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Nucleotides
Author(s) -
Kvasyuk Evgeny I.,
Mikhailopulo Igor A.,
Homan Joseph W.,
Iacono Kathryn T.,
Muto Nicholas F.,
Suhadolnik Robert J.,
Pfleiderer Wolfgang
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990113)82:1<19::aid-hlca19>3.0.co;2-g
Subject(s) - chemistry , deoxyadenosine , reverse transcriptase , stereochemistry , phosphoramidite , nucleotide , integrase , adenosine , cordycepin , microbiology and biotechnology , syncytium , biochemistry , rna , oligonucleotide , dna , cell , gene , biology
The new (2′ – 5′)oligoadenylate trimers 26 – 34 containing 5′‐amino‐5′‐deoxyadenosine or 5′‐amino‐3′,5′‐dideoxyadenosine or their lipophilic 5′‐deoxy‐5′‐(hexadecanoylamino) derivatives at the 5′‐terminus, and adenosine or 3′‐deoxyadenosine (=cordycepin) at the penultimate and 2′‐end position of the trimers were synthesized by the phosphoramidite method. The newly synthesized trimers 26 – 34 inhibited, at 100 μ M concentration, HIV‐1‐induced syncytia formation (SYN) by 19 – 96% and reverse‐transcriptase activity (RT) by 27 – 100% (see Table ). The two hexadecanoylamino derivatives 27 and 30 which were found to be potent inhibitors of SYN and RT showed also a 73 and 49% inhibition, respectively, of expression of HIV‐1 p24 antigen (p24‐EX). The same compounds 27 and 30 inhibited also, with a 100% efficacy, an amplification of HIV‐1 partial reverse transcripts (PCR) and HIV‐1 integrase activity (INT), respectively.