Bis-naphthalene diimide exhibiting an effective bis-threading intercalating ability.
Bis-naphthalene diimide (1) was successfully synthesized from Fmoc-Lys(Boc)-OH and Fmoc-Lys(NDI)-OH on the automated peptide synthesizer. The absorption spectra of 1 suggested intramolecular stacking of the naphthalene diimide parts in buffer solution. Viscometric titration of a double stranded DNA (dsDNA) solution with 1 suggested that both of the naphthalene diimide parts of 1 are involved in threading intercalation. Kinetic studies suggested that 1 binds to dsDNA with a large affinity constant (K = 106 M(-1)) by "bis-threading intercalation" rather than by electrostatic binding between the cationic sites of lysine parts and phosphate anions of DNA.
D007094:Imides; D007364:Intercalating Agents / Q000737:chemistry*; D009281:Naphthalenes; D010618:Phenanthrolines / Q000737:chemistry*; D055672:Static Electricity; D014783:Viscosity
D007094:Imides; D007364:Intercalating Agents; D009281:Naphthalenes; D010618:Phenanthrolines; C542131:naphthalenediimide