Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load

Abstract

A minimalist fluorogenic probe is presented capable of the mapping of aldehydic load through live cell microscopy.

Phytochemicals toward Green (Bio)sensing

“…In another work, the fluorescent CDs synthesized from picrocrocin (Figure - 29 ), extracted from saffron, which showed low toxicity at concentrations significantly higher than the required usual doses (less than 1 g L –1 ) for cell labeling/imaging, were used for cell bioimaging applications . Anthranilates (2-aminobenzoates) or methyl 5-MeO- N -aminoanthranilate (Figure - 30 ) was employed as a fluorescence probe for aldehyde sensing and its imaging in HEK293 cells and subsequently for studying the oxidative degradation of lipids in live cells (HEK293 cells refer to human embryonic kidney 293 cells) . Green fluorescent folic acid-CDs, which have been synthesized via carbonization of dandelion (as a natural carbon source) and then amino-functionalized with ethylenediamine (as the nitrogen source) by a one-step hydrothermal process (Figure - 35 ), were applied for cancer cell imaging by Zhao et al As shown in Figure f, the developed folic acid/CDs-based probe was selectively bound with folate receptors on the surface of cancerous cells membrane and displayed green fluorescence, wherein noncancerous cells do not express folate receptors and show very weak fluorescence compared to cancerous cells.…”

“…188 Anthranilates (2-aminobenzoates) or methyl 5-MeO-N-aminoanthranilate (Figure 12-30) was employed as a fluorescence probe for aldehyde sensing and its imaging in HEK293 cells and subsequently for studying the oxidative degradation of lipids in live cells (HEK293 cells refer to human embryonic kidney 293 cells). 217 Green fluorescent folic acid-CDs, which have been synthesized via carbonization of dandelion (as a natural carbon source) and then amino-functionalized with ethylenediamine (as the nitrogen source) by a one-step hydrothermal process (Figure 12-35), were applied for cancer cell imaging by Zhao et al As shown in Figure 10f, the developed folic acid/CDs-based probe was selectively bound with folate receptors on the surface of cancerous cells membrane and displayed green fluorescence, wherein noncancerous cells do not express folate receptors and show very weak fluorescence compared to cancerous cells. The fluorescence images of noncancerous (PC-12) and cancerous (HepG-2 and MCF-7) cells incubated with folic acid-CDs are displayed in Figure 10g, which clearly indicate the accumulation of the folic acid-CDs in cancer cells.…”

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

“…The enhancement of fluorescence relative to 119 only was recorded with λ ex /λ em 375/480 nm following 1 min of incubation of 1 μM solutions of 119 in PBS (pH 7.2) with 5 equiv of MDA (black bar), simple aliphatic aldehydes (red bars), dialdehydes, and complex aldehydes (blue bars), ketones (purple bars), glutathione (yellow bar), and biogenic metal cations (orange bars). Reproduced with permission from ref . Copyright 2019 The Royal Society of Chemistry.…”

“…Among the already described fluorogenic hydrazines ( cf . section ), methyl 5-MeO- N -aminoanthranilate 119 was tested as a probe for aliphatic ketones and showed a small (unquantified) increase in fluorescence emission upon conjugation …”

“…It was used to measure the concentration of aldehydes in cells. 312 The reaction with their test substate (malondialdehyde) immediately led to the formation of a blue-green fluorescent species (λ em = 480 nm), followed by a rapid decay of the signal (50% within 5 min; Figure 35). Still, initial enhancement of fluorescence with aliphatic aldehydes was between 5-and 20-fold.…”