US2014162309A1PendingUtilityA1
Arsenical Fluorescent Agents and Assays
Est. expiryMar 19, 2030(~3.6 yrs left)· nominal 20-yr term from priority
G01N 33/582C09B 21/00G01N 2333/44C12Q 1/04C09B 19/00C07F 9/88C09B 17/00C07F 9/80C09B 11/24
49
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Claims
Abstract
The invention provides methods and compositions for labeling dithiol-containing analytes, including a substituted, optionally hydro-, optionally hetero-, monoarsenical anthracene compound comprising a 4′ rotation blocking group and a 5′ arsenic, and that exhibits a detectable increase or shift in fluorescence when the arsenic reacts with two thiols of a rotation-blocking binding target molecule.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A substituted, optionally hydro-, optionally hetero-, monoarsenical anthracene compound comprising a 4′ rotation blocking group and a 5′ arsenic, and that exhibits a detectable increase or shift in fluorescence when the arsenic reacts with two thiols of a rotation-blocking binding target molecule, the compound having the structure I:
wherein:
R1 is O, S, NRα, or CRα 2 ;
R2 is C or N;
R3 is H, optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy;
R4 and R5 are independently carbonyl, carbonothioyl, NRα 2 , ORα, or SRα;
R6 and R7 are Rα, halide, ORα, NRα 2 , ORα, SRα, or nitro (—NO 2 );
R8 and R9 are Rα, halide, ORα, NRα 2 , ORα, SRα, or nitro (—NO 2 );
R10 is a rotational blocking group;
R11 is an arsenic protecting group displaced by reaction of the arsenic with the thiols of the target molecule;
Rα groups are independently H, optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy;
wherein one or more of the pairs R4-R6, R6-R8, R5-R7, and R7-R9 may be covalently joined in one or more rings;
and tautomers, anhydrides and salts of the compound.
2 . The compound of claim 1 wherein R11 is carbonyl, 1,2 ethanedithiol, or dihydroxyl.
3 . The compound of claim 1 wherein the rotation blocking group is an optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy.
4 . The compound of claim 1 wherein:
R11 is carbonyl, 1,2 ethanedithiol, or dihydroxyl; and
the rotation blocking group is an optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy.
5 . The compound of claim 1 wherein:
R1 is O, S, N, or C;
6 . The compound of claim 1 wherein:
R1 is O, S, N, or C;
R11 is carbonyl, 1,2 ethanedithiol, or dihydroxyl; and
the rotation blocking group is an optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy.
7 . The compound of claim 1 wherein:
R1 is O;
R1 is O;
R1 is O;
R2 is C;
R2 is C;
R2 is C;
R3 is 2-carboxyphenyl;
R3 is 2-carboxyphenyl;
R3 is 2-carboxyphenyl;
R4 is hydroxyl;
R4 is hydroxyl;
R4 is amine;
R5 is carbonyl;
R5 is carbonyl;
R5 is amine;
R6 and R7 are H; and
R6 and R7 are H or Cl;
R6 and R7 are H; and
R8 and R9 are H;
R8 and R9 are H; and
R8 and R9 are H;
R10 is methyl or benzyl;
R1 is O;
R1 and R2 are N;
R1 is O;
R2 is C;
R3 is H or methyl;
R2 is N;
R3 is 2-carboxyphenyl;
R4 and R5 are O, S, or N;
R3 is H or methyl;
R4 is hydroxyl;
R6 and R7 are H; and
R4 is hydroxyl;
R5 is carbonyl;
R8 and R9 are H;
R5 is carbonyl;
R6 and R7 are Br or nitro (—NO 2 );
R6 and R7 are H; and
and R8 and R9 are H;
R8 and R9 are H;
R1 is S;
R1 is S;
R1 and R2 are C;
R2 is N;
R2 is C;
R3 is H or C;
R3 is H or C;
R3 is 2-carboxyphenyl;
R4 and R5 are O, S, N;
R4 is hydroxyl;
R4 is hydroxyl;
R6 and R7 are H; and
R5 is carbonyl;
R5 is carbonyl;
R8 and R9 are H;
R6 and R7 are H; and
R6 and R7 are H; and
R8 and R9 are H;
R8 and R9 are H;
R1 is N;
R1 is N;
R1 is N;
R2 is C;
R2 is C;
R2 is C;
R3 is H or C;
R3 is H;
R3 is H;
R4 and R5 are O, S, or N;
R4 and R5 are NH 2 ;
R4 and R5 are N(CH 3 ) 2 ;
R6 and R7 are H; and
R6 and R7 are CH 3 ; and
R6 and R7 are H; and
R8 and R9 are H;
R8 and R9 are H; or
R8 and R9 are H.
8 . The compound of claim 7 wherein:
R11 is carbonyl, 1,2 ethanedithiol, or dihydroxyl; and
the rotation blocking group is an optionally substituted-, optionally hetero-alkyl, optionally substituted-, optionally hetero-alkenyl, optionally substituted-, optionally hetero-alkynyl, optionally substituted-, optionally hetero-aryl, or optionally substituted-, optionally hetero-alkoxy.
9 . A compound of claim 1 selected from:
10 . The compound of claim 1 wherein the arsenic is reacted with two thiols of a rotation-blocking binding target molecule forming a conjugate having the general structure II:
wherein AC is the anthracene core, RBG is the rotation blocking group and TM is the target molecule, and tautomers, anhydrides and salts of the compound.
11 . A method of using a compound of claim 1 comprising the step of:
contacting the compound with the target molecule wherein the arsenic reacts with the thiols.Join the waitlist — get patent alerts
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