Abstract
Nitrobenzamido ligands linked to the DNA intercalator 9-aminoacridine via poly(methylene) chains induce single-strand nicks in DNA upon irradiation with long-wavelength ultraviolet light (lambda greater than or equal to 300 nm). Optimal photocleavage activity was found for the reagent 9-[[6-(4-nitrobenzamido)hexyl]amino]-acridine. Removal of the acridinyl ligand or changing the position of the nitro group from the 4- to the 2-position caused a 10-fold decrease in photocleavage efficiency, whereas a change to the 3-position caused a 30-fold reduction. The DNA cleavage was 5-fold enhanced by subsequent piperidine treatment and showed some sequence dependency with predominant cleavage at G and T residues. Furthermore, significant differences in cleavage preference were observed when the poly(methylene) linker length was changed.
| Original language | English |
|---|---|
| Journal | Biochemistry |
| Volume | 27 |
| Issue number | 17 |
| Pages (from-to) | 6338-43 |
| Number of pages | 6 |
| ISSN | 0006-2960 |
| Publication status | Published - 23 Aug 1988 |
Keywords
- Aminoacridines/chemical synthesis
- Benzamides/pharmacology
- DNA/drug effects
- Indicators and Reagents
- Nitro Compounds/pharmacology
- Photolysis
- Plasmids/drug effects
- Structure-Activity Relationship