Alkyl phosphotriesters of dinucleotides and oligonucleotides. 4. Synthesis of oligodeoxyribonucleotide ethyl phosphotriesters and their specific complex formation with transfer ribonucleic acid

Sites in nucleic acids reacting with alkylating agents of differing carcinogenicity or mutagenicity

“…Ts'o and collaborators, who studied the properties of oligodeoxytrinucleotides containing a triester, report that such trinucleotides exhibit changes in a number of properties that are likely to affect normal replication (Miller et al, 1971(Miller et al, , 1974Kan et al, 1973).…”

Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability

“…Phosphotriester (PTE) ON is one of the phosphate-backbone-modified ONs developed in the 1970s. 2,3 PTE ON is a promising candidate for effective antisense ON as the phosphate modification increases resistance to nuclease digestion in cell culture 4 and improves cell membrane permeability due to the absence of negative charges on the phosphate moieties. 5 More recently, bioreversible PTE linkage-contained RNA were developed as effective RNAi prodrugs.…”

Conjugates of oligonucleotides and modified oligonucleotides: a review of their synthesis and properties

“…In their early studies of uncharged methylphosphonates and triesters, Miller and Ts'o found that racemic di-to tetramers hybridized to unmodified strands with greater affinity than the parent phosphodiesters (275,276). While diastereoisomers of dimers differed from each other, both formed more stable hybrids than the natural, charged compounds and were less effected by salt concentration.…”