Colorimetric Fluorescent Sensors for Hemoglobin Based on BODIPY Dyes

Abstract

Colorimetric fluorescent chemosensors 4 and 5 based on mono- and di- styryl borondipyrromethenes (BODIPY) linked methyl malonyl were designed for detection of hemoglobin (HgB). Their sensing behavior toward various analytes (Br, EDTA, Glucose, CO, Fe, Fe, I, NO, PO, SO,Cl, Urea, K, Mg, Na, NH, Zn,Ca,Cd, Li, Pb, Cs, Ag, Mn, Cr, Ni, Hg, Al) were investigated by fluorescence spectroscopies. Addition of HgB to acetone: water (4:1) solutions of BODIPYs 4 and 5 solutions gave visual color changes, as well as significantly quenched fluorescence emissions, while other analytes induced no or much smaller spectral changes. The sensing method for both BODIPYs 4 and 5 was successfully applied to measure the HgB in human blood with satisfactory results. Spike and recovery tests in human blood samples exhibit good recovery rates for the spiked concentrations close to the limit of detection. It was found that BODIPYs 4 and 5 constituted the HgB selective fluorescent chemosensor (ON-OFF) and the detection limits were calculated to be 1.773 μg. mL and 1. 295 μg.mL respectively.

Novel probes for selective fluorometric sensing of Fe(II) and Fe(III) based on BODIPY dyes

“…Thus, for further studies to investigate interaction between BODIPYs (2 and 3), the influence of Fe 2+ and Fe 3+ ions on fluorescence response Job's plots studies were carried out. As expected, via metal ion coordination to BODIPYs malonyl units, fluorescence intensities decreased, which confirmed the formation of coordination complex between BODIPYs 2 and 3 with Fe 2+ and Fe 3+ ions (16,17,(20)(21)(22). Jobs plots have suggested that BODIPYs 2 and 3 formed 2:1 (Ligand: metal) complexes with Fe 2+ and Fe 3+ ions (Figure 3).…”

“…The related BODIPY derivative (1) was previously synthesized by a simple one-pot reaction modified according to the procedure reported by Gabe and co-workers (17,18). 13 S5).…”

“…The synthetic pathway is shown in Scheme 1. The one-pot synthesis of compound 1 has been previously described by Gabe and coworkers and involved a condensation of 4hydroxybenzaldehyde and 2,4-dimethylpyrrole in the presence of trifluoroacetic acid as catalyst in dichloromethane under argon atmosphere followed by oxidization by p-chloranil and complexation with BF3OEt2 (17,18). Acceptable yields have been obtained on a routine basis using substitution reaction between compound 1 with methylmalonyl chloride and malonyl chloride achieved by addition of corresponding BODIPY derivatives (2 and 3).…”

“…Because BODIPY-based probes exhibit convenient spectral properties like photostability, high fluorescence quantum yield and amenability to alterations in photophysical and photochemical properties via small and facile alteration on molecules (14-16). Recently we have devised fluorescence chemosensors based on methyl malonylconjugates of mono-and di-styryl BODIPY dyes for determination of HgB via Fe ion complexation as an alternative approach to the classical sensing systems of HgB (17). These results have been encouraged us to synthesize new systems based on malonyl unit on meso position of BODIPYs as fluorescence probe by using the advantage of the low cost and rapid process of fluorescence systems.…”

Investigating the Potential of 8-Amidoquinoline Derivatives as a Fluorescent Probe for Zinc Detection: A Systematic Literature Review

“…Therefore, chemosensors have been playing an essential role in detecting various analyte in many diverse fields, especially in analytical chemistry, bio-medicinal science, and environmental chemistry [4][5][6][7][8][9]. There are various types of chemosensor, including fluorescent sensors using spectrophotometry and fluorimeter to detect analytes [10][11][12][13][14][15][16][17][18][19].…”