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Chiral analysis of alfa-diimine Ru(II) and Fe(II) complexes by capillary electrophoresis using sulfated cyclodextrins as stereoselectors
Sázelová, Petra; Koval, Dušan; Severa, Lukáš; Teplý, Filip; Kašička, Václav
2014 - English
A fast and efficient capillary electrophoretic method was developed for enantioseparation of Ru(II) and Fe(II) polypyridyl complexes using anionic randomly sulfated alfa-, beta-, and gamma-cyclodextrins (S-alfa-CD, S-beta-CD, and S-gamma-CD) and their heptakis-(2,3-diacetyl-6-sulfato)-derivatives (Ac-S-alfa-CD, Ac-S-beta-CD, and Ac-S-gamma-CD) as chiral selectors. S-alfa-CD and S-gamma-CD were found to be the best chiral selectors providing high resolutions and short analysis times. The method was applied for the assessment of chiral purity of some batches of [Ru(bpy)3]2+ catalyst.
Keywords:
capillary electrophoresis; chiral analysis; metal-polypyridyl complexes
Available at various institutes of the ASCR
Chiral analysis of alfa-diimine Ru(II) and Fe(II) complexes by capillary electrophoresis using sulfated cyclodextrins as stereoselectors
A fast and efficient capillary electrophoretic method was developed for enantioseparation of Ru(II) and Fe(II) polypyridyl complexes using anionic randomly sulfated alfa-, beta-, and ...
Polymerase synthesis of base-modified DNA: New methods and new applications
Balintová, Jana; Daďová, Jitka; Kielkowski, Pavel; Ménová, Petra; Vaníková, Zuzana; Riedl, Jan; Raindlová, Veronika; Fojta, Miroslav; Hocek, Michal
2014 - English
Diverse base-modified oligonucleotides and double-stranded DNA molecules were prepared by polymerase incorporation of modified nucleoside triphosphates. The methods include primer extension, PCR, nicking enzyme amplification reaction and mixed incorporations. The modified nucleic acids were used in redox and fluorescence labelling and coding, as well as regulation of binding and cross-linking with proteins.
Keywords:
nucleic acids; base-modified DNA; dNTPs
Available at various institutes of the ASCR
Polymerase synthesis of base-modified DNA: New methods and new applications
Diverse base-modified oligonucleotides and double-stranded DNA molecules were prepared by polymerase incorporation of modified nucleoside triphosphates. The methods include primer extension, PCR, ...
Acyclic nucleoside bisphosphonates as inhibitors of 6-oxopurine phosphoribosyltransferases: Potential antimalarial and antibacterial agents
Hocková, Dana; Keough, D. T.; Špaček, Petr; Janeba, Zlatko; Edstein, M. D.; Chavchich, M.; Wang, T. H.; Eng, W. S.; West, N. P.; de Jersey, J.; Guddat, L. W.
2014 - English
Acyclic nucleoside phosphonates (ANPs) that contain a 6-oxopurine base are good inhibitors of the human, Plasmodium falciparum, P. vivax, Escherichia coli and Mycobacterium tuberculosis 6-oxopurine phosphoribosyltransferases (PRTases), key enzymes of the purine salvage pathway. Chemical modifications based on the crystal structures of several inhibitors in complex with human HGPRTase have led to the design of new ANPs. These novel compounds contain a second phosphonate group attached to the ANP scaff old. The crystal structures of these inhibitors in complex with human HGPRTase show that they can fill three critical locations in the active site: the binding sites of the purine base, the 5’-phosphate group and pyrophosphate. Prodrugs have been synthesized and have been shown to arrest the growth of P. falciparum in erythrocyte culture. Prodrugs of selected ANPs also inhibit the growth of Mycobacterium tuberculosis in cell-based assays.
Keywords:
nucleotide analogues; enzyme inhibitors; Plasmodium
Available at various institutes of the ASCR
Acyclic nucleoside bisphosphonates as inhibitors of 6-oxopurine phosphoribosyltransferases: Potential antimalarial and antibacterial agents
Acyclic nucleoside phosphonates (ANPs) that contain a 6-oxopurine base are good inhibitors of the human, Plasmodium falciparum, P. vivax, Escherichia coli and Mycobacterium tuberculosis 6-oxopurine ...
Oligonucleotides modified with acyclic nucleoside phosphonate (HPEP) units
Kaiser, Martin Maxmilian; Novák, Pavel; Rosenbergová, Šárka; Poštová Slavětínská, Lenka; Rosenberg, Ivan; Janeba, Zlatko
2014 - English
Two acyclic nucleoside phosphonates bearing 9-[3-hydroxy-2-(phosphonoethoxy)propyl] (HPEP) moiety and either adenine and thymine as nucleobase were synthetically converted into a suitable building blocks for the subsequent automated solid phase synthesis of modified oligonucleotides. Phosphoramidite chemistry was used for the synthesis of a series of complementary nonamers where the modified acyclic monomers were incorporated using the phosphotriester method. Determination of thermal characteristics of the complexes of the modified nonamers with the complementary strands revealed a destabilizing effect of the introduced acyclic modifications.
Keywords:
acyclic nucleoside phosphonate; HPEP; oligonucleotides
Available at various institutes of the ASCR
Oligonucleotides modified with acyclic nucleoside phosphonate (HPEP) units
Two acyclic nucleoside phosphonates bearing 9-[3-hydroxy-2-(phosphonoethoxy)propyl] (HPEP) moiety and either adenine and thymine as nucleobase were synthetically converted into a suitable building ...
Preparation of modified oligonucleotides by nicking enzyme amplification reaction
Ménová, Petra; Hocek, Michal
2014 - English
A method for the enzymatic synthesis of short (10-22 nt) base-modified oligonucleotides was developed, based on the nicking enzyme amplification reaction. The methodology, including product isolation and purification, was scaled up to nanomolar amounts. The modified oligonucleotides were successfully used as primers in primer extension and PCR, affording primer-modified oligonucleotides and DNA. Two simple and efficient methods for fluorescent labelling of the PCR products were also developed.
Keywords:
dNTPs; DNA; oligonucleotides
Available at various institutes of the ASCR
Preparation of modified oligonucleotides by nicking enzyme amplification reaction
A method for the enzymatic synthesis of short (10-22 nt) base-modified oligonucleotides was developed, based on the nicking enzyme amplification reaction. The methodology, including product isolation ...
New oxidative labels for electrochemical detection of DNA
Simonova, Anna; Havran, Luděk; Fojta, Miroslav; Hocek, Michal
2014 - English
New dCTP and dATP derivatives bearing oxidizable labels have been synthesized and incorporated to DNA for studying their electrochemical properties in different sequences of DNA.
Keywords:
dNTPs; DNA; electrochemical properties
Available at various institutes of the ASCR
New oxidative labels for electrochemical detection of DNA
New dCTP and dATP derivatives bearing oxidizable labels have been synthesized and incorporated to DNA for studying their electrochemical properties in different sequences of DNA.
Acyclic nucleoside bis-phosphonates as potent inhibitors of 6-oxopurine phosphoribosyltransferases
Špaček, Petr; Keough, D. T.; Vrbková, Silvie; Slavětínská, Lenka; Janeba, Zlatko; Naesens, L.; Edstein, M. D.; Chavchich, M.; Wang, T. H.; de Jersey, J.; Guddat, L. W.; Hocková, Dana
2014 - English
Hypoxanthine-guanin-(xanthine) phosphoribosyltransferase (HG(X)PRT) is critical for the survival of malarial parasites Plasmodium falciparum and Plasmodium vivax. These parasites rely on HG(X)PRT to make 6-oxopurine nucleoside monophosphates. Specific acyclic nucleoside phosphonates (ANPs) inhibit HG(X)PRT and thus have an anti-plasmodial activity. Crystal structures of human HGPRT in complex with several ANP-based inhibitors suggested that attachment of the second phosphonate group which could occupy the pyrophosphate binding site may lead to increased affinity of these compounds.
Keywords:
nucleotide analogues; enzyme inhibitors; Plasmodium
Available at various institutes of the ASCR
Acyclic nucleoside bis-phosphonates as potent inhibitors of 6-oxopurine phosphoribosyltransferases
Hypoxanthine-guanin-(xanthine) phosphoribosyltransferase (HG(X)PRT) is critical for the survival of malarial parasites Plasmodium falciparum and Plasmodium vivax. These parasites rely on HG(X)PRT to ...
Utilisation of enzymatic labelling with 4-aminophtalimide and 4-hydroxybenzylideneimidazolinone fluorescent derivates for monitoring of DNA-protein interaction
Orság, Petr; Pivoňková, Hana; Riedl, Jan; Hocek, Michal; Fojta, Miroslav
2014 - English
The 5’-substituted deoxycytosine triphosphates with conjugated solvatochromic derivates of 4-aminophtalimide (API) and derivates of the green fluorescent protein, 4-hydroxybenzylideneimidazolinone (HBI) were synthetized and successfully tested for enzymatic incorporation using primer extension assay. Site specifically labelled oligonucleotide probes were prepared and tested for interaction with p53 and SSB proteins, displaying distinct DNA-binding properties. The incorporation of multiple fluorescent labels did not interfere with natural protein binding and protein interaction leaded in both cases the to the gradual ratiometric increase of the fluorescence intensity moreover accompanied with the changes of the fluorescence emission spectra profile. Neither effect was observed after incubation with BSA, non-DNA binding protein, confirming the specificity of the interaction. Modified nucleoside triphosphates with conjugated fluorescence labels derivates of API and HBI can be used as substrates for preparation of the specific oligonucleotide labelled probes and provide the novel tool for studying and monitoring the DNA-protein interaction.
Keywords:
DNA-protein interaction; API; HBI
Available at various institutes of the ASCR
Utilisation of enzymatic labelling with 4-aminophtalimide and 4-hydroxybenzylideneimidazolinone fluorescent derivates for monitoring of DNA-protein interaction
The 5’-substituted deoxycytosine triphosphates with conjugated solvatochromic derivates of 4-aminophtalimide (API) and derivates of the green fluorescent protein, 4-hydroxybenzylideneimidazolinone ...
Searching for Electrochemical Reduction Mechanism of Azidophenyl DNA Labels
Daňhel, Aleš; Trošanová, Zuzana; Balintová, Jana; Hocek, Michal; Fojta, Miroslav
2014 - English
This contribution brings new information to sporadic scientific results concerned to electrochemical reduction of aromatic azides. Selected compounds used as perspective DNA labels or their structural constituents such as, 4-azidophenyltrifluoroboronic acid, 4-azidophenyl modified deoxycytidine and next probable analogous compounds and/or products of their reduction, were voltammetrically studied and compared to each other in order to reveal a mechanism of their electrochemical reduction at mercury electrodes in aqueous media. Preliminary results obtained by cyclic voltammetry at mercury and carbon based electrodes and by mass spectrometry of the products isolated from batch electrolysis on mercury pool by preparative chromatography are discussed.
Keywords:
aromatic azides; DNA labels; mercury electrode; reduction mechanism; voltammetry
Available at various institutes of the ASCR
Searching for Electrochemical Reduction Mechanism of Azidophenyl DNA Labels
This contribution brings new information to sporadic scientific results concerned to electrochemical reduction of aromatic azides. Selected compounds used as perspective DNA labels or their structural ...
Sulfur-containing phosphonate monomers for oligonucleotide synthesis
Kostov, Ondřej; Zborníková, Eva; Buděšínský, Miloš; Novák, Pavel; Rosenberg, Ivan
2014 - English
A series of novel compounds, protected S-MOP nucleoside-5’-O-methylphosphonothioates, was prepared as monomers for solid phase synthesis of phosphonothioate oligonucleotides. In addition we have examined the synthetic potential of nucleoside-5’-O-methyl-(H)-phosphinates for phosphonate oligonucleotide assembly.
Keywords:
S-MOP; oligonucleotides
Available at various institutes of the ASCR
Sulfur-containing phosphonate monomers for oligonucleotide synthesis
A series of novel compounds, protected S-MOP nucleoside-5’-O-methylphosphonothioates, was prepared as monomers for solid phase synthesis of phosphonothioate oligonucleotides. In addition we have ...
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