N-Boc-N'-biotinyl-3,6,9-trioxaundecane-1,11-diamine | 418759-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-Boc-N'-biotinyl-3,6,9-trioxaundecane-1,11-diamine
• 英文别名: Biotin-PEG3-NHBoc；tert-butyl N-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethyl]carbamate
• CAS: 418759-44-1
• 化学式: C₂₃H₄₂N₄O₇S
• 分子量: 518.675
• InChiKey: UHGWQQXHARZYIQ-BJLQDIEVSA-N

物化性质

• 沸点：
  763.6±60.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-N'-biotinyl-3,6,9-trioxaundecane-1,11-diamine 在 TEA 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 11-D-biotinamide-N-[3,6,9-trioxaundecane]-N-palmitoyl-1-amino-1-deoxymelitol
  参考文献：
  名称：

  Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120

  摘要：

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00325-x
• 作为产物：
  描述：

  3,6,9-三氧杂十一烷-1,11-二胺 在 4-二甲氨基吡啶 、 TEA 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N-Boc-N'-biotinyl-3,6,9-trioxaundecane-1,11-diamine
  参考文献：
  名称：

  Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120

  摘要：

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00325-x

文献信息

• Discovery of ARD-69 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Androgen Receptor (AR) for the Treatment of Prostate Cancer
  作者：Xin Han、Chao Wang、Chong Qin、Weiguo Xiang、Ester Fernandez-Salas、Chao-Yie Yang、Mi Wang、Lijie Zhao、Tianfeng Xu、Krishnapriya Chinnaswamy、James Delproposto、Jeanne Stuckey、Shaomeng Wang

  DOI：10.1021/acs.jmedchem.8b01631

  日期：2019.1.24

  We report herein the discovery of highly potent PROTAC degraders of androgen receptor (AR), as exemplified by compound 34 (ARD-69). ARD-69 induces degradation of AR protein in AR-positive prostate cancer cell lines in a dose- and time-dependent manner. ARD-69 achieves DC50 values of 0.86, 0.76, and 10.4 nM in LNCaP, VCaP, and 22Rv1 AR+ prostate cancer cell lines, respectively. ARD-69 is capable of reducing

  我们在此报告了雄激素受体 (AR) 的高效 PROTAC 降解剂的发现，例如化合物34 (ARD-69)。ARD-69 在 AR 阳性前列腺癌细胞系中以剂量和时间依赖性方式诱导 AR 蛋白降解。ARD-69 达到 DC 50在 LNCaP、VCaP 和 22Rv1 AR+ 前列腺癌细胞系中的值分别为 0.86、0.76 和 10.4 nM。ARD-69 能够将这些前列腺癌细胞系中的 AR 蛋白水平降低 >95%，并有效抑制 AR 调节的基因表达。ARD-69 有效抑制这些 AR 阳性前列腺癌细胞系中的细胞生长，并且比 AR 拮抗剂强 100 倍以上。单剂量的 ARD-69 可有效降低小鼠异种移植肿瘤组织中 AR 蛋白的水平。进一步优化 ARD-69 可能最终导致一种新的治疗 AR+、去势抵抗性前列腺癌的方法。
• Cyto-mechanoresponsive Polyelectrolyte Multilayer Films
  作者：Johanna Davila、Armelle Chassepot、Johan Longo、Fouzia Boulmedais、Andreas Reisch、Benoît Frisch、Florent Meyer、Jean-Claude Voegel、Philippe J. Mésini、Bernard Senger、Marie-Hélène Metz-Boutigue、Joseph Hemmerlé、Philippe Lavalle、Pierre Schaaf、Loïc Jierry

  DOI：10.1021/ja208970b

  日期：2012.1.11

  Cell adhesion processes take place through mechanotransduction mechanisms where stretching of proteins results in biological responses. In this work, we present the first cyto-mechanoresponsive surface that mimics such behavior by becoming cell-adhesive through exhibition of arginine glycine aspartic acid (RGD) adhesion peptides under stretching. This mechanoresponsive surface is based on polyelectrolyte multilayer films built on a silicone sheet and where RGD-grafted polyelectrolytes are embedded under antifouling phosphorylcholine-grafted polyelectrolytes. The stretching of this film induces an increase in fibroblast cell viability and adhesion.
• Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120
  作者：Katherine D McReynolds、Abhijit Bhat、John C Conboy、S.Scott Saavedra、Jacquelyn Gervay-Hague

  DOI：10.1016/s0968-0896(01)00325-x

  日期：2002.3

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.