IP Library Granted Patent US 10,253,006
Granted Patent B2
US 10,253,006 · App. 15/130,137 · Granted Apr 9, 2019

Assay for the detection of the phenylpiperazine family

Inventors: Elouard Benchikh (Crumlin, GB); Ivan McConnell (Crumlin, GB); Philip Lowry (Crumlin, GB); Peter Fitzgerald (Crumlin, GB)
Assignee: Randox Laboratories Limited
C07D295/155C07D241/04C07D295/096C07K14/47C07K14/765C07K16/44G01N33/5308C07K2317/76
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Quick Facts
Patent No.
US 10,253,006
App. No.
15/130,137
Granted
Apr 9, 2019
Kind
B2
Abstract

The current invention describes novel immunogens which are used in the production of novel antibodies with unique binding properties in that they cross-react with a variety of phenylpiperazine derivatives. These antibodies enable methods and kits to detect and/or determine phenylpiperazine derivatives (for example mCPP, TFMPP and MeOPP) in an in vitro sample which are advantageous over currently available analytical methods in terms of cost, ease of use, speed and sensitivity.

Claims (23)

1. A polyclonal antibody raised against an immunogen, wherein the immunogen is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to bovine thyroglobulin;

wherein the polyclonal antibody has a cross-reactivity of 100% to 1-(3-chlorophenyl)piperazine, 129% to 1-(3-methylphenyl)piperazine), 106% to 1-phenylpiperazine, 68% to 1-(4-methoxyphenyl)piperazine, 57% to 1-(4-hydroxyphenyl)piperazine, 54% to 1-(4-fluorophenyl) piperazine, 31% to 1-(3-hydroxypheyl)piperazine, 13% to 1-(3-trifluoromethylphenyl)piperazine, and less than 1% to each of 4-(4-chlorophenyl)-4-hydroxypiperidine, 1-benzylpiperazine, 1-(2-methoxyphenyl)piperazine, mephedrone, mescaline, (+)-pseudoephedrine, MDPBP, JWH-018, JWH-250, salvinorin A, piperazine, 1-methyl-3-phenylpiperazine, trazodone, MCPCP and 3-amino-2-hydroxybenzotrifluoride;

wherein the cross reactivity is measured in the presence of a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase.

2. A polyclonal antibody raised against an immunogen, wherein the immunogen is a conjugate of 1-(3-carboxyphenyl)piperazine linked through the carboxy group to bovine thyroglobulin;

wherein the polyclonal antibody has a cross-reactivity of 100% to 1-(3-chlorophenyl)piperazine, 230% to 1-(3-methylphenyl)piperazine), 140% to 1-phenylpiperazine, 20% to 1-(4-methoxyphenyl)piperazine, 10% to 1-(4-hydroxyphenyl)piperazine, 38% to 1-(4-fluorophenyl) piperazine, 156% to 1-(3-hydroxyphenyl)piperazine, 61% to 1-(3-trifluoromethylphenyl)piperazine, 34% to 1-(2-methoxyphenyl)piperazine; and less than 1% to each of 4-(4-chlorophenyl)-4-hydroxypiperidine, 1-benzylpiperazine, mephedrone, mescaline, (+)-pseudoephedrine, MDPBP, JWH-018, JWH-250, salvinorin A, piperazine, 1-methyl-3-phenylpiperazine, trazodone, MCPCP and 3-amino-2-hydroxybenzotrifluoride;

wherein the cross reactivity is measured in the presence of a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase.

3. A method of detecting one or more piperazine derivatives comprising:

contacting a sample with the polyclonal antibody of claim 1 and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase; and

detecting the detecting agent.

4. The method of claim 3 , wherein the piperazine derivative is 1-(3-chlorophenyl)piperazine, 1-(3-methylphenyl)piperazine), 1-phenylpiperazine, 1-(4-methoxyphenyl)piperazine, 1-(4-hydroxyphenyl)piperazine, 1-(4-fluorophenyl) piperazine, 1-(3-hydroxyphenyl)piperazine, or 1-(3-trifluoromethylphenyl)piperazine.

5. A method of detecting one or more piperazine derivatives comprising:

contacting a sample with the polyclonal antibody of claim 2 and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase; and

detecting the detecting agent.

6. The method of claim 5 , wherein the piperazine derivative is 1-(3-chlorophenyl)piperazine, 1-(3-methylphenyl)piperazine), 1-phenylpiperazine, 1-(4-methoxyphenyl)piperazine, 1-(4-hydroxyphenyl)piperazine, 1-(4-fluorophenyl) piperazine, 1-(3-hydroxyphenyl)piperazine, 1-(3-trifluoromethylphenyl)piperazine; or 1-(2-methoxyphenyl)piperazine.

7. A method of detecting one or more piperazine derivatives comprising:

contacting a sample with the polyclonal antibody of claim 1 , the polyclonal antibody of claim 1 , and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase; and

detecting the detecting agent.

8. The method of claim 7 , wherein the piperazine derivative is 1-(3-chlorophenyl)piperazine, 1-(3-methylphenyl)piperazine), 1-phenylpiperazine, 1-(4-methoxyphenyl)piperazine, 1-(4-hydroxyphenyl)piperazine, 1-(4-fluorophenyl) piperazine, 1-(3-hydroxyphenyl)piperazine, 1-(3-trifluoromethylphenyl)piperazine; or 1-(2-methoxyphenyl)piperazine.

9. A kit comprising the polyclonal antibody of claim 1 and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase.

10. A kit comprising the polyclonal antibody of claim 2 and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase.

11. A kit comprising the polyclonal antibody of claim 1 , the polyclonal antibody of claim 1 , and a detecting agent, wherein the detecting agent is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to horseradish peroxidase.

12. A method of making the polyclonal antibody of claim 1 comprising administering to a mammal an immunogen, wherein the immunogen is a conjugate of 1-(4-carboxymethyletherphenyl)piperazine linked through the carboxy group to bovine thyroglobulin.

13. A method of making the polyclonal antibody of claim 2 comprising administering to a mammal an immunogen, wherein the immunogen is a conjugate of 1-(3-carboxyphenyl)piperazine linked through the carboxy group to bovine thyroglobulin.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVENYANCE PREVIOUSLY RECORDED AT REEL: 055950 FRAME: 0471. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Apr 20, 2021
From: RANDOX LABORATORIES LIMITED
To: NORTHERN BANK LIMITED
Reel/Frame 056210/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2021
From: RANDOX LABORATORIES LIMITED
To: NORTHERN BANK LIMITED
Reel/Frame 055950/0471 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2018
From: BENCHIKH, ELOUARD; MCCONNELL, IVAN; LOWRY, PHILIP; FITZGERALD, PETER
To: RANDOX LABORATORIES LIMITED
Reel/Frame 045446/0539 →
Priority Claims (1)
GB 1203266 · Feb 24, 2012 · national
Continuity (2)
Continuation 13774518 · Feb 22, 2013
Related Publication 20160229824A1 · Aug 11, 2016