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1. 发明申请

US20090232831A1 METHODS AND COMPOSITIONS FOR THE TREATMENT OR PREVENTION OF HUMAN IMMUNODEFICIENCY VIRUS INFECTION 审中-公开
标题翻译：治疗或预防人类免疫缺陷病毒感染的方法和组合
公开(公告)号：US20090232831A1
公开(公告)日：2009-09-17
申请号：US12338987
申请日：2008-12-18
申请人： Chi-Huey Wong , Sheng-Kai Wang , Pi-Hui Liang
发明人： Chi-Huey Wong , Sheng-Kai Wang , Pi-Hui Liang
IPC分类号： A61K39/42 , A61K31/715 , C07H1/00 , C12Q1/70
CPC分类号： A61K31/715 , A61K39/00 , G01N33/56988 , G01N33/6854 , G01N2400/00 , G01N2500/04
摘要： A conserved cluster of oligomannose glycans on gp120 has been identified as the epitope recognized by the broadly HIV-1-neutralizing monoclonal antibody 2G12. Oligomannose glycans are also the ligands for DC-SIGN, a C-type lectin found on the surface of dendritic cells. Multivalency is fundamental for carbohydrate-protein interactions, and mimicking of the high glycan density on the virus surface has become essential for designing carbohydrate-based HIV vaccines and antiviral agents. Synthesis of oligomannose dendrons, which display multivalent oligomannoses in high density, and characterize their interaction with 2G12 and DC-SIGN by a glycan microarray binding assay is disclosed. These glycodendrons inhibit the binding of gp120 to 2G12 and recombinant dimeric DC-SIGN with IC50 in the nanomolar range. A second-generation Man9 dendron was identified as a potential immunogen for HIV vaccine development and as a potential antiviral agent.
摘要翻译：已经鉴定了gp120上寡聚糖单糖聚糖的保守簇，被广泛的HIV-1中和单克隆抗体2G12识别为表位。寡聚甘露糖聚糖也是DC-SIGN的配体，DC-SIGN是树突细胞表面上发现的C型凝集素。多值是碳水化合物 - 蛋白质相互作用的基础，并且模仿病毒表面上的高聚糖密度对于设计基于碳水化合物的HIV疫苗和抗病毒剂已变得至关重要。公开了通过聚糖微阵列结合测定法显示高密度多价寡糖单糖的寡甘露糖树突的合成，并表征其与2G12和DC-SIGN的相互作用。这些甘草酮抑制gp120与2G12的结合和重组二聚体DC-SIGN，其IC50在纳摩尔范围。第二代Man9树突被鉴定为HIV疫苗开发的潜在免疫原，并被认为是潜在的抗病毒剂。

2. 发明授权

US08906832B2 Quantitative analysis of carbohydrate-protein interactions using glycan microarrays: determination of surface and solution dissociation constants 有权
标题翻译：使用聚糖微阵列对碳水化合物 - 蛋白质相互作用的定量分析：测定表面和溶液解离常数
公开(公告)号：US08906832B2
公开(公告)日：2014-12-09
申请号：US12423733
申请日：2009-04-14
申请人： Chi-Huey Wong , Pi-Hui Liang
发明人： Chi-Huey Wong , Pi-Hui Liang
IPC分类号： C07H3/00 , C40B40/12 , B01J19/00 , C40B30/04 , C40B20/02
CPC分类号： G01N33/5308 , B01J19/0046 , C40B30/04 , C40B40/12 , G01N2400/00 , G01N2400/10
摘要： A method, system and device to identify, study and/or mimic carbohydrate-protein interactions on cell surfaces and in solution measured by a glycan microarray. In some instances the method, system and device uses very small quantities of carbohydrate as low as attomol. In some instances the system, method and device is high-throughput. The small quantity sensitivity may allow for close placement of carbohydrate array members wherein due to close proximity multivalent interactions with proteins may be identified.
摘要翻译：鉴定，研究和/或模拟细胞表面和聚糖微阵列测量溶液中碳水化合物 - 蛋白质相互作用的方法，系统和装置。在某些情况下，该方法，系统和装置使用非常少量的碳水化合物，与阿托莫尔一样低。在某些情况下，系统，方法和设备是高吞吐量的。小量的灵敏度可以允许碳水化合物阵列成员的紧密放置，其中由于与蛋白质的近似多价相互作用可以被鉴定。

3. 发明授权

US08273788B2 Five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis therapeutics 有权
标题翻译：五元亚氨基环醇衍生物作为选择性和有效的糖苷酶抑制剂：用于抗病毒药物和骨关节炎治疗剂的新结构
公开(公告)号：US08273788B2
公开(公告)日：2012-09-25
申请号：US13033692
申请日：2011-02-24
申请人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
发明人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
IPC分类号： C07D207/00 , A61K31/40
CPC分类号： A61K31/4015 , Y02A50/385 , Y02A50/389
摘要： Novel 5-membered iminocyclitol derivatives were found to be a potent and selective inhibitors of the glycoprotein processing α- and β-glucosidase which were further found to be active antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus and human β-hexosaminidase, a new target for development of osteoarthritis therapeutics.
摘要翻译：发现新的5元亚氨基环醇衍生物是糖蛋白加工α-和β-葡萄糖苷酶的有效和选择性抑制剂，其进一步被发现是针对日本脑炎病毒，登革热病毒血清型2（DEN-2）的活性抗病毒剂，人类SARS冠状病毒和人类 - 糖尿病病毒，是骨关节炎治疗发展的新靶点。

4. 发明申请

US20120046337A1 Novel Five-Membered Iminocyclitol Derivatives as Selective and Potent Glycosidase Inhibitors: New Structures for Antivirals and Osteoarthritis Therapeutics 有权
标题翻译：新型五元咪嗪环醇衍生物作为选择性和强力糖苷酶抑制剂：用于抗病毒和骨关节炎治疗的新结构
公开(公告)号：US20120046337A1
公开(公告)日：2012-02-23
申请号：US13033692
申请日：2011-02-24
申请人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
发明人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
IPC分类号： A61K31/40 , A61P19/02 , C07D207/12
CPC分类号： A61K31/4015 , Y02A50/385 , Y02A50/389
摘要： Novel 5-membered iminocyclitol derivatives were found to be a potent and selective inhibitors of the glycoprotein processing α- and β-glucosidase which were further found to be active antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus and human β-hexosaminidase, a new target for development of osteoarthritis therapeutics.
摘要翻译：发现新的5元亚氨基环醇衍生物是糖蛋白加工α-和β-葡萄糖苷酶的有效和选择性抑制剂，其进一步被发现是针对日本脑炎病毒，登革热病毒血清型2（DEN-2）的活性抗病毒剂，人类SARS冠状病毒和人类 - 糖尿病病毒，是骨关节炎治疗发展的新靶点。

5. 发明授权

US07919521B2 Five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis therapeutics 有权
标题翻译：五元亚氨基环醇衍生物作为选择性和有效的糖苷酶抑制剂：用于抗病毒药物和骨关节炎治疗剂的新结构
公开(公告)号：US07919521B2
公开(公告)日：2011-04-05
申请号：US12086025
申请日：2006-12-05
申请人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
发明人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
IPC分类号： C07D207/00 , A61K31/40
CPC分类号： A61K31/4015 , Y02A50/385 , Y02A50/389
摘要： Novel 5-membered iminocyclitol derivatives were found to be a potent and selective inhibitors of the glycoprotein processing α- and β-glucosidase which were further found to be active antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus and human β-hexosaminidase, a new target for development of osteoarthritis therapeutics.
摘要翻译：发现新的5元亚氨基环醇衍生物是糖蛋白加工α-和β-葡萄糖苷酶的有效和选择性抑制剂，其进一步被发现是针对日本脑炎病毒，登革热病毒血清型2（DEN-2）的活性抗病毒剂，人类SARS冠状病毒和人类 - 糖尿病病毒，是骨关节炎治疗发展的新靶点。

6. 发明授权

US08383554B2 Quantitative microarray of intact glycolipid CD1d interaction and correlation with cell-based cytokine production 有权
标题翻译：完整糖脂CD1d相互作用的定量微阵列和与细胞因子生成的相关性
公开(公告)号：US08383554B2
公开(公告)日：2013-02-26
申请号：US12423728
申请日：2009-04-14
申请人： Chi-Huey Wong , Pi-Hui Liang
发明人： Chi-Huey Wong , Pi-Hui Liang
IPC分类号： C40B60/00 , C40B40/12 , C07G3/00
CPC分类号： C40B30/04 , C40B40/12 , G01N2333/70539 , G01N2405/10
摘要： The protein CD1d binds self and foreign glycolipids for presentation to CD1-restricted T cells by means of TCR recognition, and activates TH1 and TH2 chemokines release. Accordingly, a variety of glycolipid ligands were attached to a microarray surface and their binding with CD1d investigated. An α-galactosyl ceramide (α-GalCer) bearing a carbamate group at the 6′-OH position was tethered to the surface and the dissociation constant with CD1d determined. Competition assays were used to determine the dissociation constants (Ki) of the new and intact glycolipids. The para-fluoroheptaphenyl-modified α-GalCer was found to bind most strongly with CD1d (Ki 0.14 μM), two orders of magnitude stronger than α-GalCer and more than three times more selective for IFN-γ release. Various α-GalCer analogs were analyzed and the results showed that the binding affinity of glycolipids to CD1d correlates well with IFN-γ production, but poorly with IL-4 secretion by NKT cells, suggesting that tighter binding ligands could bias cytokine release through the TH1 pathway.
摘要翻译：蛋白质CD1d通过TCR识别结合自身和外来糖脂呈递给CD1限制性T细胞，并激活TH1和TH2趋化因子释放。因此，将各种糖脂配体连接到微阵列表面，并研究它们与CD1d的结合。在6'-OH位置带有氨基甲酸酯基的α-半乳糖神经酰胺（α-GalCer）被固定在表面，测定了CD1d的解离常数。使用竞争测定来确定新的和完整的糖脂的解离常数（Ki）。发现对 - 氟苯哌啶修饰的α-GalCer与CD1d（Ki0.14μM）最强结合，比α-GalCer强两个数量级，对于IFN-γ释放是选择性的三倍以上。分析各种α-GalCer类似物，结果表明，糖脂对CD1d的结合亲和力与IFN-γ产生良好相关，但与NKT细胞的IL-4分泌差异较小，表明更严格的结合配体可能通过TH1偏置细胞因子释放途径。

7. 发明申请

US20090275484A1 QUANTITATIVE ANALYSIS OF CARBOHYDRATE-PROTEIN INTERACTIONS USING GLYCAN MICROARRAYS: DETERMINATION OF SURFACE AND SOLUTION DISSOCIATION CONSTANTS 审中-公开
标题翻译：使用谷氨酸微量元素测定碳水化合物 - 蛋白质相互作用的定量分析：表面和溶液分散常数的测定
公开(公告)号：US20090275484A1
公开(公告)日：2009-11-05
申请号：US12423733
申请日：2009-04-14
申请人： Chi-Huey Wong , Pi-Hui Liang
发明人： Chi-Huey Wong , Pi-Hui Liang
IPC分类号： C40B30/04 , C40B60/12
CPC分类号： G01N33/5308 , B01J19/0046 , C40B30/04 , C40B40/12 , G01N2400/00 , G01N2400/10
摘要： A method, system and device to identify, study and/or mimic carbohydrate-protein interactions on cell surfaces and in solution measured by a glycan microarray. In some instances the method, system and device uses very small quantities of carbohydrate as low as attomol. In some instances the system, method and device is high-throughput. The small quantity sensitivity may allow for close placement of carbohydrate array members wherein due to close proximity multivalent interactions with proteins may be identified.
摘要翻译：鉴定，研究和/或模拟细胞表面和聚糖微阵列测量溶液中碳水化合物 - 蛋白质相互作用的方法，系统和装置。在某些情况下，该方法，系统和装置使用非常少量的碳水化合物，与阿托莫尔一样低。在某些情况下，系统，方法和设备是高吞吐量的。小量的灵敏度可以允许碳水化合物阵列成员的紧密放置，其中由于与蛋白质的近似多价相互作用可以被鉴定。

8. 发明申请

US20090306174A1 Novel Five-Membered Iminocyclitol Derivatives as Selective and Potent Glycosidase Inhibitors: New Structures for Antivirals and Osteoarthritis Therapeutics 有权
标题翻译：新型五元咪嗪环醇衍生物作为选择性和强力糖苷酶抑制剂：用于抗病毒和骨关节炎治疗的新结构
公开(公告)号：US20090306174A1
公开(公告)日：2009-12-10
申请号：US12086025
申请日：2006-12-05
申请人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
发明人： Pi-Hui Liang , Yi-Ling Lin , Chi-Huey Wong
IPC分类号： A61K31/40 , C07D207/36 , A61P31/04
CPC分类号： A61K31/4015 , Y02A50/385 , Y02A50/389
摘要： Novel 5-membered iminocyclitol derivatives were found to be a potent and selective inhibitors of the glycoprotein processing α- and β-glucosidase which were further found to be active antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus and human β-hexosaminidase, a new target for development of osteoarthritis therapeutics.
摘要翻译：发现新的5元亚氨基环醇衍生物是糖蛋白加工α-和β-葡糖苷酶的有效和选择性抑制剂，其进一步被发现是针对日本脑炎病毒，登革病毒血清型2（DEN-2），人类 SARS冠状病毒和人β-氨基己糖苷酶是骨关节炎治疗发展的新靶点。

9. 发明申请

US20090275483A1 QUANTITATIVE MICROARRAY OF INTACT GLYCOLIPID CD1D INTERACTION AND CORRELATION WITH CELL-BASED CYTOKINE PRODUCTION 有权
标题翻译：定量微晶玻璃纤维素CD1D相互作用和与细胞因子生产的相关性
公开(公告)号：US20090275483A1
公开(公告)日：2009-11-05
申请号：US12423728
申请日：2009-04-14
申请人： Chi-Huey Wong , Pi-Hui Liang
发明人： Chi-Huey Wong , Pi-Hui Liang
IPC分类号： C40B30/04 , C40B40/12
CPC分类号： C40B30/04 , C40B40/12 , G01N2333/70539 , G01N2405/10
摘要： The protein CD1d binds self and foreign glycolipids for presentation to CD1-restricted T cells by means of TCR recognition, and activates TH1 and TH2 chemokines release. Accordingly, a variety of glycolipid ligands were attached to a microarray surface and their binding with CD1d investigated. An α-galactosyl ceramide (α-GalCer) bearing a carbamate group at the 6′-OH position was tethered to the surface and the dissociation constant with CD1d determined. Competition assays were used to determine the dissociation constants (Ki) of the new and intact glycolipids. The para-fluoroheptaphenyl-modified α-GalCer was found to bind most strongly with CD1d (Ki 0.14 μM), two orders of magnitude stronger than α-GalCer and more than three times more selective for IFN-γ release. Various α-GalCer analogs were analyzed and the results showed that the binding affinity of glycolipids to CD1d correlates well with IFN-γ production, but poorly with IL-4 secretion by NKT cells, suggesting that tighter binding ligands could bias cytokine release through the TH1 pathway.
摘要翻译：蛋白质CD1d通过TCR识别结合自身和外来糖脂呈递给CD1限制性T细胞，并激活TH1和TH2趋化因子释放。因此，将各种糖脂配体连接到微阵列表面，并研究它们与CD1d的结合。在6'-OH位置带有氨基甲酸酯基团的α-半乳糖神经酰胺（α-GalCer）被束缚于表面，并且确定了CD1d的解离常数。使用竞争测定来确定新的和完整的糖脂的解离常数（Ki）。发现对 - 氟苯哌啶修饰的α-GalCer与CD1d（Ki0.14μM）最强结合，比α-GalCer强两个数量级，对于IFN-γ释放是选择性的三倍以上。分析各种α-GalCer类似物，结果表明，糖脂对CD1d的结合亲和力与IFN-γ产生良好相关，但与NKT细胞的IL-4分泌差异较小，表明更紧密的结合配体可能通过TH1偏置细胞因子释放途径。

10. 发明授权

US09816981B2 Alkynyl sugar analogs for labeling and visualization of glycoconjugates in cells 有权
公开(公告)号：US09816981B2
公开(公告)日：2017-11-14
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 , G01N33/50 , G01N33/533
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.

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