[WR]₅ | 1352757-27-7

• 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: [WR]₅
• 英文别名: 1-[3-[(2S,5S,8S,11S,14S,17S,20S,23S,26S,29S)-8,14,20,26-tetrakis(3-carbamimidamidopropyl)-3,6,9,12,15,18,21,24,27,30-decahydroxy-5,11,17,23,29-pentakis(1H-indol-3-ylmethyl)-1,4,7,10,13,16,19,22,25,28-decazacyclotriaconta-3,6,9,12,15,18,21,24,27,30-decaen-2-yl]propyl]guanidine
• CAS: 1352757-27-7
• 化学式: C₈₅H₁₁₀N₃₀O₁₀
• 分子量: 1712.0
• InChiKey: ZAECRZKMCOYFJV-RQJUBWCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  125
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  692
• 氢给体数：
  25
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  在 茴香硫醚 、 1,2-乙二硫醇 、 苯甲醚 、 三氟乙酸 作用下， 反应 2.0h， 生成 [WR]₅
  参考文献：
  名称：

  穿透细胞的手性环肽作为靶向核分子的转运蛋白。

  摘要：

  绕圈走：两亲性L环肽促进细胞吸收荧光标记的拉米夫定和磷酸肽。相应的荧光标记的缀合物F- [W 5 R 4 K]在结肠腺癌，乳腺癌和人卵巢腺癌的核中显示出高效的转运（见图）。

  DOI：

  10.1002/anie.201102572

文献信息

• Cyclic Peptide-Capped Gold Nanoparticles for Enhanced siRNA Delivery
  作者：Amir Shirazi、Karissa Paquin、Niall Howlett、Dindyal Mandal、Keykavous Parang

  DOI：10.3390/molecules190913319

  日期：——

  Previously, we have reported the synthesis of a homochiral l-cyclic peptide [WR]5 and its use for delivery of anti-HIV drugs and biomolecules. A physical mixture of HAuCl4 and the peptide generated peptide-capped gold nanoparticles. Here, [WR]5 and [WR]5-AuNPs were tested for their efficiency to deliver a small interfering RNA molecule (siRNA) in human cervix adenocarcinoma (HeLa) cells. Flow cytometry investigation revealed that the intracellular uptake of a fluorescence-labeled non-targeting siRNA (200 nM) was enhanced in the presence of [WR]5 and [WR]5-AuNPs by 2- and 3.8-fold when compared with that of siRNA alone after 24 h incubation. Comparative toxicity results showed that [WR]5 and [WR]5-AuNPs were less toxic in cells compared to other available carrier systems, such as Lipofectamine.

  之前，我们报道了同手性l-环肽[WR]5的合成及其在抗HIV药物和生物分子递送中的应用。 HAuCl4与肽的物理混合物产生了肽封端的金纳米颗粒。 在此，我们测试了[WR]5和[WR]5-AuNPs在人类宫颈癌（HeLa）细胞中递送小干扰RNA分子（siRNA）的效率。 流式细胞仪研究表明，与单独的siRNA相比，在[WR]5和[WR]5-AuNPs存在的情况下，荧光标记的非靶向siRNA（200 nM）的细胞内摄取在24 h培养后分别提高了2倍和3.8倍。 比较毒性结果表明，与其他可用的载体系统（如Lipofectamine）相比，[WR]5和[WR]5-AuNPs在细胞中的毒性较低。
• Cyclic peptides containing tryptophan and arginine as Src kinase inhibitors
  作者：Amir Nasrolahi Shirazi、Rakesh Kumar Tiwari、Alex Brown、Dindyal Mandal、Gongqin Sun、Keykavous Parang

  DOI：10.1016/j.bmcl.2013.03.124

  日期：2013.6

  A number of cyclic and linear peptides containing various combinations of amino acids were evaluated for their Src kinase inhibitory potency. Among all the peptides, cyclic decapeptide C[RW](5) containing alternative arginine (R) and tryptophan (W) residues was found to be the most potent Src kinase inhibitor. C[RW](5) showed higher inhibitory activity (IC50 = 2.8 mu M) than C[KW](5), L(KW)(5), C[RW](4), and C[RW](3) with IC50 values of 46.9, 69.1, 21.5, and 25.0 mu M, respectively, as determined in a fluorescence intensity-based assay. Thus, the cyclic nature, the presence of arginine, ring size, and the number of amino acids in the structure of the peptide were found to be critical in Src kinase inhibitory potency. The IC50 value of C[RW](5) was found to be 0.8 mu M in a radioactive assay using [gamma-P-32]-ATP and polyE(4)Y as the substrate. C[RW](5) was a noncompetitive Src kinase inhibitor, showing approximately fourfold more selectivity towards Src than Abl. (C) 2013 Elsevier Ltd. All rights reserved.