Water-soluble compound for detection of beta-amyloid

Patent metadata

Field	Value
Publication number	US-12498375-B2
Application number	US-202117520972-A
Country	US
Kind code	B2
Filing date	Nov 8, 2021
Priority date	Nov 19, 2020
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

The present invention relates to a water-soluble compound for the detection of beta-amyloid, and a production method thereof. The compound according to the present invention has excellent water-soluble properties, and thus can provide a water-soluble formulation for the detection of beta-amyloid. Accordingly, there is an effect that the compound can be useful as a composition for the detection of beta-amyloid through retinal imaging.

First claim

The invention claimed is:

1 . A method for detecting the presence of beta-amyloid plaque in a sample, the method comprising:
contacting the sample with a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof; and measuring an increase or shift in a fluorescence signal generated by the compound of Chemical Formula 1 upon binding to the beta-amyloid plaque:

in Chemical Formula 1,
Y is S or O,
A is phenylpiperazine, N-methylaniline or N, N-dimethylaniline,
R 1 and R 2 are each independently hydrogen or a C 1 to C 10 alkyl group,
x is an integer of 1 to 10, and
n and m are each independently an integer of 0 or greater, and n+m≥1,
wherein the increase or shift in the fluorescence signal, as compared to a fluorescence of the compound in the absence of beta-amyloid plaque, indicates the presence of beta-amyloid plaque in the sample.

2 . The method for detecting the presence of beta-amyloid plaque of claim 1 , wherein the method is for providing the information about the increase or shift in the fluorescence signal for the diagnosis of a disease caused by beta-amyloid plaque overproduction.

3 . The method for detecting the presence of beta-amyloid plaque of claim 2 , wherein the disease caused by beta-amyloid plaque overproduction is a disease selected from the group consisting of dementia, Alzheimer's disease, Down syndrome, amyloid angiopathy, cerebral amyloid angiopathy, systemic amyloidosis, Dutch-type amyloidosis, inclusion body myositis, Mediterranean fever, Muckle-Wells Syndrome, idiopathic myeloma, amyloid polyneuropathy, amyloid cardiomyopathy, systemic senile amyloidosis, amyloidosis hereditary cerebral hemorrhage, scrapie, Creutzfeldt-Jakob disease, Kuru disease, Gerstmann-Straussler-Scheinker syndrome, medullary thyroid carcinoma, muscular weakness disease, and islet of Langerhans type II diabetes.

4 . The method for detecting the presence of beta-amyloid plaque of claim 1 , wherein n and m are each independently an integer of 0 to 10.

5 . The method for detecting the presence of beta-amyloid plaque of claim 1 , wherein R 1 and R 2 are each a methyl group.

6 . The method for detecting the presence of beta-amyloid plaque of claim 1 , wherein x is 4.

7 . The method for detecting the presence of beta-amyloid plaque of claim 1 ,
in Chemical Formula 1, Y is S, A is phenylpiperazine, N-methylaniline or N,N-dimethylaniline, R 1 and R 2 are each a methyl group, x is 4, n is 1, and m is 0 or 1.

8 . The method for detecting the presence of beta-amyloid plaque of claim 1 , wherein the compound represented by Chemical Formula 1 is at least one selected from the group consisting of (E)-3-(2-4-(dimethylamino)styryl)-1,1-dimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate, (E)-4-(2-(2-(5-(4-(dimethylamino)phenyl)thiophen-2-yl)vinyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate, (E)-4-(1,1-dimethyl-2-(4-(piperazin-1-yl)styryl)-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate, and (E)-4-(1,1-dimethyl-2-(2-(5-(4-(methylamino)phenyl)thiophen-2-yl)vinyl)-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate.

Assignees

• Korea Atomic Energy Res

Inventors

• Park Yong Dae
• Jeon Jong Ho
• Joe Min Ho
• Lee Dong Eun

Classifications

• G01N33/6896

  Neurological disorders, e.g. Alzheimer's disease · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D409/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D209/60 Primary

  Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles · CPC title

• A61K51/0446

  having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil · CPC title