The molecular properties concerning size, shape,and electric charges of the planar aromatic DNA intercalatorsare still poorly understood. Herein, a series of water-solubleperylene bisimide (PBI) derivatives containing a rigid andplanar aromatic nanoscaffold with different size, shape, andelectric charges were synthesized. Using histochemistry and cellviability assays on animal tissues and cancer cells, we revealedthe molecular properties required for successful DNA
intercalators to localize in cell nuclei and inhibit cancer cells.Small molecular size and the strong polarity of hydrophilicsubstituents are prerequisites for PBI-based DNA intercalators. A large number of charges facilitate the nucleic accumulation ofthese DNA intercalators, while fewer charges and planararomatic nanoscaffold more efficiently inhibit cancer cellgrowth.