Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity

MOLECULES(2021)

引用 1|浏览4
暂无评分
摘要
Quinone methide precursors 1a-e, with different alkyl linkers between the naphthol and the naphthalimide chromophore, were synthesized. Their photophysical properties and photochemical reactivity were investigated and connected with biological activity. Upon excitation of the naphthol, Forster resonance energy transfer (FRET) to the naphthalimide takes place and the quantum yields of fluorescence are low (phi(F) approximate to 10(-2)). Due to FRET, photodehydration of naphthols to QMs takes place inefficiently (phi(R) approximate to 10(-5)). However, the formation of QMs can also be initiated upon excitation of naphthalimide, the lower energy chromophore, in a process that involves photoinduced electron transfer (PET) from the naphthol to the naphthalimide. Fluorescence titrations revealed that 1a and 1e form complexes with ct-DNA with moderate association constants K-a approximate to 10(5)-10(6) M-1, as well as with bovine serum albumin (BSA) K-a approximate to 10(5) M-1 (1:1 complex). The irradiation of the complex 1e@BSA resulted in the alkylation of the protein, probably via QM. The antiproliferative activity of 1a-e against two human cancer cell lines (H460 and MCF 7) was investigated with the cells kept in the dark or irradiated at 350 nm, whereupon cytotoxicity increased, particularly for 1e (>100 times). Although the enhancement of this activity upon UV irradiation has no imminent therapeutic application, the results presented have importance in the rational design of new generations of anticancer phototherapeutics that absorb visible light.
更多
查看译文
关键词
naphthols,naphthalimides,FRET,PET,quinone methides,antiproliferative activity
AI 理解论文
溯源树
样例
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要