N-Hydroxysuccinimido iminobiotinate | 84171-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-Hydroxysuccinimido iminobiotinate
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 5-[(3aS,4S,6aR)-2-amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoate
• CAS: 84171-51-7
• 化学式: C₁₄H₂₀N₄O₄S
• 分子量: 340.403
• InChiKey: RVNCPTOYUFIJGP-RVBZMBCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-5-[[(2S)-6-amino-1-[[(2S)-1-carboxy-4-(2,6-dimethylbenzoyl)oxy-3-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid 、 N-Hydroxysuccinimido iminobiotinate 以 水 为溶剂， 反应 12.0h， 生成 (4S)-5-[[(2S)-6-[5-[(3aS,4S,6aR)-2-amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoylamino]-1-[[(2S)-1-carboxy-4-(2,6-dimethylbenzoyl)oxy-3-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
  参考文献：
  名称：

  Synthesis of Novel Caspase Inhibitors for Characterization of the Active Caspase Proteome in Vitro and in Vivo

  摘要：

  Caspases are cysteine proteases that are essential for cytokine maturation and apoptosis. To facilitate the dissection of caspase function in vitro and in vivo, we have synthesized irreversible caspase inhibitors with biotin attached via linker arms of various lengths (12a-d) and a 2,4-dinitrophenyl labeled inhibitor (13). Affinity labeling of apoptotic extracts followed by blotting reveals that these affinity probes detect active caspases. Using the strong affinity of avidin for biotin, we have isolated affinity-labeled caspase 6 from apoptotic cytosolic extracts of cells overexpressing procaspase 6 by treatment with 12c, which contains biotin attached to the N-epsilon-lysine of the inhibitor by a 22.5 A linker arm, followed by affinity purification on monomeric avidin-sepharose beads. Compound 13 has proven sufficiently cell permeable to rescue cells from apoptotic execution. These novel caspase inhibitors should provide powerful probes for the study of the active caspase proteome during apoptosis both in vitro and in vivo.

  DOI：

  10.1021/jm060385h

文献信息

• Structure-based design of a streptavidin mutant specific for an artificial biotin analogue
  作者：Tatsuya Kawato、Eiichi Mizohata、Yohei Shimizu、Tomohiro Meshizuka、Tomohiro Yamamoto、Noriaki Takasu、Masahiro Matsuoka、Hiroyoshi Matsumura、Tatsuhiko Kodama、Motomu Kanai、Hirofumi Doi、Tsuyoshi Inoue、Akira Sugiyama

  DOI：10.1093/jb/mvv004

  日期：2015.6

  using antibodies, a streptavidin mutant with low immunogenicity, termed low immunogenic streptavidin mutant No. 314 (LISA-314), was produced previously as a drug delivery tool. However, endogenous biotins (BTNs) with high affinity (Kd < 10(-10) M) for the binding pocket of LISA-314 prevents access of exogenous BTN-labelled anticancer drugs. In this study, we improve the binding pocket of LISA-314 to

  对于使用抗体的多步骤预靶向方法，先前制备了具有低免疫原性的链霉亲和素突变体，称为低免疫原性链霉亲和素突变体No.314（LISA-314），作为药物递送工具。但是，对LISA-314结合袋具有高亲和力（Kd <10（-10）M）的内源性生物素（BTN）阻止了外源性BTN标记的抗癌药物的进入。在这项研究中，我们改善了LISA-314的结合口袋，以消除其对内源BTN物种的亲和力，因此确保新设计的LISA-314仅结合人工BTN类似物。分两个步骤进行三个氨基酸残基的置换，以开发出称为V212的突变体，该突变体可选择性结合6-（5-（（3aS，4S，6aR）-2-亚氨基六氢-1H-硫代[3,4-d ]咪唑-4-基）戊酰胺基）己酸（亚氨基生物素长尾巴，IMNtail）。表面等离振子共振结果表明，V212对IMNtail的Kd值为5.9×10（-7）M，但对内源BTN种类没有结合亲和力。该V212 /
• MODIFIED BIOTIN, STREPTAVIDIN MUTANT, AND USAGE OF THEM
  申请人：Savid Therapeutics Inc.

  公开号：EP3842440A2

  公开（公告）日：2021-06-30

  An object of this invention is to provide a streptavidin mutant reduced in affinity to the naturally-occurring biotin, and to provide a modified biotin which shows a high affinity to such streptavidin mutant reduced in affinity to the naturally-occurring biotin. This invention can provide a compound composed of a dimer of modified biotin, a streptavidin mutant, angsd usage of them.

  本发明的目的是提供一种对天然存在的生物素的亲和力降低的链霉亲和素突变体，并提供一种对这种对天然存在的生物素的亲和力降低的链霉亲和素突变体显示出高亲和力的改性生物素。本发明可以提供一种由改性生物素的二聚体、链霉亲和素突变体以及它们的用法组成的化合物。
• AFFINITY-BASED CONTROLLED RELEASE SYSTEM
  申请人：SHOICHET Molly Sandra

  公开号：US20140187487A1

  公开（公告）日：2014-07-03

  Prolonged or extended release of bioactive protein is achieved using an affinity-based approach which exploits the specific binding of Src homology 3 (SH3) domain with short proline-rich peptides. Specifically, methylcellulose was modified with SH3-binding peptides (MC-peptide) with either a weak affinity or strong affinity for SH3. Controlled release of chondroitinase ABC (ChABC) is also described.
• US9498539B2
  申请人：——

  公开号：US9498539B2

  公开（公告）日：2016-11-22
• Synthesis of Novel Caspase Inhibitors for Characterization of the Active Caspase Proteome in Vitro and in Vivo
  作者：Alexander J. Henzing、Helen Dodson、Joel M. Reid、Scott H. Kaufmann、Robert L. Baxter、William C. Earnshaw

  DOI：10.1021/jm060385h

  日期：2006.12.1

  Caspases are cysteine proteases that are essential for cytokine maturation and apoptosis. To facilitate the dissection of caspase function in vitro and in vivo, we have synthesized irreversible caspase inhibitors with biotin attached via linker arms of various lengths (12a-d) and a 2,4-dinitrophenyl labeled inhibitor (13). Affinity labeling of apoptotic extracts followed by blotting reveals that these affinity probes detect active caspases. Using the strong affinity of avidin for biotin, we have isolated affinity-labeled caspase 6 from apoptotic cytosolic extracts of cells overexpressing procaspase 6 by treatment with 12c, which contains biotin attached to the N-epsilon-lysine of the inhibitor by a 22.5 A linker arm, followed by affinity purification on monomeric avidin-sepharose beads. Compound 13 has proven sufficiently cell permeable to rescue cells from apoptotic execution. These novel caspase inhibitors should provide powerful probes for the study of the active caspase proteome during apoptosis both in vitro and in vivo.