# US 8,772,501 B2 · Fluorescent dyes and uses thereof

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- Number: US 8,772,501 B2
- Document ID: US8772501B2
- Status: Granted
- Kind: B2
- Application number: 13/748,756
- Filed: 2013-01-24
- Published: 2013-05-23
- Granted: 2014-07-08
- Earliest claimed: 2009-07-16
- Assignees: Beckman Coulter, Inc.
- Applicants: Beckman Coulter, Inc.
- Inventors: Hashem Akhavan-Tafti; Renuka De Silva; Guoping Wang; Robert A. Eickholt; Ravinder Gupta; Lakshmi S. Kaanumalle
- Web page: https://patentgrep.com/patent/US8772501B2

## CPC

- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C09B 7/00: Indigoid dyes
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

The present invention provides fluorescent dyes that are based on firefly luciferin structure. These dyes are optimally excited at shorter wavelengths and have Stokes shift of at least 50 nm. The fluorescent dyes of the invention are useful for preparation of dye-conjugates, which can be used in detection of an analyte in a sample.

## Claims

### Claim 1

A dye-conjugate having the formula:
wherein
X1 and X2 are independently S or O;
Y1 and Y2 separately represent halogen, or Y1 is CF3 and Y2 is H;
Z1 is H or alkyl;
wherein Z1 and one of the W groups may be absent and, if absent, are replaced with an additional bond between C4 and C5 in ring C;
L is selected from the group consisting of a carbonyl group (C═O), —C(═O)NH(CH2)nC(O)— wherein n is an integer from 1-5, and —(CH2)nC(═O)— wherein n is an integer from 1-5; and
wherein CM is a covalently linked conjugated molecule comprising a protein.

### Claim 2 (depends on 1)

The dye-conjugate of claim 1 wherein the protein is an antibody, or a fragment of an antibody.

### Claim 3 (depends on 2)

The dye-conjugate of claim 2 wherein the antibody is selected from the group consisting of an anti CD3 antibody, an anti CD4 antibody, and an anti CD45 antibody.

### Claim 4 (depends on 1)

The dye-conjugate of claim 1 wherein Y1 and Y2 are each a halogen.

### Claim 5 (depends on 1)

The dye-conjugate of claim 1 wherein Y1 and Y2 are each chlorine.

### Claim 6 (depends on 1)

The dye-conjugate of claim 1 wherein Y1 and Y2 are each fluorine.

### Claim 7 (depends on 1)

The dye-conjugate of claim 1 wherein Y1 is CF3 and Y2 is H.

### Claim 8 (depends on 1)

The dye-conjugate of claim 1 wherein each W is alkyl.

### Claim 9 (depends on 1)

The dye-conjugate of claim 1 wherein each W is methyl.

### Claim 10 (depends on 1)

The dye-conjugate of claim 1 wherein more than one dye molecule is conjugated to the protein.

### Claim 11 (depends on 1)

The dye-conjugate of claim 1 wherein X1 and X2 are both S atoms.

### Claim 12 (depends on 1)

The dye-conjugate of claim 1 wherein X1 is an S atom and X2 is an O atom.