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    FLUORESCENT PROBE FOR USE IN DETECTION OF BRAIN TUMOR
    3.
    发明申请
    FLUORESCENT PROBE FOR USE IN DETECTION OF BRAIN TUMOR 有权

    公开(公告)号：US20220341922A1

    公开(公告)日：2022-10-27

    申请号：US17612378

    申请日：2020-05-19

    Applicant: The University of Tokyo

    Inventor： Yosuke KITAGAWA ,  Shota TANAKA ,  Nobuhito SAITO ,  Yugo KURIKI ,  Mako KAMIYA ,  Yasuteru URANO

    IPC: G01N33/533 ,  C07K5/06 ,  C09B11/24 ,  G01N33/574

    Abstract: Provided is a novel fluorescent probe which can be used in a spray manner, has an outstandingly high sensitivity-specificity with instantaneousness, and enables detection of a brain tumor.
    A fluorescent probe for detecting a brain tumor, including a compound of the following formula (I) or a salt thereof: wherein P1 represents an arginine residue, a histidine residue or a tyrosine residue, P2 represents a proline residue or a glycine residue, where P1 is linked to an adjacent N atom by forming an amide bond, and P2 is linked to P1 by forming an amide bond; R1 represents a hydrogen atom, or 1 to 4 identical or different substituents each independently selected from the group consisting of an optionally substituted alkyl group, a carboxyl group, an ester group, an alkoxy group, an amide group and an azide group; R2, R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group or a halogen atom; R8 and R9 each independently represent a hydrogen atom or an alkyl group;
    X represents O, Si(Ra)(Rb), Ge(Ra)(Rb), Sn(Ra)(Rb), C(Ra) (Rb) or P(═O)(Ra); Ra and Rb each independently represent a hydrogen atom, an alkyl group or an aryl group; and Y represents a C1-C3 alkylene group.

    SUPER-RESOLUTION FLUORESCENT IMAGING PROBE
    4.
    发明申请
    SUPER-RESOLUTION FLUORESCENT IMAGING PROBE 审中-公开

    公开(公告)号：US20180052109A1

    公开(公告)日：2018-02-22

    申请号：US15551149

    申请日：2016-02-23

    Applicant: The University of Tokyo

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Akihiko MOROZUMI ,  Shinnosuke UNO ,  Keitaro UMEZAWA

    IPC: G01N21/64 ,  A61K49/00 ,  C09K11/06

    CPC classification number: G01N21/6458 ,  A61K49/0019 ,  A61K49/005 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1074 ,  C09K2211/1096 ,  G01N21/6428 ,  G01N33/533 ,  G01N33/68 ,  G01N2021/6439 ,  G02B21/0076 ,  G02B27/58

    Abstract: [Problem] To provide a novel fluorescent probe for super-resolution imaging that uses fluorescent light emission characteristics that originate from an intermolecular nucleophilic addition-dissociation equilibrium reaction, and to provide a super-resolution fluorescent imaging method that uses the probe. [Solution] A fluorescent probe for super-resolution imaging that comprises a compound represented by formula (I) or a salt thereof(in the formula, X represents an oxygen atom, C(Ra) (Rb), or Si(Ra) (Rb) (wherein Ra and Rb each independently represent a hydrogen atom or an alkyl group), R1 represents a hydrogen atom or an optionally substituted aryl (provided that, if R1 is a phenyl group, the benzene ring of the phenyl group does not have a substituent at position 2 or position 6), R2 and R3 each independently represent 1-3 identical or differing substituents that are independently selected from the group that consists of hydrogen atoms, hydroxyl groups, halogen atoms, optionally substituted alkyl groups, optionally substituted sulfo groups, optionally substituted carboxyl groups, optionally substituted ester groups, optionally substituted amide groups, and optionally substituted azide groups, R4 and R5 each independently represent a hydrogen atom or an optionally substituted alkyl group or N(R4) (R5) forms an amide group or a carbamate group (provided that, if R4 or R5 is an alkyl group, each may form, together with R2, a ring structure that contains the nitrogen atom that is bonded thereto), and R6 and R7 each independently represent a hydrogen atom or an optionally substituted alkyl group or N(R6)(R7) forms an amide group or a carbamate group (provided that, if R6 or R7 is an alkyl group, each may form, together with R3, a ring structure that contains the nitrogen atom that is bonded thereto)), the fluorescent probe for super-resolution imaging being characterized in that the compound represented by formula (I) or the salt thereof undergoes a nucleophilic addition-dissociation equilibrium reaction with a nucleophilic compound that contains an —SH group.

    ENZYME-SPECIFIC FLUORESCENT COMPOUND CAPABLE OF BEING RETAINED IN CELLS
    5.
    发明申请
    ENZYME-SPECIFIC FLUORESCENT COMPOUND CAPABLE OF BEING RETAINED IN CELLS 有权
    在细胞中保留的酶特异性荧光化合物

    公开(公告)号：US20170073321A1

    公开(公告)日：2017-03-16

    申请号：US15310641

    申请日：2015-05-13

    Applicant: The University of Tokyo

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Tomohiro DOURA

    IPC: C07D311/04 ,  C12Q1/40

    CPC classification number: C07D311/04 ,  C07H17/04 ,  C12Q1/40 ,  G01N2333/938

    Abstract: Provided is an enzyme-specific fluorescent compound capable of being retained in cells, which can emit fluorescence specifically in a target cell, particularly a cell capable of expressing a reporter enzyme such as β-galactosidase, and can covalently bind to a protein in the cell to exhibit an excellent property of being retained in the cell. The fluorescent compound comprises a compound represented by formula (I′) or a salt thereof. In formula (I′), A, X, Y and R1 to R9 are as described in claim 1.

    Abstract translation: 提供能够保留在细胞中的酶特异性荧光化合物，其可以在靶细胞，特别是能够表达报告酶如β-半乳糖苷酶的细胞中特异性发射荧光，并且可以共价结合细胞中的蛋白质 以表现出保留在细胞中的优异性质。 荧光化合物包含由式（I'）表示的化合物或其盐。 在式（I'）中，A，X，Y和R 1至R 9如权利要求1所述。

    RED FLUORESCENT PROBE FOR USE IN DETECTION OF PEPTIDASE ACTIVITY
    7.
    发明申请
    RED FLUORESCENT PROBE FOR USE IN DETECTION OF PEPTIDASE ACTIVITY 审中-公开

    公开(公告)号：US20200087516A1

    公开(公告)日：2020-03-19

    申请号：US16485962

    申请日：2018-02-16

    Applicant: The University of Tokyo

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Ryo TACHIBANA

    IPC: C09B11/24 ,  C12Q1/37 ,  A61K49/00

    Abstract: [Problem]A problem addressed by the present invention is to provide a novel fluorescent probe having excellent tissue permeability that is capable of detecting the peptidase activity expressed at a high level in cancer cells and the like as a response of long-wavelength red fluorescence.[Solution]A compound represented by formula (I) or a salt thereof: [In the formula, A represents a ring structure selected from the group consisting of a thiophene ring, a cyclopentene ring, a cyclopentadiene ring, and a furan ring; X represents a C0-C3 alkylene group; Y represents O, S, C(═O)O, or NH, Z represents O, C(Ra) (Rb), Si(Ra) (Rb), Ge(Ra) (Rb), Sn(Ra) (Rb), Se, P(Rc), or P(Rc) (═O) (where Ra and Rb each independently represent a hydrogen atom or an alkyl group, and Rc represents a hydrogen atom, an alkyl group, or an aryl group); R1 and R2 each independently represent from one to three of the same or different substituents selected from the group consisting of a hydrogen atom, a hydroxyl group, a halogen atom, and an alkyl group, a sulfo group, a carboxyl group, an ester group, an amide group, and an azide group each of which may be substituted; R3 represents an acyl residue derived from an amino acid (where the acyl residue is a residue obtained by removing an OH group from a carboxyl group of the amino acid); R4 and R5 each independently represent a hydrogen atom or an alkyl group (where when R4 or R5 is an alkyl group, the R4 or R5, together with R2, may form a ring structure comprising a nitrogen atom to which R4 and R5 are bonded).]

    ENZYME-SPECIFIC INTRACELLULARLY-RETAINED RED FLUORESCENT PROBE
    8.
    发明申请
    ENZYME-SPECIFIC INTRACELLULARLY-RETAINED RED FLUORESCENT PROBE 审中-公开

    公开(公告)号：US20190256544A1

    公开(公告)日：2019-08-22

    申请号：US16313357

    申请日：2017-06-23

    Applicant: The University of Tokyo

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Hiroki ITO ,  Yu KAWAMATA

    IPC: C07H17/04 ,  C12Q1/34 ,  G01N33/58

    Abstract: It is an object of the present invention to provide a fluorescence imaging probe capable of selectively visualizing target cells such as cells expressing β-galactosidase (lacZ expressing cells) at a single-cell level in a red fluorescence region, and of performing co-staining together with GFP.An intracellularly-retainable red fluorescent probe comprising a compound represented by the following formula (I) or a salt thereof: wherein: A represents a monovalent group cleaved by an enzyme; R1 represents a hydrogen atom, or one to four of the same or different substituents bonded to a benzene ring; R3, R4, R5, and R6 each independently represent —CFR10R11, —CF2R12, a hydrogen atom, a hydroxyl group, an alkyl group, or a halogen atom, wherein at least one of R3, R4, R5, and R6 is —CFR10R11 or —CF2R12; R2 and R7 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group, or a halogen atom; R8 and R9 each independently represent a hydrogen atom or an alkyl group; R10, R11, and R12 each independently represent a hydrogen atom, an alkyl group, or an alkenyl group; X represents Si(Ra) (Rb), wherein Ra and Rb each independently represent a hydrogen atom or an alkyl group; and Y is —C(═O)— or —RcC(═O)—, wherein Rc is an alkylene group having 1-3 carbon atoms.

    GLUTATHIONE-DETECTING FLUORESCENT PROBE
    9.
    发明申请
    GLUTATHIONE-DETECTING FLUORESCENT PROBE 审中-公开
    荧光检测荧光探针

    公开(公告)号：US20170045525A1

    公开(公告)日：2017-02-16

    申请号：US15116661

    申请日：2015-02-24

    Applicant: THE UNIVERSITY OF TOKYO

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Keitaro UMEZAWA ,  Masafumi YOSHIDA

    IPC: G01N33/68 ,  C09K11/07 ,  C09B19/00 ,  G01N33/58 ,  G01N21/64 ,  C09B11/24

    CPC classification number: G01N33/68 ,  C07F7/081 ,  C07F7/0812 ,  C09B11/08 ,  C09B11/24 ,  C09B11/28 ,  C09B19/00 ,  C09K11/06 ,  C09K11/07 ,  C09K2211/1007 ,  C09K2211/1033 ,  C09K2211/1055 ,  C09K2211/1088 ,  C09K2211/1096 ,  G01N21/6428 ,  G01N21/6458 ,  G01N33/582 ,  G01N33/6815 ,  G01N2021/6439 ,  G01N2021/6441

    Abstract: [Problem] To provide the following: a novel fluorescent probe for detecting a compound, such as glutathione, that contains a —SH group; a detection method using said fluorescent probe; and a detection kit containing said probe.[Solution] A fluorescent probe for detecting a compound containing an —SH group, wherein the fluorescent probe comprises a compound represented by formula (I) or a salt thereof (In the formula, X represents Si(Ra)(Rb), Ge(Ra)(Rb), Sn(Ra)(Rb), C(Ra)(Rb), or O (wherein Ra and Rb each independently represent a hydrogen atom or alkyl group); R1 represents a hydrogen atom, or 1-4 identical or different substituents independently selected from the group consisting of a cyano group, alkyl group, carboxyl group, ester group, alkoxy group, amide group, and azide group, each of which may be optionally substituted; R2 represents a hydrogen atom, halogen atom, hydroxyl group, cyano group, or an alkyl group, alkynyl group, alkoxy group, aryl, or heteroaryl, each of which may be optionally substituted; R3 and R4 each independently represent a hydrogen atom or 1-3 identical or different substituents independently selected from the group consisting of a hydroxyl group, halogen atom, or an alkyl group, sulfo group, carboxyl group, ester group, amide group and azide group, each of which may be optionally substituted; R5, R6, R7 and R8 each independently represent a hydrogen atom or alkyl group, wherein, R5 or R6, respectively together with R3, may form a ring structure including the nitrogen atoms bonded thereto, or R7 or R8, respectively together with R4, may form a ring structure including the nitrogen atoms bonded thereto).

    Abstract translation: [解决方案]用于检测含有-SH基团的化合物的荧光探针，其中所述荧光探针包含由式（I）表示的化合物或其盐（在该式中，X表示Si（Ra）（Rb），Ge Ra）（Rb），Sn（Ra）（Rb），C（Ra）（Rb）或O（其中Ra和Rb各自独立地表示氢原子或烷基）; R1表示氢原子或1-4 相同或不同的取代基，其独立地选自氰基，烷基，羧基，酯基，烷氧基，酰胺基和叠氮基，其各自可以被任选取代; R 2表示氢原子，卤素原子 ，羟基，氰基或烷基，炔基，烷氧基，芳基或杂芳基，其各自可以被任选取代; R 3和R 4各自独立地表示氢原子或1-3个相同或不同的独立选择的取代基 由羟基，卤素原子或烷基基团组成的组 p，磺基，羧基，酯基，酰胺基和叠氮基，其各自可以任选被取代; R 5，R 6，R 7和R 8各自独立地表示氢原子或烷基，其中，R 5或R 6分别与R 3一起形成包含与其结合的氮原子的环结构，或者R 7或R 8与R 4， 可以形成包括与其结合的氮原子的环结构）。

    FLUORESCENT PROBE FOR DETECTING ACTIVATION OF SIALIDASE
    10.
    发明申请
    FLUORESCENT PROBE FOR DETECTING ACTIVATION OF SIALIDASE 有权

    公开(公告)号：US20220186286A1

    公开(公告)日：2022-06-16

    申请号：US17593009

    申请日：2020-03-05

    Applicant: The University of Tokyo

    Inventor： Yasuteru URANO ,  Mako KAMIYA ,  Charlotte RIVAS

    IPC: C12Q1/40 ,  C07H17/04

    Abstract: A fluorescent probe for sialidase activity detection, is a compound represented by the following general formula or a salt thereof. R1, if present, represents the same or different monovalent substituent present on a benzene ring. R2 and R3 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogen atom. R4 and R5 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogen atom. R6 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 5 carbon atoms. R6′ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R6′ may form, together with R3 or R5 a five to seven-membered heterocyclyl or heteroaryl containing a nitrogen atom to which R6′ is bonded.

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