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US 11,530,352 B2Granted
Fluorescent detection of amines and hydrazines and assaying methods thereof
AssigneeIllumina, Inc.
InventorsAli Asadi, Jian-Sen Li
Life of this patent
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Abstract
Provided herein are processes for preparing fluorescent 1-cyano-2-substituted isoindole compounds or N-substituted phthalazinium compounds, comprising reacting an aromatic dialdehyde or aromatic aldehyde-ketone compound with a material that contains primary amino or hydrazine groups, and assaying methods involving the processes thereof.
Claims20
A process for assaying a compound of R—NH2, comprising:
- forming a compound of Formula (I):
- by reacting a compound of Formula (III):
- with the compound of R—NH2 in the presence of a cyanide ion;
- and
- detecting and measuring the fluorescence of the compound of Formula (I),
- wherein:
- X is CRa or N,
- R1 and R2 are Ra;
- or R1 and R2 together with the carbon atoms they are attached to form a monocyclic or multicyclic fused aryl or heteroaryl ring, which is optionally substituted with one or more Ra1;
- R3 is hydrogen, alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- each of which is optionally substituted with one or more Rb;
- R is a moiety, which is attached to a solid support directly or via a linker;
- each instance of Ra is independently hydrogen, halogen, alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, hydroxyl, alkoxy, cycloalkoxy, heterocyclyloxy, aryloxy, heteroaryloxy, cyano, nitro, amino, amido, carboxyl, sulfonyl, sulfonamido, acyl, acyloxy, alkoxycarbonyl, or phosphate;
- each of which is optionally substituted with one or more Rb;
- each instance of Ra1 is independently halogen, alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, hydroxyl, alkoxy, cycloalkoxy, heterocyclyloxy, aryloxy, heteroaryloxy, cyano, nitro, amino, amido, carboxyl, sulfonyl, sulfonamido, acyl, acyloxy, alkoxycarbonyl, or phosphate;
- each of which is optionally substituted with one or more Rb;
- and
- each instance of Rb is independently halogen, alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, hydroxyl, alkoxy, cycloalkoxy, heterocyclyloxy, aryloxy, heteroaryloxy, cyano, nitro, amino, amido, carboxyl, sulfonyl, sulfonamido, acyl, acyloxy, alkoxycarbonyl, or phosphate;
- each of which is optionally substituted with one or more halogen, alkyl, or alkoxy;
- and
- wherein the reaction between the compound of Formula (III) and R—NH2 occurs under a mildly basic condition having a pH of from 7.5 to 9.5.
18 more elements
Dependencies are inferred from the claim text.