Synthesized Two New Water‐Soluble Fluorescents Calix[4]arene 4‐sulfo‐1,8‐naphthalimide Derivatives Inhibit Proliferation of Human Colorectal Carcinoma Cells

Abstract

AbstractSynthesis of 1,8‐naphthalimide derivatives and biochemical studies using them as anti‐cancer and cellular imaging agents have attracted significant attention in recent years. This study aimed to synthesize two new fluorescent narrow rim‐functionalized 4‐sulfo‐1,8‐naphthalimide derivatives of calix[4]arenes (4 and 7) and examination of their cytotoxic properties for cancerous cells. For this purpose, p‐tert‐butylcalix[4]arene bearing dihydrazide (3) or diaminopropyl (6) units on its narrow rim were reacted with 4‐sulfo‐1,8‐naphthalic anhydrate. The structure of these synthesized compounds has been characterized using 1H‐NMR, 13C‐NMR, and FTIR techniques. To investigate the anti‐cancer properties, compounds 4, 7, and N,N‐dimethylaminoethyl‐1,8‐naphthalimide (8) were tested on the human colorectal cancer cell line (DLD‐1) as well as healthy colon epithelial cell line (CCD‐18Co). The IC50 values of 4 and 7 were determined as 12.95 μM and 16.13 μM, respectively, on DLD‐1 cells. Furthermore, following the treatment of CCD‐18Co cells with 4 and 7, the IC50 values were determined as 508 μM and 269 μM, respectively. However, it was observed that compound 8 had no cytotoxic effect on both DLD‐1 cells and CCD‐18Co cells. Furthermore, the fluorescence imaging of human colorectal cancer cells treated with the synthesized compounds (4, 7, and 8) was performed on living cells.