Specific detection of D-glucose by a tetraphenylethene-base fluorescent sensor

• US 9,051,598 B2
• Filed: 05/02/2012
• Issued: 06/09/2015
• Est. Priority Date: 05/02/2011
• Status: Active Grant

• Current Assignee: Hong Kong University of Science and Technology
• Original Assignee: Hong Kong University of Science and Technology
• Inventors: Liu, Yi, Qin, Anjun, Tang, Benzhong, Sun, Jingzhi, Hu, Rongrong
• Primary Examiner(s): Soderquist, Arlen
• Application Number:
  US13/462,183
• Publication Number:
  US 20120282703A1
• Time in Patent Office: 1,133 Days
• Field of Search: 436 93- 95, 436/166, 436/172
• US Class Current: 1/1
• CPC Class Codes: C12Q 1/54 involving glucose or galactose
• CPC Class Codes: G01N 2021/6439 with indicators, stains, dyes, tags, labels, marks
• CPC Class Codes: G01N 21/64 Fluorescence; Phosphorescence
• CPC Class Codes: G01N 21/6428 Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" in vivo A61B5/00; immunoassay G01N33/53
• CPC Class Codes: G01N 21/6486 Measuring fluorescence of biological material, e.g. DNA, RNA, cells G01N21/6428 takes precedence
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: G01N 33/66 involving blood sugars, e.g. galactose
• CPC Class Codes: Y10T 436/144444 Glucose

Abstract

A method of detecting the presence or absence of saccharide or saccharide level in a biological or artificial sample comprising contacting the sample with a water-soluble tetraphenylethene-cored probe having multiple functionalities of boronic acid and aggregation induced emission (AIE) characteristics, and detecting fluorescence. A method for detecting pH in a sample solution with a certain pH value comprising contacting the sample solution with a water-soluble tetraphenylethene-cored probe having multiple functionalities of boronic acid and aggregation induced emission (AIE) characteristics, and detecting fluorescence.

Claims

1. A method for detecting the presence or absence of glucose or the glucose level in a sample, comprising contacting the sample with a water-soluble tetraphenylethene-cored probe having multiple functionalities of boronic acid and aggregation induced emission (AIE) characteristics, and detecting fluorescence, wherein the water-soluble tetraphenylethene-cored probe is dissolved in a buffer at a pH of at least 9.74, wherein the sample is in aqueous media containing DMSO.

2. The method of claim 1, wherein the water-soluble tetraphenylethene-cored probe contains diboronic acid.

3. The method of claim 2, wherein the water-soluble tetraphenylethene-cored probe is (1,2-diphenylethene-1,2-diyl)bis(1,4-phenylene)-1,1′

-diboronic acid (TPEDB).

4. The method of claim 3, wherein the glucose level is from 0.2 mM to 10.0 mM.

5. The method of claim 4, wherein the emission of TPEDB is boosted nearly 5.4 fold when the concentration of D-glucose reaches 5.0 mM.

6. The method of claim 2, wherein the tetraphenylethene-cored probe oligomerizes with D-glucose in solution and activates the fluorescence of the probe.

7. The method of claim 6, wherein the glucose level is 5.0 mM.

8. The method of claim 1, wherein the sample is a solution of D-glucose contained in deionized water.

9. The method of claim 1, wherein the sample is a biological sample.

10. The method of claim 9, wherein the biological sample is a urine solution.

11. The method of claim 1, wherein the sample is contacted with a solution of the water-soluble tetraphenylethene-cored probe in carbonate buffer.

12. The method of claim 11, wherein the carbonate buffer contains 4.0 vol % of dimethyl sulfoxide.

13. The method of claim 11, wherein the carbonate buffer has a concentration of 0.4 M.

14. The method of claim 11, wherein the carbonate buffer has a pH value of 10.5.

15. A method for detecting pH in the range of 8.61 to 9.74 in a sample solution with a certain pH value, comprising contacting the sample solution with a water-soluble tetraphenylethene-cored probe having multiple functionalities of boronic acid and aggregation induced emission (AIE) characteristics, and detecting fluorescence, wherein the water-soluble tetraphenylethene-cored probe is dissolved in a buffer at a pH of at least 8.61, wherein the sample is in aqueous media containing DMSO.

16. The method of claim 15, wherein the water-soluble tetraphenylethene-cored probe is a 2.0 mL stock solution and the sample solution is 2.0 mL standard buffer solution.

17. The method of claim 15, wherein the water-soluble tetraphenylethene-cored probe is (1,2-Diphenylethene-1,2-diyl)bis(1,4-phenylene)-1,1′

-diboronic acid (TPEDB).

18. The method of claim 15, wherein the sample solution is a sodium hydroxide solution.

19. The method of claim 18, wherein the sodium hydroxide solution contains 4.0 vol % DMSO.

20. The method of claim 18, wherein the concentration of the sodium hydroxide solution is 0.01 M.

21. The method of claim 15, wherein the sample solution is prepared using Britton-Robinson buffers.