A boron dipyrromethene-derivative fluorescent probes for β-cyclodextrin and maltooligotose hydrophobicity recognition

Abstract

This study introduces a novel approach to oligosaccharide sensing utilizing hydrophobic interaction-driven fluorescent probes. The design involves three Boron dipyrromethene (BODIPY)-based Oligosaccharide sensing Fluorescent dyes (BOliFluor) with varying hydrophobic moieties synthesized to detect oligosaccharides precisely. The probes demonstrated sensitivity to linear maltooctaose and cyclic β-cyclodextrin, with a distinct response profile. The hydrophobic nature of the benzyl group in BOliFluor 2 enhanced interaction with β-cyclodextrin, resulting in a linear response with a low detection limit of 0.06 mM. In contrast, BOliFluor 1 and 3 exhibited a sigmoidal response according to Hill's equation, F = Fmax·cn/(Kd + cn), suggesting a complex interaction mechanism influenced by the conformational flexibility of the recognition groups. The study also explored the impact of chaotropic salts on the binding mode of BOliFluor to β-cyclodextrin, revealing a salt-dependent response. Overall, this research presents a promising strategy for selective oligosaccharide detection through hydrophobic interactions, paving the way for enhanced sensitivity and specificity in this field. The findings contribute to developing a comprehensive analytical method for oligosaccharides, addressing existing challenges in their detection and quantification.

Keywords

• Oligosaccharide sensing
• BODIPY-based fluorescent probes
• Hydrophobic interaction
• β-cyclodextrin
• Maltooligotose recognition
• Entropy loss