Ultra bright dimeric or polymeric dyes with spacing linker groups

Patent metadata

Field	Value
Publication number	US-12461106-B2
Application number	US-202418436594-A
Country	US
Kind code	B2
Filing date	Feb 8, 2024
Priority date	Apr 6, 2016
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

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 R1, R2, R3, R4, R5, L1, L2, L3, L4, 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 compound having the following structure (IA):

or a stereoisomer, salt or tautomer thereof, wherein:
M is, at each occurrence, independently a fluorescent dye, wherein at least one occurrence of M has absorbance for use in fluorescence resonance energy transfer (FRET), and at least one occurrence of M has emissions for use in FRET;
L 1 is at each occurrence, independently either i) an alkylene linker; ii) a heteroalkylene linker including at least one nitrogen atom; or iii) a linker comprising a triazolyl functional group;
L 2 and L 3 are, at each occurrence, independently an alkylene or heteroalkylene linker;
R 1 is, at each occurrence, H;
R 2 is Q, or a protected form thereof, or a linker comprising a covalent bond to Q;
R 3 comprises a deoxythymidine (dT) group;
R 4 is, at each occurrence, OH, O − or OR d ;
R 5 is, at each occurrence, oxo;
R d is a counter ion;
Q is a moiety comprising a sulfhydryl, disulfide, activated ester, isothiocyanate, azide, alkyne, alkene, diene, dienophile, acid halide, sulfonyl halide, phosphine, «-haloamide, biotin, amino or maleimide functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester, and wherein the azide is an alkyl azide or acyl azide;
m is, at each occurrence, independently an integer of one to 10;
n is an integer of one to 32; and
z is an integer from 2 to 25.

2 . The compound of claim 1 , wherein for at least one occurrence of L 1 , L 1 -M has the following structure:

wherein L 1a and L 1b are each independently optional linkers.

3 . The compound of claim 1 , wherein for at least one occurrence of L 1 , L 1 -M has the following structure:

wherein L 1a and L 1b are each independently optional linkers.

4 . The compound of claim 2 , wherein L 1a or L 1b , or both, is absent.

5 . The compound of claim 2 , wherein L 1a or L 1b , or both, is present.

6 . The compound of claim 5 , wherein L 1a and L 1b , when present, are each independently alkylene or heteroalkylene.

7 . The compound of claim 5 , wherein L 1a and L 1b , when present, independently have one of the following structures:

8 . The compound of claim 1 , wherein R 4 is, at each occurrence, O − .

9 . The compound of claim 1 , wherein Q is capable of forming a covalent bond with a targeting moiety that is an antibody or cell surface receptor antagonist.

10 . The compound of claim 1 , wherein L 2 and L 3 are, at each occurrence, a methylene linker.

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

12 . The compound of claim 1 , wherein L 2 -R 3 comprises the following structure:

13 . The compound of claim 1 , wherein Q is a moiety selected from

14 . The compound of claim 1 , wherein Q is capable of forming a covalent bond with an analyte molecule that is a nucleic acid, amino acid or a polymer thereof, an enzyme, receptor, receptor ligand, antibody, glycoprotein, aptamer or prion.

15 . The compound of claim 1 , wherein one M is a FRET acceptor.

16 . The compound of claim 1 , wherein z is an integer from 2 to 10.

17 . The compound of claim 1 , wherein z is an integer from 3 to 6.

18 . The compound of claim 1 , wherein R 2 comprises alkylene oxide.

19 . The compound of claim 1 , wherein R 3 comprises alkylene oxide.

Assignees

• Sony Group Corp

Inventors

• Matray Tracy
• Singh Sharat

Classifications

• C09B69/109

  containing other specific dyes · CPC title

• C09B69/102

  containing a perylene dye · CPC title

• C09B69/101

  containing an anthracene dye · CPC title

• C09B11/26

  Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic {(phthaleins C09B11/24)} · CPC title

• C09B3/14

  Perylene derivatives · CPC title