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On the complex formation of acridine dyes with DNA. VII. Dependence of the binding on the dye structure
Author(s) -
Löber G.,
Achtert G.
Publication year - 1969
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.1969.360080504
Subject(s) - proflavine , chemistry , acridine orange , acridine , steric effects , fluorescence , dna , ring (chemistry) , intercalation (chemistry) , stereochemistry , photochemistry , crystallography , organic chemistry , biochemistry , apoptosis , physics , quantum mechanics
Abstract The binding constants for the complex formation of more than twenty ring nitrogen‐and amino‐substituted acridine derivatives with calf thymas DNA were measured by a fluorescence method. DNA quenches the fluorescence of the aminoacridine dyes so long as both amino hydrogens are not substituted. These dyes show an enhancement of their fluorescence intensity in the presence of DNA. Typical representatives of both are proflavine and acridine orange derivatives, respectively. A discussion of steric and electronic influences of various substituents attached to the ring nitrogen and amino groups on the binding led to the concept of different conformations for intercalated acridines without amino groups and the aminoacridines. The electrostatic binding site of the former seems to be the positively charged ring nitrogen, while the binding sites in the aminoacridines are so located that the amino groups are directed towards the negatively charged DNA phosphates.