Acetonitrilated Unsymmetric BODIPYs having glycine fluorescence responsive quenching: Design, synthesis and spectroscopic properties

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 233; p. 118211
• Main Authors: Xiao, Fuyan, Wang, Yuling, Shao, Tingyu, Jin, Guofan
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 05.06.2020
• Subjects: 5-FU; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; BODIPY; Boron Compounds - chemistry; Boron Compounds - pharmacology; Cell Line, Tumor; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - pharmacology; Glycine; Glycine - chemistry; Glycine - pharmacology; Humans; IC50; Microscopy, Fluorescence; Neoplasms - drug therapy; Neoplasms - pathology; UV-PL; BODIPY; Glycine; UV-PL; IC50; 5-FU; IC
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2020.118211

A series of novel N≡C-CH2-B-F system BODIPY were designed and synthesized by introducing aldehyde and acetonitrile units which gave positive influence to spectroscopic and chemical properties of BODIPY derivatives. The effects of glycine (Gly) on the target products were studied via ultraviolet and visible spectrophotometry (UV–Vis) and photoluminescence (PL) under different conditions of the presence and absence of cations (K+, Ca2+, Zn2+). It was showed that glycine has an intense quenching effect on the compounds in both the presence and absence of ions with a dramatic color change from notable red to light orange owing to the addition of Gly. With regard to cells imaging investigation, the products showed the prominent fluorescence in cholangiocarcinoma cells. The luminescent effect of compounds 1 and 3 entering the cells was significantly stronger than that of compound 2. In addition, pertaining to anticancer properties, two human cancer cell lines (RBE, HCCC-9810) and one normal cell line (L−02) were evaluated for in vitro cytotoxicity. The target compounds, 1–3, exhibited moderate antitumor activity, of which compound 1 was found to be the most potent derivative with IC50 values of 119.31 ± 6.25, 114.73 ± 3.25, and 106.33 ± 5.22 against RBE, HCCC-9810, and L-02 cells, respectively, slightly weaker than the positive control 5-FU. [Display omitted] •Synthesis of three highly fluorescent Acetonitrilated Unsymmetric BODIPYs and synthetic routes are proposed.•The response of glycine is realized based on the characteristics of the three synthetic BODIPY derivatives.•Related researches are performed on cell biological activity and cell imaging.