Deoxyribonucleic acid intercalation

Povirk LF, Dattagupta N, Warf BC, Goldberg IH (1981) Neocarzinostatin chromophore binds to deoxyribonucleic acid by intercalation. Biochemistry 20 4007-4014 Powers EL, Gampel-Jobbagy Z (1972) Water-derived radicals and radiation sensitivity of bacteriophage T7. Int J Radiat Biol 21 353-359... 

There is less information in the literature about binding of alkaloids to ribonucleic acid than there is for deoxyribonucleic acid but such binding does occur. However, since ribonucleic acid is single-stranded, the intercalation mechanism does not apply. Binding of the purine alkaloids caffeine and theophylline follows the reverse order from their binding to DNA — theopylline binds with 10,000 times the affinity of caffeine [345], Elliptinium acetate, best-known for its intercalation into DNA, is easily oxidized to an A-ring quinone amine that binds to the 2 -oxygen atom of ribose units in RNA. The first product then cyclizes to a spiro derivative [346]. 

Ashikawa, I., Kinosita, K., Dcegami. A.. Nishimura, Y, l ibot, M.. Watanabe, K., Iso, K., and Nakano. T. 1983, Inlemal motion of deoxyribonucleic acid in chromatin. Nanosecond fluoiescencestud-ies of intercalated ethidium, fiiochemutry 22 6018-6026. 

The final example in the table (example 5, Table 6.9) is one of a class of similar cyclizations found in several families of antibiotics. For example, it has been argued that the activity of antibiotics such as Dynemicin A (Figure 6.17) results from initial binding (intercalation) of the antibiotic into the minor groove of deoxyribonucleic acid (DNA Chapter 14) followed by cycloaromatization of the enediyne system to produce a diradical intermediate. The diradical then irreversibly finks to the DNA by hydrogen abstraction, damaging it permanently. 

An intercalation-based mechanism resulting from quinone insertion between two deoxyribonucleic acid (DNA) base pairs causing disturbance of DNA transcription and replication by inhibition of DNA topoisomerases. 

J. Bernard and G. F. Riou, In vivo effects of intercalating and nonintercalating drugs on the tertiary structure of kinetoplast deoxyribonucleic acid, Biochem., 1980, 19, 4197-4178. 

---