Ultra bright dimeric or polymeric dyes with spacing linker groups

Patent metadata

Field	Value
Publication number	US-10866244-B2
Application number	US-201715801035-A
Country	US
Kind code	B2
Filing date	Nov 1, 2017
Priority date	Apr 6, 2016
Publication date	Dec 15, 2020
Grant date	Dec 15, 2020

Abstract

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I):

or a stereoisomer, tautomer or salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , L 1 , L 2 , L 3 , L 4 , M, m and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.

First claim

What is claimed is:

1. A fluorescent compound comprising Y number of fluorescent moieties M, wherein each of the fluorescent moieties M independently having one of the following structures:

wherein:
each M is covalently bound to at least one other M by a linker comprising L 1 , L 2 , L 3 and a polyethylene oxide, wherein the polyethylene oxide having the following structure:

L 1 , L 2 and L 3 are each independently alkylene or heteroalkylene;
m is an integer from 2 to 10;
z is an integer from 2 to 30; and
each independently indicates a point of attachment to L 1 , L 2 or L 3 ,
wherein the fluorescent compound has a peak fluorescence emission upon excitation with a predetermined wavelength of ultraviolet light of at least 85% of Y times greater than the peak fluorescence emission of a single M moiety upon excitation with the same wavelength of ultraviolet light, and wherein Y is an integer of 2 to 10, and the single M moiety is an M moiety not covalently bound to the polyethylene oxide having the following structure:

2. The fluorescent compound of claim 1 , having a peak fluorescence emission of at least 90% of Y times greater than the peak fluorescence emission of a single M moiety.

3. The fluorescent compound of claim 1 , having a peak fluorescence emission of at least 95% of Y times greater than the peak fluorescence emission of a single M moiety.

4. The fluorescent compound of claim 1 , having a peak fluorescence emission of at least 97% of Y times greater than the peak fluorescence emission of a single M moiety.

5. The fluorescent compound of claim 1 , having a peak fluorescence emission of at least 99% of Y times greater than the peak fluorescence emission of a single M moiety.

6. The fluorescent compound of claim 1 , wherein the peak fluorescence emission is at a wavelength ranging from about 500 to about 550 nm.

7. A composition comprising the fluorescent compound of claim 1 and an analyte.

8. The fluorescent compound of claim 1 , wherein the fluorescent compound further comprises a covalent bond to a nucleic acid, amino acid or a polymer thereof, or an antibody, cell surface receptor antagonist, enzyme, receptor, receptor ligand, antibody, glycoprotein, aptamer or prion.

9. The fluorescent compound of claim 1 , wherein z is 3.

10. The fluorescent compound of claim 1 , wherein z is 6.

11. The fluorescent compound of claim 1 , wherein z is an integer from 20 to 25.

12. The fluorescent compound of claim 1 , wherein m is an integer from 2 to 5.

13. The fluorescent compound of claim 1 , wherein the fluorescent compound further comprises a covalent bond to a nucleic acid sequence.

14. The fluorescent compound of claim 13 , wherein the nucleic acid sequence is a DNA sequence.

15. The fluorescent compound of claim 1 , wherein the fluorescent compound further comprises a covalent bond to an antibody.

Assignees

• Sony Corp
• Sony Corp America

Inventors

• Matray Tracy
• Singh Sharat

Classifications

• G01N33/52

  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 title

• C09B69/109

  containing other specific dyes · CPC title

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title

• C09B69/102

  containing a perylene dye · CPC title

• C09B69/101

  containing an anthracene dye · CPC title