RRRRRRRRR-NH₂ | 208646-06-4

• 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: RRRRRRRRR-NH₂
• 英文别名: H-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-NH2；(2S)-2-amino-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-5-(diaminomethylideneamino)pentanamide
• CAS: 208646-06-4
• 化学式: C₅₄H₁₁₁N₃₇O₉
• 分子量: 1422.72
• InChiKey: FGJSGYCPMWPZLA-VXJRNSOOSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.2
• 重原子数：
  100
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  882
• 氢给体数：
  28
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (E)-cyclooct-4-en-1-yl (4-nitrophenyl) carbonate 、 RRRRRRRRR-NH₂ 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 17.0h， 生成 (E)-cyclooct-4-en-1-yl ((6S,9S,12S,15S,18S,21S,24S,27S,30S)-1,35-diamino-6-carbamoyl-9,12,15,18,21,24,27-heptakis(3-guanidinopropyl)-1,35-diimino-8,11,14,17,20,23,26,29-octaoxo-2,7,10,13,16,19,22,25,28,34-decaazapentatriacontan-30-yl)carbamate
  参考文献：
  名称：

  用于研究细胞中MDM2-p53抑制剂的生物正交探针以及用于药物发现的高内涵筛选方法的开发

  摘要：

  为了研究MDM2-p53抑制剂在疾病相关细胞模型中的行为，我们开发并验证了一组生物正交探针，这些探针可以在细胞中进行荧光标记并用于高含量筛选试验。通过使用具有单细胞分辨率的自动化图像分析，我们可以通过共定位可视化化合物的细胞内靶标结合并量化骨肉瘤模型中MDM2-p53抑制后的靶标上调。此外，我们开发了一种高通量检测方法，可通过竞争对非标记MDM2-p53抑制剂的目标占有率进行定量，并鉴定出新的化学物质。这种方法可以扩展到潜在客户发现应用程序的其他目标。

  DOI：

  10.1002/anie.201608568
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 生成 RRRRRRRRR-NH₂
  参考文献：
  名称：

  An easy-to-detect nona-arginine peptide for epidermal targeting

  摘要：

  一种与Re-三羰基IR和荧光探针（SCoMPI）结合的非九精氨酸肽在表皮积累，而不到达真皮层。

  DOI：

  10.1039/c4cc08737b

文献信息

• Bioorthogonal Probes for the Study of MDM2-p53 Inhibitors in Cells and Development of High-Content Screening Assays for Drug Discovery
  作者：Pier Luca D'Alessandro、Nicole Buschmann、Markus Kaufmann、Pascal Furet、Frederic Baysang、Reto Brunner、Andreas Marzinzik、Thomas Vorherr、Therese-Marie Stachyra、Johannes Ottl、Dimitrios E. Lizos、Amanda Cobos-Correa

  DOI：10.1002/anie.201608568

  日期：2016.12.23

  To study the behavior of MDM2‐p53 inhibitors in a disease‐relevant cellular model, we have developed and validated a set of bioorthogonal probes that can be fluorescently labeled in cells and used in high‐content screening assays. By using automated image analysis with single‐cell resolution, we could visualize the intracellular target binding of compounds by co‐localization and quantify target upregulation

  为了研究MDM2-p53抑制剂在疾病相关细胞模型中的行为，我们开发并验证了一组生物正交探针，这些探针可以在细胞中进行荧光标记并用于高含量筛选试验。通过使用具有单细胞分辨率的自动化图像分析，我们可以通过共定位可视化化合物的细胞内靶标结合并量化骨肉瘤模型中MDM2-p53抑制后的靶标上调。此外，我们开发了一种高通量检测方法，可通过竞争对非标记MDM2-p53抑制剂的目标占有率进行定量，并鉴定出新的化学物质。这种方法可以扩展到潜在客户发现应用程序的其他目标。
• Bombesin/oligoarginine fusion peptides for gastrin releasing peptide receptor (GRPR) targeted gene delivery
  作者：Anjuman Ara Begum、Yu Wan、Istvan Toth、Peter M. Moyle

  DOI：10.1016/j.bmc.2017.12.013

  日期：2018.1

  The development of non-viral gene delivery systems, with the capacity to overcome most of the biological barriers facing gene delivery, is challenging. We have developed peptide-based, multicomponent, non-viral delivery systems, incorporating: a bombesin peptide ligand (BBN(6-14)), to selectively target the gastrin releasing peptide receptor (GRPR); oligoarginine peptides (hexa- (R-6) and nona-arginine (R-9)), for plasmid DNA (pDNA) condensation; and GALA, to facilitate endosome escape. The uptake and endosome escape efficiency of bombesin/oligoarginine and bombesin/oligoarginine/GALA fusion peptides for oligonucleotide delivery was evaluated in terms of their complex size, cellular uptake, endosome escape, and cellular toxicity. Complex size and cell uptake studies demonstrated that the nona-arginine/bombesin delivery system was more efficient at condensing and delivering pDNA into PC-3 prostate cancer cells compared to the hexa-arginine/bombesin delivery system. Further, competition with free bombesin peptide, and comparative uptake studies in Caco-2 cells, which express GRPR at a lower level, suggested that GRPR contributes to the targeted uptake of this system. The addition of GALA into the nona-arginine/bombesin-based system further increased the pDNA cellular uptake at all tested N/P ratios; facilitated endosomal pDNA release; and had limited effects on cell viability. In conclusion, the delivery system combining BBN(6-14) with nona-arginine and GALA had optimal characteristics for the delivery of pDNA into the GRPR overexpressing cell line PC-3. (C) 2017 Elsevier Ltd. All rights reserved.
• An easy-to-detect nona-arginine peptide for epidermal targeting
  作者：Sylvain Clède、Nicolas Delsuc、Cécile Laugel、François Lambert、Christophe Sandt、Arlette Baillet-Guffroy、Clotilde Policar

  DOI：10.1039/c4cc08737b

  日期：——

  A nona-arginine peptide conjugated with a Re-tricarbonyl IR and fluorescent probe (SCoMPI) accumulates at the epidermis without reaching the dermis.

  一种与Re-三羰基IR和荧光探针（SCoMPI）结合的非九精氨酸肽在表皮积累，而不到达真皮层。