Labelling compounds and their use in assays

• US 9,822,398 B2
• Filed: 10/08/2014
• Issued: 11/21/2017
• Est. Priority Date: 10/08/2013
• Status: Active Grant

• Current Assignee: Binx Health Limited
• Original Assignee: Atlas Genetics Limited
• Inventors: Marsh, Barrie J., Frost, Christopher G., Sharp, Jonathan
• Primary Examiner(s): Bakshi, Pancham
• Application Number:
  US15/026,454
• Publication Number:
  US 20160244815A1
• Time in Patent Office: 1,140 Days
• Field of Search: 556138, 556140, 556143
• CPC Class Codes: C07F 15/02 Iron compounds
• CPC Class Codes: C07F 17/02 of metals of Groups 8, 9 or 10 of the Periodic System
• CPC Class Codes: C12Q 1/6816 characterised by the detection means C12Q1/6804 takes precedence
• CPC Class Codes: C12Q 1/689 for bacteria
• CPC Class Codes: C12Q 2563/113 the label being electroactive, e.g. redox labels
• CPC Class Codes: G01N 27/3276 being a hybridisation with immobilised receptors using a FET type sensor G01N27/4145; concerning the hybridisation C12Q1/68
• CPC Class Codes: G01N 33/58 involving labelled substances G01N33/53 takes precedence

Abstract

The invention provides monoferrocenyl compounds of general formula (I). The invention also provides substrates labelled with the compounds, functionalised derivatives of the compounds and methods of using the compounds, functionalised derivatives and labelled substrates in electrochemical assays.

Claims

1. A compound of formula IA

2. The compound of claim 1, wherein a+b=1.

3. The compound of any one of claims 1-2, wherein b is 0.

4. The compound of any one of claims 1-3 according to formula IB

5. The compound of any one of claims 1-4 wherein each X is independently selected from the group consisting of halo, vinyl, SR, S(O)R, alkyl, P(O)R₂, S(O)₂R, and SiR_3.

6. The compound of claim 1 wherein a is 4, b is 5 and each X is methyl.

8. The compound of claim 5, wherein each X is independently selected from the group consisting of SR, S(O)R, and S(O)₂R.

7. A compound selected from the group consisting of

3-(nonamethylferrocenylmethoxy)propan-1-ol;

3-((1′

-chloro)-ferrocenylmethoxy)propan-1-ol;

3-((2-tert-butylthio)-ferrocenylmethoxy)propan-1-ol;

3-((2-tert-butylsulfinyl)-ferrocenylmethoxy)propan-1-ol;

3-((2-tert-butylsulfonyl)-ferrocenylmethoxy)propan-1-ol;

3-((2-di-tert-butylphospinyl)-ferrocenylmethoxy)propan-1-ol;

3-(2-tributylstannyl-ferrocenylmethoxy)propan-1-ol;

3-(2-trimethylsilyl-ferrocenylmethoxy)propan-1-ol;

3-(2-tributylsilyl-ferrocenylmethoxy)propan-1-ol;

3-(2-trimethylstannyl-ferrocenylmethoxy)propan-1-ol;

3-(2-vinyl-ferrocenylmethoxy)propan-1-ol;

3-(2-iodo-ferrocenylmethoxy)propan-1-ol;

2-(3-ferrocenylpropoxy)ethanol;

2-(3-(2-tert-butylthio)-ferrocenylpropoxy)ethanol;

2-(3-(2-tert-butylsulfinyl)-ferrocenylpropoxy)ethanol; and

2-(3-(2-tert-butylsulfonyl)-ferrocenylpropoxy)ethanol.