# US 12,180,183 B2 · Water-soluble fluorescent probe and nanoparticals with aggregation-induced emission effect for ovarian cancer and preparation method and use thereof

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- Number: US 12,180,183 B2
- Document ID: US12180183B2
- Status: Granted
- Kind: B2
- Application number: 17/257,884
- Filed: 2019-06-24
- Published: 2021-09-02
- Granted: 2024-12-31
- Earliest claimed: 2018-07-05
- Assignees: Hunan Targeting Detection Technology Co., Ltd
- Applicants: Hunan Targeting Detection Technology Co., Ltd
- Inventors: Wenbin Zeng; Shi Li; Zuyuan Liu; Xueyan Huang; Tang Gao
- Web page: https://patentgrep.com/patent/US12180183B2

## CPC

- C07D 401/14: containing three or more hetero rings
- C09K 11/06: containing organic luminescent materials
- G01N 21/6428: {Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" (in vivo A61B5/00; immunoassay G01N33/53)}
- G01N 33/57545: of the ovaries
- G01N 33/582: {with fluorescent label}
- G01N 33/92: involving lipids, e.g. cholesterol {, lipoproteins, or their receptors (steroid hormones G01N33/743)}
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- C09K 2211/1018: Heterocyclic compounds
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES

## Abstract

Disclosed are a water-soluble fluorescent probe and nanoparticles with an aggregation induced emission (AIE) effect and preparation methods and the application. The fluorescent probe molecule includes one imidazole ring substituted by two methoxyphenyls and one phenyl and two quaternary ammonium salt structures. It has good dispersion in water, may form micelles. It has the characteristics of AIE effect and a large Stokes shift etc. It is suitable for fluorescence detection. Under the induction of lysophosphatidic acid, the probe can be self-assembled so as to aggregate and generate yellow fluorescence. Lysophosphatidic acid may be quantitatively analyzed by measuring the intensity of emitted fluorescence.

## Claims

### Claim 1

A fluorescent molecular probe, wherein the fluorescent molecular probe has a structure of Formula 1:
wherein the fluorescent molecular probe is water-soluble and has an aggregation-induced emission effect, and the fluorescent molecular probe is used for specifically recognizing lysophosphatidic acid.

### Claim 2 (depends on 1)

The fluorescent molecular probe of claim 1, wherein the fluorescent molecular probe is formed by linking a tetra-substituted imidazole ring, a dodecyl chain and a pyridine ring with formation of a salt.

### Claim 3 (depends on 1)

A fluorescent nanoprobe, wherein the fluorescent nanoprobe is formed by self-assembly of the fluorescent molecular probe of claim 1, and the fluorescent nanoprobe is used for specifically recognizing the lysophosphatidic acid.

### Claim 4 (depends on 1)

A method for preparing the fluorescent molecular probe of claim 1, wherein the method comprises the following steps:
1) 4-formylpyridine, aniline and anisil undergoing a one-pot cyclization reaction in an acetic acid/ammonium acetate system, to obtain an intermediate of Formula 2;
2) the intermediate of Formula 2 and 1,12-dibromododecane undergoing a nucleophilic substitution reaction, to obtain an intermediate of Formula 3; and
3) the intermediate of Formula 3 and pyridine undergoing a nucleophilic substitution reaction, to obtain a target product,

### Claim 5 (depends on 4)

The method of claim 4, wherein:
a reaction process in the step 1) is as follows: dissolving the 4-formylpyridine and the aniline in a glacial acetic acid solvent and stirring for 0.5-1.5 hours at room temperature, and then adding the anisil and ammonium acetate, reacting for 6-12 hours at 120° C.;
reaction conditions in the step 2) are as follows: using acetonitrile as a solvent, and reacting for 6-10 hours at 90° C.; and
reaction conditions in the step 3) are as follows: using the pyridine as a solvent, reacting for 6-10 hours at 90° C.

### Claim 6 (depends on 3)

A method for preparing the fluorescent nanoprobe of claim 3, comprising: dissolving the fluorescent molecular probe into an organic solvent, to yield an obtained mixture, adding the obtained mixture into an aqueous solution, performing ultrasonic treatment, and obtaining the fluorescent nanoprobe.

### Claim 7 (depends on 6)

The method of claim 6, wherein the organic solvent is selected from at least one of methanol, ethanol, dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, acetone, or acetonitrile, and the aqueous solution is selected from pure water, physiological saline, a phosphate buffer solution (PBS), a tris(hydroxymethyl)aminomethane hydrochloride buffer solution or a 4-hydroxyethylpiperazine ethanesulfonic acid buffer solution.