Water‐Soluble Triarylboron Compound for ATP Imaging In Vivo Using Analyte‐Induced Finite Aggregation

Abstract

Adenosine 5'-triphosphate (ATP) is a multifunctional molecule that participates in many important biological processes. Currently, fluorescence indicators for ATP with high performance are in demand. Reported herein is a novel water-soluble triarylboron compound which displays an apparent ATP-dependent fluorescence enhancement when dispersed in water. It can selectively recognize ATP from other bioactive substances in vitro and in vivo. The ATP-induced finite aggregation endows the indicator with appreciable photostability and superior tolerance to environmental electrolytes. This indicator has been successfully applied to the ATP imaging in NIH/3T3 fibroblast cells. The difference in the ATP levels within the membrane and cytosol is clearly visible.

A Ga3+self-assembled fluorescent probe for ATP imaging in vivo

“…5, apparent fluorescence signal occurred in the cytoplasm and cell membrane, but not in the nucleus. The distribution of ATP is in line with the reported (Ojida et al, 2002(Ojida et al, , 2006(Ojida et al, , 2008Li et al, 2014). To further confirm that fluorescent domain was triggered by ATP, apyrase was used to treat the cells prior to the staining procedure.…”

“…We also reported a molecular assembly of a squaraine dye with cationic surfactant for selectively fluorescence response to ATP (Xu et al, 2011). Very recently, Yang and coworkers reported a water-soluble triarylboron compound for ATP imaging through analyte-induced finite aggregation (Li et al, 2014). These sensors take advantage of different receptors binding, i.e., hydrogen bonding, electrostatic interactions, π-π interactions, or combinations of them, to achieve good selectivity.…”

“…Accordingly, considerable efforts have been devoted to develop fluorescent sensors for ATP (Ojida et al, 2002(Ojida et al, , 2006(Ojida et al, , 2008Weitz et al, 2012;Xu et al, 2009Xu et al, , 2011Li et al, 2014;Rao et al, 2012;Strianese et al, 2012;Moro et al, 2010;Shi et al, 2013;Zhang et al, 2013aZhang et al, , 2013bNgo et al, 2012;Zhao et al, 2012;Schäferling and Wolfbeis, 2007). Hamachi and co-workers reported a zinc dipicolyl-tethered xanthenes (Ojida et al, 2008), acridine (Ojida et al, 2006), or anthracene (Ojida et al, 2002) as turn-on type fluorescent sensors for ATP.…”

Water‐Soluble Triarylborane Chromophores for One‐ and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells

“…They and two other groups made use of a similar method for the preparation of water‐soluble triarylboranes with phosphonium substituents for anion sensing . Recently, a water‐soluble, non‐ionic triarylborane containing polyethylene glycol chains as the hydrophilic groups was reported by Yang and co‐workers as an efficient fluorescence indicator for ATP in the cytoplasm and cell membrane . Furthermore, while our work was in progress, the same authors reported a water‐soluble triarylborane‐containing Cu II ‐cyclen.…”

Sensing for intracellular thiols by water-insoluble two-photon fluorescent probe incorporating nanogel

“…Furthermore, p-conjugated triarylboron derivatives show high fluorescence quantum yield and excellent photostability. Triarylboron luminogens, therefore, have promising applications in diverse areas, such as temperature measurement [24][25][26], adenosine triphosphate (ATP) detection [27], fluoride detection [28] and two-photon absorption antenna [29]. Considering outstanding features of p-conjugated triarylboron derivatives, we designed and synthesized a "turn-on" twophoton fluorescent probe DMDP-M (Scheme 1) based on a p-conjugated triarylboron luminogen 4-(dimesitylboryl)-N,Ndiphenylaniline (DMDP) bearing a maleimide moiety linked by methylene spacer for selective detection of thiols.…”