Detection of intercalation-induced changes in DNA structure by reaction with diethyl pyrocarbonate or potassium permanganate. Evidence against the induction of Hoogsteen base pairing by echinomycin

Peter E. Nielsen

Detection of intercalation-induced changes in DNA structure by reaction with diethyl pyrocarbonate or potassium permanganate. Evidence against the induction of Hoogsteen base pairing by echinomycin

Transcription, RNA, and Gene Medicine Program

43 Citationer (Scopus)

Abstract

Binding of the bis-intercalators echinomycin and N,N'-di(9-acridinyl)spermidine or the mono-intercalators 9-aminoacridine and ethidium to DNA induces hypersensitivity of adenines towards reaction with diethyl pyrocarbonate. It is proposed that this hyperreactivity is due to the DNA helix unwinding and extension induced by intercalation, thereby exposing N7 in the major groove, and not as previously suggested to the formation of Hoogsteen base pairing. Hypersensitivity of thymines towards oxidation with permanganate is also induced upon binding of these drugs (especially the bis-intercalators) to DNA. This thymine hyperreactivity is both sequence- and intercalator-dependent, thereby indicating the potential of KMnO4 as a useful probe for analyzing the structure of intercalator-DNA complexes in solution.

Originalsprog	Engelsk
Tidsskrift	FEBS Letters
Vol/bind	231
Udgave nummer	1
Sider (fra-til)	172-6
Antal sider	5
ISSN	0014-5793
Status	Udgivet - 11 apr. 1988

Citationsformater

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title = "Detection of intercalation-induced changes in DNA structure by reaction with diethyl pyrocarbonate or potassium permanganate. Evidence against the induction of Hoogsteen base pairing by echinomycin",

abstract = "Binding of the bis-intercalators echinomycin and N,N'-di(9-acridinyl)spermidine or the mono-intercalators 9-aminoacridine and ethidium to DNA induces hypersensitivity of adenines towards reaction with diethyl pyrocarbonate. It is proposed that this hyperreactivity is due to the DNA helix unwinding and extension induced by intercalation, thereby exposing N7 in the major groove, and not as previously suggested to the formation of Hoogsteen base pairing. Hypersensitivity of thymines towards oxidation with permanganate is also induced upon binding of these drugs (especially the bis-intercalators) to DNA. This thymine hyperreactivity is both sequence- and intercalator-dependent, thereby indicating the potential of KMnO4 as a useful probe for analyzing the structure of intercalator-DNA complexes in solution.",

keywords = "Base Composition, Base Sequence, DNA/drug effects, Diethyl Pyrocarbonate/pharmacology, Echinomycin/pharmacology, Formates/pharmacology, Intercalating Agents/pharmacology, Plasmids/drug effects, Potassium Permanganate/pharmacology, Quinoxalines/pharmacology, Structure-Activity Relationship",

author = "Nielsen, {Peter E.}",

year = "1988",

month = apr,

day = "11",

language = "English",

volume = "231",

pages = "172--6",

journal = "F E B S Letters",

issn = "0014-5793",

publisher = "JohnWiley & Sons Ltd",

number = "1",

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TY - JOUR

T1 - Detection of intercalation-induced changes in DNA structure by reaction with diethyl pyrocarbonate or potassium permanganate. Evidence against the induction of Hoogsteen base pairing by echinomycin

AU - Nielsen, Peter E.

PY - 1988/4/11

Y1 - 1988/4/11

N2 - Binding of the bis-intercalators echinomycin and N,N'-di(9-acridinyl)spermidine or the mono-intercalators 9-aminoacridine and ethidium to DNA induces hypersensitivity of adenines towards reaction with diethyl pyrocarbonate. It is proposed that this hyperreactivity is due to the DNA helix unwinding and extension induced by intercalation, thereby exposing N7 in the major groove, and not as previously suggested to the formation of Hoogsteen base pairing. Hypersensitivity of thymines towards oxidation with permanganate is also induced upon binding of these drugs (especially the bis-intercalators) to DNA. This thymine hyperreactivity is both sequence- and intercalator-dependent, thereby indicating the potential of KMnO4 as a useful probe for analyzing the structure of intercalator-DNA complexes in solution.

AB - Binding of the bis-intercalators echinomycin and N,N'-di(9-acridinyl)spermidine or the mono-intercalators 9-aminoacridine and ethidium to DNA induces hypersensitivity of adenines towards reaction with diethyl pyrocarbonate. It is proposed that this hyperreactivity is due to the DNA helix unwinding and extension induced by intercalation, thereby exposing N7 in the major groove, and not as previously suggested to the formation of Hoogsteen base pairing. Hypersensitivity of thymines towards oxidation with permanganate is also induced upon binding of these drugs (especially the bis-intercalators) to DNA. This thymine hyperreactivity is both sequence- and intercalator-dependent, thereby indicating the potential of KMnO4 as a useful probe for analyzing the structure of intercalator-DNA complexes in solution.

KW - Base Composition

KW - Base Sequence

KW - DNA/drug effects

KW - Diethyl Pyrocarbonate/pharmacology

KW - Echinomycin/pharmacology

KW - Formates/pharmacology

KW - Intercalating Agents/pharmacology

KW - Plasmids/drug effects

KW - Potassium Permanganate/pharmacology

KW - Quinoxalines/pharmacology

KW - Structure-Activity Relationship

M3 - Journal article

C2 - 3360122

SN - 0014-5793

VL - 231

SP - 172

EP - 176

JO - F E B S Letters

JF - F E B S Letters

IS - 1

ER -

Detection of intercalation-induced changes in DNA structure by reaction with diethyl pyrocarbonate or potassium permanganate. Evidence against the induction of Hoogsteen base pairing by echinomycin

Abstract

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