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Wyszukujesz frazę "oligonucleotide" wg kryterium: Temat


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Tytuł:
Synteza modyfikowanych oligonukleotydów zawierających stereozdefiniowane internukleotydowe wiązania tiofosforanowe
Synthesis of modified oligonucleotides containing stereodefined internucleotide phosphorothioate bonds
Autorzy:
Radzikowska, E.
Kaczmarek, R.
Baraniak, J.
Powiązania:
https://bibliotekanauki.pl/articles/172219.pdf
Data publikacji:
2015
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
oligonukleozydotiofosforany
oligonukleotydy antysensowe
synteza modyfikowanych oligonukleotydów
synteza stereospecyficzna
oligo(deoxy)ribonucleoside phosphorothioates
antisense oligonucleotides
synthesis of modified oligonucleotide
stereospecific synthesis
Opis:
Synthetic oligonucleotides constitute an important class of compounds which can exhibit biological activity. As potential drugs they could be employed in antisense strategy by acting on the pathogenic mRNA, causing inactivation of the target molecules during the translation process [1]. Ideal antisense agent (ASO) should be resistant to exo and/or endonucleases, exhibit a suitable pharmacological and pharmacokinetic profile and exhibits high binding affinity towards the target mRNA. To improve some properties of the ASO plethora of the chemical modifications introduced within the nucleobase, sugar unit and internucleotide linkage are investigated [3]. Among them, phosphorothioate oligonucleotides (PS-oligo), created by replacing one of the nonbridging oxygen atoms with a sulfur atom, are the major representatives of DNA analogs. PS-oligo display several attractive features like nuclease resistance, activation of RNase H, and good pharmacokinetic properties [1]. Replacement of one of two nonbridging oxygens at phosphorus by sulfur induces asymmetry at the phosphorus atom. Hence, the synthesized oligo(nucleoside phosphorothioate) is a mixture of 2n diastereomers (where n is the number of internucleotide phosphorothioate functions). Therefore the actual biological activity of the P-chiral oligonucleotide analogues, (e.g., interactions with proteins or nucleic acids) may depend on stereochemical factors [7]. One has to keep in mind that the phosphoramidite [5] and H-phosphonate [32] methodologies (commonly used to prepare PS-oligo) are nonstereospecific and give a mixture of 2n diastereomers. Thus, various methods have been elaborated to synthesize these P-chiral oligonucleotide analogs in a stereocontrolled manner [15, 17], among them the oxathiaphospholane method developed by Stec et al. [18], the method utilizing nucleoside 3’-O-(3-N-acyl)oxazaphospholidine derivatives as monomer units [19], and the method based on a stereoselective synthesis of nucleoside 3’-O-oxazaphospholidine monomers [21, 22] are the most significant.
Źródło:
Wiadomości Chemiczne; 2015, 69, 11-12; 957-981
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
Tytuł:
Wykorzystanie reakcji 1,3-dipolarnej cykloaddycji Huisgena do modyfikacji nukleozydów i ligonukleotydów
An application of the Huisgen 1,3-dipolar cycloaddition to modify nukleosides and oligonucleotides
Autorzy:
Radzikowska, E.
Powiązania:
https://bibliotekanauki.pl/articles/171872.pdf
Data publikacji:
2011
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
1,3-dipolarna cykloaddycja
analogi nukleozydów
chemia click
synteza modyfikowanych oligonukleotydów
1,2,3-triazole
biokoniugaty
1,3-dipolar cycloaddition
analogues of nucleosides
click chemistry
synthesis of modified oligonucleotide
bioconjugates
Opis:
The 1,3-dipolar cycloaddition reaction between azides and terminal alkynes, known as the Huisgen reaction, constitutes a powerful tool for the synthesis of versatile molecules containing carbon – heteroatom bond. The use of a copper(I) salt in this reaction allowed Sharpless to develop the concept of „click chemistry” [1]. This strategy is based on reactions between small units characterized by mild reaction conditions, versatility, high yields and stereospecificity. The chemistry of nucleic acids and nucleoside analogues is undergoing rapid developments and numerous compounds from these classes of compounds are used in medicinal treatment. Analogues of nucleoside constitute a class of drugs that possesses either anticancer or/and antiviral activity (against HIV, HSV, VZV or HCV viruses) [3]. Many modified oligonucleotides show biological activity. As potential drugs oligonucleotides are employed in antisense, antigen and aptamer strategies. An antisense therapeutic agent acts on the pathogenic mRNA causing inactivation of the target whereas an antigen agent acts on DNA and aptamer on unwanted protein. It is not surprising that number of research groups are trying to join the concept of click chemistry with nucleic acids chemistry. In this way, it is possible to obtain new molecules like base- or sugar-modified nucleosides, nucleosides, bioconjugates and olignucleotides. The copper-catalyzed 1,3-dipolar cycloaddition CuAAC allows to functionalize DNA, for example by labelling it through attaching small molecules to DNA. Two general strategies have been developed for this purpose: presynthetic and postsynthetic labelling. In the presynthetic method nucleotide monomers are labelled before DNA synthesis and purification. In the postsynthetic strategy DNA containing small reactive groups is synthesized first and then it is conjugated with the desired molecules. CuAAC is also a convenient method for the synthesis of modified oligonucleotides in which phosphodiester linkage is replaced by 1,2,3- -triazole or for a solid phase synthesis. Such molecules appear to be useful in medicine, molecular diagnostic (e.g. fluorescent dyes) or mechanistic molecular model in the future.
Źródło:
Wiadomości Chemiczne; 2011, 65, 3-4; 207-234
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
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