Water soluble fluorescent or colored dyes and methods for their use

Patent metadata

Field	Value
Publication number	US-2016208100-A1
Application number	US-201414913675-A
Country	US
Kind code	A1
Filing date	Aug 22, 2014
Priority date	Aug 22, 2013
Publication date	Jul 21, 2016
Grant date	—

Abstract

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): including stereoisomers, salts and tautomers thereof, wherein R 1 , R 2 , R 3 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , M 1 , M 2 , A, q, w and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.

First claim

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

wherein:
M 1 and M 2 are, at each occurrence, independently a moiety comprising two or more double bonds and at least one degree of conjugation, and at least one occurrence of M 1 is a moiety comprising three or more aryl or heteroaryl rings, or combinations thereof;
L 1 , L 3 , L 4 L 6 , L 7 and L 8 are, at each occurrence, independently optional alkylene or heteroalkylene linkers;
R 1 is, at each occurrence, independently H, alkyl or alkoxy;
R 2 is an electron pair, H, alkyl, alkylether, hydroxylalkyl, aminoalkyl, hydroxylalkylether, sulfhydrylalkyl, sulfyhdrylalkylether, cyanoalkyl, phospho, thiophospho, alkylphospho, alkylthiophospho, alkyletherphospho, alkyletherthiophospho, phosphoalkyl, phosphoalkylether, thiophosphoalkyl or thiophosphoalkylether, or R 2 is a linker comprising a covalent bond to a biomolecule or microparticle;
R 3 is H, OH, SH, —NH 2 , alkyl, alkylether, hydroxylalkyl, aminoalkyl, hydroxylalkylether, sulfhydrylalkyl, sulfyhdrylalkylether, cyanoalkyl, —Oaralkyl, phosphate, thiophosphate, alkylphospho, alkylthiophospho, —Oalkylphospho, —Oalkylthiophospho, alkyletherphospho, alkyletherthiophospho, —Oalkyletherphospho, —Oalkyletherthiophospho phosphoalkyl, phosphoalkylether, thiophosphoalkyl, thiophosphoalkylether, —Ophosphoalkyl, O-phosphoalkylether, —Othiophosphoalkyl or —Othiophosphoalkylether;
R 4 is, at each occurrence, independently O − , S − , OZ, SZ or N(R 6 ) 2 , where Z is a cation and each R 6 is independently H or alkyl;
R 5 is, at each occurrence, independently oxo, thioxo or absent;
n is an integer from 2 to 20; and
q and w are each independently 0 or 1 for each integral value of n, wherein q is 1 for at least two integral values of n, or wherein q and w are each independently one for at least one integral value of n.

2 . (canceled)

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

wherein:
M 1 is, at each occurrence, independently a moiety comprising two or more double bonds and at least one degree of conjugation, and at least one occurrence of M 1 is a moiety comprising four or more aryl or heteroaryl rings, or combinations thereof;
L 1 , L 7 and L 3 are, at each occurrence, independently optional alkylene or heteroalkylene linkers;
R 1 is, at each occurrence, independently H, alkyl or alkoxy;
R 2 is H, alkyl, alkylether, hydroxylalkyl, aminoalkyl, hydroxylalkylether, sulfhydrylalkyl, sulfyhdrylalkylether, cyanoalkyl, phospho, thiophospho, alkylphospho, alkylthiophospho, alkyletherphospho, alkyletherthiophospho, phosphoalkyl, phosphoalkylether, thiophosphoalkyl or thiophosphoalkylether, or R 2 is a linker comprising a covalent bond to a biomolecule or microparticle;
R 3 is H, OH, SH, —NH 2 , alkyl, alkylether, hydroxylalkyl, aminoalkyl, hydroxylalkylether, sulfhydrylalkyl, sulfyhdrylalkylether, cyanoalkyl, —Oaralkyl, phosphate, thiophosphate, alkylphospho, alkylthiophospho, —Oalkylphospho, —Oalkylthiophospho, alkyletherphospho, alkyletherthiophospho, —Oalkyletherphospho, —Oalkyletherthiophospho phosphoalkyl, phosphoalkylether, thiophosphoalkyl, thiophosphoalkylether, —Ophosphoalkyl, O-phosphoalkylether, —Othiophosphoalkyl or —Othiophosphoalkylether;
R 4 is, at each occurrence, independently O − , S − , OZ, SZ or N(R 6 ) 2 , where Z is a cation and each R 6 is independently H or alkyl;
R 5 is, at each occurrence, independently oxo, thioxo or absent; and
n is an integer from 2 to 10.

4 . (canceled)

5 . The compound of claim 4 , wherein the compound has one of the following structures (IIc), (IId), (IIe) or (IIf):

6 . (canceled)

7 . The compound of claim 1 , wherein the compound has the following structure (IIIb):

wherein:
R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are, at each occurrence, independently H or alkyl; and
x 1 , x 2 , y 1 , y 2 , z 1 and z 2 are, at each occurrence, independently an integer from 0 to 5.

8 - 10 . (canceled)

11 . The compound of claim 14 , wherein R 2 has one of the following structures:

wherein:
R 2a is —OH, —NH 2 , or —SH; and
a is an integer from 1 to 10.

12 . (canceled)

13 . The compound of claim 1 , wherein R 2 has one of the following structures:

wherein:
R 2a is —OH, —SH, —NH 2 , phosphate or thiophosphate;
R 4a and R 4b are independently O − , S − , OZ or SZ, where Z is a cation;
R 5a and R 5b are independently oxo, or thioxo; and
a, b and c are each independently integers from 1 to 10.

14 . The compound of claim 1 , wherein R 3 is OH.

15 . (canceled)

16 . The compound of claim 1 , wherein R 3 has one of the following structures:

wherein:
R 3a is —OH, —SH, —NH 2 , phosphate or thiophosphate;
R 4a and R 4b are independently O − , S − , OZ or SZ, where Z is a cation;
R 5a and R 5b are independently oxo, or thioxo; and
b and c are each independently integers from 1 to 10.

17 - 28 . (canceled)

29 . A compound having the following structure (IV):

wherein:
M 1 is, at each occurrence, independently a moiety comprising two or more double bonds and at least one degree of conjugation, and at least one occurrence of M 1 is a moiety comprising three or more aryl or heteroaryl rings, or combinations thereof;
L 1 , L 3 , and L 7 are, at each occurrence, independently optional alkylene or heteroalkylene linkers;
R 1 is, at each occurrence, independently H, alkyl or alkoxy;
R 2 is phospho, thiophospho, alkylphospho, alkylthiophospho, alkyletherphospho, alkyletherthiophospho, phosphoalkyl, phosphoalkylether, thiophosphoalkyl or thiophosphoalkylether, or R 2 is a linker comprising a covalent bond to a biomolecule or microparticle;
R 3 is H, OH, SH, —NH 2 , alkyl, alkylether, hydroxylalkyl, aminoalkyl, hydroxylalkylether, sulfhydrylalkyl, sulfyhdrylalkylether, phosphate, thiophosphate, alkylphospho, alkylthiophospho, —Oalkylphospho, —Oalkylthiophospho, alkyletherphospho, alkyletherthiophospho, —Oalkyletherphospho, —Oalkyletherthiophospho phosphoalkyl, phosphoalkylether, thiophosphoalkyl, thiophosphoalkylether, —Ophosphoalkyl, O-phosphoalkylether, —Othiophosphoalkyl or —Othiophosphoalkylether;
R 4 is, at each occurrence, independently O − , S − , OZ, SZ or N(R 6 ) 2 , where Z is a cation and each R 6 is independently H or alkyl;
R 5 is, at each occurrence, independently oxo, thioxo or absent;
n is an integer from 1 to 20.

30 - 44 . (canceled)

45 . A compound having the following structure (Ih):

wherein:
M 1 is a moiety comprising three or more

Assignees

• Sony Corp
• Sony Corp America

Inventors

• Matray Tracy
• Sherif Hesham
• Battrell C Frederick

Classifications

• C07F9/5765

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• G01N33/582

  with fluorescent label · CPC title

• C07H21/04

  with deoxyribosyl as saccharide radical · CPC title

• C09B69/109

  containing other specific dyes · CPC title

• C09B3/14 Primary

  Perylene derivatives · CPC title