α‐Acrylaldehyde 3‐Pyrrolyl BODIPY as a Specific Optical Sensor for Cysteine and Homocysteine

Abstract

A new fluorophore, α-acrylaldehyde 3-pyrrolyl BODIPY was synthesized by treating 3-pyrrolyl BODIPY with a mixture of 3-(dimethylamino) acrolein and POCl 3 under Vilsmeier-Haack reaction conditions. The X-ray structure revealed that the fluorophore was almost planar, and the appended pyrrole was in the same plane with a small deviation from the mean plane. We investigated the potential use of α-acrylaldehyde 3-pyrrolyl BODIPY for sensing thiol containing amino acids such as cysteine/homocysteine (Cys/Hcy). Our studies showed that the α-acrylaldehyde-3-pyrrolyl BODIPY was found to be useful for exclusive sensing of Cys/Hcy and to exhibit different optical signaling responses to Cys and Hcy at physiological pH in aq. CH 3 CN (1 : 1 v/v, PBS) medium. The enhancement in optical properties for Cys and quenching in same properties for Hcy was attributed to different binding modes of Cys/Hcy with αacrylaldehyde 3-pyrrolyl BODIPY.

Synthesis and properties of covalently linked phenyl bridged 3-pyrrolyl BODIPY–BODIPY dyads

“…13 However, the synthesis of the BF 2 complex of a-pyrrolyl dipyrrin has not been thoroughly explored in previous studies due to the inaccessibility of a-pyrrolyl dipyrrin ligands. Recently, we [14][15][16][17][18][19][20][21] and others [22][23][24][25] developed a simple and facile synthetic route for BF 2 complexes of meso-aryl a-pyrrolyl dipyrrins 3a (Fig. 1).…”

BODIPY(aryl)iodonium salts in the efficient synthesis of diversely functionalized BODIPYs and selective detection of serum albumin

“…1,[8][9][10] Although, traditional approaches to prepare BODIPYs are also available, they generally require multistep processes starting from pyrrole or related unstable intermediates. 11,12 Direct C-H bond functionalization of BODIPY chromophores is a highly attractive way of exploring the diversity of the BODIPY moieties. You and Wu described a late-stage regioselective decarboxylative direct C-H arylation using substituted benzoic acids as coupling partners of BODIPY in the presence of palladium acetate, PCy 3 •HBF 4 as a ligand and silver carbonate at 140 °C for 24 h. 13 Jiao, Hao and co-workers developed a direct β-selective styrylation of BODIPYs involving the reaction of BODIPY with styrene in the presence of palladium acetate and silver acetate as an oxidant in PivOH at 80 °C.…”

“…1,8–10 Although, traditional approaches to prepare BODIPYs are also available, they generally require multistep processes starting from pyrrole or related unstable intermediates. 11,12…”

Synthesis, Structure, Spectral, Electrochemical, and Theoretical Studies of Ru(II) Complexes of 3-Pyrrolyl BODIPY-Based Ligands

“…There are different methods − available for the synthesis of prodigiosin 1 . Interestingly, α-pyrrolyl dipyrrins readily complex with the BF 2 unit to form BF 2 -complex of α-pyrrolyl dipyrrins known as 3-pyrrolyl BODIPYs (BODIPY: 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) which are highly fluorescent and have been used extensively as biological probes and for other applications. − A few years back, we ,− and others − reported a straightforward synthesis of meso -aryl 3-pyrrolyl BODIPYs 2 and explored their physicochemical properties. We also showed that the α-position of the appended pyrrole can be easily functionalized with functional groups such as −CHO 3 , and the functionalized meso -aryl 3-pyrrolyl BODIPYs have been used to synthesize several interesting fluorescent 3-pyrrolyl BODIPY-based conjugates .…”