Exploring the use of APTS as a fluorescent reporter dye for continuous glucose sensing

Abstract

The anionic fluorescent dye, aminopyrene trisulfonic acid (APTS), was synthesized and used in a solution-based two-component glucose-sensing system comprising the dye and a boronic acid-appended viologen. The fluorescence of the dye was quenched in the presence of the viologen and the fluorescence restored upon glucose addition. An important feature of this fluorophore is that it can be covalently bonded to a polymer through the amine group without a significant effect on optical properties. Two APTS derivatives, functionalized with polymerizable groups, were synthesized and immobilized in hydroxyethyl methacrylate (HEMA)-based hydrogels. The latter were used to continuously monitor glucose. The fluorescence signal modulation, signal stability, reversibility, reproducibility, and pH sensitivity of the hydrogels were evaluated. The APTS dyes described herein are insensitive to pH changes within the physiological range, both in solution and when immobilized in a hydrogel. When APTS is used in conjunction with boronic acid-appended viologens to sense glucose, the system displays some pH sensitivity because of the presence of the boronic acid.

Enzymatic Glycosylation of Small Molecules: Challenging Substrates Require Tailored Catalysts

“…Progress in this endeavor is documented in a series of publications detailing the chemistry of the system and the development of sensors based on immobilization of the sensing components in hydrogels. [199][200][201][202][203][204][205][206][207][208] The sensor will be commercialized for continuous glucose monitoring in intensive care units. [209] In collaboration with the laboratory of Schiller [41,210] the sensing system was used to go beyond continuous glucose sensing, [210] such as multivariate analysis, [199,202] hydrogels in multiwell plates, [211] and enzyme assays.…”

Dual‐fluorophore Raspberry‐like Nanohybrids for Ratiometric pH Sensing

“…HPTS has been utilized as a fluorescent pH indicator dye in the near‐neutral region by many researchers . The pH sensitivity of HPTS is due to the presence of a hydroxyl moiety on the pyrene ring in its structure . The deprotonated form of HPTS is highly fluorescent.…”

“…[14,25] The pH sensitivity of HPTS is due to the presence of ah ydroxyl moiety on the pyrene ringi ni ts structure. [26] The deprotonated form of HPTS is highly fluorescent. As HPTS gets protonated, its fluorescencei ntensity decreases, thus providing fluorescencer esponse with varying pH.…”

Chemical Biology: What is Its Role in Drug Discovery?

“…A ruthenium-based metallocrown complex senses the presence of Li + ions in both water and in serum providing a fluorescent readout (Rochat et al, 2009). Sensors for other compounds including glucose (Sharrett et al, 2009), spermidine and spermine (Tanima et al, 2009), palmatine and dehydrocorydaline (Chunju Li et al, 2009), and acetylcholine (Dumartin et al, 2009) have also been described. A novel ditopic receptor based on resocinarene has been reported for the binding of acetylcholine and ammonium cations (Salorinne et al, 2009).…”