1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

Anne  B Eldrup; Gerald Haaima; Peter E. Nielsen

1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

Anne B Eldrup, Gerald Haaima, Peter E. Nielsen

Transcription, RNA, and Gene Medicine Program

9 Citationer (Scopus)

Abstract

A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7 degrees C per unit) or pseudoisocytosine (1.5 degrees C per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions ( approximately 3 degrees C per unit).

Originalsprog	Engelsk
Tidsskrift	Bioorganic & Medicinal Chemistry Letters
Vol/bind	12
Udgave nummer	21
Sider (fra-til)	3121-3124
Antal sider	4
ISSN	0960-894X
Status	Udgivet - 4 nov. 2002

Citationsformater

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title = "1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems",

abstract = "A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7 degrees C per unit) or pseudoisocytosine (1.5 degrees C per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions ( approximately 3 degrees C per unit).",

keywords = "Bridged Bicyclo Compounds/chemical synthesis, Cytosine/chemistry, DNA/chemistry, Drug Stability, Guanine/chemistry, Hot Temperature, Hydrogen Bonding, Indicators and Reagents, Molecular Mimicry, Naphthyridines/chemical synthesis, Peptide Nucleic Acids/chemistry, Stereoisomerism",

author = "Eldrup, {Anne B} and Gerald Haaima and Nielsen, {Peter E.}",

year = "2002",

month = nov,

day = "4",

language = "English",

volume = "12",

pages = "3121--3124",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Pergamon Press",

number = "21",

}

TY - JOUR

T1 - 1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

AU - Eldrup, Anne B

AU - Haaima, Gerald

AU - Nielsen, Peter E.

PY - 2002/11/4

Y1 - 2002/11/4

N2 - A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7 degrees C per unit) or pseudoisocytosine (1.5 degrees C per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions ( approximately 3 degrees C per unit).

AB - A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7 degrees C per unit) or pseudoisocytosine (1.5 degrees C per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions ( approximately 3 degrees C per unit).

KW - Bridged Bicyclo Compounds/chemical synthesis

KW - Cytosine/chemistry

KW - DNA/chemistry

KW - Drug Stability

KW - Guanine/chemistry

KW - Hot Temperature

KW - Hydrogen Bonding

KW - Indicators and Reagents

KW - Molecular Mimicry

KW - Naphthyridines/chemical synthesis

KW - Peptide Nucleic Acids/chemistry

KW - Stereoisomerism

M3 - Journal article

C2 - 12372515

SN - 0960-894X

VL - 12

SP - 3121

EP - 3124

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 21

ER -

1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

Abstract

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