8‐(4‐aminophenyl)BODIPYs as fluorescent pH probes: facile synthesis, computational study and lysosome imaging. Issue 1 (23rd December 2015)

• Record Type: Journal Article
• Authors: Zhang , Yuan; Fang, Hong‐mei; Zhang, Xiao‐tai; Wang, Shu; Xing, Guo‐wen
• Is Part Of: ChemistrySelect. Volume 1:Issue 1(2016)
• Page Start: 1
• Page End: 6
• Publication Date: 2015-12-23
• Subjects: BODIPY -- fluorescent probe -- lysosome; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201500016
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Five novel BODIPY‐based dyes (3 a ‐e ) were facilely synthesized via Buchwald‐Hartwig cross coupling reaction. The 8‐(4‐aminophenyl)BODIPYs can be used as fluorescent pH probes with broad response ranges. Low fluorescence intensities of3a–e were observed under neutral or weak acidic conditions, whereas, the fluorescence signals significantly increased with further decreasing pH values, indicating that they are highly sensitive to acidic pH alterations. Fluorescence response mechanism of the probes to pH is based on the photo‐induced electron transfer (PET), which was investigated by density functional theory (DFT) and time dependent‐density functional theory (TD‐DFT) calculations. Cell imaging experiments demonstrated3 b (pKa 3.59) was a novel lysosome‐targeting probe with excellent membrane permeability, high sensitivity and selectivity, as well as low cytotoxicity. In addition, probes3 a and3 d with pKa 2.66, 2.51 could be potential for detecting extremely acidic conditions in bacteria. Abstract : Five novel BODIPY‐based dyes (3a–e ) were facilely synthesized via Buchwald‐Hartwig cross coupling reaction. The 8‐(4‐aminophenyl)BODIPYs can be used as fluorescent pH probes with broad pH response ranges. Cell imaging experiments demonstrated3 b is a novel lysosome‐targeting probe with excellent membrane permeability, high sensitivity and selectivity, and low cytotoxicity.