2-((2-((tert-butyldimethylsilyl)oxy)ethyl)disulfanyl)ethanol | 1001648-93-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-((2-((tert-butyldimethylsilyl)oxy)ethyl)disulfanyl)ethanol
• 英文别名: 2-((2-((tert-butyldimethylsilyl)oxy)ethyl)disulfanyl)ethan-1-ol；2-[2-[Tert-butyl(dimethyl)silyl]oxyethyldisulfanyl]ethanol；2-[2-[tert-butyl(dimethyl)silyl]oxyethyldisulfanyl]ethanol
• CAS: 1001648-93-6
• 化学式: C₁₀H₂₄O₂S₂Si
• 分子量: 268.517
• InChiKey: VDTMXQHYCPADDR-UHFFFAOYSA-N

物化性质

• 沸点：
  309.7±27.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2-((tert-butyldimethylsilyl)oxy)ethyl)disulfanyl)ethanol 在 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.75h， 生成
  参考文献：
  名称：

  DNA‐Damage‐Response‐Targeting Mitochondria‐Activated Multifunctional Prodrug Strategy for Self‐Defensive Tumor Therapy

  摘要：

  AbstractWe report a novel multifunctional construct, M1, designed explicitly to target the DNA damage response in cancer cells. M1 contains both a floxuridine (FUDR) and protein phosphatase 2A (PP2A) inhibitor combined with a GSH‐sensitive linker. Further conjugation of the triphenylphosphonium moiety allows M1 to undergo specific activation in the mitochondria, where mitochondria‐mediated apoptosis is observed. Moreover, M1 has enormous effects on genomic DNA ascribed to FUDR's primary function of impeding DNA/RNA synthesis combined with diminishing PP2A‐activated DNA repair pathways. Importantly, mechanistic studies highlight the PP2A obtrusion in FUDR/5‐fluorouracil (5‐FU) therapy and underscore the importance of its inhibition to harbor therapeutic potential. HCT116 cell xenograft‐bearing mice that have a low response rate to 5‐FU show a prominent effect with M1, emphasizing the importance of DNA damage response targeting strategies using tumor‐specific microenvironment‐activatable systems.

  DOI：

  10.1002/anie.202117075
• 作为产物：
  描述：

  2-羟乙基二硫化物 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-((2-((tert-butyldimethylsilyl)oxy)ethyl)disulfanyl)ethanol
  参考文献：
  名称：

  靶向化疗的还原反应性两亲甲氨蝶呤-鬼臼毒素缀合物。

  摘要：

  由于天然高毒性，水溶性差以及鬼臼毒素（PPT）的其他副作用，其应用受到限制。为了解决这些问题，我们开发了一种新的PPT递送系统，其中亲水性药物甲氨蝶呤（MTX）和疏水性药物PPT通过还原反应性二硫键相连，形成两亲性药物-药物偶联物前体（MTX-SS- PPT）。该缀合物可以在水溶液中自组装成球形纳米聚集体并自递送至肿瘤组织。此外，MTX可以靶向叶酸受体阳性细胞。肿瘤细胞中谷胱甘肽的过度表达破坏了二硫键并释放出游离药物。体内外实验表明，纳米药物可以有效提高生物相容性，降低PPT的毒性。

  DOI：

  10.1002/asia.201901070

文献信息

• A fluoresceinylcarbonate-based fluorescent probe for the sensitive detection of biothiols in a HEPES buffer and its cellular expression
  作者：Keum-Hee Hong、Dae Il Kim、Hyockman Kwon、Hae-Jo Kim

  DOI：10.1039/c3ra42935k

  日期：——

  A fluoresceinylcarbonate-based fluorescent probe (1) with a disulfide bond was designed for the detection of biothiols in an aqueous solvent. The probe showed a more rapid and sensitive response to biothiols than other various amino acids through the disulfide bond cleavage and the subsequent intramolecular cyclization. When glutathione was added to the probe, fluorescence of 1 was significantly enhanced and was observable with the naked eye and in living cells.

  一种基于荧光素碳酸酯的荧光探针（1），具有二硫键，被设计用于在水中检测生物硫醇。该探针通过二硫键断裂及随后的分子内环化，对生物硫醇的响应速度和灵敏度均高于其他多种氨基酸。当谷胱甘肽加入到该探针中时，1的荧光显著增强，可通过肉眼观察到，并在活细胞中可视。
• 新規核酸プロドラッグおよびその使用方法
  申请人：オントリー、インコーポレイテッド

  公开号：JP2015205910A

  公开（公告）日：2015-11-19

  PROBLEM TO BE SOLVED: To provide prodrugs of stereodefined oligonucleotides to impart additional stability to oligonucleotide molecules in many in-vitro and in-vivo applications.SOLUTION: A nucleic acid prodrug has a structure represented by the formula (1), where each instance of Ba is independently a blocked or unblocked adenine, cytosine, guanine, thymine, uracil or modified nucleobase.

  问题要解决的是：提供立体定义寡核苷酸的前药，以在许多体外和体内应用中赋予寡核苷酸分子额外的稳定性。解决方案：核酸前药具有由公式（1）表示的结构，其中每个Ba的实例独立地是阻断或未阻断的腺嘌呤、胞嘧啶、鸟嘌呤、胸腺嘧啶、尿嘧啶或修饰的核碱基。
• Molecularly pure miktoarm spherical nucleic acids: preparation and usage as a scaffold for abiotic intracellular catalysis
  作者：Bohan Zhang、Silei Bai、Xiangyu Chao、Tong Wu、Zhiyong Chen、Zehong Cheng、Yue Xiao、Ke Zhang、Yugang Bai

  DOI：10.1039/d1sc04833c

  日期：——

  We present a fullerene-based strategy that allows the synthesis of molecularly pure miktoarm spherical nucleic acids (SNAs) with diverse structures, which, with post-functionalization, could serve as efficient scaffolds for intracellular catalysis. The SNA structure promotes cell permeability, nucleic acid stability, and catalytic efficiency, making the platform ideal for in cellulo reactions. Consequently

  我们提出了一种基于富勒烯的策略，可以合成具有不同结构的分子纯miktoarm球形核酸（SNA），通过后功能化，可以作为细胞内催化的有效支架。 SNA 结构可促进细胞通透性、核酸稳定性和催化效率，使该平台成为纤维素反应的理想选择。因此，带有三（三唑）的 miktoarm SNA 能够有效介导细胞内铜催化的纳摩尔水平的炔-叠氮环加成反应，并促进活体斑马鱼中的相同反应。
• Integrin-Mediated Targeted Cancer Therapy Using c(RGDyK)-Based Conjugates of Gemcitabine
  作者：Theodora Chatzisideri、George Leonidis、Theodoros Karampelas、Eleni Skavatsou、Angeliki Velentza-Almpani、Francesca Bianchini、Constantin Tamvakopoulos、Vasiliki Sarli

  DOI：10.1021/acs.jmedchem.1c01468

  日期：2022.1.13
• Stimuli-responsive biotin-anchored prodrug for the targeted delivery of anti-cancer agent NBDHEX with turn-on NIR fluorescence
  作者：Rahul Kesarwani、Nikita Pal、Krishna P. Bhabak

  DOI：10.1039/d4cc00210e

  日期：2024.3.21

  Biothiol-responsive turn-on fluorogenic prodrug RK-296 was developed for the sustained delivery of the anti-cancer agent and GSTP1 inhibitor NBDHEX with turn-on NIR fluorescence.