2,5-dioxopyrrolidin-1-yl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate | 1345692-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-dioxopyrrolidin-1-yl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate
• CAS: 1345692-52-5
• 化学式: C₁₅H₁₈BNO₆S
• 分子量: 351.188
• InChiKey: KLIJNQOMJQHMCO-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(5-bromothiophen-2-yl)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole 、 2,5-dioxopyrrolidin-1-yl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以75%的产率得到5'-(4-thienyl-2,1,3-benzothiadiazole)-[2,2']-bithiophenyl-5-carboxylic acid (2,5-dioxopyrrolidin-1-yl) ester
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522
• 作为产物：
  描述：

  2-噻吩甲酸 、 异丙醇频哪醇硼酸酯 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 38.0h， 生成 2,5-dioxopyrrolidin-1-yl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522

文献信息

• Human Serum Albumin–Oligothiophene Bioconjugate: A Phototheranostic Platform for Localized Killing of Cancer Cells by Precise Light Activation
  作者：Andrea Cantelli、Marco Malferrari、Alice Soldà、Giorgia Simonetti、Sonny Forni、Edoardo Toscanella、Edoardo J. Mattioli、Francesco Zerbetto、Alberto Zanelli、Matteo Di Giosia、Mattia Zangoli、Giovanna Barbarella、Stefania Rapino、Francesca Di Maria、Matteo Calvaresi

  DOI：10.1021/jacsau.1c00061

  日期：2021.7.26

  exploitation of oligothiophenes in photodynamic therapy is hindered by their intrinsic hydrophobicity that lowers their biocompatibility and availability in water environments. Here, we developed human serum albumin (HSA)–oligothiophene bioconjugates that afford the use of insoluble oligothiophenes in physiological environments. UV–vis and electrophoresis proved the conjugation of the oligothiophene sensitizers

  噻吩基材料的电子、光学和氧化还原特性使其在纳米科学和纳米技术中发挥着关键作用。然而，低聚噻吩在光动力疗法中的应用受到其固有疏水性的阻碍，降低了其在水环境中的生物相容性和可用性。在这里，我们开发了人血清白蛋白（HSA）-低聚噻吩生物缀合物，可在生理环境中使用不溶性低聚噻吩。紫外可见分光光度计和电泳证明了低聚噻吩敏化剂与蛋白质的结合。动态光散射和圆二色性测量证实，该生物结合物是水溶性的且具有生物相容性，不具有任何“暗毒性”，并且以生理单体形式保留HSA。相比之下，在超低光剂量照射下，生物结合物有效地产生活性氧（ROS）并导致癌细胞的完全根除。实时监测 HSA-低聚噻吩生物共轭物的光杀伤活性表明，活细胞在照射后会“爆炸”。光依赖性和剂量依赖性细胞凋亡是生物缀合物辐照激活的细胞死亡的主要机制之一。该生物结合物是一种新型治疗诊断平台，能够在细胞内产生 ROS，并通过寡聚噻吩的荧光提供成像。它也是一个