Base-modified oligodeoxynucleotides. I. effect of 5-alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines on duplex stability and hydrophobicity

Properties of oligodeoxynucleotides essential for the antisense effect can be favourably modified by substitution of the heterocyclic base moiety. This is shown here for duplex stability by 5 alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines in the self-complementary (dT-dA) 10...

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Published inTetrahedron letters Vol. 34; no. 13; pp. 2191 - 2194
Main Authors Sági, János, Szemzö, Attila, Ébinger, Katalin, Szabolcs, Anna, Sági, Gyula, Ruff, Éva, Ötvös, László
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 26.03.1993
Elsevier
Subjects
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Substituent effect
Aqueous medium
Chemical stability
Solubility
Oligonucleotide
Hydrophobicity
Deoxyribonucleotide
Oligodeoxyribonucleotide
Pyrimidine nucleotide
Duplex
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Summary:Properties of oligodeoxynucleotides essential for the antisense effect can be favourably modified by substitution of the heterocyclic base moiety. This is shown here for duplex stability by 5 alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines in the self-complementary (dT-dA) 10 and (dC-dG) 6 oligomers as well as for the hydrophobic character of the (dT-dA) 10 series. 5-Alkyluracils decrease, whereas 5-alkyl-cytosines and 5-(1-alkynyl)- substituted pyrimidines retain or increase duplex stability. Hydrophobicity of the base-modified oligonucleotides is strongly enhanced.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)60379-9