# US 11,897,902 B1 · Nano-sized mixed ligand [4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine- phenanthroline] Ru(III) complex for medicinal applications

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- Number: US 11,897,902 B1
- Document ID: US11897902B1
- Status: Granted
- Kind: B1
- Application number: 18/372,657
- Filed: 2023-09-25
- Granted: 2024-02-13
- Earliest claimed: 2023-09-25
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Latef Ahmed; Mai Mostafa Khalaf Ali; Tarek El-Dabea; Seraj Alzahrani; Ahmed M. Abu-Dief
- Web page: https://patentgrep.com/patent/US11897902B1

## CPC

- C07F 15/0053: {without a metal-carbon linkage}
- A61K 9/51: Nanocapsules; {Nanoparticles; (nanotubes A61K9/0092; polymeric micelles A61K9/1075; polymersomes A61K9/1273; pure drug nanoparticles A61K9/14; drug nanoparticles with adsorbed surface modifiers A61K9/141; conjugates, e.g. between drug and non-active nanoparticles, A61K47/50; preparations for in vivo diagnosis A61K49/00; with radioactive substances A61K51/00)}
- A61K 47/547: {Chelates, e.g. Gd-DOTA or Zinc-amino acid chelates; Chelate-forming compounds, e.g. DOTA or ethylenediamine being covalently linked or complexed to the pharmacologically- or therapeutically-active agent}
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- B82Y 5/00: Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- B82Y 40/00: Manufacture or treatment of nanostructures
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES

## Abstract

A compound 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex, its synthesis, and its use for pharmaceutical applications.

## Claims

### Claim 1

A 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex having the formula I:

### Claim 2 (depends on 1)

The 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1, wherein the complex is formed as nanoparticles.

### Claim 3 (depends on 2)

The 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 2, wherein the nanoparticles have a semi-spherical shape.

### Claim 4 (depends on 2)

The 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 2, wherein the nanoparticles have an average size of about 25 nm to 30 nm.

### Claim 5 (depends on 2)

The 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 2, wherein the nanoparticles have an average particle size of about 28 nm.

### Claim 6 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1 and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1.

### Claim 8 (depends on 7)

The method of claim 7, wherein the microbial infection is caused by one or more of Escherichia coli and Aspergillus flavus.

### Claim 9 (depends on 1)

A method of treating cancer in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1.

### Claim 10 (depends on 9)

The method of treating cancer of claim 9, wherein the cancer is breast cancer.

### Claim 11 (depends on 1)

A method of promoting an antioxidant effect in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1.

### Claim 12 (depends on 1)

A method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 1, the method comprising:
adding a solution of Ruthenium (III) chloride (RuCl3) in ethanol to a 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine ligand in ethanol ethanol to obtain a first mixture;
sonicating the first mixture;
adding phenanthroline to the first mixture to obtain a second mixture;
sonicating the second mixture; and
obtaining the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex.

### Claim 13 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the RuCl3 is added stepwise.

### Claim 14 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the first mixture is sonicated for at least 30 minutes.

### Claim 15 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the second mixture is sonicated for at least 30 minutes.

### Claim 16 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the RuCl3 and the phenanthroline are mixed in an about 1:1 molar ratio.

### Claim 17 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex is a dark brown crystalline powder.

### Claim 18 (depends on 12)

The method of making the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex of claim 12, wherein the 4-bromo-2-(quinolin-2-yliminomethyl)-phenol imine]-Ru(III)-phenanthroline complex is a nanosized complex.
