# US 12,111,320 B2 · 1,1′-[(substituted alkyl)imino]bis(alkylene)]bis-ferrocenes and their use in electrochemical assays by labelling substrates of interest

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- Number: US 12,111,320 B2
- Document ID: US12111320B2
- Status: Granted
- Kind: B2
- Application number: 18/485,575
- Filed: 2023-10-12
- Published: 2024-02-22
- Granted: 2024-10-08
- Earliest claimed: 2012-06-22
- Assignees: Binx Health Limited
- Applicants: Binx Health Limited
- Inventors: Barrie Marsh; Christopher Frost; David Pearce
- Web page: https://patentgrep.com/patent/US12111320B2

## CPC

- G01N 33/58: involving labelled substances (G01N33/53 takes precedence)
- C07F 17/02: of metals of Groups 8, 9 or 10 of the Periodic Table
- C12Q 1/6816: characterised by the detection means (C12Q1/6804 takes precedence)
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES

## Abstract

Compounds of general formula I wherein Fc and Fc′ may be the same or different and are substituted ferrocenyl moieties having at least one ring substituent selected from sulfur-containing groups, phosphorus-containing groups, iodo, chloro, silyl, fluoroalkyl groups containing two or more fluorine atoms, heteroaryl, substituted phenyl, and cyano, wherein if present as sole substituent the cyano group is located on the proximal cyclopentadienyl ring; X is a spacer, Y is a spacer, Z is a spacer; and R is a linker group. Compound I may be used to make labelled substrates, functionalised compounds for making labelled substrates and may be used as labels in an electrochemical assay.

## Claims

### Claim 1

A compound selected from the group consisting of:
6-(bis((1′-iodoferrocenyl)1-methylferrocenyl)amino)hexan-1-ol;
6-(bis((1′-(4-nitrophenyl)ferronceyl)1-methylferrocenyl)amino) hexan-1-ol;
6-(bis((1′-(1-furanyl)ferrocenyl)1-methylferrocenyl)amino)hexan-1-ol; and
6-(bis((2-cyano)1-methylferrocenyl)amino)hexan-1-ol.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is 6-(bis((1′-iodoferrocenyl)1-methylferrocenyl)amino)hexan-1-ol.

### Claim 3 (depends on 2)

A nucleic acid labeled with the compound of claim 2.

### Claim 4 (depends on 2)

A paramagnetic particle labeled with the compound of claim 2, wherein the paramagnetic particle is a microparticle or a nanoparticle.

### Claim 5 (depends on 2)

An amino acid labeled with the compound of claim 2.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is 6-(bis((1′-(4-nitrophenyl)ferronceyl)1-methylferrocenyl)amino)hexan-1-ol.

### Claim 7 (depends on 6)

A nucleic acid labeled with the compound of claim 6.

### Claim 8 (depends on 6)

A paramagnetic particle labeled with the compound of claim 6, wherein the paramagnetic particle is a microparticle or a nanoparticle.

### Claim 9 (depends on 6)

An amino acid labeled with the compound of claim 6.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is 6-(bis((1′-(1-furanyl)ferrocenyl)1-methylferrocenyl)amino)hexan-1-ol.

### Claim 11 (depends on 10)

A nucleic acid labeled with the compound of claim 10.

### Claim 12 (depends on 10)

A paramagnetic particle labeled with the compound of claim 10, wherein the paramagnetic particle is a microparticle or a nanoparticle.

### Claim 13 (depends on 10)

An amino acid labeled with the compound of claim 10.

### Claim 14 (depends on 1)

The compound of claim 1, wherein the compound is 6-(bis((2-cyano)1-methylferrocenyl)amino)hexan-1-ol.

### Claim 15 (depends on 14)

A nucleic acid labeled with the compound of claim 14.

### Claim 16 (depends on 14)

A paramagnetic particle labeled with the compound of claim 14, wherein the paramagnetic particle is a microparticle or a nanoparticle.

### Claim 17 (depends on 14)

An amino acid labeled with the compound of claim 14.