IP Library Granted Patent US 11,981,820
Granted Patent B2
US 11,981,820 · App. 17/458,938 · Granted May 14, 2024

Ultra bright dimeric or polymeric dyes

Inventors: Tracy Matray (Snohomish, WA); Sharat Singh (Rancho Santa Fe, CA); Michael VanBrunt (Covington, WA)
Assignee: SONY GROUP CORPORATION
C09B69/102C07C215/68C07F9/091C07F9/2408C09B69/103C09B69/109G01N33/582
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Quick Facts
Patent No.
US 11,981,820
App. No.
17/458,938
Granted
May 14, 2024
Kind
B2
Abstract

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

Claims (44)

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

or a stereoisomer, salt or tautomer thereof, wherein:

G is, at each occurrence, independently a moiety comprising an aldehyde, oxime, hydrazone, alkyne, amine, azide, acylazide, acylhalide, nitrile, nitrone, sulfhydryl, disulfide, sulfonyl halide, isothiocyanate, activated ester, ketone, α, β-unsaturated carbonyl, alkene, maleimide, α-haloimide, epoxide, aziridine, tetrazine, tetrazole, phosphine, biotin, or thiirane functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;

L 1a , L 2 and L 3 are, at each occurrence, independently an optional alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, heteroalkynylene or heteroatomic linker;

L 4 is, at each occurrence, independently an alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linker;

R 1 is, at each occurrence, independently H, alkyl or alkoxy;

R 2 and R 3 are each independently H, OH, SH, alkyl, alkoxy, alkylether, —OP(═R a )(R b )R c , Q, a linker comprising a covalent bond to Q, a linker comprising a covalent bond to an analyte molecule, a linker comprising a covalent bond to a solid support or a linker comprising a covalent bond to a further compound of structure (II), wherein: R a is O or S; R b is OH, SH, O − , S − , OR d or SR d ; R c is OH, SH, O − , S − , OR d , SR d , alkyl, alkoxy, alkylether, alkoxyalkylether, phosphate, thiophosphate, phosphoalkyl, thiophosphoalkyl, phosphoalkylether or thiophosphoalkylether; and R d is a counter ion;

R 4 is, at each occurrence, independently OH, SH, O − , S − , OR d or SR d ;

R 5 is, at each occurrence, independently oxo, thioxo or absent;

Q is, at each occurrence, independently a moiety comprising a sulfhydryl, disulfide, activated ester, isothiocyanate, azide, alkyne, alkene, diene, dienophile, acid halide, sulfonyl halide, phosphine, a-haloamide, biotin, amino or maleimide functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;

m is, at each occurrence, independently an integer of zero or greater, provided that at least one occurrence of m is an integer of one or greater; and

n is an integer of one or greater.

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

3. The compound of claim 1 , wherein L 4 is, at each occurrence, independently C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene.

4. The compound of claim 1 , wherein the compound has the following structure (IIA):

wherein:

L 1a and L 1b are, at each occurrence, independently optional linkers; and

x 1 , x 2 , x 3 and x 4 are, at each occurrence, independently an integer from 0 to 6.

5. The compound of claim 1 , wherein the compound has the following structure (IIB):

wherein:

x 1 , x 2 , x 3 and x 4 are, at each occurrence, independently an integer from 0 to 6; and

y is an integer from 1 to 6.

6. The compound of claim 5 , wherein G is, at each occurrence, independently

7. The compound of claim 5 , wherein y is 2 for each integral value of m.

8. The compound of claim 5 , wherein, at each occurrence,

x 1 , x 2 , x 3 and x 4 are each 1; or

x 2 and x 4 are each 0, and x 3 is 1.

9. The compound of claim 5 , wherein:

R 4 is, at each occurrence, independently OH, O— or OR d ; and

R 5 is, at each occurrence, oxo.

10. The compound of claim 1 , wherein the compound has one of the following structures (IID) or (IIE):

11. The compound of claim 10 , wherein:

R 2 and R 3 are each independently OH or —OP(═R a )(R b )R c ;

one of R 2 or R 3 is OH or —OP(═R a )(R b )R c , and the other of R 2 or R 3 is Q or a linker comprising a covalent bond to Q; or

one of R 2 or R 3 is OH or —OP(═R a )(R b )R c , and the other of R 2 or R 3 is a linker comprising a covalent bond to an analyte molecule or a linker comprising a covalent bond to a solid support.

12. The compound of claim 1 , wherein Q is a moiety comprising one of the following structures:

wherein

X is halo; and

EWG is an electron withdrawing group.

13. The compound of claim 1 , wherein the analyte molecule is a nucleic acid, amino acid, a polymer, an enzyme, receptor, receptor ligand, antibody, glycoprotein, aptamer or prion.

14. The compound of claim 1 , wherein the solid support is a polymeric bead or nonpolymeric bead.

15. The compound of claim 1 , wherein m is, at each occurrence, independently an integer from 3 to 10.

16. The compound of claim 1 , wherein m is, at each occurrence, independently an integer from 7 to 9.

17. The compound of claim 1 , wherein n is an integer from 1 to 100.

Assignments (1)
CHANGE OF NAME Recorded May 17, 2023
From: SONY CORPORATION
To: SONY GROUP CORPORATION
Reel/Frame 063693/0164 →
Continuity (3)
Division 15543885
Provisional Application 62317192 · Apr 1, 2016
Related Publication 20210395530A1 · Dec 23, 2021
Cited By (3)
US 12,461,106 US 12,577,403 US 12,629,425