Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity

Aya Ogata, Chihiro Furukawa, Kohei Sakurai, Hideo Iba, Yukio Kitade, Yoshihito Ueno

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5′-terminus of one strand. We found that incorporation of biaryl units at the 5′-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes.

Original languageEnglish
Pages (from-to)7299-7302
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number24
DOIs
Publication statusPublished - 15-12-2010

Fingerprint

MicroRNAs
RNA-Induced Silencing Complex
Untranslated RNA
Nucleotides
Genes
Messenger RNA
Processing

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Ogata, Aya ; Furukawa, Chihiro ; Sakurai, Kohei ; Iba, Hideo ; Kitade, Yukio ; Ueno, Yoshihito. / Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity. In: Bioorganic and Medicinal Chemistry Letters. 2010 ; Vol. 20, No. 24. pp. 7299-7302.
@article{b9dae27ffc724448ab0a42ddf26307ab,
title = "Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity",
abstract = "MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5′-terminus of one strand. We found that incorporation of biaryl units at the 5′-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes.",
author = "Aya Ogata and Chihiro Furukawa and Kohei Sakurai and Hideo Iba and Yukio Kitade and Yoshihito Ueno",
year = "2010",
month = "12",
day = "15",
doi = "10.1016/j.bmcl.2010.10.077",
language = "English",
volume = "20",
pages = "7299--7302",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "24",

}

Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity. / Ogata, Aya; Furukawa, Chihiro; Sakurai, Kohei; Iba, Hideo; Kitade, Yukio; Ueno, Yoshihito.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 24, 15.12.2010, p. 7299-7302.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity

AU - Ogata, Aya

AU - Furukawa, Chihiro

AU - Sakurai, Kohei

AU - Iba, Hideo

AU - Kitade, Yukio

AU - Ueno, Yoshihito

PY - 2010/12/15

Y1 - 2010/12/15

N2 - MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5′-terminus of one strand. We found that incorporation of biaryl units at the 5′-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes.

AB - MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5′-terminus of one strand. We found that incorporation of biaryl units at the 5′-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes.

UR - http://www.scopus.com/inward/record.url?scp=78449272613&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78449272613&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2010.10.077

DO - 10.1016/j.bmcl.2010.10.077

M3 - Article

C2 - 21067927

AN - SCOPUS:78449272613

VL - 20

SP - 7299

EP - 7302

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 24

ER -