Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates

• Wang-Yong Yang,
• Samantha A. Marrone,
• Nalisha Minors,
• Diego A. R. Zorio and
• Igor V. Alabugin

Beilstein J. Org. Chem. 2011, 7, 813–823, doi:10.3762/bjoc.7.93

• cytotoxicity) value of 1.49 × 10−7 M. Keywords: cancer cell proliferation assay; DNA alkylation; lysine conjugate; photocycloaddition; photo-DNA cleavage; plasmid relaxation assay; triplet excitation; Introduction Triggering chemical processes with light offers numerous practical advantages. Not only does

• DNA photocleavage The results of plasmid relaxation assay with three lysine conjugates are summarized in Figure 7. These experiments were carried out on 15 μM of lysine conjugate with 30 μM/base pair of pBR322 plasmid DNA at pH 6, 7 and 8. The DNA-cleaving ability of conjugates does not directly

• for the isomeric acetylenes 3–5. Supporting Information Supporting information features details for experimental procedures, emission titration spectra, fluorescence decay traces, picture of plasmid relaxation assay, characterization data, and NMR spectra (1H, 13C NMR, HSQC, and HMBC). Supporting