title: Synthesis and evaluation of the functional oligonucleotides-PEG conjugates.
abstract: We have previously demonstrated that the phenylsulfide and phenylsulfoxide derivatives of 2-amino-6-vinylpurine exhibit efficient cross-linking with high selectivity towards cytidine through synchronous activation within duplex. In this study, we synthesized their conjugates with PEG for possible application to in vitro as well as in vivo antisense agents. Thus, the ODN (2) with the antisense sequence toward luciferase was synthesized, having the 2-amino-6-vinylpurine nucleoside analog at the reactive site for targeting C and the amino linker at the 3' terminal. The vinyl group was transformed to the corresponding substituted phenylsulfide derivatives (3), and then the amino group of the 3' end was converted to the thiopropionyl group (4). The thiol nucleophile of 4 was reacted to the acid-responsive PEG2 in good isolated yields (55-62%).
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
authors.forename: Ali Md
authors.initials: AM
authors.lastname: Monsur
authors.forename: Fumi
authors.initials: F
authors.lastname: Nagatsugi
authors.forename: Motoi
authors.initials: M
authors.lastname: Oishi
authors.forename: Yukio
authors.initials: Y
authors.lastname: Nagasaki
authors.forename: Kazunari
authors.initials: K
authors.lastname: Kataoka
authors.forename: Shigeki
authors.initials: S
authors.lastname: Sasaki
mesh_terms: D002851:Chromatography, High Pressure Liquid; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D011092:Polyethylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D009841:Oligonucleotides; D011092:Polyethylene Glycols