35002-96-1Relevant academic research and scientific papers
Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability
Hayashi, Junsuke,Hamada, Tomoko,Sasaki, Ikumi,Nakagawa, Osamu,Wada, Shun-Ichi,Urata, Hidehito
, p. 3610 - 3615 (2015/08/11)
A spermine-conjugated ethyl phosphotriester oligonucleotide was obtained by solid-phase synthesis based on phosphoramidite chemistry. The ethyl phosphotriester linkage was robust to exonuclease digestion and stable in fetal bovine serum. Cell membrane permeability of the spermine-conjugated ethyl phosphotriester oligonucleotide was studied by fluorescence experiments. The effective cell penetrating potency of the spermine-conjugated ethyl phosphotriester oligonucleotide was determined by confocal laser scanning microscopy and measurement of intracellular fluorescence intensity.
Transformation of Dinucleoside S-Aryl Phosphorothioates into the Corresponding O-Alkyl Phosphates by Use of Tributyltin Alkoxides
Ohuchi, Shokichi,Ayukawa, Hiroshi,Hata, Tsujiaki
, p. 1501 - 1504 (2007/10/02)
Several alkyl dinucleoside phosphotriesters were easily obtained by use of the reaction of S-aryl dinucleoside phosphorothioates with tributyltin alkoxides.This reaction proceeds at room temperature under neutral conditions.
OLIGOTHIMIDYLATES COMPORTANT LA STRUCTURE ALTERNEE ALKYLPHOSPHOTRIESTER-PHOSPHODIESTER ET LIES DE FACON COVALENTE A UN AGENT INTERCALANT
Asseline, U.,Barbier, C.,Thuong, N. T.
, p. 63 - 74 (2007/10/02)
Four oligothymidylates involving alternating alkylphosphotriester-phosphodiester backbones with the same steric configuration for all the phosphotriester groups have been synthesized by the phosphotriester method in solution from each pure α and β isomers of the ethylated 5b or neopentylated 5c dinucleoside.This partial esterification of the phosphate groups stabilizes the nucleic acid chain against nucleolytic attack by P1 and S1 nucleases.This effect increases with the size of the alkyl groups.It also depends upon the steric configuration of the alkylphosphotriester groups: the β isomers are more resistant to S1 nuclease than the α isomers.Tetrathymidylates bearing two "neopentyl" groups (Tp(CH2CMe3)Tp)2(CH2)5Acr 2cα and 2cβ give specific complexes with poly r(A) and the β isomer 2c binds a little stronger than the tetrathymidylate (Tp)n(CH2)5Acr.The neopentyl group is stable under the conditions required for the synthesis of oligodeoxynucleotides involving the four nucleic acid bases.It can be used for the partial esterification of the phosphodiester groups.
