PhTX-343-L-arginin-amide | 130203-22-4

• 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: PhTX-343-L-arginin-amide
• 英文别名: PhTX-343-arginine；(2S)-2-amino-N-[3-[4-[3-[[(2S)-2-(butanoylamino)-3-(4-hydroxyphenyl)propanoyl]amino]propylamino]butylamino]propyl]-5-(diaminomethylideneamino)pentanamide
• CAS: 130203-22-4
• 化学式: C₂₉H₅₃N₉O₄
• 分子量: 591.798
• InChiKey: OIZCSHUACZAXHP-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  42
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  222
• 氢给体数：
  9
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  PhTX-343-L-arginin-amide 在 dipotassium hydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 碘 作用下， 以 甲醇 、 水 为溶剂， 生成 <127I2>PhTX-343-arginine
  参考文献：
  名称：

  Synthesis of glutamate receptor antagonist philanthotoxin-433 (PhTX-433) and its analogs

  摘要：

  DOI：

  10.1016/s0040-4020(01)85463-6
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 PhTX-343-L-arginin-amide
  参考文献：
  名称：

  Synthesis of glutamate receptor antagonist philanthotoxin-433 (PhTX-433) and its analogs

  摘要：

  DOI：

  10.1016/s0040-4020(01)85463-6

文献信息

• Solid-phase synthesis of neuroactive spider–wasp hybrid toxin analogues using a backbone amide linker
  作者：Christian A. Olsen、Matthias Witt、Henrik Franzyk、Jerzy W. Jaroszewski

  DOI：10.1016/j.tetlet.2006.11.074

  日期：2007.1

  Polyamine toxins isolated from the venoms of spiders and wasps and their synthetic analogues are uncompetitive antagonists of ligand-gated ionotropic receptors in the central- and peripheral nervous systems, and have proved valuable as tools for the investigation of receptor structure and function. In the present letter we describe the efficient solid-phase synthesis (SPS) of novel hybrid toxins using

  从蜘蛛和黄蜂的毒液中分离的多胺毒素及其合成类似物是中枢神经系统和外周神经系统中非竞争性配体门控离子受体的拮抗剂，并已被证明可作为研究受体结构和功能的有价值的工具。在本信中，我们描述了使用BAL树脂的新型杂化毒素的有效固相合成（SPS）。该策略可实现毒素分子的双向构建，并且在化学类似的毒素类似物文库的SPS中具有用于结构-活性关系（SAR）研究的潜力。
• Synthesis and binding of [125I2]philanthotoxin-343, [125I2]philanthotoxin-343-lysine, and [125I2]philanthotoxin-343-arginine to rat brain membranes
  作者：R. A. Goodnow、R. Bukownik、K. Nakanishi、P. N. R. Usherwood、A. T. Eldefrawi、N. A. Anis、M. E. Eldefrawi

  DOI：10.1021/jm00112a012

  日期：1991.8

  I-125(2)-iodinated philanthotoxin-343 (PhTX-343) (10), [I-125(2)]PhTX-343-arginine (11), and [I-125(2)]PhTX-343-lysine (12) were synthesized and evaluated as probes for glutamate receptors in rat brain synaptic membranes. It was found that these probes were not specific for the glutamate receptors but may be useful for investigating the polyamine binding site. Filtration assays with Whatman GF/B fiber glass filters were unsuitable because the iodinated PhTX-343 analogues exhibited high nonspecific binding to the filters, thus hindering detection of specific binding to membranes. When binding was measured by a centrifugal assay, [I-125(2)]PhTX-343-lysine (12) bound with low affinity (K(D) = 11.4 +/- 2-mu-M) to a large number of sites (37.2 +/- 9.1 nmol/mg of protein). The binding of [I-125(2)]PhTX-343-lysine was sensitive only to the polyamines spermine and spermidine, which displaced [I-125(2)]PhTX-343-lysine (12) with K(i) values of (3.77 +/- 1.4) X 10(-5) M and (7.51 +/- 0.77) X 10(-5) M, respectively. The binding was insensitive to glutamate receptor agonists and antagonists. Binding results with [I-125(2)]PhTX-343-arginine (11) were similar to those of [I-125(2)]PhTX-343-lysine. Considering the high number of toxin binding sites (10000-fold more than glutamate) in these membranes and the insensitivity of the binding to almost all drugs that bind to glutamate receptors, it is evident that most of the binding observed is not to glutamate receptors. On the other hand, PhTX analogues with photoaffinity labels may be useful in the isolation/purification of various glutamate and nicotinic acetylcholine receptors; they could also be useful in structural studies of receptors and their binding sites.
• GOODNOW, R. (JR);KONNO, K.;NIWA, M.;KALLIMOPOULOS, T.;BUKOWNIK, R.;LENARE+, TETRAHEDRON, 46,(1990) N, C. 3267-3286
  作者：GOODNOW, R. (JR)、KONNO, K.、NIWA, M.、KALLIMOPOULOS, T.、BUKOWNIK, R.、LENARE+

  DOI：——

  日期：——
• NAKANISHI, KOJI;GOODNOW, R.;KONNO, K.;NIWA, M.;BUKOWNIK, RUDOLPH;KALLIMOP+, PURE AND APPL. CHEM., 62,(1990) N, C. 1223-1230
  作者：NAKANISHI, KOJI、GOODNOW, R.、KONNO, K.、NIWA, M.、BUKOWNIK, RUDOLPH、KALLIMOP+

  DOI：——

  日期：——
• GOODNOW, R. A. (JR);BUKOWNIK, R.;NAKANISHI, K.;USHERWOOD, P. N. R.;ELDEFR+, J. MED. CHEM., 34,(1991) N, C. 2389-2394
  作者：GOODNOW, R. A. (JR)、BUKOWNIK, R.、NAKANISHI, K.、USHERWOOD, P. N. R.、ELDEFR+

  DOI：——

  日期：——