IP Library Granted Patent US 9,429,568
Granted Patent B2
US 9,429,568 · App. 13/993,891 · Granted Aug 30, 2016

Silaanthracene as a red and near infrared sensor and a method to manufacture such a sensor

Inventors: Daniel Dyer (Carbondale, IL); Colleen Scott (Carbondale, IL); Matthew McCarroll (Carbondale, IL); Lichang Wang (Carbondale, IL); Narsimha Sattenapally (Carbondale, IL); Quinn Best (Carbondale, IL)
Assignee: Board of Trustees of Southern Illinois University on Behalf of Southern Illinois University Carbondale
G01N33/52C07F7/0812C07F7/0818G01N21/6428
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Quick Facts
Patent No.
US 9,429,568
App. No.
13/993,891
Granted
Aug 30, 2016
Kind
B2
Abstract

Silaanthracene compounds and methods of producing silaanthracene compounds, in particular silaanthracene fluorophores for use as red or near infrared sensors, probes, dyes, and tags are provided.

Claims (52)

1. A compound of Formula (I):

wherein:

X is selected from the group consisting of hydrogen and halogen;

R 1 is selected from the group consisting of amino and hydroxy;

R 2 is selected from the group consisting of amino, imino, hydroxy, and keto;

R 3 is selected from the group consisting of

 and wherein R, R 4 and R 5 are independently chosen from alkyls.

2. The compound of claim 1 , wherein R 1 and R 2 are aminos.

3. The compound of claim 1 , wherein R 1 is an amino and R 2 is an imino.

4. The compound of claim 1 , wherein R 1 and R 2 are hydroxys.

5. The compound of claim 1 , wherein R 1 is a hydroxy and R 2 is a ketone.

6. A chemical sensor/probe comprising Formula (I):

Wherein:

X is selected from the group consisting of hydrogen and halogen;

R 1 is selected from the group consisting of amino and hydroxy;

R 2 is selected from the group consisting of amino, imino, hydroxy, and keto;

R 3 is selected from the group consisting of

wherein R, R 4 and R 5 are independently chosen from alkyls;

wherein the chemical sensor/probe produces one or more analytically useful signals when contacted with at least one analyte; and

wherein the one or more analytically useful signals are selected from the group consisting of absorption of light at one or more characteristic wavelengths ranging from about 570 nm to about 663 nm, emission of red or NIR light at one or more characteristic wavelengths in response to at least one excitatory light pulse delivered at a wavelength ranging from about 430 nm to about 655 nm, emission of light at a characteristic peak intensity ranging from about 40,000 a.u. to about 800,000 a.u. observed at a wavelength ranging from about 430 nm to about 663 nm, a color change in solution, and any combination thereof.

7. The composition of claim 6 , wherein one or more analytically useful signals is a mathematical combination of two or more other signals of the one or more analytically useful signals, wherein the mathematical combination is selected from the group consisting of signal sums, signal differences, signal products, signal ratios, signal integrations, signal rates, and any combination thereof.

8. The composition of claim 7 , wherein the chemical sensor/probe produces one signal when contacted with one analyte.

9. The composition of claim 7 , wherein the chemical sensor/probe produces one signal when contacted with two or more analytes.

10. The composition of claim 7 , wherein the chemical sensor/probe produces two or more signals when contacted with two or more analytes, wherein each of the two or more signals is associated uniquely with one of the two or more analytes.

11. The composition of claim 6 , wherein the analyte is selected from the group consisting of a cell, a subcellular structure, a chemical compound, and a chemical condition.

12. A dye/tag comprising Formula (I):

wherein

X is selected from the group consisting of hydrogen and halogen;

R 1 is selected from the group consisting of amino and hydroxy;

R 2 is selected from the group consisting of amino, imino, hydroxy, and keto;

R 3 is selected from the group consisting of

wherein the dye/tag is mixed with or attached to an entity, and one or more analytically useful signals produced by the dye/tag are monitored; and

wherein the one or more analytically useful signals are selected from the group consisting of absorption of light at one or more characteristic wavelengths ranging from about 570 nm to about 663 nm, emission of red or NIR light at one or more characteristic wavelengths in response to at least one excitatory light pulse delivered at a wavelength ranging from about 430 nm to about 655 nm, emission of light at a characteristic peak intensity ranging from about 40,000 a.u. to about 800,000 a.u. observed at a wavelength ranging from about 430 nm to about 663 nm, a color change in solution, and any combination thereof.

13. The composition of claim 12 , wherein the entity is selected from the group consisting of a peptide, a protein, a biomolecule, and a biological cell.

14. The composition of claim 12 , wherein the one or more analytically useful signals are monitored continuously.

15. The composition of claim 14 , wherein one or more analytically useful signals are used to track at least one movement of the entity.

16. The composition of claim 12 , wherein the one or more analytically useful signals are monitored non-continuously.

17. The composition of claim 16 , wherein the one or more analytically useful signals are used to track the location of the entity.

18. A compound of Formula (II):

wherein:

X is selected from the group consisting of hydrogen and halogen;

R 3 is selected from the group consisting of

19. A chemical sensor/probe comprising Formula (II):

wherein X is selected from the group consisting of hydrogen and halogen;

R 3 is selected from the group consisting of

wherein the chemical sensor/probe produces one or more analytically useful signals when contacted with at least one analyte; and

wherein the one or more analytically useful signals are selected from the group consisting of absorption of light at one or more characteristic wavelengths ranging from about 570 nm to about 663 nm, emission of red or NIR light at one or more characteristic wavelengths in response to at least one excitatory light pulse delivered at a wavelength ranging from about 430 nm to about 655 nm, emission of light at a characteristic peak intensity ranging from about 40,000 a.u. to about 800,000 a.u. observed at a wavelength ranging from about 430 nm to about 663 nm, a color change in solution, and any combination thereof.

20. A dye/tag comprising Formula (II):

wherein X is selected from the group consisting of hydrogen and halogen; and

R 3 is selected from the group consisting of

wherein the dye/tag produces one or more analytically useful signals when contacted with at least one analyte; and

wherein the one or more analytically useful signals are selected from the group consisting of absorption of light at one or more characteristic wavelengths ranging from about 570 nm to about 663 nm, emission of red or NIR light at one or more characteristic wavelengths in response to at least one excitatory light pulse delivered at a wavelength ranging from about 430 nm to about 655 nm, emission of light at a characteristic peak intensity ranging from about 40,000 a.u. to about 800,000 a.u. observed at a wavelength ranging from about 430 nm to about 663 nm, a color change in solution, and any combination thereof.

Assignments (4)
CONFIRMATORY LICENSE Recorded Sep 11, 2023
From: SOUTHERN ILLINOIS UNIVERSITY CARBONDALE
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 064857/0276 →
CONFIRMATORY LICENSE Recorded Jun 13, 2023
From: SOUTHERN ILLINOIS UNIVERSITY CARBONDALE
To: NATIONAL INSTITUTES OF HEALTH
Reel/Frame 063934/0838 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2014
From: SCOTT, COLLEEN; MCCARROLL, MATTHEW; WANG, LICHANG; BEST, QUINN; SATTENAPALLY, NARSIMHA
To: BOARD OF TRUSTEES OF SOUTHERN ILLINOIS UNIVERSITY ON BEHALF OF SOUTHERN ILLINOIS UNIVERSITY CARBONDALE
Reel/Frame 031913/0712 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2014
From: DYER, DENISE DEANNE
To: BOARD OF TRUSTEES OF SOUTHERN ILLINOIS UNIVERSITY ON BEHALF OF SOUTHERN ILLINOIS UNIVERSITY CARBONDALE
Reel/Frame 031886/0048 →
Continuity (2)
Provisional Application 61423974 · Dec 16, 2010
Related Publication 20150185209A1 · Jul 2, 2015