Tytuł
Nukleozydo i oligonukleozydo boranofosfoniany - metody syntezy i wybrane właściwości biologiczne
Autorzy
[ 1 ] Instytut Chemii Bioorganicznej Polskiej Akademii Nauk, Polska Akademia Nauk | [ P ] pracownik
Dyscyplina naukowa (Ustawa 2.0)
Wariant tytułu
EN NUCLEOSIDE AND OLIGONUCLEOSIDE BORANEPHOSPHONATES –SYNTHETIC METHODS AND SELECTED BIOLOGICAL PROPERTIES
Rok publikacji
2020
Opublikowano w
Typ artykułu
artykuł naukowy
Język publikacji
polski
Słowa kluczowe
Streszczenie
EN Interest in boron-containing compounds has grown in recent years due to their potential medicinal and biochemical applications. Nucleoside boranephosphonatesare analogues of naturally occurring nucleoside phosphates in which one of the non-bridging oxygen atom has been replaced by a BH3group [1]. This modification imparts unique biological properties to nucleotides and nucleic acids. DNA and RNA fragments containing boranephosphonate internucleotide linkages are resistant to various nucleases, stimulate the RNase H activity, and reveal high lipophilicity, which significantly enhances their cellular uptake [2]. The hydrolytic stability and nuclease resistance make these compounds attractive candidates in designing new therapeutics and medicinal diagnostics. Considering these characteristics nucleoside boranephosphonates constitute a promising class of nucleotide analogues worth exploring for biological purposes. For this reason over the past decades chemists strived to develop efficient synthetic strategies for incorporation of the borane group (-BH3) into the phosphate moiety of nucleotides and oligonucleotides. This review presents in the first part different approaches for the introduction of the boranephosphonate structural motif into nucleotides by using phosphoramidite method, H-phosphonate strategy, and by employing dedicated boranephosphonylating reagents. Next, recent chemical approaches for the preparation of oligonucleoside boranephosphonates are presented together with enzymatic methods for the incorporation of the BH3group into DNA and RNA fragments. The last part of this review is dedicated to the selected biological properties of nucleoside and oligonucleoside boranephosphonate, their interaction with enzymes, potency of these compounds for gene suppression, and their possible use as new class of active pharmaceutical ingredients (API).
Strony (od-do)
477 - 506
Typ licencji
CC BY (uznanie autorstwa)
Wersja tekstu w otwartym dostępie
ostateczna wersja opublikowana
Data udostępnienia
07.2020
Czas udostępnienia publikacji w sposób otwarty
w momencie opublikowania
Punktacja Ministerstwa / czasopismo
5
Punktacja Ministerstwa / czasopismo w ewaluacji 2017-2021
5
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