A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum

Abstract

A general approach toward highly fluorogenic probes across the visible spectrum for various analytes offers significant potential for engineering a wide range of bioprobes with diverse sensing and imaging functions. Here we show a facile and general strategy that involves introducing a new fluorogenic mechanism in boron dipyrromethene (BODIPY) dyes, based on the principle of stimuli-triggered dramatic reduction in the electron-withdrawing capabilities of the meso-substituents of BODIPYs. The fluorogenic mechanism has been demonstrated to be applicable in various BODIPYs with emission maxima ranging from green to far red (509, 585, and 660 nm), and the synthetic strategy allows access to a panel of highly fluorogenic bioprobes for various biomolecules and enzymes (HO, HS, and protease) via introducing specific triggering motifs. The potency of the general design strategy is exemplified by its application to develop a mitochondria-targeting far-red probe capable of imaging of endogenous HO in living cells.

A H2O2-Responsive Boron Dipyrromethene-Based Photosensitizer for Imaging-Guided Photodynamic Therapy

“…And 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was purchased from Gen View Co., Ltd., Tallahassee, FL, USA. Compounds 1, 2 , 3 [37] were prepared as described.…”

“…Herein, we synthesize a H 2 O 2 -responsive photosensitizer for near infrared (NIR) fluorescence imaging-guided photodynamic therapy. As depicted in Scheme 1, in the presence of H 2 O 2 , the arylboronate group is broken, the meso -ester-substituted dye converts to highly labile intermediates, followed by the linker self-immolation to form meso -carboxylate-substituted BODIPY with strong fluorescence emission [37]. And when exposed to the near-infrared light, it would generate singlet oxygen to kill the cancer cells.…”

Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

“…Thus, vanillin 9 was readily converted to nitriles 11 and 13 (Scheme ). Vanillin 9 was first converted to its 2‐hydroxyethyl derivative 10 . Treatment of aldehyde 10 with hydroxylamine, triethylamine and SO 2 F 2 produced nitrile 11 .…”

“…Vanillin 9 wasf irst converted to its 2-hydroxyethyl derivative 10. [46] Treatment of aldehyde 10 with hydroxylamine, triethylamine and SO 2 F 2 produced nitrile 11.T he mesylatedd erivative 12 also gave the desired nitrile 13 in high yield. The compatibility of the reaction with variousf unctional groups allowed for the synthesis of azide functionalized nitrile 14 startingf rom vanillin in excellent yield.…”

BODIPY-based Fluorescent Probe for the Detection of Cysteine in Living Cells

“…[34][35][36][37][38][39][40][41][42][43] BODIPY dyes have emerged as a fascinating class, attribute able to their various favorable features, such as high photo-stability, favorable fluorescence quantum yields and molar absorption coefficients. 34,[44][45][46][47][48][49][50] The meso position, as the most sensitive position of BODIPY, could be fine-tuned by the electronic property of the substituent to impact maximum emission and absorption. 49 We have demonstrated that steric congestion at 1-and 7-positions may affect the SNArrearrangement cascade reaction of individual biothiol species that allow differentiation of bithiol species from dual emission channels.…”