Fluorescent water-solvated conjugated polymers

Patent metadata

Field	Value
Publication number	US-10604657-B2
Application number	US-201715642216-A
Country	US
Kind code	B2
Filing date	Jul 5, 2017
Priority date	Jul 7, 2016
Publication date	Mar 31, 2020
Grant date	Mar 31, 2020

Abstract

Water solvated polymeric dyes and polymeric tandem dyes are provided. The polymeric dyes include a water solvated light harvesting multichromophore having a conjugated segment of aryl or heteroaryl co-monomers linked via covalent bonds, vinylene groups or ethynylene groups. The polymeric tandem dyes further include a signaling chromophore covalently linked to the multichromophore in energy-receiving proximity therewith. Also provided are labeled specific binding members that include the subject polymeric dyes. Methods of evaluating a sample for the presence of a target analyte and methods of labeling a target molecule in which the subject polymeric dyes find use are also provided. Systems and kits for practicing the subject methods are also provided.

First claim

What is claimed is:

1. A water solvated light harvesting multichromophore comprising a conjugated segment having the structure of formula (I):

wherein:
each L is independently a covalent bond, a vinylene group or an ethynylene group;
M 1 and M 2 are independently an aryl co-monomer or heteroaryl co-monomer;
M 1 does not comprise fluorene and M 2 does not comprise fluorene;
each * is a site for covalent attachment to the unsaturated backbone of a conjugated polymer;
n is an integer from 1 to 100,000; and
one or more of:
(i) the conjugated segment has the structure of formula (II):

wherein:
each W is independently selected from an alkyl, a substituted alkyl, an aralkyl, a substituted aralkyl, an aryl, a substituted aryl, a heteroaryl, a substituted heteroaryl, a PEG or modified PEG group and a water soluble group (WSG); and q is 1, 2, 3 or 4; and

(ii) M 2 is selected from one of the following structures:

wherein:
Y 8 is C(R 3 ) 2 , —C(R 3 ) 2 C(R 3 ) 2 —, NR 3 or Si(R 3 ) 2 ;
Y 9 is C(R 4 ) 2 , —C(R 4 ) 2 C(R 4 ) 2 - or Si(R 4 ) 2 ;
X is S or O;
R 1 and R 2 are independently selected from H, halogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, acyl, substituted acyl, sulfonic acid, cyano, alkoxy, substituted alkoxy and T 1 -Z 1 , or R 1 and R 2 together form a 5- or 6-membered fused aryl or heteroaryl ring which can be optionally substituted;
each R 3 is independently H, amino, substituted amino, halogen, cyano, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, acyl, substituted acyl, sulfonic acid, cyano, alkoxy, substituted alkoxy and -T 1 -Z 1 ;
each R 4 is independently alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, acyl, substituted acyl, sulfonic acid, cyano, alkoxy, substituted alkoxy and -T 1 -Z 1 ;
Z 1 is a chemoselective functional group or a linked signaling chromophore; and
T 1 is a linker.

2. The water solvated light harvesting multichromophore according to claim 1 , wherein each M 1 is a substituted phenyl co-monomer.

3. The water solvated light harvesting multichromophore according to claim 1 , wherein the conjugated segment has the structure of formula (II):

wherein:
each W is independently selected from an alkyl, a substituted alkyl, an aralkyl, a substituted aralkyl, an aryl, a substituted aryl, a heteroaryl, a substituted heteroaryl, a PEG or modified PEG group and a water soluble group (WSG); and
q is 1, 2, 3 or 4.

4. The water solvated light harvesting multichromophore according to claim 1 , wherein the multichromophore has the structure of formula (V):

wherein:
M 2 , M 3 and M 4 are independently an aryl co-monomer or heteroaryl co-monomer;
each L is an ethynylene linking unit, or each L is a vinylene group, or at least two L are covalent bonds;
each n is independently an integer from 1 to 10,000;
each m is independently 0 or an integer from 1 to 10,000;
p is an integer from 1 to 100,000; and
G 1 and G 2 are each independently selected from a terminal group, a t conjugated segment, a linker and a linked specific binding member.

5. The water solvated light harvesting multichromophore according to claim 4 , wherein the multichromophore has the structure of formula (IX):

wherein:
each W is independently selected from an alkyl, a substituted alkyl, an aralkyl, a substituted aralkyl, an aryl, a substituted aryl, a heteroaryl, a substituted heteraryl, a PEG or modified PEG group and a WSG; and
q is 1, 2, 3 or 4.

6. The water solvated light harvesting multichromophore according to claim 5 , wherein the multichromophore has the structure of formula (XI):

wherein:
W 1 and W 2 are as defined for W;
Z 1 is a chemoselective functional group or a linked signaling chromophore; and
T 1 is a linker.

7. The water solvated light harvesting multichromophore according to claim 5 , wherein the multichromophore has the structure of formula (XIII):

wherein:
W 3 , W 4 and W 5 are as defined for W.

8. The water solvated light harvesting multichromophore according to claim 5 , wherein the multichromophore has the structure of formula (XIV):

wherein:
W 3 and W 5 are as defined for W;
Z 2 is a chemoselective functional group or a linked specific binding member; and
T 2 is a linker.

9. The water solvated light harvesting multichromophore according to claim 5 , wherein the multichromophore has the structure of formula (XV):

wherein:
W 3 , W 4 and W 5 are as defined for W;
Z 1 is a chemoselective functional group or a linked signaling chromophore; and
T 1 is a linker.

10. The water solvated light harvesting multichromophore according to claim 4 , wherein the conjugated segment comprises the structure of formula (XVII):

wherein:
each W is independently selected from H, an alkyl, a substituted alkyl, an aralkyl, a substituted aralkyl, an aryl, a substituted aryl, a heteroaryl, a substituted heteroaryl, a PEG or modified PEG group and a WSG;
and q is 1, 2, 3 or 4.

11. The water solvated light harvesting multichromophore according to claim 10 , wherein M 2 is selected from one of the following structures:

Assignees

• Becton Dickinson Co

Inventors

• Bartholomew Glenn P
• Liang Yongchao
• Gaylord Brent S

Classifications

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• C08G2261/3327

  alkene-based · CPC title

• C08G61/123

  derived from five-membered heterocyclic compounds · CPC title

• C08G2261/3328

  alkyne-based · CPC title

• C09B69/105 Primary

  containing a methine or polymethine dye · CPC title