Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

Abstract

The fluorescence imaging technologies are becoming the most powerful and noninvasive diagnostic tools in cellular biology and modern medicine where abnormal cell arrangements are associated with diseases. Thus, these techniques require new fluorescent dyes with excellent chemical, physical, and photophysical properties. A series of four new Boron Schiff bases (1–4) has been prepared by condensation between phenylboronic acid with the corresponding ligand. The compounds were characterized by NMR (1H, 13C, and 11B), UV/vis, fluorescence spectroscopy, and high‐resolution mass spectrometry. The crystal structures of three compounds showed tetracoordinated Boron atoms with semiplanar skeleton ligands. Interesting organoboron response to viscosity on their fluorescence (Φ: more than 3‐fold). Additionally, compounds 1 and 2 were found to serve as a fluorescent dye for cell imaging (B16F10, CaCo, and A‐431 cells) since it has the capability to rapidly accumulate within the cells and gave bright green fluorescence, it showed low cytotoxicity activity and high photostability in solution. Additionally, the compounds have also been investigated using DFT.

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…For example, boron Schiff bases have indeed been employed in OLEDs (Vidyasagar et al, 2019) and as non-linear optical chromophores (Reyes et al, 2002;Lamère et al, 2006;Muñoz et al, 2008;Jiménez-Pérez et al, 2015a;Jiménez-Pérez et al, 2015b). In addition, they are used in bioimaging (António et al, 2019;Ibarra-Rodríguez et al, 2019;Russo et al, 2020).…”

Boron Schiff bases derived from α-amino acids as nucleoli/cytoplasm cell-staining fluorescent probes in vitro

“…In previous works, we reported the rst uorescent probes derived from BOSHIBAs with application in cellular staining (Scheme 2). [23][24][25] These probes, in contrast to those mentioned above, presented low cost, easy synthesis, and high quantum yields.…”

Rotors of BOSCHIBAs as endoplasmic reticulum fluorescent probes in HeLa and human umbilical vein endothelial cells

“…The bulky groups on compound I allow improving the solubility in organic solvents and thus single crystals and their molecular structure were elucidated; however, the staining in B16F10 and A-431 cells was weak (10 μg mL −1 ). 13–15…”