Water soluble fluorescent or colored dyes and methods for their use

Patent metadata

Field	Value
Publication number	US-9689877-B2
Application number	US-201515112395-A
Country	US
Kind code	B2
Filing date	Jan 16, 2015
Priority date	Jan 16, 2014
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

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.

First claim

What is claimed is:

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.

Assignees

• Sony Corp
• Sony Corp America

Inventors

• Matray Tracy
• Sherif Hesham

Classifications

• G01N21/6428

  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 title

• C07F9/2408

  of hydroxyalkyl compounds · CPC title

• C07F9/093 Primary

  Polyol derivatives esterified at least twice by phosphoric acid groups · CPC title

• C07F9/094

  with arylalkanols · CPC title

• G01N33/583 Primary

  with non-fluorescent dye label · CPC title