IP Library Granted Patent US 9,720,005
Granted Patent B2
US 9,720,005 · App. 14/723,724 · Granted Aug 1, 2017

Immunoassay for compounds of the NBOMe family

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Quick Facts
Patent No.
US 9,720,005
App. No.
14/723,724
Granted
Aug 1, 2017
Kind
B2
Abstract

An immunoassay method for detecting and determining ‘NBOMe’ family designer drugs is described. Also described are components for use in implementing the method, namely, antibodies, detection agents, solid state devices and kits as well as immunogens used to raise the antibodies.

Claims (16)

1. An antibody which binds to epitope of Structure (Y)

in which R 1 is selected from the group consisting on a halogen, hydrogen, hydroxyl, C 1-3 alkyl, C 1-3 thioalkyl, C 1-3 alkoxy, perfluoromethyl and nitro; R 3 and R 4 are H and R 2 is methoxy;

wherein the antibody shows a cross-reactivity of 75 to 200% to the epitope of the Structure (Y) and a cross-reactivity of less than 5% to 2-(4-Iodo-2,5-dimethoxyphenyl) ethanamine (2C-I), 2-(4-ethyl-2,5-dimethoxyphenyl)ethanamine (2C-E), 2,5-dimethoxy-4-bromoamphetamine (DOB) and 2-(4-bromo-dimethoxyphenyl)ethanamine (2C-B); and

wherein the cross-reactivity is relative to 100% cross-reactivity of the antibody to 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl] ethanamine (25I-NB)Me).

2. The antibody of claim 1 , which binds to an epitope of at least one of 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl] ethanamine (25I-NBOMe), 2-(2,5 dimethoxy-4-propylphenyl)-N-(2-methoxybenzyl)ethanamine (25P-NBOMe), Mescaline-[(2-methoxvpheny)methy]ethanamine (Mescaline-NBOMe), 2-(4-Bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl] ethanamine (25B-NBOMe), 2-(2,5-Dimethoxy-4-methylphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25D-NBOMe), 2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25E-NBOMe), 2-(2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25H-NBOMe), 2-(2,5-dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethanamine (25N-NBOMe), 2-[2,5-dimethoxy-4-(-methylsulfanyl)phenyl]-N-(2-methoxybenzyl)ethanamine (25T2-NBOMe), 2-[(4-isopropylsulfanyl)-2,5-dimethoxyphenyl]-N-(2-methoxybenzyl)ethanamine (25T4-NBOMe) and 2-[2,5-dimethoxy-4(propylsulfanyl)phenyl]-N-(2-methoxybenzyl)ethanamine (25T7-NBOMe).

3. The antibody of claim 1 with an antibody sensitivity of IC50 of 0.2 ng/ml or less for 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl] ethanamine (25I-NBOMe), 2-(2,5 dimethoxy-4-propylphenyl)-N-(2-methoxybenzyl)ethanamine (25P-NBOMe), mescaline-2-methoxyphenyl)methyl]ethanamine (mescaline-NBOMe), 2 (4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25B-NBOMe), dimethoxy-4-methylphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25D-NBOMe), 2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25E-NBOMe) 2-(2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25H-NBOMe), 2-(2,5-dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethanamine (25N-NBOMe), 2-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]-N-(2-methoxybenzyl)ethanamine (25T2-NBOMe), 2-[4-isopropylsulfanyl)-2,5-dimethoxyphenyl]-N-(2-methoxybenzyl)ethanamine (25T4-NBOMe) and 2-[2,5-dimethoxy-4(propylsulfanyl)phenyl]-N-(2-methoxybenzyl)ethanamine (25T7-NBOMe).

4. The antibody of claim 1 further characterized by being derived from an immunogen of structure II

wherein X is a cross-linking group and Y is an antigenicity-conferring carrier.

5. The antibody of claim 4 wherein X is -(A)-(B)n-, where A is O, S or N and B is a C 1-6 substituted or unsubstituted straight chain alkylene or arylene moiety and n is either 0 or 1.

6. The antibody of claim 1 , which binds to an epitope of at least one of 25I-NBOMe, 25P-NBOMe, Mescaline-NBOMe, 25B-NBOMe, 25D-NBOMe, 25E-NBOMe, 25H-NBOMe, 25N-NBOMe, 25T2-NBOMe, 25T4-NBOMe and 25T7-NBOMe.

7. The antibody of claim 1 with an IC50 of 0.2 ng/ml or less for 25I-NBOMe, 25P-NBOMe, Mescaline-NBOMe, 25B-NBOMe, 25D-NBOMe, 25E-NBOMe 25H-NBOMe, 25N-NBOMe, 25T2-NBOMe, 25T4-NBOMe and 25T7-NBOMe.

8. The antibody of claim 1 further characterized by being derived from an immunogen of structure II

wherein X is a cross-linking group and Y is an antigenicity-conferring carrier.

9. A substrate comprising an antibody of one of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 or 8 , wherein optionally the substrate is either a microtitre plate or a biochip.

10. A kit comprising an antibody according to one of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 or 8 , and optionally one or more detecting agents of structure III

in which X is a cross-linking group and Y is a labelling agent which is detectable; and optionally wherein X is -(A)-(B) n1 —, where A is O, S or N and B is a C 1-6 substituted or unsubstituted straight chain alkylene or arylene moiety and n1 is either 0 or 1; wherein, optionally, X is -(A)-(B) n1 —, where A is O, S or N and B is a C 1-6 substituted or unsubstituted straight chain alkylene terminating, before conjugation with the labelling agent, with a terminal reactive group and n1 is either 0 or 1; wherein, further optionally, X is -(A)-(B) n1 —, where A is N and B is a C 1-6 substituted or unsubstituted straight chain alkylene terminating, before conjugation with the labelling agent, with a terminal reactive group and n1 is either 0 or 1.

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 Aug 5, 2015
From: MCCONNELL, IVAN ROBERT; BENCHIKH, ELOUARD; FITZGERALD, PETER; LOWRY, ANDREW PHILIP
To: RANDOX LABORATORIES LIMITED
Reel/Frame 036255/0535 →