# US 9,872,917 B2 · Anion-paired cationic metallocene-containing compounds and polymers as antimicrobial agents

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- Number: US 9,872,917 B2
- Document ID: US9872917B2
- Status: Granted
- Kind: B2
- Application number: 15/194,724
- Filed: 2016-06-28
- Published: 2017-03-23
- Granted: 2018-01-23
- Earliest claimed: 2013-04-04
- Assignees: University of South Carolina
- Applicants: University of South Carolina
- Inventors: Chuanbing Tang; Jiuyang Zhang; Yung-Pin Chen; Alan W. Decho
- Web page: https://patentgrep.com/patent/US9872917B2

## CPC

- A61K 47/58: obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A01N 37/12: containing the group [IMAGE cpc-sch-A01N-0932.gif], wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
- A01N 55/02: containing metal atoms
- A61K 31/43: Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula [IMAGE cpc-sch-A61K-0952.gif], e.g. penicillins, penems
- A61K 31/546: containing further heterocyclic rings, e.g. cephalothin
- C08F 220/282: {and containing two or more oxygen atoms}
- 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)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

Anion-paired metallocene-containing compounds are generally provided, along with methods of making the same. In one embodiment, the anion-paired metallocene-containing compound includes a cationic metallocene moiety covalently connected to an organic functional group, and an anion paired to the cationic metallocene moiety. Generally, the cationic metallocene moiety comprises two cyclopentadienyl anions bound to a metal center in the oxidation state I.

## Claims

### Claim 1

A anion-paired metallocene-containing polymer, comprising; at least one monomeric unit comprising a cationic metallocene moiety paired to an anion, wherein the cationic metallocene moiety comprises two cyclopentadienyl anions bound to a metal center in the oxidation state I, and wherein the anion comprises an anionic antibiotic compound.

### Claim 2 (depends on 1)

The anion-paired metallocene-containing polymer of claim 1, wherein the anion comprises a hexafluorophosphate anion, a tetraphenylborate anion, a tetrafluoroborate anion, a trifluoromethanesulfonate anion, F—, Cl—, Br—, I—, NO3-, an acetate anion, a sulfate anion, a hydrogen sulfate anion, a perchlorate anion, a bromate anion, a cyanide anion, a thiocyanate anion, a hydroxide anion, a dihydrogen phosphate anion, or a formate anion.

### Claim 3 (depends on 1)

The anion-paired metallocene-containing polymer of claim 1, wherein the anionic antibiotic compound comprises a penicillin anion or related compound, a carbapenem anion or related compound, or a cephalosporin anion or related compound.

### Claim 4 (depends on 1)

The anion-paired metallocene-containing polymer of claim 1, wherein the metal center comprises comprises iron, cobalt, rhodium, or ruthenium.

### Claim 5 (depends on 1)

The anion-paired metallocene-containing polymer of claim 1, wherein the anion-paired metallocene-containing polymer is a homopolymer.

### Claim 6 (depends on 1)

The anion-paired metallocene-containing polymer of claim 1, wherein the anion-paired metallocene-containing polymer is a copolymer comprising the at least one monomeric unit comprising the cationic metallocene moiety paired to the anion and a comonomeric unit.