# US 2019/0170757 A1 · Ultraviolet Absorbing Polymeric Dyes and Methods for Using the Same

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- Number: US 2019/0170757 A1
- Document ID: US20190170757A1
- Status: Published application
- Kind: A1
- Application number: 16/256,582
- Filed: 2019-01-24
- Published: 2019-06-06
- Earliest claimed: 2015-03-12
- Assignees: Becton, Dickinson and Company
- Applicants: Becton, Dickinson and Company
- Inventors: Yongchao Liang; Frank P. Uckert; Glenn P. Bartholomew; Barry E. Leonard; Brent S. Gaylord
- Web page: https://patentgrep.com/patent/US20190170757A1

## CPC

- G01N 33/582: {with fluorescent label}
- C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G 2261/124: alternating
- C08G 2261/1424: containing ether groups, including alkoxy
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/1644: comprising other functional groups, e.g. OH groups, NH groups, COOH groups or boronic acid
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Water soluble light harvesting multichromophores that have an ultraviolet absorption maximum are provided. In some embodiments, the multichromophores include a conjugated segment including a fused 6-5-6 tricyclic co-monomer and a UV absorbance-modifying co-monomer. The multichromophores may include an acceptor chromophore covalently linked to the multichromophore in energy-receiving proximity therewith. In some embodiments, a specific binding member is covalently linked to the multichromophore. Also provided are methods of evaluating a sample for the presence of a target analyte and methods of labelling a target molecule using compositions including the light harvesting multichromophores. Kits and systems for practicing the subject methods are also provided.

## Claims

### Claim at position 1

1-99. (canceled)

### Claim 100

A method of evaluating a sample for the presence of a target analyte, the method comprising:
(a) contacting the sample with a polymeric dye conjugate that specifically binds the target analyte to produce a labelling composition contacted sample, wherein the polymeric dye conjugate comprises:
(i) a water-soluble light harvesting multichromophore comprising a repeat unit comprising:
a fused 6-5-6 tricyclic co-monomer; and
a UV absorbance-modifying co-monomer that is a substituted aryl co-monomer or a substituted or unsubstituted heteroaryl co-monomer; and
(ii) a specific binding member covalently linked to the multichromophore; and
(b) assaying the labelling composition contacted sample for the presence of a polymeric dye conjugate-target analyte binding complex to evaluate whether the target analyte is present in the sample.

### Claim 101 (depends on 100)

The method according to claim 100, wherein the polymeric dye conjugate further comprises an acceptor chromophore covalently linked to the multichromophore in energy-receiving proximity therewith.

### Claim 102 (depends on 101)

The method according to claim 101, wherein the acceptor chromophore is selected from cyanine dye, xanthene dye, coumarin dye, thiazine dye and acridine dye.

### Claim 103 (depends on 100)

The method according to claim 100, wherein the fused 6-5-6 tricyclic co-monomer comprises a central 5-membered ring that is a heterocycle.

### Claim 104 (depends on 103)

The method according to claim 103, wherein the fused 6-5-6 tricyclic co-monomer is a carbazole co-monomer.

### Claim 105 (depends on 100)

The method according to claim 100, wherein the fused 6-5-6 tricyclic co-monomer is a fluorene co-monomer linked via positions 2 and 7 to a polymer backbone.

### Claim 106 (depends on 100)

The method according to claim 100, wherein the fused 6-5-6 tricyclic co-monomer is a fluorene co-monomer linked via positions 3 and 6 to a polymer backbone.

### Claim 107 (depends on 105)

The method according to claim 105, wherein the fused 6-5-6 tricyclic co-monomer is of the structure:
wherein:
Z is —C(R1)2— or —N(R1)—;
each R is H; and
each R1 is independently selected from alkyl, substituted alkyl, aralkyl, substituted aralkyl, PEG moiety, water solubilizing group and -L1-Z1, where L1 is a linker and Z1 is a chemoselective tag.

### Claim 108 (depends on 107)

The method according to claim 107, wherein each R1 is substituted alkyl comprising one or more water solubilizing groups or substituted aralkyl comprising one or more water solubilizing groups.

### Claim 109 (depends on 100)

The method according to claim 100, wherein the UV absorbance-modifying co-monomer is selected from substituted 1,4-phenyl, substituted 1,3-phenyl, substituted or unsubstituted 2,5-pyridyl, and substituted or unsubstituted 2,6-pyridyl.

### Claim 110 (depends on 100)

The method according to claim 100, wherein the UV absorbance-modifying co-monomer is selected from one of the following:
wherein:
Z2-Z5 are each independently CR or N, wherein at least one Z2-Z5 is N; and
each R and R11-R16 are independently selected from the group consisting of hydrogen, halogen, cyano, alkoxy, substituted alkoxy, alkyl and substituted alkyl.

### Claim 111 (depends on 110)

The method according to claim 110, wherein the UV absorbance-modifying co-monomer is selected from one of the following:
wherein n is 1-20 and R′ is H or lower alkyl.

### Claim 112 (depends on 110)

The method according to claim 110, wherein the substituted aryl co-monomer is of the structure:
wherein R11 and R13 are each independently an alkyl or a substituted alkyl.

### Claim 113 (depends on 110)

The method according to claim 110, wherein the substituted aryl co-monomer is of the structure:
wherein R11 is an alkyl or a substituted alkyl,

### Claim 114 (depends on 100)

The method according to claim 100, wherein:
the multichromophore comprises 25% or more by molarity of the UV absorbance-modifying co-monomer; and
the multichromophore is a conjugated polymer comprising 5 or more monomeric repeat units.

### Claim 115 (depends on 100)

The method according to claim 100, wherein the multichromophore has an absorption maximum wavelength in the range of 300 to 400 nm and an emission maximum wavelength in the range of 375 to 900 nm, wherein 80% or more of the integrated absorption intensity is in the UV region.

### Claim 116 (depends on 100)

The method according to claim 100, wherein the target analyte is associated with a cell.

### Claim 117 (depends on 116)

The method according to claim 116, wherein the target analyte is a cell surface marker of the cell.

### Claim 118 (depends on 116)

The method according to claim 116, wherein the target analyte is an intracellular target, and the method further comprises lysing the cell.

### Claim 119 (depends on 100)

The method according to claim 100, wherein the method further comprises flow cytometrically analyzing the polymeric dye conjugate-target analyte binding complex.