biocytin imidazolide | 101187-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: biocytin imidazolide
• 英文别名: (3aS,4S,6aR)-4-[5-(1H-imidazol-1-yl)-5-oxopentyl]tetrahydro-1H-thieno-[3,4-d]imidazol-2(3H)-one；(3aS,4S,6aR)-4-(5-imidazol-1-yl-5-oxopentyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
• CAS: 101187-31-9
• 化学式: C₁₃H₁₈N₄O₂S
• 分子量: 294.378
• InChiKey: OXJQZMNIPOHIJV-NHCYSSNCSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  biocytin imidazolide 在 4-carbonyldiimidazole 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.03h， 生成 methyl {31-[(3aS,4S,6aR)-2-oxahexahydro-1H-thieno[3,4-d]imidazol-4-yl]-16,27-dioxo-20,23-dioxa-17,26-diazahentriacont-1-yl} malonate
  参考文献：
  名称：

  Synthesis of a Biotinated Lipofullerene as a New Type of Transmembrane Anchor

  摘要：

  DOI：

  10.1002/1099-0690(200004)2000:7<1173::aid-ejoc1173>3.0.co;2-i
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 D-生物素 以 N,N-二甲基甲酰胺 为溶剂， 生成 biocytin imidazolide
  参考文献：
  名称：

  来自三氮烯基前体的放射性标记生物素酰胺：合成、结合和体内特性

  摘要：

  N-(4-[127/125/123l]碘苄基)生物素酰胺4a-4c的合成通过N-[4-(3',3'-二甲基三氮烯基)苄基)生物素酰胺与碘化钠的直接分解进行描述了 CF3COOH 的存在。以这种方式碘化的生物素与抗生物素蛋白 (Kd = 2.84 ± 0.45 × 10−15 M, n = 3.9 ± 0.6) 形成稳定的复合物，其在过量天然生物素存在下以 0.034 ± 0.006 hr1 的速率常数解离。血液清除研究和甲状腺摄取不足表明该化合物在体内未脱碘，并且在循环中的表现与天然生物素非常相似。这种芳基三氮烯前体方法适用于用短寿命放射性卤化物进行标记。它可用于生产无载体添加的生物素衍生物，用于涉及抗生物素蛋白或链霉抗生物素蛋白的生物学研究和测定。

  DOI：

  10.1002/jlcr.2580341203

文献信息

• [EN] KETONE INHIBITORS OF LYSINE GINGIPAIN<br/>[FR] INHIBITEURS CÉTONE DE LYSINE GINGIPAÏNE
  申请人：CORTEXYME INC

  公开号：WO2018053353A1

  公开（公告）日：2018-03-22

  The present invention provides compounds according to Formula (I) as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.

  本发明提供了如下式（I）所述的化合物，以及它们用于抑制牙龈假单胞菌（Porphyromonas gingivalis）的赖氨酸基因底物蛋白酶（Kgp）的用途。还描述了牙龈蛋白酶活性探针化合物和测定牙龈蛋白酶活性的方法，以及用于治疗与牙龈假单胞菌感染相关的疾病的方法，包括阿尔茨海默病等脑部疾病。
• Synthesis and biological evaluation of biotin-conjugated <i>Portulaca oleracea</i> polysaccharides
  作者：Qianqian Han、Lirong Huang、Qiang Luo、Ying Wang、Mingliang Wu、Shixin Sun、Hongmei Zhang、Yanqing Wang

  DOI：10.1039/d1ra02226a

  日期：——

  Biotinylated Portulaca oleracea polysaccharide (Bio-POP) conjugates were successfully prepared by the esterification reaction. The biotinylated polysaccharide products were an off-white powder with an average degree of substitution of 42.5%. After grafting biotin onto POP, the thermal stability of Bio-POP conjugates was much higher than that of POP and the surface topography of Bio-POP was a loose

  通过酯化反应成功制备了生物素化马齿苋多糖（Bio-POP）缀合物。生物素化多糖产品为灰白色粉末，平均取代度为42.5%。将生物素接枝到POP上后，Bio-POP缀合物的热稳定性远高于POP，并且Bio-POP的表面形貌为疏松多孔的交联结构。体外细胞毒性试验表明，POP、生物素和Bio-POP缀合物对HeLa、MCF-7、LO-2和A549表现出不同的细胞毒性，特别是POP对A549细胞系生长的抑制作用强于其他细胞系。核染色法显示Bio-POP结合物在一定程度上干扰A549细胞的凋亡，免疫荧光染色照片显示Bio-POP结合物诱导A549细胞表现出免疫活性。因此，生物素与马齿苋多糖的组合对A549细胞具有免疫协同治疗作用，可应用于抗肿瘤结合药物领域。
• Ketone inhibitors of lysine gingipain
  申请人：CORTEXYME, INC.

  公开号：US10730826B2

  公开（公告）日：2020-08-04

  The present invention provides compounds according to Formula I as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.

  本发明提供了根据本文所述式 I 的化合物及其用于抑制牙龈卟啉单胞菌的赖氨酸gingipain蛋白酶（Kgp）的用途。本发明还描述了龈肽酶活性探针化合物和检测龈肽酶活性的方法，以及治疗与牙龈卟啉单胞菌感染有关的疾病（包括阿尔茨海默病等脑部疾病）的方法。
• Synthesis and biological actions of highly potent and prolonged acting biotin-labeled melanotropins
  作者：Dhirendra N. Chaturvedi、James J. Knittel、Victor J. Hruby、Ana Maria de L. Castrucci、Mac E. Hadley

  DOI：10.1021/jm00377a005

  日期：1984.11

  Biocytin derivatives of a superpotent analogue of alpha-melanotropin, [Nle4,D-Phe7]-alpha-MSH, were prepared. [N alpha-Bct-Ser1, Nle4,D-Phe7]-alpha-MSH and [12-Bct-N alpha-dodecanoyl-Ser1,Nle4,D-Phe 7]- alpha-MSH were synthesized by solid-phase techniques, and the coupling of biotin and 12-aminododecanoic acid was achieved through their succinimido esters. These melanotropins possessed almost identical actions to [Nle4,D-Phe 7]- alpha-MSH as determined by several melanocyte bioassays. Both biocytin derivatives were highly potent agonists and exhibited prolonged biological activity as determined in the frog and lizard skin bioassays. Both biotinylated peptides were at least equipotent to alpha-MSH in stimulating Cloudman S91 mouse melanoma tyrosinase activity. The analogues were resistant to inactivation by alpha-chymotrypsin.
• Carbohydrate Dependent Targeting of Cancer Cells by Bleomycin−Microbubble Conjugates
  作者：Jean-Charles Chapuis、Ryan M. Schmaltz、Krystal S. Tsosie、Marek Belohlavek、Sidney M. Hecht

  DOI：10.1021/ja8091104

  日期：2009.2.25

  Biotinylated bleomycin A(5) was attached to streptavidin-derivatized microbubbles, and a solution containing the conjugate was passed over a monolayer of cultured MCF-7 cells. The bleomycin-derivatized microbubbles adhered to the MCF-7 cells, and the association could be monitored by the use of a microscope. Three other cancer cell lines gave similar results. The bleomycin-microbubble conjugate did not bind to a normal breast cell tine (MCF-10A) or to the matched noncancer cell lines corresponding to the other cancer cell lines targeted by bleomycin. No binding to any tested cell tine was observed when the microbubbles; tacked conjugated bleomycin A(5) or when the microbubble contained a bleomycin A(5) analogue tacking the carbohydrate moiety.