Novel seven-membered ring-fused naphthalimide derivatives with potentials for cancer theranostics

Naphthalimide derivatives have good planarity and large conjugated structure and therefore possess pho-tophysical properties and biological activities. Previously, our group discovered seven-membered hetero-cyclic derivatives via modifying 4-and 5-positions of naphthalimide skeleton and found the derivatives had good water solubility and showed large stokes shift and strong fluorescence in water. In this arti-cle, we designed and synthesized more seven-membered ring-fused naphthalimide derivatives ( Y1 -Y16 ) by introducing different substitutions on the imide group. Among them, Y1 , Y5 , Y9 were found to show similar cytotoxic activities with Amonafide against A549 and HL60 cells, with IC50 values at 10 -6 mol/L. What is more, the asymmetry derivatives ( Y1 and Y5 ) showed high fluorescent quantum yields in the aqueous phase ( CYRILLIC CAPITAL LETTER EF = 0.47). Considering the great fluorescence quantum yields in water and the potent anti-tumor activities of the representative seven-membered ring-fused naphthalimides, they have poten-tials to be used as agents for cancer theranostics.(c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

In this study, a series of seven-membered ring-fused naphthalimide derivatives were designed and synthesized. Three derivatives, Y1, Y5, and Y9, showed similar cytotoxic activities to Amonafide against A549 and HL60 cells. Moreover, these derivatives exhibited high fluorescent quantum yields in water.