4-(N-(S-glutathionylacetyl)amino)phenylarsonic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(N-(S-glutathionylacetyl)amino)phenylarsonic acid
• 英文别名: 4-(N-((S-glutathionyl)acetyl)amino)benzenearsonic acid；(2S)-2-amino-5-[[(2R)-3-[2-(4-arsonoanilino)-2-oxoethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₈H₂₅AsN₄O₁₀S
• 分子量: 564.405
• InChiKey: WORJSYLULCAJOK-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  271
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-(N-(S-glutathionylacetyl)amino)phenylarsonic acid 、 fluorescein-5-EX succinimidyl ester 以 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Noninvasive Imaging of Cell Death Using an Hsp90 Ligand

  摘要：

  Cell death plays a central role in normal physiology and in disease. Common to apoptotic and necrotic cell death is the eventual loss of plasma membrane integrity. We have produced a small organoarsenical compound, 4-(N-(S-glutathionylacetyl)amino)phenylarsonous add, that rapidly accumulates in the cytosol of dying cells coincident with loss of plasma membrane integrity. The compound is retained in the cytosol predominantly by covalent reaction with the 90 kDa heat shock protein (Hsp90), the most abundant molecular chaperone of the eukaryotic cytoplasm. The organoarsenical was tagged with either optical or radioisotope reporting groups to image cell death in cultured cells and in murine tumors ex vivo and in situ. Tumor cell death in mice was noninvasively imaged by SPECT/CT using an (111)In-tagged compound. This versatile compound should enable the imaging of cell death in most experimental settings.

  DOI：

  10.1021/ja110226y
• 作为产物：
  描述：

  对氨基苯砷酸 在 碳酸氢钠 、 sodium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 4-(N-(S-glutathionylacetyl)amino)phenylarsonic acid
  参考文献：
  名称：

  Noninvasive Imaging of Cell Death Using an Hsp90 Ligand

  摘要：

  Cell death plays a central role in normal physiology and in disease. Common to apoptotic and necrotic cell death is the eventual loss of plasma membrane integrity. We have produced a small organoarsenical compound, 4-(N-(S-glutathionylacetyl)amino)phenylarsonous add, that rapidly accumulates in the cytosol of dying cells coincident with loss of plasma membrane integrity. The compound is retained in the cytosol predominantly by covalent reaction with the 90 kDa heat shock protein (Hsp90), the most abundant molecular chaperone of the eukaryotic cytoplasm. The organoarsenical was tagged with either optical or radioisotope reporting groups to image cell death in cultured cells and in murine tumors ex vivo and in situ. Tumor cell death in mice was noninvasively imaged by SPECT/CT using an (111)In-tagged compound. This versatile compound should enable the imaging of cell death in most experimental settings.

  DOI：

  10.1021/ja110226y

文献信息

• Induction of the mitochondrial permeability transition
  申请人：Hogg John Philip

  公开号：US20060166208A1

  公开（公告）日：2006-07-27

  The present invention relates to process for identifying a compound which induces the mitochondrial permeability transition (MPT) in proliferating cells, wherein said process comprises contacting a cell or cell extract with a compound, determining whether compound binds to adenine nucleotide translocator (ANT), and determining whether the compound selectively induces the MPT in proliferating cells.

  本发明涉及一种用于识别在增殖细胞中诱导线粒体通透性转换（MPT）的化合物的过程，其中所述过程包括将细胞或细胞提取物与化合物接触，确定化合物是否结合腺嘌呤核苷酸转运蛋白（ANT），并确定该化合物是否选择性地诱导增殖细胞中的MPT。
• Substantially cell membrane impermeable compound and use thereof
  申请人：New South Innovations PTY Limited

  公开号：US07074766B1

  公开（公告）日：2006-07-11

  The present invention relates to a compound according to Formula (I): A-(L-Y)p, wherein A comprises at least one substantially cell-membrane impermeable pendant group; L comprises any suitable linker and/or spacer group; Y comprises at least one arsenoxide or arsenoxide equivalent; p is an integer from 1 to 10; and the sum total of carbon atoms in A and L together, is greater than 6.

  本发明涉及一种化合物，其符合以下式（I）：A-(L-Y)p，其中A包括至少一个基本上细胞膜不透性的吊挂基团；L包括任何合适的连接基团和/或间隔基团；Y包括至少一个砷酸盐或砷酸盐等效物；p为1至10的整数；A和L中碳原子的总和大于6。
• Noninvasive Imaging of Cell Death Using an Hsp90 Ligand
  作者：Danielle Park、Anthony S. Don、Tania Massamiri、Amol Karwa、Beth Warner、Jan MacDonald、Christine Hemenway、Arati Naik、Kah-Tiong Kuan、Pierre J. Dilda、Jason W. H. Wong、Kevin Camphausen、Lori Chinen、Mary Dyszlewski、Philip J. Hogg

  DOI：10.1021/ja110226y

  日期：2011.3.9

  Cell death plays a central role in normal physiology and in disease. Common to apoptotic and necrotic cell death is the eventual loss of plasma membrane integrity. We have produced a small organoarsenical compound, 4-(N-(S-glutathionylacetyl)amino)phenylarsonous add, that rapidly accumulates in the cytosol of dying cells coincident with loss of plasma membrane integrity. The compound is retained in the cytosol predominantly by covalent reaction with the 90 kDa heat shock protein (Hsp90), the most abundant molecular chaperone of the eukaryotic cytoplasm. The organoarsenical was tagged with either optical or radioisotope reporting groups to image cell death in cultured cells and in murine tumors ex vivo and in situ. Tumor cell death in mice was noninvasively imaged by SPECT/CT using an (111)In-tagged compound. This versatile compound should enable the imaging of cell death in most experimental settings.