US 11,667,945 B2
Detection method and detection probe for colibactin and colibactin-producing bacteria
Kenji Watanabe, Shizuoka (JP); Yuta Tsunematsu, Shizuoka (JP); and Michio Sato, Shizuoka (JP)
Assigned to Shizuoka Prefecture Public University Corporation, Shizuoka (JP)
Appl. No. 16/642,696
Filed by SHIZUOKA PREFECTURE PUBLIC UNIVERSITY CORPORATION, Shizuoka (JP)
PCT Filed Aug. 27, 2018, PCT No. PCT/JP2018/031489
§ 371(c)(1), (2) Date Jun. 1, 2020,
PCT Pub. No. WO2019/044736, PCT Pub. Date Mar. 7, 2019.
Claims priority of application No. JP2017-163079 (JP), filed on Aug. 28, 2017.
Prior Publication US 2021/0010051 A1, Jan. 14, 2021
Int. Cl. G01N 33/53 (2006.01); C12Q 1/04 (2006.01); C07D 311/18 (2006.01); C09K 11/07 (2006.01); G01N 33/569 (2006.01)
CPC C12Q 1/04 (2013.01) [C07D 311/18 (2013.01); C09K 11/07 (2013.01); G01N 33/56911 (2013.01)] 6 Claims
 
1. A compound or a fluorescent probe selected from the group consisting of:
(A) a compound or a fluorescent probe obtained by connecting an amino group of a coumarin fluorescent dye having the amino group at position 7 of a coumarin skeleton and a carboxyl group of myristoyl asparagine via an amide bond;
(B) a compound or a fluorescent probe obtained by connecting an amino group of a naphthalimide fluorescent dye having the amino group at position 4 of a naphthalimide skeleton and a carboxyl group of myristoyl asparagine via an amide bond;
(C) a compound or a fluorescent probe obtained by connecting an amino group of naphthalene, pyrene or anthracene having the amino group at position 2 thereof and a carboxyl group of myristoyl asparagine via an amide bond;
(D) a compound or a fluorescent probe obtained by connecting one or both of amino groups of a rhodamine fluorescent dye having the amino group at position 3 and/or 9 of a xanthene skeleton and carboxyl group(s) of myristoyl asparagine via an amide bond;
(E) a compound or a fluorescent probe obtained by connecting one or both of amino groups of Bodipy fluorescent dye having the amino group at position 1 and/or 7 of Bodipy mother nucleus and the carboxyl group(s) of myristoyl asparagine via an amide bond;
(F) a compound or a fluorescent probe obtained by connecting said carboxyl group and said amino group in any one of (A) to (E) via alanine (—NH—CH(CH3)-CO—) (each forms an amide bond with alanine);
(G) a compound or a fluorescent probe obtained by connecting a carboxyl group of myristoyl asparagine and a hydroxyl group of oFlu, which is a fluorescent group that exhibits fluorescence when the hydroxyl group is released, via a self-cleavable linker, wherein the selfcleavable linker is connected to the carboxyl group of myristoyl asparagine via an amide bond;
and the hydroxyl group of oFlu is liberated when the amide bond is decomposed by hydrolysis; and
(H) a compound or fluorescent probe having a fluorescent dye connected to a carboxyl group of myristoyl asparagine via an amide bond, wherein fluorescence is emitted after the amide bond is cleaved in a ClbP dependent manner.