A water-soluble two-photon ratiometric triarylboron probe with nucleolar targeting by preferential RNA binding

Abstract

By functionalizing triarylboron with cyclen, we developed a two-photon fluorescence probe, TAB-2, which can selectively bind RNA with a ratiometric readout. We tested TAB-2 in NIH/3T3 fibroblast cells, and demonstrated its capability in visualizing nucleoli and analyzing microenvironment polarity by two-photon and fluorescence-lifetime imaging microscopy.

The Effect of Branching on the One‐ and Two‐Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging

“…[25] They reported cell-membrane permeability and a preferentiald istribution at mitochondria, [25] whereas the same compound, withoutC u II binding, was used one year later to stain nucleoli and cytoplasm. [26] However,a two-photon brightnesso fo nly 30 GM in DMSO was measured for this compound. Very recently,a no ctupolar dye was reported which stains nucleoli as well as the nuclear membrane, nuclear matrix,n uclear pore and the cytoplasm, while binding to RNA.…”

“…The Yang group sensed H 2 S with a Cu II ‐cyclen‐substituted triarylborane . They reported cell‐membrane permeability and a preferential distribution at mitochondria, whereas the same compound, without Cu II binding, was used one year later to stain nucleoli and cytoplasm . However, a two‐photon brightness of only 30 GM in DMSO was measured for this compound.…”

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

“…We recently reported the water-soluble and stable cationic bis-triarylborane derivative 1 as an ew fluorophore applicable for one-and two-photon excited fluorescence imaging in cells. [3] Given that only af ew examples of water-soluble triarylboranes have been reported to date, [4][5][6][7][8][9][10][11][12][13] such borane-based chromophores could be considered to be novel fluorophores for biochemical applications;t hey are already widely used in nonlinearo ptical materials, organic electronics, organic lightemitting diodes or anion sensors. [14][15][16][17][18][19][20][21][22] However,f luorescence of 1 only enabled intracellularl ocalisation of ad ye, but did not allow fort he determination of at argeted biomacromolecule (for example, protein or DNA or RNA).…”

Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

“…Furthermore, they could sense H 2 S with a Cu II -cyclen-substituted triarylborane 108. They reported cell-membrane permeability and a preferential distribution at mitochondria,108 while the same compound, without Cu II binding, was used one year later to stain nucleoli and cytoplasm 109. However, a two-photon brightness of only 30 GM in DMSO was measured for this compound.…”