title: Synthesis of antisense oligonucleotides containing acyclic alkynyl nucleoside analogs and their biophysical and biological properties.
abstract: The synthesis of oligonucleotide (ON) analogs, which can be used as antisense molecules, has recently gained much attention. Here, we report the synthesis and properties of an ON analog containing acyclic thymidine and cytidine analogs with a 4-pentyl-1,2-diol instead of the d-ribofuranose moiety. The incorporation of these analogs into the ON improved its nuclease resistance to 3'-exonucleases. Furthermore, it was found that the incorporation of the acyclic thymidine analog into a DNA/RNA duplex accelerates the RNA cleavage of a DNA/RNA duplex by Escherichia coli RNase H.
authors.affiliation: United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Aya
authors.initials: A
authors.lastname: Ogata
authors.affiliation: Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Maeda
authors.affiliation: United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. Electronic address: uenoy@gifu-u.ac.jp.
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Ueno
mesh_terms: D055592:Biophysical Phenomena; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry; D004926:Escherichia coli / Q000201:enzymology; D006868:Hydrolysis; D009690:Nucleic Acid Conformation; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D012313:RNA / Q000737:chemistry / Q000378:metabolism; D016914:Ribonuclease H / Q000378:metabolism; D013816:Thermodynamics
chemical_list: D016376:Oligonucleotides, Antisense; D012313:RNA; D004247:DNA; D016914:Ribonuclease H
keywords: Acyclic nucleoside; Alkyne; Antisense oligonucleotide; Nuclease resistance; RNase H; Thermal stability