Red‐to‐Near‐Infrared Emitting PyrrolylBODIPY Dyes: Synthesis, Photophysical Properties and Bioimaging Application

Abstract

Near-infrared (NIR) fluorophores with characteristics such as deep tissue penetration, minimal damage to the biological samples, and low background interference, are highly sought-after materials for in vivo and deep-tissue fluorescence imaging. Herein, series of 3-pyrrolylBODIPY derivatives and 3,5-dipyrrolylBODIPY derivatives have been prepared by a facile regioselective nucleophilic aromatic substitution reaction (S N Ar) on 3,5-halogenated BODIPY derivatives (3,5-dibromo or 2,3,5,6-tetrachloroBODIPYs) with pyrroles. The installation of a pyrrolic unit onto the 3-position of the BODIPY chromophore leads to a dramatic red shift of both the absorption (up to 160 nm) and the emission (up to 260 nm) in these resultant 3-pyrrolylBODIPYs with respect to that of the BODIPY chromophore. Their further 5-positional functionalization provides a facile way to fine tune their photophysical properties, and these resulting dipyrrolylBODI-PYs and functionalized pyrrolylBODIPYs show strong absorption in the deep red-to-NIR regions (595-684 nm) and intense NIR fluorescence emission (650-715 nm) in dichloromethane.To demonstrate the applicability of these functionalized pyrrolylBODIPYs as NIR fluorescent probes for cell imaging, pyrrolylBODIPY 6 a containing mitochondrion-targeting butyltriphenylphosphonium cationic species was also prepared. It selectively localized in mitochondria of HeLa cells, with low cytotoxicity and intense deep red fluorescence emission.

3‐Pyrrolyl BODIPY Based Schiff Base Fluorophores: A Selective Chemodosimetric and Optical Sensor for Diethyl Chlorophosphate

“…Substituted 3‐pyrrolyl BODIPY based molecular probes are remarkable for in situ detection and intracellular monitoring of various analytes/bioanalytes, estimation of their concentration level, and dynamics due to more cellular penetrating power in the context of bio‐molecular optical imaging [28] . As a result, assessment of the accumulation of such toxic DCP from contaminated soil and water along with other requisite nutrients in potential plant species, particularly those with medicinal values, demands monitoring the concentration level of such metabolites.…”

Roles of DNA Target in Cancer Cell-Selective Cytotoxicity by Dicopper Complexes with DNA Target/Ligand Conjugates

“…Fluorescence Imaging. 26 Onto observation dishes (φ14 mm), HeLa cells in a culture medium (600 μL) were seeded and grown in a humidified atmosphere of 5% CO 2 at 37 °C for 24 h. The dishes were rinsed twice with PBS(−). A solution of 1 P1 , 1 P2 , or 1 P3 (200 μM, 600 μL) in the culture medium was added to the dishes and incubated at 37 °C for 1 h. After rinsing twice with PBS(−), to the dishes was added a solution of Mito Tracker Deep Red FM (Thermo Fisher) (50 nM, 600 μL) in a complete culture medium for mitochondrial staining.…”

A white light emitting single halochromic hydrazine bridged bis(3-pyrrolyl BODIPY) fluorophore

“…Furthermore, the appended pyrrole of 3-pyrrolyl BODIPY is highly susceptible to functionalization at the a-position and the a-functionalized 3-pyrrolyl BODIPYs are very useful synthons to synthesize several interesting fluorescent 3-pyrrolyl BODIPY based conjugates. In due course of time, we [22][23][24][25][26][27][28] and others [29][30][31] have developed a simple method for the synthesis of 3-pyrrolyl meso-aryl BODIPY based derivatives and they have been used in fluorescence sensing, photodynamic therapy, biotechnology, bioimaging, lightharvesting systems, etc. We also developed a method 32 to remove BF 2 units from BODIPYs and the resulting ligands have been used in coordination chemistry.…”