Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Chenguang Lou; Qiang Xiao; Lavinia Brennan; Mark E Light; Nuria Vergara-Irigaray; Elizabeth M Atkinson; Lindy M Holden-Dye; Keith R Fox; Tom Brown

doi:10.1016/j.bmc.2010.07.005

Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Chenguang Lou, Qiang Xiao, Lavinia Brennan, Mark E Light, Nuria Vergara-Irigaray, Elizabeth M Atkinson, Lindy M Holden-Dye, Keith R Fox, Tom Brown

Department of Physics, Chemistry and Pharmacy

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

Original language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	18
Issue number	17
Pages (from-to)	6389-6397
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmc.2010.07.005
Publication status	Published - 2010

Keywords

DNA Footprinting
Humans
Nucleic Acid Conformation
Oligodeoxyribonucleotides
Structure-Activity Relationship
Uridine

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10.1016/j.bmc.2010.07.005

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Lou, Chenguang ; Xiao, Qiang ; Brennan, Lavinia ; Light, Mark E ; Vergara-Irigaray, Nuria ; Atkinson, Elizabeth M ; Holden-Dye, Lindy M ; Fox, Keith R ; Brown, Tom. / Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine. In: Bioorganic & Medicinal Chemistry Letters. 2010 ; Vol. 18, No. 17. pp. 6389-6397.

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title = "Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine",

abstract = "2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.",

keywords = "DNA Footprinting, Humans, Nucleic Acid Conformation, Oligodeoxyribonucleotides, Structure-Activity Relationship, Uridine",

author = "Chenguang Lou and Qiang Xiao and Lavinia Brennan and Light, {Mark E} and Nuria Vergara-Irigaray and Atkinson, {Elizabeth M} and Holden-Dye, {Lindy M} and Fox, {Keith R} and Tom Brown",

year = "2010",

doi = "10.1016/j.bmc.2010.07.005",

language = "English",

volume = "18",

pages = "6389--6397",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Pergamon Press",

number = "17",

}

Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine. / Lou, Chenguang; Xiao, Qiang; Brennan, Lavinia; Light, Mark E; Vergara-Irigaray, Nuria; Atkinson, Elizabeth M; Holden-Dye, Lindy M; Fox, Keith R; Brown, Tom.

In: Bioorganic & Medicinal Chemistry Letters, Vol. 18, No. 17, 2010, p. 6389-6397.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

AU - Lou, Chenguang

AU - Xiao, Qiang

AU - Brennan, Lavinia

AU - Light, Mark E

AU - Vergara-Irigaray, Nuria

AU - Atkinson, Elizabeth M

AU - Holden-Dye, Lindy M

AU - Fox, Keith R

AU - Brown, Tom

PY - 2010

Y1 - 2010

N2 - 2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

AB - 2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

KW - DNA Footprinting

KW - Humans

KW - Nucleic Acid Conformation

KW - Oligodeoxyribonucleotides

KW - Structure-Activity Relationship

KW - Uridine

U2 - 10.1016/j.bmc.2010.07.005

DO - 10.1016/j.bmc.2010.07.005

M3 - Journal article

C2 - 20674370

VL - 18

SP - 6389

EP - 6397

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

SN - 0960-894X

IS - 17

ER -

Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Abstract

Keywords

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