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    Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo
    1.
    发明授权
    Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo 有权
    用于体内岩藻糖基化聚糖荧光成像的糖蛋白质组学探针

    公开(公告)号：US08329413B2

    公开(公告)日：2012-12-11

    申请号：US13053192

    申请日：2011-03-21

    申请人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R Hanson ,  Masaaki Sawa

    发明人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R Hanson ,  Masaaki Sawa

    IPC分类号： G01N33/53

    CPC分类号： G01N33/582 ,  G01N1/30 ,  G01N2400/00

    摘要： Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.

    摘要翻译： 提供了通过含有包含炔基的探针的Cu（I）催化的[3 + 2]环加成的荧光标记来标记携带叠氮基的细胞聚糖的方法。 通过Cu（I）催化的[3 + 2]环加成的探针的炔基与叠氮改性的糖，从非荧光前体4-乙炔基-N-乙基-1,8-萘二甲酰亚胺生成荧光探针是 提供。 公开了通过岩藻糖补救途径将叠氮基岩藻糖类似物掺入糖缀合物。 公开了通过用用点击激活的荧光探针或生物素化的炔标记的6-叠氮基聚糖处理的细胞的流式细胞术的岩藻糖基化细胞的荧光可视化。 公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内位置。

    Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo
    2.
    发明申请
    Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo 有权
    用于体内岩藻糖基化聚糖荧光成像的糖蛋白质组学探针

    公开(公告)号：US20080241856A1

    公开(公告)日：2008-10-02

    申请号：US12079228

    申请日：2008-03-24

    申请人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R. Hanson ,  Masaaki Sawa

    发明人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R. Hanson ,  Masaaki Sawa

    IPC分类号： G01N33/53 ,  C12P19/44 ,  C12Q1/00

    CPC分类号： G01N33/582 ,  G01N1/30 ,  G01N2400/00

    摘要： The disclosure provides a method of labeling of cellular glycans bearing azide groups via a fluorescent labeling technique based on Cu(I)-catalyzed [3+2]cycloaddition (click activation) of a probe comprising an alkynyl group. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2]cycloaddition of the alkyne group of the probe with an azido-modified sugar. The disclosure further provides a method of incorporating an azido-containing fucose analog into glycoconjugates via the fucose salvage pathway. The disclosure provides a method of fluorescent visualization of fucosylated cells by flow cytometry when cells treated with 6-azidofucose are labeled with the click-activated fluorogenic probe or biotinylated alkyne. A method of visualizing the intracellular localization of fucosylated glycoconjugates by fluorescence microscopy is also disclosed.

    摘要翻译： 本公开提供了通过基于包含炔基的探针的Cu（I）催化的[3 + 2]环加成（点击活化）的荧光标记技术来标记携带叠氮基的细胞聚糖的方法。 该方法需要通过Cu（I）催化的[3 + 2]环加成的探针的炔基与非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺的生成荧光探针， 改性糖。 本公开进一步提供了通过岩藻糖补救途径将含叠氮基岩藻糖类似物掺入糖缀合物的方法。 本公开内容提供了当用6-叠氮基聚糖处理的细胞用点击激活的荧光探针或生物素化的炔被标记时，流式细胞仪荧光显示岩藻糖基化细胞的方法。 还公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内定位的方法。

    GLYCOPROTEOMIC PROBES FOR FLUORESCENT IMAGING OF FUCOSYLATED GLYCANS IN VIVO
    3.
    发明申请
    GLYCOPROTEOMIC PROBES FOR FLUORESCENT IMAGING OF FUCOSYLATED GLYCANS IN VIVO 有权
    血液中富含荧光成像的GLYCOPROTEOMIC PROBES

    公开(公告)号：US20110257376A1

    公开(公告)日：2011-10-20

    申请号：US13053192

    申请日：2011-03-21

    申请人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R. Hanson ,  Masaaki Sawa

    发明人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R. Hanson ,  Masaaki Sawa

    IPC分类号： C07K14/47 ,  C07H19/207

    CPC分类号： G01N33/582 ,  G01N1/30 ,  G01N2400/00

    摘要： Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.

    摘要翻译： 提供了通过含有包含炔基的探针的Cu（I）催化的[3 + 2]环加成的荧光标记来标记携带叠氮基的细胞聚糖的方法。 通过Cu（I）催化的[3 + 2]环加成的探针的炔基与叠氮改性的糖，从非荧光前体4-乙炔基-N-乙基-1,8-萘二甲酰亚胺生成荧光探针是 提供。 公开了通过岩藻糖补救途径将叠氮基岩藻糖类似物掺入糖缀合物。 公开了通过用用点击激活的荧光探针或生物素化的炔标记的6-叠氮基聚糖处理的细胞的流式细胞术的岩藻糖基化细胞的荧光可视化。 公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内位置。

    Glycoproteomic probes for fluorescent imaging fucosylated glycans in vivo
    4.
    发明授权
    Glycoproteomic probes for fluorescent imaging fucosylated glycans in vivo 有权
    用于体内荧光成像岩藻糖基化聚糖的糖蛋白质组学探针

    公开(公告)号：US07910319B2

    公开(公告)日：2011-03-22

    申请号：US12079228

    申请日：2008-03-24

    申请人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R Hanson ,  Masaaki Sawa

    发明人： Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah R Hanson ,  Masaaki Sawa

    IPC分类号： G01N33/53

    CPC分类号： G01N33/582 ,  G01N1/30 ,  G01N2400/00

    摘要： The disclosure provides a method of labeling of cellular glycans bearing azide groups via a fluorescent labeling technique based on Cu(I)-catalyzed [3+2]cycloaddition (click activation) of a probe comprising an alkynyl group. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2]cycloaddition of the alkyne group of the probe with an azido-modified sugar. The disclosure further provides a method of incorporating an azido-containing fucose analog into glycoconjugates via the fucose salvage pathway. The disclosure provides a method of fluorescent visualization of fucosylated cells by flow cytometry when cells treated with 6-azidofucose are labeled with the click-activated fluorogenic probe or biotinylated alkyne. A method of visualizing the intracellular localization of fucosylated glycoconjugates by fluorescence microscopy is also disclosed.

    摘要翻译： 本公开提供了通过基于包含炔基的探针的Cu（I）催化的[3 + 2]环加成（点击活化）的荧光标记技术来标记携带叠氮基的细胞聚糖的方法。 该方法需要通过Cu（I）催化的[3 + 2]环加成的探针的炔基与非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺的生成荧光探针， 改性糖。 本公开进一步提供了通过岩藻糖补救途径将含叠氮基岩藻糖类似物掺入糖缀合物的方法。 本公开内容提供了当用6-叠氮基聚糖处理的细胞用点击激活的荧光探针或生物素化的炔被标记时，流式细胞仪荧光显示岩藻糖基化细胞的方法。 还公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内定位的方法。

    ALKYNYL SUGAR ANALOGS FOR LABELING AND VISUALIZATION OF GLYCOCONJUGATES IN CELLS
    5.
    发明申请
    ALKYNYL SUGAR ANALOGS FOR LABELING AND VISUALIZATION OF GLYCOCONJUGATES IN CELLS 审中-公开
    用于在细胞中标记和观察甘油三酯的ALKYNYL糖模拟物

    公开(公告)号：US20120149887A1

    公开(公告)日：2012-06-14

    申请号：US13159339

    申请日：2011-06-13

    申请人： Masaaki Sawa ,  Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah Hanson

    发明人： Masaaki Sawa ,  Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah Hanson

    IPC分类号： C07H15/04 ,  C07H19/10

    CPC分类号： G01N33/5005 ,  G01N33/5008 ,  G01N33/533 ,  G01N2400/00

    摘要： Methods for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates are disclosed. Alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars are incorporated into cellular glycoconjugates. Chemical probes comprising an azide group and a visual or fluorogenic probe and used to label alkyne-derivatized sugar-tagged glycoconjugates are disclosed. Chemical probes bind covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and are visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA, confocal microscopy, and mass spectrometry.

    摘要翻译： 公开了将衍生的含炔烃类似物作为细胞糖缀合物的“标签”的代谢寡糖工程方法。 将炔基衍生的Fuc和炔基衍生的ManNAc糖掺入细胞糖缀合物中。 公开了包含叠氮基和视觉或荧光探针并用于标记炔衍生的糖标记的糖缀合物的化学探针。 化学探针通过Cu（I）催化的[3 + 2]叠氮炔环加成与炔基共价结合，并在细胞表面，细胞内或细胞提取物中显现。 标记的糖缀合物能够通过流式细胞术，SDS-PAGE，Western印迹，ELISA，共聚焦显微镜和质谱检测。

    Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells
    7.
    发明授权
    Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells 有权
    炔基糖类似物用于细胞中糖缀合物的标记和可视化

    公开(公告)号：US07960139B2

    公开(公告)日：2011-06-14

    申请号：US12079226

    申请日：2008-03-24

    申请人： Masaaki Sawa ,  Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah Hanson

    发明人： Masaaki Sawa ,  Chi-Huey Wong ,  Tsui-Ling Hsu ,  Sarah Hanson

    IPC分类号： G01N33/53

    CPC分类号： G01N33/5005 ,  G01N33/5008 ,  G01N33/533 ,  G01N2400/00

    摘要： The present disclosure relates to a method for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates. The disclosed method incorporates alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars into a cellular glycoconjugate. A chemical probe comprising an azide group and a visual probe or a fluorogenic probe is used to label the alkyne-derivatized sugar-tagged glycoconjugate. In one aspect, the chemical probe binds covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and is visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA or confocal microscopy, and mass spectrometry.

    摘要翻译： 本公开内容涉及将衍生的含炔烃类似物作为“标签”掺入细胞糖缀合物的代谢寡糖工程方法。 所公开的方法将炔基衍生化的Fuc和炔基衍生的ManNAc糖引入细胞糖缀合物中。 使用包含叠氮化物基团和视觉探针或荧光探针的化学探针来标记炔衍生的糖标记的糖缀合物。 在一个方面，化学探针通过Cu（I）催化的[3 + 2]叠氮炔环加成共价结合到炔基上，并且在细胞表面，细胞内或细胞提取物中可视化。 标记的糖缀合物能够通过流式细胞术，SDS-PAGE，Western印迹，ELISA或共聚焦显微镜和质谱检测。

    NOVEL FURANONE DERIVATIVE
    10.
    发明申请
    NOVEL FURANONE DERIVATIVE 有权
    新鲜的呋喃酮衍生物

    公开(公告)号：US20140018533A1

    公开(公告)日：2014-01-16

    申请号：US14008488

    申请日：2012-03-30

    申请人： Takayuki Irie ,  Ayako Sawa ,  Masaaki Sawa ,  Tokiko Asami ,  Yoko Funakoshi ,  Chika Tanaka

    发明人： Takayuki Irie ,  Ayako Sawa ,  Masaaki Sawa ,  Tokiko Asami ,  Yoko Funakoshi ,  Chika Tanaka

    IPC分类号： C07D471/04

    CPC分类号： C07D471/04 ,  A61K31/437 ,  A61K31/4375 ,  A61K31/444 ,  A61K31/4545 ,  A61K31/4709 ,  A61K31/496 ,  A61K31/506 ,  A61K31/5355 ,  A61K31/541 ,  C07D519/00

    摘要： To provide a novel furanone derivative, and a medicine including the same. The furanone derivative is represented by the formula (I): wherein A represents —COOR1 or a hydrogen atom; R1 represents a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocycle; R2 and R3 are the same or different and each independently represent a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted phenyl group, an optionally substituted heterocycle, an optionally substituted heterocyclic fused ring, or an optionally substituted amino group; or alternatively, R2 and R3, taken together with the nitrogen atom to which they are attached, may form an optionally substituted heterocycle or an optionally substituted heterocyclic fused ring; and R4 represents a hydrogen atom or a halogen atom; with the proviso that when A represents —COOR1, R2 and R3 are not optionally substituted amino groups at the same time, and when A represents a hydrogen atom, R3 represents a hydrogen atom.

    摘要翻译： 提供一种新颖的呋喃酮衍生物，以及包含该呋喃酮衍生物的药物。 呋喃酮衍生物由式（I）表示：其中A表示-COOR 1或氢原子; R1表示氢原子，任选取代的烃基或任选取代的杂环; R2和R3相同或不同，并且各自独立地表示氢原子，任选取代的烃基，任选取代的苯基，任选取代的杂环，任选取代的杂环稠合环或任选取代的氨基; 或者R2和R3与它们所连接的氮原子一起可以形成任选取代的杂环或任选取代的杂环稠环; R4代表氢原子或卤原子; 条件是当A表示-COOR 1时，R2和R3不同时为任选取代的氨基，当A表示氢原子时，R 3表示氢原子。