[2-(2-{2-[2-(11-tritylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid | 769931-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [2-(2-{2-[2-(11-tritylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid
• 英文别名: 1,1,1-triphenyl-14,17,20,23,26-pentaoxa-2-thiaoctacosan-28-oic acid；S-trityl-26-mercapto-3,6,9,12,15-pentaoxahexacosan-1-oic acid；2-[2-[2-[2-[2-(11-Tritylsulfanylundecoxy)ethoxy]ethoxy]ethoxy]ethoxy]acetic acid
• CAS: 769931-27-3
• 化学式: C₄₀H₅₆O₇S
• 分子量: 680.946
• InChiKey: NCUJOZTVKXWXMS-UHFFFAOYSA-N

物化性质

• 沸点：
  757.5±55.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  48
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2-(2-{2-[2-(11-tritylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (S)-2-{2-[2-(2-{2-[2-(11-Tritylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetylamino}-succinic acid
  参考文献：
  名称：

  Tunable Inhibition and Denaturation of α-Chymotrypsin with Amino Acid-Functionalized Gold Nanoparticles

  摘要：

  Water-soluble gold nanoparticles bearing diverse L-amino acid terminals have been fabricated to probe the effect of receptor surface on protein surface binding. The interaction of these nanoparticles with a-chymotrypsin (ChT) was investigated by activity assay, gel electrophoresis, zeta-potential, circular dichroism, and fluorescence spectroscopy. The results show that both electrostatic and hydrophobic interactions between the hydrophobic patches of receptors and the protein contribute to the stability of the complex. The microscopic binding constants for these receptor-protein systems are 10(6)-10(7) M-1, with the capacity of the nanoparticle receptors to bind proteins determined by both their surface area and their surface charge density. Furthermore, it is found that the hydrophilic side chains destabilize the ChT structure through either competitive hydrogen bonding or breakage of salt bridges, whereas denaturation was much slower with hydrophobic amino acid side chains. Significantly, correlation between the hydrophobicity index of amino acid side chains and the binding affinity and denaturation rates was observed.

  DOI：

  10.1021/ja0512881
• 作为产物：
  描述：

  [2-(2-{2-[2-(11-acetylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid ethyl ester 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 [2-(2-{2-[2-(11-tritylsulfanyl-undecyloxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid
  参考文献：
  名称：

  Arrays for the Combinatorial Exploration of Cell Adhesion

  摘要：

  A new method for the fabrication of arrays of self-assembled monolayers (SAMs) of alkane thiols (ATs) on gold to combinatorially assay surfaces for cell adhesion is reported. A fluorous SAM, which is both cytophobic and solvophobic, was used as the background between the array features. The resulting solvophobic background permits the application of an assembly after conjugation strategy for fabrication. SAMs containing mixtures of ATs and peptide-terminated ATs were generated. Multiple cell types demonstrated differential and specific binding to these surfaces. Additionally, pluripotent human embryonic stem cells proliferated on surfaces generated by this method.

  DOI：

  10.1021/ja0474291

文献信息

• Isomeric Control of Protein Recognition with Amino Acid- and Dipeptide-Functionalized Gold Nanoparticles
  作者：Chang-Cheng You、Sarit S. Agasti、Vincent M. Rotello

  DOI：10.1002/chem.200701234

  日期：2008.1

  Amino acid and dipeptide-functionalized gold nanoparticles (NPs) possessing L/D-leucine and/or L/D-phenylalanine residues have been constructed in order to target the surfaces of alpha-chymotrypsin (ChT) and cytochrome c (CytC). Isothermal titration calorimetry (ITC) was conducted to evaluate the binding thermodynamics and selectivity of these NP-protein interactions. The chirality of the NP end-groups

  具有L / D-亮氨酸和/或L / D-苯丙氨酸残基的氨基酸和二肽功能化的金纳米颗粒（NPs）已被构建出来，以靶向α-胰凝乳蛋白酶（ChT）和细胞色素c（CytC）的表面。进行了等温滴定热分析（ITC），以评估这些NP-蛋白质相互作用的结合热力学和选择性。NP端基的手性实质上影响所得的复合物稳定性，在相同疏水性的颗粒之间观察到多达20倍的差异，表明来自配体的结构信息可用于控制蛋白质识别。
• Direct photopatterning of light-activated gold nanoparticles
  作者：Chandramouleeswaran Subramani、Xi Yu、Sarit. S. Agasti、Bradley Duncan、Serkan Eymur、Murat Tonga、Vincent M. Rotello

  DOI：10.1039/c1jm11035g

  日期：——

  Photoactivatable gold NPs were patterned viaphotolithography. In this approach, charge reversal of the ligands on NPs upon UV irradiation induces crosslinking to generate stable NP patterns.

  可光活化金 NPs 采用紫外光刻技术制成图案。在这种方法中，NPs 上的配体在紫外线照射下发生电荷反转，从而诱导交联，生成稳定的 NP 图案。
• Acylsulfonamide-Functionalized Zwitterionic Gold Nanoparticles for Enhanced Cellular Uptake at Tumor pH
  作者：Tsukasa Mizuhara、Krishnendu Saha、Daniel F. Moyano、Chang Soo Kim、Bo Yan、Young-Kwan Kim、Vincent M. Rotello

  DOI：10.1002/anie.201411615

  日期：2015.5.26

  A nanoparticle design featuring pH‐responsive alkoxyphenyl acylsulfonamide ligands is reported herein. As a result of ligand structure, this nanoparticle is neutral at pH 7.4, becoming positively charged at tumor pH (<6.5). The particle uptake and cytotoxicity increase over this pH range. This pH‐controlled uptake and toxicity makes this particle a promising tool for tumor selective therapy.

  本文报道了一种具有 pH 响应性烷氧基苯基酰基磺酰胺配体的纳米粒子设计。由于配体结构，该纳米颗粒在 pH 7.4 时呈中性，在肿瘤 pH (<6.5) 时带正电。在此 pH 范围内，颗粒摄取和细胞毒性会增加。这种 pH 值控制的摄取和毒性使该颗粒成为肿瘤选择性治疗的有前途的工具。
• Regulation of α-chymotrypsin activity on the surface of substrate-functionalized gold nanoparticles
  作者：Chang-Cheng You、Rochelle R. Arvizo、Vincent M. Rotello

  DOI：10.1039/b605508g

  日期：——

  A gold nanoparticle functionalized with substrates for α-chymotrypsin was fabricated to afford an enzyme modulator that exhibited enzyme-specific activation coupled with general inhibition of other proteases.

  用δ-糜蛋白酶底物功能化的金纳米粒子制成了一种酶调节剂，它既能激活酶的特异性，又能普遍抑制其他蛋白酶。
• Light-Regulated Release of DNA and Its Delivery to Nuclei by Means of Photolabile Gold Nanoparticles
  作者：Gang Han、Chang-Cheng You、Byoung-jin Kim、Rosemary S. Turingan、Neil S. Forbes、Craig T. Martin、Vincent M. Rotello

  DOI：10.1002/anie.200600214

  日期：2006.5.5