A dual-channel responsive near-infrared fluorescent probe for multicolour imaging of cysteine in living cells

Abstract

Aberrant levels of cysteine (Cys) in living cells are closely related to some diseases; thusin situvisualization of intracellular Cys is very helpful for the investigation of physiological and pathological processes.

BODIPY‐Based Fluorescent Probes for Biothiols

“…Bao, Zeng, and co-workersh ave reported three NIR fluorescent probes( 78, 79,a nd 80)b earing the NBD fluorophore at the meso position of BODIPY or 3,5-position of the aza-BODIPY scaffoldt hrough an ether bond ( Figure 19). [108][109][110] Lately,o ur group incorporated the NBD fluorophore with the BODIPY scaffold by as elfimmolative linker as NIRs ensor 81 fort he differentiation of GSH/H 2 Sa nd Cys/Hcy (Figure 19). [111] These probesall could be applied in biological samples.…”

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

“…Many previously reported efforts have focused on the synthesis of dyes for cysteine detection, with at least 24 synthetic dye-based reported to function in detecting cysteine in the past five years (Table 2) [ 257 , 258 , 259 , 260 , 261 , 262 , 263 , 271 , 272 , 273 , 274 , 275 , 276 , 277 , 278 , 279 , 280 , 281 , 282 , 283 , 284 , 285 , 286 , 287 , 288 ]. Of these, several can be targeted to the mitochondria [ 262 , 282 , 285 , 286 ], the Golgi apparatus [ 259 , 276 ], the endoplasmic reticulum [ 274 , 275 ] and the lysosome [ 277 ].…”

“…Of these, several can be targeted to the mitochondria [ 262 , 282 , 285 , 286 ], the Golgi apparatus [ 259 , 276 ], the endoplasmic reticulum [ 274 , 275 ] and the lysosome [ 277 ]. Five act as non-specific sensors, detecting cysteine and other molecules that contain thiol groups or cysteine metabolites, with some using different wavelengths to distinguish between the different ligands [ 258 , 271 , 273 , 280 , 283 ]. These synthetic sensors all require irreversible reactions to detect cysteine, negatively affecting kinetics and requiring at least 5 min to an hour for maximum fluorescence [ 257 , 259 , 260 , 262 , 271 , 272 , 273 , 274 , 275 , 276 , 277 , 278 , 279 , 280 , 281 , 282 , 283 , 284 , 285 , 286 , 288 ].…”

Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies

“…Since an NBD-S bond will quench the fluorescence of NBD, H 2 S, PhSH, GSH, and thiol-containing proteins cannot restore it. Therefore, NBD-O ether can be used for distinguishing Cys or Hcy from other RSSs based on the fluorescence recovery of fluorophores and the change of NBD fluorescence [208] , [209] , [210] , [211] .…”