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Abstract
Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.
Highlights
Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are important mediators in many physiological and pathological vivo leads to processes.[1]
Our design strategy for an azulene chemodosimeter imaging probe is centered on the concept of an inversion of internal charge transfer (ICT) directionality upon reaction with the analyte
Our approach involves the use of a pinacol boronate ester as a receptor motif, whose reaction with ROS/RNS leads to the desired reversal of the direction of ICT
Summary
Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are important mediators in many physiological and pathological vivo leads to processes.[1]. The ester groups will stabilize the hydroxyazulene product 2 of reaction with ROS/RNS, they will enhance the contribution of the resonance effect that reinforces the inherent polarity of azulene, as shown in Scheme 2c. The pretreated with H2O2 (2 mM) fluorescence intensity of cells pretreated with ROS was shown to increase nearly 3-fold (Figure 6b-c), compared to negative control (Figure 6a, cells stained with probe 1 only). 1 showed strong fluorescence intensity, increasing by approximately 2-fold, as compared with the control group (Figure 6d,e,g). Compared to negative control (Figure 7b,c) whereas fluorescence did not increase above basal levels upon cotreatment with SIN-1 and ebselen (200 μM) (Figure 7d,f) This confirms that our probe can directly detect endogenous ROS in living tissues with TPM
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