A “Turn-On” Fluorescent Sensor for Methylglyoxal

Abstract

Methylglyoxal (MGO), a dicarbonyl metabolite produced by all living cells, has been associated with a number of human diseases. However, studies of the role(s) MGO plays biologically have been handicapped by a lack of direct methods for its monitoring and detection. To address this limitation, we have developed a fluorescent sensor (methyl diaminobenzene-BODIPY, or "MBo") that can detect MGO under physiological conditions. We show that MBo is selective for MGO over other biologically relevant dicarbonyls and is suitable for detecting MGO in complex environments, including that of living cells. In addition, we demonstrate MBo's utility in estimating plasma concentrations of MGO. The results reported herein have the potential to advance both clinical and basic science research and practice.

A fluorogenic assay for methylglyoxal

“…The response is potentiated markedly by addition of exogenous MG. Similar findings were reported with the BODIPY-related probe by Wang et al [27]. DAF-2DA was also used to assess whether increased fluorescence could be detected in cells using a microplate based-cell assay with A549 cells cultured in 96-well plates.…”

“…We have shown in our studies that MG reacts with DAF-2 and DAR-1 to produce a characteristic fluorophore and, moreover, the development of related increased fluorescence can be used to report on MG and other dicarbonyl concentrations. Wang et al [27] recently synthesized MBo (methyl -1 studies). a.u., arbitrary units.…”

“…of the zero analyte control in calibration curves). MBo was also used to estimate MG in mouse plasma, finding 0.51-0.99 μM MG [27]. Interferencefree estimates of MG in human plasma are lower than this at 100-300 nM [35,36].…”

“…In the present article, we describe the reaction of MG with DAF-2 and DAR-1 and the strengths and limitations of their use to detect MG and related dicarbonyl metabolites, including in live cells. A similar approach was taken independently in preparing a 1,2-diaminophenyl derivative of BODIPY [27].…”

Colorimetric and Fluorometric Discrimination of Geometrical Isomers (Maleic Acid vs Fumaric Acid) with Real-Time Detection of Maleic Acid in Solution and Food Additives

“…Compared to the large number of chromogenic receptors for the sensing of metal ions, [11][12][13] very few chromogenic receptors for anions and small molecules have been developed that are based on recognition approaches. [13][14][15][16] In fact, a thorough literature survey revealed that there are very few colorimetric or fluorogenic sensors which dealt with the use of synthetically constructed receptors in carboxylic acids sensing purpose. [17][18] Supramolecular concepts [19][20] in designing new optical chemosensors has become a very common trend in recent-past based on changes in fluorescence [21][22][23] and in absorbance [24][25][26] as the output signals.…”