Optical determination of glucose utilizing boronic acid adducts

a technology of boronic acid and glucose, applied in the field of optical determination of glucose utilizing boronic acid adducts, can solve the problems of inability to develop and commercialize in vivo monitoring systems, all prior art sensors are deficient in one or more aspects

Inactive Publication Date: 2004-02-12
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in spite of the intense effort, no practical system has been developed and commercialized for in vivo monitoring.
All of these prior art sensors are deficient...

Method used

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  • Optical determination of glucose utilizing boronic acid adducts
  • Optical determination of glucose utilizing boronic acid adducts
  • Optical determination of glucose utilizing boronic acid adducts

Examples

Experimental program
Comparison scheme
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preparation b

Synthesis of 8-acetoxy-pyrene-1,3,6-trisulfonyl Chloride

[0237] Trisodium-8-acetoxy-pyrene-1,3,6-trisulfonate (acetoxy-HPTS, 11.33 g, 20 mmol) was suspended in 30 mL of thionyl chloride to which 5 drops of dimethylformamide was added. The suspension was refluxed for 3 hr., during which time it became a brown solution. The solution was then cooled to 25.degree. C. under an argon atmosphere. Thionyl chloride was then distilled off under vacuum (2 Torr) leaving a yellow residue. The yellow residue was transferred to three separate centrifuge tubes along with 60 mL of dichloromethane. The suspensions were then centrifuged and the supernatant solutions transferred to a dry round bottom flask. The residue remaining in the centrifuge tubes was washed an additional four times each with 10 mL portions of dichloromethane. The supernatant solutions were combined and left overnight under an argon atmosphere and some precipitation was observed.

[0238] The dichloromethane solution was added to 250 ...

preparation d

Synthesis of N-benzyl-4-ethenyl-4,7-phenanthrolinium Chloride (4,7-Phen SV)

[0240] A flame dried, side armed 100-mL round bottom flask, equipped with a magnetic stirring bar, was cooled under argon and charged with 4,7-phenanthroline (2.14 g, 11.86 mmols). The flask was equipped with a reflux condenser attached to an argon (g) line and charged with 4-(chloromethyl)styrene (0.905 g, 0.836 mL, 5.93 mmols) and anhydrous CH.sub.3CN (20 mL) through the side arm. The solution was heated to reflux under argon (g) for 17 h, then cooled to room temperature and precipitated with diethyl ether (30 mL). The suspension was allowed to settle and the supernatant removed via cannula. The remaining residue along with 15 mL of solvent was cannulated into a centrifuge tube, triturated with acetone (20 mL), and centrifuged (process repeated 4 times). The brownish / pink solid was triturated with diethyl ether (3.times.20 mL) and dried under reduced pressure. Yield: 0.376 g, 1.13 mmols (19%). .sup.1H NMR (...

example 1

Synthesis of 4,4'-N,N'-bis-(benzyl-3-boronic Acid) Dipyridinium Dibromide

[0242] An oven-dried, 50-mL centrifuge tube was cooled under argon, fitted with a magnetic stirring bar, and charged with 4,4'-bipyridyl (0.469 g, 3 mmols). The tube was sealed with a septum and charged with CH.sub.3OH (7 mL). The homogenous solution was stirred at room temperature while freshly prepared dimethyl-(3-bromomethyl)-benzeneboronate (1.82 g, 7.5 mmols) was added via syringe. After stirring the solution for 15 hours, the reaction vessel was centrifuged (4 min at 3200 RPM) and the CH.sub.3OH cannulated to a separate flask. The remaining yellow solid was triturated with acetone:water (24:1, V / V, 25 mL), stirred vigorously on a vortex mixer and centrifuged. The acetone solution was removed by cannula and the trituration process repeated two more times. The solid was then triturated with diethyl ether using the same process. The pale yellow solid, in the centrifuge tube, was then dried on the high vacuum...

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Abstract

The present invention concerns an improved optical method and optical sensing device for determining the levels of polyhydroxyl-substituted organic molecules in vitro and/or in vivo in aqueous media. In particular, a sensory devise is implemented in a mammal to determine sugar levels. Specifically, a dye is combined with a conjugated nitrogen-containing heterocyclic aromatic boronic acid-substituted bis-onium compound in the presence of a sugar, such as fructose or glucose. The viologens are preferred as the aromatic conjugated nitrogen-containing boronic acid substituted compounds. The method is useful to determine sugar levels in a human being.

Description

[0001] This application is a continuation-in-part of U.S. Ser. No. 09 / 731,323, filed Dec. 5, 2000 and also PCT International application PCT / US01 / 46658 filed Dec. 5, 2001. Both applications are incorporated herein by reference in their entirety.[0002] 1. Field of the Invention[0003] This invention relates to an improved optical method and / or sensor for polyhydroxy substituted organic molecules that measure the concentration of these molecules in aqueous or organic media. In one application, the method and sensor monitor the concentration of sugars, i.e. glucose or fructose, in aqueous solution in vitro. In particular, the method and sensor monitor the concentration of sugars, i.e. glucose or fructose, in aqueous solution in vivo. The determination of glucose in fluids in vivo and in vitro is of importance. The in vivo sensing device is implanted in a human being. Some of the novel components of the optical method and device are also considered to be inventions in their own right.[00...

Claims

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Application Information

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IPC IPC(8): G01N33/52G01N33/543G01N21/64
CPCG01N33/52
Inventor SINGARAM, BAKTHANWESSLING, RITCHIE A.
Owner RGT UNIV OF CALIFORNIA
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