# US 2024/0201177 A1 · Fluorescent compound for immunohischemistry and diagnosis composition for detecting biological material comprising the same

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- Number: US 2024/0201177 A1
- Document ID: US20240201177A1
- Status: Published application
- Kind: A1
- Application number: 18/073,644
- Filed: 2022-12-02
- Published: 2024-06-20
- Earliest claimed: 2022-11-24
- Assignees: Bioacts Corporation
- Applicants: Bioacts Corporation
- Inventors: JIN WOO PARK; KIWON KIM; SU JUNG JANG; MINA KIM
- Web page: https://patentgrep.com/patent/US20240201177A1

## CPC

- G01N 33/533: with fluorescent label
- C07D 403/14: containing three or more hetero rings
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided is a fluorescent compound for labeling a biomaterial having the following Chemical Formula 1: In Chemical Formula 1 above, n is an integer of 1 to 6, X1 and X2 are the same as or different from each other, and each independently selected from H, —SO3− and —SO3H, R1 and R2 are the same as each other or each independently selected from C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, —(CH2)m1SO3−, —(CH2)m2SO3H, and m1 is an integer of 1 to 7, m2 is an integer of 1 to 7, p1 is an integer of 1 to 10, q1 is an integer of 0 to 10, r1 is an integer of 1 to 10, and Y1 is selected from H, —OH, halogen and o1 is an integer of 1 to 10.

## Claims

### Claim 1

A fluorescent compound for labeling a biomaterial having the following Chemical Formula 1:
In Chemical Formula 1 above,
n is an integer of 1 to 6,
X1 and X2 are the same as or different from each other, and each independently selected from H, —SO3− and —SO3H,
R1 and R2 are the same as each other or each independently selected from C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, —(CH2)m1SO3−, —(CH2)m2SO3H, and
m1 is an integer of 1 to 7,
m2 is an integer of 1 to 7,
p1 is an integer of 1 to 10,
q1 is an integer of 0 to 10,
r1 is an integer of 1 to 10, and
Y1 is selected from H, —OH, halogen and
o1 is an integer of 1 to 10,
Z1 is selected from H, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s1 is an integer of 1 to 10, and
Ar1 is selected from H, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
t1 is an integer of 1 to 10,
u1 is an integer of 1 to 10, and
R5 is selected from H, OH, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, and
R3 and R4 are the same as or different from each other and each independently selected from substituted or unsubstituted C1-7 alkyl, substituted, unsubstituted C8-20 alkyl and
p2 is an integer of 1 to 10,
q2 is an integer of 1 to 10,
r2 is an integer of 1 to 10, and
Y2 is selected from H, —OH, halogen and
o2 is an integer of 1 to 10,
Z2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s2 is an integer of 1 to 10, and
Ar2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
and
t2 is an integer of 1 to 10,
u2 is an integer of 1 to 10,
R6 is selected from H, —OH, substituted or unsubstituted C1-7 alkyl and substituted or unsubstituted C8-20 alkyl.

### Claim 2 (depends on 1)

The fluorescent compound of claim 1, wherein the compound of Chemical Formula 1 above
n is an integer of 1 to 3,
X1 and X2 are the same as or different from each other, and each independently selected from —SO3− and —SO3H,
R1 and R2 are the same as each other or each independently selected from C1-4 straight chain alkyl, —(CH2)m1SO3−, —(CH2)m2SO3H, and
m1 is an integer of 1 to 5,
m2 is an integer of 1 to 5,
p1 is an integer of 1 to 5,
q1 is an integer of 1 to 6,
r1 is an integer of 1 to 6, and
Y1 is selected from —OH, —Cl− and
o1 is an integer of 1 to 4,
Z1 is selected from H, C1-4 straight chain alkyl and
s1 is an integer of 1 to 4, and
Ar1 is selected from C1-4 straight chain alkyl, C1-4 aminoalkyl and
t1 is an integer of 1 to 4,
u1 is an integer of 1 to 4,
R5 is selected from H, OH, C1-4 straight chain alkyl.

### Claim 3 (depends on 1)

The fluorescent compound of claim 1, wherein the compound of Chemical Formula 1 above
R3 and R4 are the same as or different from each other and each independently selected from substituted or unsubstituted C1-7 alkyl, substituted, unsubstituted C8-20 alkyl and
p2 is an integer of 1 to 10,
q2 is an integer of 1 to 10,
r2 is an integer of 1 to 10, and
Y2 is selected from H, —OH, halogen and
o2 is an integer of 1 to 10,
Z2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s2 is an integer of 1 to 10, and
Ar2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
and
t2 is an integer of 1 to 10,
u2 is an integer of 1 to 10,
R6 is selected from H, —OH, substituted or unsubstituted C1-7 alkyl and substituted or unsubstituted C8-20 alkyl.

### Claim 4 (depends on 1)

The fluorescent compound of claim 1, wherein the compound of Chemical Formula 1 above
R3 and R4 are the same as or different from each other and each independently selected from C1-4 straight chain alkyl and
and
p2 is an integer of 1 to 5,
q2 is an integer of 1 to 5,
r2 is an integer of 1 to 6, and
Y2 is selected from —OH, —Cl− and
o2 is an integer of 1 to 4,
Z2 is selected from H, C1-4 straight chain alkyl and
and,
s2 is an integer of 1 to 4, and
Ar2 is selected from C1-4 straight chain alkyl, C1-4 aminoalkyl and
and
t2 is an integer of 1 to 4,
u2 is an integer of 1 to 6,
R6 is selected from H, OH, C1-4 straight chain alkyl.

### Claim 5 (depends on 1)

The fluorescent compound of claim 1, wherein the compound of Chemical Formula 1 above is any one selected from compounds represented by the following Chemical Formulas 1-12.

### Claim 6 (depends on 1)

The fluorescent compound of claim 1, wherein the compound is for immunohistochemistry.

### Claim 7 (depends on 1)

The fluorescent compound of claim 1, wherein the compound is for immunohistochemistry which simultaneously stains multiple markers.

### Claim 8

An immunohistochemical composition for detecting a biomaterial comprising a fluorescent compound represented by the following Chemical Formula 1:
In Chemical Formula 1 above,
n is an integer of 1 to 6,
X1 and X2 are the same as or different from each other, and each independently selected from H, —SO3− and —SO3H,
R1 and R2 are the same as each other or each independently selected from C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, —(CH2)m1SO3−, —(CH2)m2SO3H, and
m1 is an integer of 1 to 7,
m2 is an integer of 1 to 7,
p1 is an integer of 1 to 10,
q1 is an integer of 0 to 10,
r1 is an integer of 1 to 10, and
Y1 is selected from H, —OH, halogen and
o1 is an integer of 1 to 10,
Z1 is selected from H, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s1 is an integer of 1 to 10, and
Ar1 is selected from H, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
t1 is an integer of 1 to 10,
u1 is an integer of 1 to 10, and
R5 is selected from H, OH, C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, and
R3 and R4 are the same as or different from each other and each independently selected from substituted or unsubstituted C1-7 alkyl, substituted, unsubstituted C8-20 alkyl and
p2 is an integer of 1 to 10,
q2 is an integer of 1 to 10,
r2 is an integer of 1 to 10, and
Y2 is selected from H, —OH, halogen and
o2 is an integer of 1 to 10,
Z2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s2 is an integer of 1 to 10, and
Ar2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
and
t2 is an integer of 1 to 10,
u2 is an integer of 1 to 10,
R6 is selected from H, —OH, substituted or unsubstituted C1-7 alkyl and substituted or unsubstituted C8-20 alkyl.

### Claim 9 (depends on 8)

An immunohistochemical composition in claim 8, wherein the Chemical Formula 1 above:
R3 and R4 are the same as or different from each other and each independently selected from substituted or unsubstituted C1-7 alkyl, substituted, unsubstituted C8-20 alkyl and
p2 is an integer of 1 to 10,
q2 is an integer of 1 to 10,
r2 is an integer of 1 to 10, and
Y2 is selected from H, —OH, halogen and
o2 is an integer of 1 to 10,
Z2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl and
s2 is an integer of 1 to 10, and
Ar2 is selected from H, substituted or unsubstituted C1-7 alkyl, substituted or unsubstituted C8-20 alkyl, C1-7 aminoalkyl and
and
t2 is an integer of 1 to 10,
u2 is an integer of 1 to 10,
R6 is selected from H, —OH, substituted or unsubstituted C1-7 alkyl and substituted or unsubstituted C8-20 alkyl.