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5-(Pyren-1-yl)uracil UNA monomers: Synthesis, hybridization studies and i-motif stability
Perlíková, Pavla; Pedersen, E. B.; Wengel, J.
2014 - English
We have used direct conjugation of a pyrene moiety to a uracil base in synthesis of novel pyrene-modified UNA building blocks. Oligonucleotides with bulge-incorporated pyrene-modified UNA monomers showed increased duplex thermal stability, whereas destabilizing effect was observed in fully matched duplexes and in i-motifs.
Keywords:
5-(pyren-1-yl)uracil UNA monomers; DNA; unlocked nucleic acids
Available at various institutes of the ASCR
5-(Pyren-1-yl)uracil UNA monomers: Synthesis, hybridization studies and i-motif stability
We have used direct conjugation of a pyrene moiety to a uracil base in synthesis of novel pyrene-modified UNA building blocks. Oligonucleotides with bulge-incorporated pyrene-modified UNA monomers ...
Insights into the mechanism of action of bactericidal lipophosphonoxins
Panova, Natalya; Zborníková, Eva; Šimák, Ondřej; Krásný, Libor; Kolář, M.; Látal, T.; Seydlová, G.; Rejman, Dominik
2014 - English
The advantages offered by antibiotics in the treatment of infectious diseases are endangered due to the increase in the number of antibiotic-resistant bacterial strains. This reduces the efficiency of antibiotic treatments and poses a serious health and economical problem. Currently, the need for novel antibiotics is becoming increasingly apparent. Recently, we discovered a series of compounds termed lipophosphonoxins exhibiting selective cytotoxicity towards gram-positive bacterial cells. The attempt to elucidate the mode of action of lipophosphonoxins is presented here.
Keywords:
lipophosphonoxins; cytotoxicity; antibiotics
Available at various institutes of the ASCR
Insights into the mechanism of action of bactericidal lipophosphonoxins
The advantages offered by antibiotics in the treatment of infectious diseases are endangered due to the increase in the number of antibiotic-resistant bacterial strains. This reduces the efficiency ...
Tyrosine-based prodrugs of acyclic nucleoside phosphonates
Tichý, Tomáš; Pomeisl, Karel; Krečmerová, Marcela; McKenna, Ch. E.
2014 - English
Prodrug approach based on masking of a phosphonate function by ester linkage to a tyrosine promoiety has been developed. Results demonstrate that tyrosine is a promoiety providing drug conjugates with good chemical stability, bioavailability and efficient activation to active drug species. Another properties like metabolic stability and antiviral activity can be tuned by modification of the carboxyl function of the promoiety. Phosphonate monoester prodrugs were prepared by PyBOP coupling of a protected tyrosine promoiety with suitably derivatized phosphonate function of the parent drug. Phosphonate diester prodrugs were prepared by "synthon" approach, emloying alkylation of purine nucleobase with pre-prepared PME synthons bearing two protected tyrosine promoieties.
Keywords:
acyclic nucleoside phosphonates; prodrug; tyrosine
Available at various institutes of the ASCR
Tyrosine-based prodrugs of acyclic nucleoside phosphonates
Prodrug approach based on masking of a phosphonate function by ester linkage to a tyrosine promoiety has been developed. Results demonstrate that tyrosine is a promoiety providing drug conjugates ...
Redox labeling and redox coding of nucleic acids
Balintová, Jana; Brázdová, Marie; Havran, Luděk; Fojta, Miroslav; Hocek, Michal
2014 - English
Modified nucleoside triphosphates (dNTPs) bearing benzofurazane, azides and triazoles were prepared by Sonogashira or Suzuki cross-coupling. Polymerase incorporations of the functionalyzed dNTPs into DNA by primer extension and their electrochemical properties have been studied.
Keywords:
nucleic acids; DNA; dNTPs
Available at various institutes of the ASCR
Redox labeling and redox coding of nucleic acids
Modified nucleoside triphosphates (dNTPs) bearing benzofurazane, azides and triazoles were prepared by Sonogashira or Suzuki cross-coupling. Polymerase incorporations of the functionalyzed dNTPs into ...
Study of DNA-protein interactions by cross-link formation using aqueous Michael addition
Daďová, Jitka; Orság, Petr; Pohl, Radek; Brázdová, Marie; Fojta, Miroslav; Hocek, Michal
2014 - English
Acrylamide and vinylsulfonamide were designed as reactive DNA modifications for covalent crosslinking with cysteine containing peptides and proteins. The corresponding functionalized cytidine triphosphates were prepared and enzymatically incorporated into DNA. These modified oligonucleotides were then used for conjugation with DNA binding domain of protein p53.
Keywords:
nucleic acids; DNA; Michael addition
Available at various institutes of the ASCR
Study of DNA-protein interactions by cross-link formation using aqueous Michael addition
Acrylamide and vinylsulfonamide were designed as reactive DNA modifications for covalent crosslinking with cysteine containing peptides and proteins. The corresponding functionalized cytidine ...
Synthesis and biological properties of polysubstituted 5-nitrosopyrimidines
Janeba, Zlatko; Čechová, Lucie; Žurek, Jiří; Procházková, Eliška; Dračínský, Martin
2014 - English
2,4,6-Triamino-5-nitrosopyrimidines have been reported to contain a strong intramolecular hydrogen bond between the 5-nitroso and 4- or 6-amino groups, thus forming an additional pseudoring. Such analogues were speculated to be good mimics of fused bicyclic derivatives, e.g. purines. A series of novel polysubstituted 2-amino-5-nitrosopyrimidines, as potential structural mimics of modifi ed purine nucleos(t)ides well-known for their important biological properties, has been designed and synthesized. The physicochemical and biological properties of the prepared polysubstituted 2-amino-5-nitrosopyrimidines are being evaluated.
Keywords:
polysubstituted 5-nitrosopyrimidines; intramolecular hydrogen bond; NMR spectroscopy
Available at various institutes of the ASCR
Synthesis and biological properties of polysubstituted 5-nitrosopyrimidines
2,4,6-Triamino-5-nitrosopyrimidines have been reported to contain a strong intramolecular hydrogen bond between the 5-nitroso and 4- or 6-amino groups, thus forming an additional pseudoring. Such ...
Competitive incorporations of modified versus natural nucleotides by DNA polymerases
Kielkowski, Pavel; Hocek, Michal
2014 - English
A series of 7-substituted 7-deazaadenosine and 5-substituted cytosine triphosphates were tested in competitive incorporations with different DNA polymerases with their natural analogs and analyzed using restriction endonucleases and compared with steady state kinetics of the modified and natural dNTPs. Data sets correlation is up to 99 % and gave us to find modified dATPs with high incorporation ratios.
Keywords:
DNA polymerases; dNTPs
Available at various institutes of the ASCR
Competitive incorporations of modified versus natural nucleotides by DNA polymerases
A series of 7-substituted 7-deazaadenosine and 5-substituted cytosine triphosphates were tested in competitive incorporations with different DNA polymerases with their natural analogs and analyzed ...
Phosphanucleosides containing 1-hydroxymethylphospholane 1-oxide ring
Páv, Ondřej; Zborníková, Eva; Buděšínský, Miloš; Rosenberg, Ivan
2014 - English
Novel phosphanucleosides containing 1-hydroxymethylphospholane 1-oxide ring were synthesized as compounds with potential biological activity. A ring-closing metathesis was employed to prepare a phospholene precursor, which was then converted into either 4-azido-3-hydroxy-1-hydroxymethylphospholane 1-oxide or 3-azido-1- hydroxymethylphospholane 1-oxide derivatives. Subsequently, nucleobase was introduced using a nucleobase construction. The biological activity of prepared compounds was evaluated.
Keywords:
phosphanucleosides; 1-hydroxymethylphospholane 1-oxide ring; biological activity
Available at various institutes of the ASCR
Phosphanucleosides containing 1-hydroxymethylphospholane 1-oxide ring
Novel phosphanucleosides containing 1-hydroxymethylphospholane 1-oxide ring were synthesized as compounds with potential biological activity. A ring-closing metathesis was employed to prepare a ...
Activation of human RNase L by 5’-C-phosphonate-modified oligoadenylates
Petrová, Magdalena; Buděšínský, Miloš; Zborníková, Eva; Panova, Natalya; Novák, Pavel; Rosenberg, Ivan
2014 - English
Adeno’sine 5’-(S)-C-phosphonate (pCOHX) was prepared as monomer suitable for oligonucleotide synthesis. Modified tetramers pCOHXAAA and pCOHXAApCOHX were assembled on solid phase and evaluated for their ability to activate human RNase L.
Keywords:
human RNase L; oligoadenylates
Available at various institutes of the ASCR
Activation of human RNase L by 5’-C-phosphonate-modified oligoadenylates
Adeno’sine 5’-(S)-C-phosphonate (pCOHX) was prepared as monomer suitable for oligonucleotide synthesis. Modified tetramers pCOHXAAA and pCOHXAApCOHX were assembled on solid phase and evaluated for ...
Pyrrolidine nucleotides conformationally constrained via hydrogen bonding
Pohl, Radek; Poštová Slavětínská, Lenka; Rejman, Dominik
2014 - English
Conformation of pyrroPME nucleotide analogues was studied by means of NMR at different pD values in D2O solutions. Surprisingly, two stable conformers were found at pD > 9 for both cis and trans configurations and their ratio depended on the acid-base properties of nucleobase attached to pyrrolidine ring. The results of conformational analysis suggest that the conformation of the pyrrolidine ring is locked via intramolecular hydrogen bond between negatively charged phosphonate oxygen atom and protonized pyrrolidine nitrogen.
Keywords:
pyrrolidine nucleotides; PMEA; hydrogen bond
Available at various institutes of the ASCR
Pyrrolidine nucleotides conformationally constrained via hydrogen bonding
Conformation of pyrroPME nucleotide analogues was studied by means of NMR at different pD values in D2O solutions. Surprisingly, two stable conformers were found at pD > 9 for both cis and trans ...
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