# US 12,180,235 B1 · Fabrication of novel nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl }-phenyl-methanone] Ru(III) complex for pharmaceutical applications

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- Number: US 12,180,235 B1
- Document ID: US12180235B1
- Status: Granted
- Kind: B1
- Application number: 18/439,677
- Filed: 2024-02-12
- Granted: 2024-12-31
- Earliest claimed: 2024-02-12
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Rafea Elamin Elgack Elgorashe; Mona M Abdel-Mawla; Rafat M. El-Khatib; Ibrahim Omar Barnawi; Amal H. Alsehli; Ahmed M. Abu-Dief
- Web page: https://patentgrep.com/patent/US12180235B1

## 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 9/5192: {Processes}
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- A61P 39/06: Free radical scavengers or antioxidants
- A61K 9/14: Particulate form, e.g. powders, {Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles (microspheres A61K9/16; microcapsules A61K9/50; nanocapsules, nanoparticles of the matrix type A61K9/51)}
- 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

## Abstract

A nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex, its synthesis, and its use as an anticancer, antioxidant, and antimicrobial agent.

## Claims

### Claim 1

A nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex having the formula I:

### Claim 2 (depends on 1)

The nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1, wherein the complex has a spherical shape.

### Claim 3 (depends on 1)

The nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1, wherein the complex has a size of about 20 nm.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (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 nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1.

### Claim 6 (depends on 5)

The method of treating cancer of claim 5, wherein the cancer is colon cancer.

### 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 nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1.

### Claim 8 (depends on 7)

The method of treating the microbial infection of claim 7, wherein the microbial infection is caused by a gram negative bacteria Pseudomonas aeruginosa.

### Claim 9 (depends on 7)

The method of treating the microbial infection of claim 7, wherein the microbial infection is caused by a fungus Aspergillus Flavus.

### Claim 10 (depends on 1)

A method of inhibiting free radicals in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1.

### Claim 11 (depends on 4)

A method of promoting an antioxidant activity in a subject, the method comprising administering to a subject in need thereof the pharmaceutical composition of claim 4.

### Claim 12 (depends on 1)

A method of making the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 1, the method comprising:
adding RuCl3 in ethanol to a 4{3,4-Bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone azomethine ligand in ethanol to obtain a reaction mixture;
sonicating the reaction mixture a first time;
adding a secondary ligand phenanthroline to the reaction mixture under sonication a second time; and
obtaining the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex.

### Claim 13 (depends on 12)

The method of making nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein the RuCl3 in ethanol is added stepwise.

### Claim 14 (depends on 12)

The method of making nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein sonicating the reaction mixture a first time lasts for about 30 minutes.

### Claim 15 (depends on 12)

The method of making nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein sonicating the reaction mixture a second time lasts for about 30 minutes.

### Claim 16 (depends on 12)

The method of making nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein the RuCl3 and the 4{3,4-Bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone azomethine ligand are added in an about 2:1 molar ratio.

### Claim 17 (depends on 12)

The method of making the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein the RuCl3, the 4{3,4-Bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone azomethine ligand, and the secondary ligand phenanthroline are added in an about 2:1:1 molar ratio.

### Claim 18 (depends on 12)

The method of making nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex of claim 12, wherein the nano-sized [4{3,4-bis-[(5-bromo-2-hydroxy-benzylidene)-amino]-phenyl}-phenyl-methanone] Ru(III) complex is obtained as a dark brown crystalline powder.