IP Library Granted Patent US 9,980,668
Granted Patent B2
US 9,980,668 · App. 13/562,403 · Granted May 29, 2018

Photoluminescent nanostructure-based sensors

Inventors: Michael S. Strano (Lexington, MA); Paul W. Barone (Jamaica Plain, MA); Jin-Ho Ahn (Cambridge, MA); Kyungsuk Yum (Cambridge, MA); Thomas P. McNicholas (Cambridge, MA)
Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
A61B5/1459A61B5/14532G01N33/542G01N33/54373G01N33/582G01N33/587G01N33/66
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Quick Facts
Patent No.
US 9,980,668
App. No.
13/562,403
Granted
May 29, 2018
Kind
B2
Abstract

A composition for sensing an analyte can include a photoluminescent nanostructure complexed to a sensing polymer, where the sensing polymer includes an organic polymer non-covalently bound to the photoluminescent nanostructure and an analyte-binding protein covalently bound to the organic polymer, and where the analyte-binding protein is capable of selectively binding the analyte, and the analyte-binding protein undergoes a substantial conformational change when binding the analyte. Separately, a composition for sensing an analyte, can include a complex, where the complex includes a photoluminescent nanostructure in an aqueous surfactant dispersion and a boronic acid capable of selectively reacting with an analyte. The compositions can be used in devices and methods for sensing an analyte.

Claims (24)

1. A composition for sensing an analyte, comprising a complex, wherein the complex includes a photoluminescent nanostructure in an aqueous dispersion and a substituted phenyl boronic acid adsorbed to the photoluminescent nanostructure, wherein the complex has a specific affinity to an analyte and binding of the analyte to the complex changes a fluorescence signal of the photoluminescent nanostructure.

2. The composition of claim 1 , wherein the photoluminescent nanostructure is a carbon nanotube.

3. The composition of claim 2 , wherein the carbon nanotube is a SWNT.

4. The composition of claim 1 , wherein the analyte is a monosaccharide.

5. The composition of claim 4 , wherein the monosaccharide is glucose.

6. The composition of claim 5 , wherein the boronic acid is selected from the group consisting of: 3-aminophenylboronic acid, 4-chlorophenylboronic acid, 4-carboxyphenylboronic acid, naphthalene-1-boronic acid, 3-nitrophenylboronic acid, benzene-1,4-diboronic acid, 2-naphthylboronic acid, 1-thianthrenylboronic acid, 4-cyanophenylboronic acid, 4-methyl-1-naphthaleneboronic acid, 6-methoxy-2-naphthaleneboronic acid, 6-ethoxy-2-naphthaleneboronic acid, 3-biphenylboronic acid, 8-quinolinylboronic acid, pyrene-1-boronic acid, 9,9-dihexylfluorene-2,7-diboronic acid, acenaphthene-5-boronic acid, 10-bromoanthracene-9-boronic acid, 4-(diphenylamino)phenylboronic acid, 4-(4′-methoxybenzyloxy)phenylboronic acid, 4-(4′-(2-pentyloxy)phenyl)phenylboronic acid, 2-(tert-butyldimethylsilyloxy)naphthalene-6-boronic acid, 9-anthraceneboronic acid, 5-bromopyridine-3-boronic acid, 9-phenanthracenylboronic acid, 4-bromo-1-naphthaleneboronic acid, 2-aminopyrimidine-5-boronic acid, indazole-4-boronic acid, fluorene-2-boronic acid, and indazole-6-boronic acid.

7. The composition of claim 1 , wherein the substituted phenyl boronic acid is a para-substituted, electron-withdrawing phenyl boronic acid.

8. A device for sensing an analyte, comprising:

a hydrogel particle encapsulating a composition, wherein the composition includes a complex, wherein the complex includes a photoluminescent nanostructure in an aqueous dispersion and a substituted phenyl boronic acid adsorbed to the photoluminescent nanostructure, wherein the complex has a specific affinity to an analyte and binding of the analyte to the complex changes a fluorescence signal of the photoluminescent nanostructure.

9. The device of claim 8 , wherein the photoluminescent nanostructure is a carbon nanotube.

10. The device of claim 9 , wherein the carbon nanotube is a SWNT.

11. The device of claim 8 , wherein the analyte is a monosaccharide.

12. The device of claim 11 , wherein the monosaccharide is glucose.

13. The device of claim 12 , wherein the boronic acid is selected from the group consisting of: 3-aminophenylboronic acid, 4-chlorophenylboronic acid, 4-carboxyphenylboronic acid, naphthalene-1-boronic acid, 3-nitrophenylboronic acid, benzene-1,4-diboronic acid, 2-naphthylboronic acid, 1-thianthrenylboronic acid, 4-cyanophenylboronic acid, 4-methyl-1-naphthaleneboronic acid, 6-methoxy-2-naphthaleneboronic acid, 6-ethoxy-2-naphthaleneboronic acid, 3-biphenylboronic acid, 8-quinolinylboronic acid, pyrene-1-boronic acid, 9,9-dihexylfluorene-2,7-diboronic acid, acenaphthene-5-boronic acid, 10-bromoanthracene-9-boronic acid, 4-(diphenylamino)phenylboronic acid, 4-(4′-methoxybenzyloxy)phenylboronic acid, 4-(4′-(2-pentyloxy)phenyl)phenylboronic acid, 2-(tert-butyldimethylsilyloxy)naphthalene-6-boronic acid, 9-anthraceneboronic acid, 5-bromopyridine-3-boronic acid, 9-phenanthracenylboronic acid, 4-bromo-1-naphthaleneboronic acid, 2-aminopyrimidine-5-boronic acid, indazole-4-boronic acid, fluorene-2-boronic acid, and indazole-6-boronic acid.

14. The composition of claim 8 , wherein the substituted phenyl boronic acid is a para-substituted, electron-withdrawing phenyl boronic acid.

15. A method for sensing an analyte, comprising:

providing a composition, wherein the composition includes a complex, wherein the complex includes a photoluminescent nanostructure in an aqueous dispersion and a substituted phenyl boronic acid adsorbed to the photoluminescent nanostructure, wherein the complex has a specific affinity to an analyte and binding of the analyte to the complex changes a fluorescence signal of the photoluminescent nanostructure; and

contacting the composition with a sample suspected of containing the analyte.

16. The method of claim 15 , wherein the photoluminescent nanostructure is a carbon nanotube.

17. The method of claim 16 , wherein the carbon nanotube is a SWNT.

18. The method of claim 15 , wherein the analyte is a monosaccharide.

19. The method of claim 18 , wherein the monosaccharide is glucose.

20. The method of claim 19 , wherein the boronic acid is selected from the group consisting of: 3-aminophenylboronic acid, 4-chlorophenylboronic acid, 4-carboxyphenylboronic acid, naphthalene-1-boronic acid, 3-nitrophenylboronic acid, benzene-1,4-diboronic acid, 2-naphthylboronic acid, 1-thianthrenylboronic acid, 4-cyanophenylboronic acid, 4-methyl-1-naphthaleneboronic acid, 6-methoxy-2-naphthaleneboronic acid, 6-ethoxy-2-naphthaleneboronic acid, 3-biphenylboronic acid, 8-quinolinylboronic acid, pyrene-1-boronic acid, 9,9-dihexylfluorene-2,7-diboronic acid, acenaphthene-5-boronic acid, 10-bromoanthracene-9-boronic acid, 4-(diphenylamino)phenylboronic acid, 4-(4′-methoxybenzyloxy)phenylboronic acid, 4-(4′-(2-pentyloxy)phenyl)phenylboronic acid, 2-(tert-butyldimethylsilyloxy)naphthalene-6-boronic acid, 9-anthraceneboronic acid, 5-bromopyridine-3-boronic acid, 9-phenanthracenylboronic acid, 4-bromo-1-naphthaleneboronic acid, 2-aminopyrimidine-5-boronic acid, indazole-4-boronic acid, fluorene-2-boronic acid, and indazole-6-boronic acid.

21. The composition of claim 15 , wherein the substituted phenyl boronic acid is a para-substituted, electron-withdrawing phenyl boronic acid.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jun 15, 2015
From: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 035905/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2013
From: STRANO, MICHAEL S.; BARONE, PAUL W.; AHN, JIN-HO; YUM, KYUNGSUK; MCNICHOLAS, THOMAS P.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 029670/0147 →
Continuity (2)
Provisional Application 61513790 · Aug 1, 2011
Related Publication 20130035567A1 · Feb 7, 2013