Luminogenic and fluorogenic compounds and methods to detect molecules or conditions

Patent metadata

Field	Value
Publication number	US-2016176830-A1
Application number	US-201414553445-A
Country	US
Kind code	A1
Filing date	Nov 25, 2014
Priority date	May 31, 2005
Publication date	Jun 23, 2016
Grant date	—

Abstract

A method to detect the presence of amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided. Compounds and compositions for carrying out the methods of the invention are also provided.

First claim

1 . A compound according to formula IIA:

wherein
Z is OR 1 ;
Z′ is O;
R is H, (C 6-30 )alkyl, saccharide, or M + wherein M is an alkali metal;
R 1 is (C 6-30 )aryl, heteroaryl, heterocycle, (C 1-20 )alkylthio, (C 1-20 )alkyl—S(O)—, (C 1-20 alkyl-SO 2 —, (C 1-20 )alkyl—SO 3 —, saccharide, (C 1-20 )alkylphosphate, (C 1-20 )alkylphosphonate, (C 6-30 )arylthio, (C 6-30 )aryl—S(O)—, (C 6-30 )aryl—SO 2 —, (C 6-30 )aryl—SO 3 —, (C 6-30 )arylphosphate, (C 6-30 )arylphosphonate, or R 1 is (C 1-20 )alkyl substituted by R 2 ;
R 2 is C( 2-20 )alkenyl, (C 2-20 )alkenyl, (C 3-20 )cycloalky, (C 1-20 )alkoxyl, (C 1-20 )alkylcarbonyl, (C 1-20 )alkylcarboxyl, hydroxyl, —COOR x , —SO 3 R x , (C 1-20 )alkylthio, (C 6-30 )arylthio, (C 1-20 )alkyl—S(O)—, (C 1-20 )alkyl—S(O) 2 —, nitro, amino, NH(C 1-6 )alkyl, NH(C 1-6 )alkynyl, N((C 1-6 )alkyl) 2 , N((C 1-6 )alkynyl) 2 , mercapto, saccharide or trifluoromethyl;
W 1 is H, halo, hydroxyl, (C 1-6 )alkyl or (C 1-6 )alkoxy;
wherein any alkyl, alkenyl, cycloalkyl, alkoxy, amino, aryl, heteroaryl or heterocycle group is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from (C 1-6 )alkyl, phenyl, halo, hydroxyl, —COOR x , —SO 2 R x , —SO 3 R x , nitro, amino, NH(C 1-6 )alkyl, NH(C 1-6 )alkynyl, N((C 1-6 )alkyl) 2 , N((C 1-6 )alkynyl) 2 , mercapto;
when Z is OR 1 , formula IIA is optionally a dimer connected at the two A rings via a linker comprising a (C 1-12 )alkyl diradical that is optionally interrupted by one to four O atoms, N atoms, or an optionally substituted aryl, heteroaryl or heterocycle group to form a bridge between the dimer of formula IIA, and the R 1 group of each 2 group connecting the dimer for formula IIA is replaced by the bridge;
or a salt thereof.

2 . A compound according to claim 1 , wherein R is H or methyl.

3 . A compound according to claim 2 , wherein R 1 is (C 1-20 ) alkyl substituted by R 2 .

4 . A compound according to claim 3 , wherein R 1 is substituted by amino.

5 . A compound according to claim 1 , wherein R 1 is selected from the group consisting of —S(O) 3 (C 6-30 )aryl.

6 . A compound according to claim 5 , wherein —S(O) 3 (C 6-30 )aryl is substituted with one or more substituents.

7 . A compound according to claim 6 , wherein the one or more substituents are selected from the group consisting of nitro, phenyl and (C 1-6 )alkyl.

8 . A compound selected from the group consisting of:

9 . A compound according to claim 8 , wherein the compound is consisting of:

Assignees

• Promega Corp

Inventors

• Cali James J
• Daily William
• Hawkins Erika
• Klaubert Dieter
• Liu Jianquan
• Meisenheimer Poncho
• Scurria Michael
• Shultz John W
• Unch James
• Valley Michael P
• Wood Keith V
• Zhou Wenhui

Classifications

• C09B11/24

  Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• C12Q1/66

  involving luciferase · CPC title

• C07D311/16

  substituted in position 7 · CPC title

• C09B19/00

  Oxazine dyes · CPC title