Deformylation reaction-based probe forin vivoimaging of HOCl

Abstract

We report a near-infrared emissive probe which can detect HOCl in vivo by both fluorescence imaging and the naked eye.

Release of Amino‐ or Carboxy‐Containing Compounds Triggered by HOCl: Application for Imaging and Drug Design

“…[12] Thet hree typical probes FDOCl-12 (series II), FDOCl-6,and FDOCl-8 (series I) were selected for the in vivo detection. [12] Thet hree typical probes FDOCl-12 (series II), FDOCl-6,and FDOCl-8 (series I) were selected for the in vivo detection.…”

“…We recently reported anew deformylation reaction based probe by delivering methylene blue (MB; FDOCl-1 in Figure 1) for rapid detection of HOCl in vivo,i nw hich, near-infrared (NIR) fluorescence is switched on when aleucomethylene (LMB) derivative is converted into MB in the presence of HOCl. [12] To further develop this system into aH OCl-responsive drug delivery system, we therefore compared the reaction efficiencya nd products of different derivatives of LMB.W ef ound that the reaction time of ad imethylamino carbamide derivative (FDOCl-4)w ith HOCl was more than 10 minutes,m uch slower than that of FDOCl-1 (Figure 1a). However,w hen the dimethylamino group of FDOCl-4 was replaced by either NH 2 or NHR, or the outer amide group was replaced by an alkyl group,t he reaction with HOCl became much faster.…”

“…In vivo studies were then carried on using mouse models of arthritis generated according to our reported method (details in the Supporting Information). [12] Thet hree typical probes FDOCl-12 (series II), FDOCl-6,and FDOCl-8 (series I) were selected for the in vivo detection. As shown in Figure S32, after injection with the same amount of probes (100 mL, 1mm), only the arthritic paw area displayed ar emarkable fluorescent signal (see Figure S32-S34).…”

A Reaction‐Based Fluorescent Probe for Imaging of Native Hypochlorous Acid

“…[10][11][12][13][14] Synthetic small molecular fluorescent probesh ave been confirmed that were superior tools for trackingH OCl due to their high sensitivity,s electivity and easy manipulation. [15][16][17][18][19][20][21][22][23][24][25][26][27] Fluorescence imaging has been considered to be ah igh biocompatible imaging technique andh as been widely used ford etection of specific speciesa tt he cellular level for its noninvasive, realtime visualization, and high spatiala nd temporal resolution. [28][29][30][31][32][33] The conjunction of fluorescent probe and fluorescence imaging could provide us powerful tools for visualization of biologically relevant species.H ence, the fluorescent probesw ith high selectivity and sensitivity would able to trace the endogenousH OCl in living organisms.…”

Fast‐Response Fluorogenic Probe for Visualizing Hypochlorite in Living Cells and in Zebrafish

“…Many fluorogenic probes for ClO − have been reported. These probes operate through different mechanisms, such as oxime oxidation to aldehydes, chlorination of thioesters and amides, and thioether‐to‐sulfonate and selenide‐to‐selenoxide transformations, Whereas most probes can be applied to image cells with low ClO − concentrations, few can be applied to detect ClO − in living organisms . In addition, because of their low sensitivities and low molar absorptions in the visible range, few of these probes can react quickly with ClO − in a manner observable to the naked eye in a few seconds.…”