearing various alkyl, amino or hetaryl groups in position 4 has been prepared and all compounds have been tested for cytostatic and antiviral activities (HCV and Dengue viruses).
Keywords:
nucleosides; cytostatics; 7-deazapurine ribonucleosides
Available at various institutes of the ASCR
Synthesis and biological activity of thiophene fused 7-deazapurine ribonucleosides
A series of thieno[2’,3’:4,5]pyrrolo[2,3-d]pyrimidine ribonucleosides bearing various alkyl, amino or hetaryl groups in position 4 has been prepared and all compounds have been tested for cytostatic ...
Analysis and characterization of antimicrobial peptides by capillary electrophoresis
Tůmová, Tereza; Monincová, Lenka; Čeřovský, Václav; Kašička, Václav
2014 - English
Capillary electrophoresis has been employed for quantitative and qualitative analysis, separation and characterization of antimicrobial peptides – halictines. In addition to purity degree of synthetic peptides, also their effective and ionic mobilities and charges within a wide pH range were determined.
Keywords:
capillary electrophoresis; halictines; physico-chemical parameters
Available at various institutes of the ASCR
Analysis and characterization of antimicrobial peptides by capillary electrophoresis
Capillary electrophoresis has been employed for quantitative and qualitative analysis, separation and characterization of antimicrobial peptides – halictines. In addition to purity degree of synthetic ...
Development and applications of ionization techniques in ambient mass spectrometry
Rejšek, Jan; Vrkoslav, Vladimír; Cvačka, Josef
2014 - English
Ambient mass spectrometry is a sharply developing subject area. Desorption electrospray ionization (DESI) and desorption atmospheric pressure photoionization (DAPPI) are two types of ionization techniques in the ambient mass spectometry. Herein, they were investigated in two research areas: (1) TLC analysis. (2) Localization of insect defense glands.
Keywords:
ambient mass spectrometry; desorption electrospray ionization; desorption atmospheric pressure photoionization; thin-layer chromatography; insect defense compounds; mass spectrometry imaging
Available at various institutes of the ASCR
Development and applications of ionization techniques in ambient mass spectrometry
Ambient mass spectrometry is a sharply developing subject area. Desorption electrospray ionization (DESI) and desorption atmospheric pressure photoionization (DAPPI) are two types of ionization ...
Voltammetric Behavior of 4-Aminophthalimide Label using Hanging Mercury Drop Electrode
Ferenčíková, Z.; Daňhel, Aleš; Riedl, Jan; Hocek, Michal; Fojta, Miroslav
2014 - English
4-aminophthalimide (API), covalently attached to nucleotide (dCTP or dATP) has recently beendesigned as a fluorescent label for the detection of DNA-protein interaction. However API is electrochemically reducible and therefore it is possible to use alternatively the API-modified nuclotides as DNA redox labels. The electrochemical behavior of labeled nucleotides and labeled DNA was studied using cyclic voltammetry and transfer stripping cyclic voltammetry at hanging mercury drop electrode. Observed CVs showed irreversible reduction signals of 4-aminophthalimide label without production of consequently oxidizable/reducible species.
Keywords:
labeled nucleotide; 4-aminophthalimide; primer extension; DNA; hanging mercury drop electrode; voltammetry
Available at various institutes of the ASCR
Voltammetric Behavior of 4-Aminophthalimide Label using Hanging Mercury Drop Electrode
4-aminophthalimide (API), covalently attached to nucleotide (dCTP or dATP) has recently beendesigned as a fluorescent label for the detection of DNA-protein interaction. However API is ...
Separation of nonpolar lipids from vernix caseosa
Háková, Eva; Míková, Radka; Vrkoslav, Vladimír; Doležal, A.; Plavka, R.; Cvačka, Josef
2014 - English
The aim of this work is to develop a separation method for characterization of unknown nonpolar lipids in vernix caseosa. Here we optimized adsorption chromatography coupled to mass spectrometry detection with exact mass measurement. A long silica gel column (250 + 250 x 4.6 mm, particle size: 5 mu m) provided the best separation of nonpolar lipids present in vernix caseosa.
Keywords:
vernix caseosa; lipids; normal-phase chromatography; mass spectrometry
Available at various institutes of the ASCR
Separation of nonpolar lipids from vernix caseosa
The aim of this work is to develop a separation method for characterization of unknown nonpolar lipids in vernix caseosa. Here we optimized adsorption chromatography coupled to mass spectrometry ...
Capillary electrophoresis applied to chiral analysis of helquats and characterization of their intermediates and interconversion barriers using randomly and single isomer sulfated cyclodextrins as stereoselectors
Kašička, Václav; Koval, Dušan; Sázelová, Petra; Severa, Lukáš; Vávra, Jan; Adriaenssens, Louis; Sonawane, Manoj R.; Teplý, Filip
2014 - English
Capillary electrophoresis in acidic sodium phosphate background electrolyte, pH 2.4, with randomly sulfated alfa-, beta- and gamma-cyclodextrins as chiral selectors was applied to fast, high-resolution separation of enantiomers of a series of 35 helquats, a new class of N-heteroaromatic dicationic helicene-like species. The developed methodology was employed for evaluation of preparative enantioresolution procedures of helquats, for monitoring their racemization and for determination of interconversion barrier of helquat enantiomers.
Keywords:
helquats; chiral analysis; capillary electrophoresis
Available at various institutes of the ASCR
Capillary electrophoresis applied to chiral analysis of helquats and characterization of their intermediates and interconversion barriers using randomly and single isomer sulfated cyclodextrins as stereoselectors
Capillary electrophoresis in acidic sodium phosphate background electrolyte, pH 2.4, with randomly sulfated alfa-, beta- and gamma-cyclodextrins as chiral selectors was applied to fast, ...
Affinity capillary electrophoresis applied for study of solvent effect on stability constant of dibenzo-18-crown-6 complex with potassium ion
Konášová, Renáta; Jaklová Dytrtová, Jana; Kašička, Václav
2014 - English
Affinity capillary electrophoresis was used for investigation of solvent effect on stability constant of dibenzo-18-crown-6 complex with potassium ion in mixed hydro-organic solvents at different water/methanol and water/ethanol ratios. The stability constant of the complex was decreasing with increasing molar fraction of water in mixed solvents and almost independent of the organic solvent used.
Keywords:
affinity capillary electrophoresis; solvent effect; binding constant
Available at various institutes of the ASCR
Affinity capillary electrophoresis applied for study of solvent effect on stability constant of dibenzo-18-crown-6 complex with potassium ion
Affinity capillary electrophoresis was used for investigation of solvent effect on stability constant of dibenzo-18-crown-6 complex with potassium ion in mixed hydro-organic solvents at different ...
Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
Procházková, Eliška; Čechová, Lucie; Žurek, Jiří; Janeba, Zlatko; Dračínský, Martin
2014 - English
The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents in the positions 4 and 6. Mixtures of two rotamers differing in the orientation of the nitroso group were observed in the NMR spectra of the compounds where two distinct intramolecular hydrogen bonds could be formed. In several cases, we were able to isolate and characterize the two hydrogen bond isomers (two conformers) by column chromatography. The ratio of the two rotamers in equilibrium depends strongly on the character of the substituents in the positions 4 and 6 and can be finely tuned in a broad range of conformation ratios. The experimental results were supported by DFT calculations.
Keywords:
intramolecular hydrogen bonds; polysubstituted 5-nitrosopyrimidines; NMR spectroscopy
Available at various institutes of the ASCR
Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents in the positions 4 and 6. Mixtures of two ...
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