US2017320830A1PendingUtilityA1
Hydrophilic high quantum yield acridinium esters with improved stability and fast light emission
Assignee: SIEMENS HEALTHCARE DIAGNOSTICS INCPriority: Jul 8, 2013Filed: Jul 4, 2014Published: Nov 9, 2017
Est. expiryJul 8, 2033(~6.9 yrs left)· nominal 20-yr term from priority
G01N 21/76C07D 219/06C09K 11/07G01N 33/582F21K 2/06G01N 33/543
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Claims
Abstract
Hydrophilic, high quantum yield, chemiluminescent acridinium compounds with increased light output, improved stability, fast light emission and decreased non specific binding are disclosed. The chemiluminescent acridinium esters possess hydrophilic, branched, electron-donating functional groups at the C2 and/or C7 positions of the acridinium nucleus.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A hydrophilic, high quantum yield acridinium ester having the following structure:
wherein,
R 1 is a methyl or sulfopropyl group;
G is a branched group independently selected at each occurrence from:
where R 2 , R 3, R 4 , R 5 , R 6 and R 7 are independently at each occurrence a methyl group or a group —(CH 2 CH 2 O) n CH 3 , where n is an integer from 1 to 5; and
R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
2 . An acridinium ester according to claim 1 wherein G is, at one or both occurrences, a group:
where R 2 and R 3 are independently at each occurrence a methyl group or a group —(CH 2 CH 2 O) n CH 3 , where n is an integer from 1 to 5.
3 . An acridinium ester according to claim 2 wherein G is a group:
at one or both occurrences.
4 . An acridinium ester according to claim 2 wherein G is a group:
at one or both occurrences.
5 . An acridinium ester according to claim 2 wherein G is a group:
at one or both occurrences.
6 . An acridinium ester according to claim 1 wherein G is, at one or both occurrences, a group:
where R 4 , R 5 , R 6 and R 7 are independently at each occurrence a methyl group or a group —(CH 2 CH 2 O) n CH 3 , where n is an integer from 1 to 5.
7 . An acridinium ester according to claim 6 wherein G is, at one or both occurrences, a group:
at one or both occurrences.
8 . An acridinium ester according to claim 6 wherein G is a group:
at one or both occurrences.
9 . An acridinium ester according to claim 1 , where R 12 is selected from the group consisting of:
(1) —OH; (2) —O—N-succinimidyl; (3) —NH—(CH 2 ) 5 —C(O)—O—N-succinimidyl; (4) —NH—(CH 2 ) 5 —COOH; (5) —NH—(C 2 H 4 O) n —C 2 H 4 NH—C(O)—(CH 2 ) 3 —C(O)—O—N-succinimidyl wherein n=1 to 5; (6) —NH—(C 2 H 4 O) n —C 2 H 4 NH—C(O)—(CH 2 ) 3 —COOH, wherein n=1 to 5; (7) —NH—(C 2 H 4 O) n —C 2 H 4 NH 2 , wherein n=1 to 5; and (8) —NH—R—NHR, wherein R is independently hydrogen, alkyl, alkenyl, alkynyl, or aralkyl; wherein R optionally comprises up to 20 heteroatoms.
10 . An acridinium ester according to claim 9 , wherein R 12 is —OH.
11 . An acridinium ester according to claim 9 , wherein R 12 is —NH—(C 2 H 4 O) n —C 2 H 4 NH 2 , wherein n=1 to 5.
12 . An acridinium ester according to claim 9 , wherein R 12 is:
—NH—(C 2 H 4 O) n —C 2 H 4 NH—C(O)—(CH 2 ) 3 —C(O)—O—R″ wherein n=1 to 5; and where R″ is hydrogen or —N-succinimidyl.
13 . An acridinium ester according to claim 1 , having the following structure:
where R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
14 . An acridinium ester according to claim 1 having the following structure:
where R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
15 . An acridinium ester according to claim 1 having the following structure:
where R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
16 . An acridinium ester according to claim 1 having the following structure:
where R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
17 . An acridinium ester according to claim 1 having the following structure:
where R 12 is an electrophilic or nucleophilic group for conjugating the acridinium compound to an analyte, an analyte analog, or a binding molecule for an analyte.
18 . The acridinium ester according to any of claims 14 - 18 , wherein R 12 is —OH.
19 . An assay for the detection or quantification of an analyte comprising the steps of:
(a) providing a conjugate comprising: (i) a binding molecule specific for an analyte; and (ii) a hydrophilic, high quantum yield and fast light emitting acridinium ester according to claim 1 ; (b) providing a solid support having immobilized thereon a second binding molecule specific for said analyte; (c) mixing the conjugate, the solid phase and a sample suspected of containing the analyte to form a binding complex; (d) separating the binding complex captured on the solid support; (e) triggering chemiluminescence of the binding complex from step (d) by adding chemiluminescence triggering reagents; (f) measuring the amount of light emission with a luminometer; and (g) detecting the presence or calculating the concentration of the analyte by comparing the amount of light emitted from the reaction mixture with a standard dose response curve which relates the amount of light emitted to a known concentration of the analyte.
20 . An assay for the detection or quantification of an analyte comprising the steps of:
(a) providing a conjugate of an analyte with a hydrophilic, high quantum yield and fast light emitting acridinium ester according to claim 1 ; (b) providing a solid support immobilized with a binding molecule specific for the analyte; (c) mixing the conjugate, solid support and a sample suspected of containing the analyte to form a binding complex; (d) separating the binding complex captured on the solid support; (e) triggering the chemiluminescence of the binding complex from step (d) by adding chemiluminescence triggering reagents; (f) measuring the amount of light with an luminometer; and (g) detecting the presence or calculating the concentration of the analyte by comparing the amount of light emitted from the reaction mixture with a standard dose response curve which relates the amount of light emitted to a known concentration of the analyte.Join the waitlist — get patent alerts
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