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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
Author(s) -
Jeppesen Claus,
Nielsen Peter E.
Publication year - 1988
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(88)80725-7
Subject(s) - chemistry , potassium permanganate , intercalation (chemistry) , potassium , base (topology) , dna , base pair , medicinal chemistry , stereochemistry , inorganic chemistry , biochemistry , organic chemistry , mathematical analysis , mathematics
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 KMnO 4 as a useful probe for analysing the structure of intercalator‐DNA complexes in solution.