Fluorescent probe

Patent metadata

Field	Value
Publication number	US-9250232-B2
Application number	US-201314378022-A
Country	US
Kind code	B2
Filing date	Feb 15, 2013
Priority date	Feb 17, 2012
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

A compound represented by the formula (I) [R 1 represents hydrogen atom or a substituent; R 2 , R 3 , R 6 , and R 7 represent hydrogen atom, an alkyl group, a halogen atom, or a hydrophilic substituent; R 4 and R 5 represent an alkyl group or an aryl group; R 8 and R 9 represent a group cleaved by contact with an object substance for measurement; and X represents silicon atom, germanium atom, or tin atom] or a salt thereof, which is useful as a fluorescent probe that emits red fluorescence by contact with an object substance for measurement.

First claim

What is claimed is:

1. A compound represented by the formula (I), or a salt thereof:

wherein, in the formula,
R 1 represents a hydrogen atom, or the same or different 1 to 4 monovalent substituents existing on the benzene ring;
R 2 and R 3 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogen atom, or a monovalent hydrophilic substituent;
R 4 and R 5 independently represent an alkyl group having 1 to 6 carbon atoms, or an aryl group having 1 to 6 carbon atoms;
R 6 and R 7 independently represent hydrogen atom, an alkyl group 1 to 6 carbon atoms, a halogen atom, or a monovalent hydrophilic substituent;
R 8 and R 9 , which are the same or different, independently represent hydrogen atom or a monovalent group that is cleaved by contact with an object substance for measurement, provided that R 8 and R 9 are not simultaneously hydrogen atoms;
and X represents a silicon atom, a germanium atom, or a tin atom.

2. The compound or a salt thereof according to claim 1 , wherein
R 1 represents a hydrogen atom or 1 to 3 monovalent substituents existing on the benzene ring wherein the substituents are selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, hydroxy group, carboxy group, sulfonyl group, an alkoxycarbonyl group, a halogen atom, and amino group,
R 2 and R 3 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogen atom, or a monovalent hydrophilic substituent having an amino group substituted with one or two carboxyalkyl groups, which may form esters, as a partial structure;
R 4 and R 5 independently represent an alkyl group having 1 to 6 carbon atoms,
R 6 and R 7 independently represent a hydrogen atom or a halogen atom,
R 8 and R 9 represent a hydrogen atom or a monovalent group that is cleaved by contact with the same object substance for measurement, provided that R 8 and R 9 are not simultaneously hydrogen atoms; and
X represents a silicon atom.

3. The compound or a salt thereof according to claim 1 , wherein
R 1 represents a hydrogen atom or 1 to 3 monovalent substituents existing on the benzene ring wherein the substituents are selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, hydroxy group, carboxy group, a halogen atom, and amino group,
R 2 and R 3 independently represent a hydrogen atom or a monovalent hydrophilic substituent having one or two amino groups substituted with two carboxymethyl groups, which may form esters, as partial structures,
R 4 and R 5 independently represent an alkyl group having 1 to 3 carbon atoms,
R 6 and R 7 are both hydrogen atoms, chlorine atoms, or fluorine atoms,
R 8 and R 9 represent a hydrogen atom or a monovalent group that is cleaved by the same reductase, oxidase, or hydrolase, provided that R 8 and R 9 are not simultaneously hydrogen atoms; and
X represents silicon atom.

4. The compound or a salt thereof according to claim 1 , wherein
R 1 represents a hydrogen atom,
R 2 and R 3 independently represent a hydrogen atom or an alkyl group having one or two amino groups substituted with two carboxymethyl groups, which may form acetoxymethyl esters, as partial structures, and wherein the alkyl group may have an oxo group, or contain an amide bond,
R 4 and R 5 independently represent an alkyl group having 1 to 3 carbon atoms,
R 6 and R 7 are both hydrogen atoms or chlorine atoms, and
R 8 and R 9 represent a monovalent group that is cleaved by an enzyme selected from the group consisting of β-lactamase, cytochrome P450 oxidase, β-galactosidase, β-glucosidase, β-glucuronidase, β-hexosaminidase, lactase, alkaline phosphatase, matrix metalloprotease, and glutamyl transferase.

5. A method for measuring an object substance for measurement, which comprises
contacting a compound represented by the formula (I) or salt thereof of claim 1 with the object substance for measurement, and then
measuring fluorescence.

Assignees

• Univ Tokyo

Inventors

• Nagano Tetsuo
• Hanaoka Kenjiro
• HIRABAYASHI Kazuhisa
• TOKI Yuko

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C07H17/04

  Heterocyclic radicals containing only oxygen as ring hetero atoms · CPC title

• C12Q1/00

  Measuring or testing processes involving enzymes, nucleic acids or microorganisms (measuring or testing apparatus with condition measuring or sensing means, e.g. colony counters, C12M1/34); Compositions therefor; Processes of preparing such compositions · CPC title

• C07H23/00

  Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12 (esters with inorganic acids C07H11/00) · CPC title

• G01N33/52 Primary

  Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper {and including single- and multilayer analytical elements (immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72)} · CPC title