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Copper-catalyzed azidealkyne cycloaddition in attaching cyanine dyes to amino acid's side chain

Synthesis of the cyanine-amino acid conjugates via copper-catalyzed azide-alkyne cycloaddition was performed in high yields with copper wire as source of Cu(I). With addition of all compounds into aqueous solution of ctDNA, big distortion of DNA backbone was observed as well as strong induced CD spectra (ICD) in region where cyanine dye absorbs (450-550 nm). Two compounds, differing in substituent on benzothiazolic part of cyanine, bind to DNA as monomer even at dye-over-DNA excess. On the contrary, other two compounds aggregate along DNA backbone as indicated with bisignate ICD spectra. One shows clockwise arrangement (negative to positive signature sequence) or P- configurated helicity, while another one has positive/negative patern thus having counter- clockwise arrangement or M-configurated helicity.

Copper-catalyzed azide-alkyne cycloaddition, cyanine-amino acid conjugates

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