IP Library Granted Patent US 9,689,877
Granted Patent B2
US 9,689,877 · App. 15/112,395 · Granted Jun 27, 2017

Water soluble fluorescent or colored dyes and methods for their use

Inventors: Tracy Matray (Snohomish, WA); Hesham Sherif (Redmond, WA)
Assignees: SONY CORPORATION; SONY CORPORATION OF AMERICA
G01N33/583C07F9/093C07F9/094C07F9/2408C09B1/00G01N21/29G01N33/52
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Quick Facts
Patent No.
US 9,689,877
App. No.
15/112,395
Granted
Jun 27, 2017
Kind
B2
Abstract

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): Formula (I), including stereoisomers, salts and tautomers thereof, wherein R 1a , R 1b , R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , R 2k , R 2l , R 2m , R 2n , R 2o , R 2p , R 2q , R 2r and R 2s are as defined herein. Methods associated with preparation and use of such compounds are also provided.

Claims (32)

1. A compound having the following structure (I):

or a salt, stereoisomer or tautomer thereof, wherein:

R 1a and R 1b are each independently hydroxyl or alkoxy; and

R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , R 2k , R 2l , R 2m , R 2n , R 2o , R 2p , R 2q , R 2r , R 2s and R 2t are each independently H, halo or -L 1 -R 3 ;

R 3 is, at each occurrence, independently an analyte molecule or alkyl substituted with one or more of hydroxyl, protected hydroxyl, amino, alkylamino, alkoxy, polyalkyether, hydroxylalkoxy, aminoalkoxy, hydroxylpolyalkyether, aminopolyalkyether, phosphate, thiophosphate, phospho, thiophospho, phosphoalkylether, Ophosphoalkylether, thiophosphoalkylether, Othiophosphoalkylether, phosphoramidite or activated phosphorous; or R 3 is a microparticle; and

L 1 is an optional linker moiety.

2. The compound of claim 1 , wherein the compound has the following structure:

3. The compound of claim 1 , wherein the compound has the following structure (If):

4. The compound of claim 1 , wherein R 1a or R 1b is hydroxyl.

5. The compound of claim 1 , wherein R 1a or R 1b , or both, is alkoxy.

6. The compound of claim 1 , wherein at least one of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g or R 2h is halo.

7. The compound of claim 6 , wherein R 2b is bromo.

8. The compound of claim 1 , wherein at least one of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g or R 2h is -L 1 -R 3 .

9. The compound of claim 8 , wherein R 2b is -L 1 -R 3 .

10. The compound of claim 1 , wherein R 3 is, at each occurrence, independently alkyl substituted with one or more of hydroxyl, protected hydroxyl, amino, alkylamino, alkoxy, polyalkyether, hydroxylalkoxy, aminoalkoxy, hydroxylpolyalkyether, aminopolyalkyether, phosphate, thiophosphate, phospho, thiophospho, phosphoalkylether, Ophosphoalkylether, thiophosphoalkylether, Othiophosphoalkylether, phosphoramidite or activated phosphorous.

11. The compound of claim 10 , wherein R 3 has, at each occurrence, independently one of the following structures:

wherein:

n 1 , n 2 and n 3 are each independently an integer from 1 to 6; and

x and y are each independently an integer from 1 to 10.

12. The compound of claim 1 , wherein R 3 is, at each occurrence, independently an analyte molecule.

13. The compound of claim 12 , wherein the analyte molecule is a nucleic acid, peptide, carbohydrate, lipid, enzyme, receptor, receptor ligand, antibody, glycoprotein, aptamer, antigen, prion, drug, vitamin or small molecule.

14. The compound of claim 1 , wherein L 1 comprises a phosphate bond to the analyte molecule.

15. The compound of claim 14 , wherein L 1 has the following structure:

wherein n 1 , n 2 and n 3 are each independently an integer from 1 to 6.

16. The compound of claim 1 , wherein the compound has one of the following structures:

wherein R 3 is an analyte molecule.

17. The compound of claim 1 , wherein the compound has the following structure (Ib):

18. The compound of claim 1 , wherein the compound has the following structure (Ic):

19. The compound of claim 1 , wherein the compound has the following structure (Id):

20. The compound of claim 1 , wherein the compound has the following structure (Ie):

21. The compound of claim 1 , wherein R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , R 2k , R 2l , R 2m , R 2n , R 2o , R 2p , R 2q , R 2r , R 2s and R 2t are each H.

22. The compound of claim 1 , wherein R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , R 2k , R 2l , R 2m , R 2n , R 2o , R 2p , R 2q , R 2r and R 2s are each independently H, halo or -L 1 -R 3 , and R 2t is H.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2020
From: SONY CORPORATION OF AMERICA
To: SONY CORPORATION
Reel/Frame 054751/0070 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 18, 2016
From: MATRAY, TRACY; SHERIF, HESHAM
To: SONY CORPORATION; SONY CORPORATION OF AMERICA
Reel/Frame 040045/0617 →
Continuity (2)
Provisional Application 61928147 · Jan 16, 2014
Related Publication 20160341736A1 · Nov 24, 2016