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Intercalation of Organic Dye Molecules into Double-Stranded DNA -- General Principles and Recent Developments

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 258))

Abstract

Several aspects of the intercalation of organic dyes into DNA are presented. After a description of general features of intercalation and the analytical evaluation of this binding mode, recent applications of the intercalation process in chemistry, biology, pharmacy, and medicine are described, with examples from representative dye classes, namely acridines, anthraquinones, cyanines, and phenanthridinium dyes. Along with references to classical work in this research field, examples are presented which demonstrate the influence of the substitution pattern of the intercalator on the selectivity and efficiency of intercalation. In addition, a survey of the recent literature is given that covers significant developments in the application of intercalating dyes as chemotherapeutic drugs, as probe or sensor molecules in biophysical chemistry and molecular biology, as photosensitizers in DNA-damage reactions, and as fluorescence stains.

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Abbreviations

A:

Adenine

Ala:

Alanine

BER:

Base Excision Repair

C:

Cytosine

CD:

Circular dichroism

ct DNA:

Calf thymus DNA

dA:

Deoxyadenosinephosphate

dC:

Deoxycytidinephosphate

dG:

Deoxyguanosinephosphate

dsDNA:

Double-stranded DNA

dT:

Deoxythymidinephosphate

ET:

Electron transfer

Gln:

Glutamine

Gly:

Glycine

G:

Guanine

LD:

Linear dichroism

Lys:

Lysine

SASA:

Solvent-accessible surface area

Ser:

Serine

ssDNA:

Single-stranded DNA

T:

Thymine

Trp:

Tryptophane

Tyr:

Tyrosine

Val:

Valine

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Ihmels, H., Otto, D. Intercalation of Organic Dye Molecules into Double-Stranded DNA -- General Principles and Recent Developments. In: Würthner, F. (eds) Supermolecular Dye Chemistry. Topics in Current Chemistry, vol 258. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b135804

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