A pyrene-based ratiometric fluorescent probe with a large Stokes shift for selective detection of hydrogen peroxide in living cells

Abstract

Hydrogen peroxide (H 2 O 2 ) plays a significant role in regulating a variety of biological processes. Dysregulation of H 2 O 2 can lead to various diseases. Although numerous fluorescent imaging probes for H 2 O 2 have been reported, the development of H 2 O 2 ratiometric fluorescent probe with large Stokes shift remains rather limited. Such probes have shown distinct advantages, such as minimized interference from environment and improved signal-to noise ratio. In this work, we reported a new pyrene-based compound Py-VPB as H 2 O 2 fluorescent probe in vitro. The probe demonstrated ratiometric detection behavior, large Stokes shift and large emission shift. In addition, the probe showed high sensitivity and selectivity towards H 2 O 2 in vitro. Based on these excellent properties, we successfully applied Py-VPB to the visualization of exogenous and endogenous H 2 O 2 in living cells. Cell imaging study also showed that our probe was localized in the mitochondria. We envision that the probe can provide a useful tool for unmasking the biological roles of mitochondrial H 2 O 2 in living systems.

White light employing luminescent engineered large (mega) Stokes shift molecules: a review

“…An extension of the acceptor strength was pursued by Chen et al in 2020, whereby a boronic moiety was engulfed to further extend the acceptor fragment. 38 Interestingly, a mega Stokes shift of up to 220 nm was observed as the compound bound to detect hydrogen peroxide, thereby reducing crosstalk between the excitation ( λ ex = 380 nm) and emission light. Chao and co-workers designed a pyrene-based colorimetric and fluorescent pH probe with a large Stokes shift of up to 145 nm.…”

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

“…In all cases, successful accumulation was observed which denotes a significant superior performance of pyrene materials when compared to other chemistries, such as cyanines, which require the presence of additional delocalized lipophilic cations (see above). Probes 124 [168] and 125 [169] (, Table 5 ) bear terminal boronate functionalization for sensing application. As such, their arguably low quantum yields (φ f =0.07 and 0.27 for 124 and 125 in DMSO and sodium borate buffer, respectively) are intended for this purpose.…”

Novel Prostate Cancer Biomarkers: Aetiology, Clinical Performance and Sensing Applications

“…Another recent study suggests the use of a new pyrene-based compound (Py-VPB) as H 2 O 2 fluorescent probe for intracellular detection in vitro and in vivo. Using HeLa cell line, H 2 O 2 was visualised inside mitochondria [42]. The most significant ions and small molecules, including their importers and mechanisms of oxidative DNA damage, are shown in Figure 2.…”