2-methyl-2-((prop-2-yn-1-yloxy)carbonyl)propane-1,3-diyl bis(2,2,5-trimethyl-1,3-dioxane-5-carboxylate) | 919988-17-3

• 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: 2-methyl-2-((prop-2-yn-1-yloxy)carbonyl)propane-1,3-diyl bis(2,2,5-trimethyl-1,3-dioxane-5-carboxylate)
• 英文别名: [2-methyl-3-oxo-3-prop-2-ynoxy-2-[(2,2,5-trimethyl-1,3-dioxane-5-carbonyl)oxymethyl]propyl] 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• CAS: 919988-17-3
• 化学式: C₂₄H₃₆O₁₀
• 分子量: 484.544
• InChiKey: RNNXIZWUJOAGDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.6±40.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-methyl-2-((prop-2-yn-1-yloxy)carbonyl)propane-1,3-diyl bis(2,2,5-trimethyl-1,3-dioxane-5-carboxylate) 在 吡啶 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Prop-2-ynyl 2-methyl-3-[2-methyl-3-(4-nitrophenoxy)carbonyloxy-2-[(4-nitrophenoxy)carbonyloxymethyl]propanoyl]oxy-2-[[2-methyl-3-(4-nitrophenoxy)carbonyloxy-2-[(4-nitrophenoxy)carbonyloxymethyl]propanoyl]oxymethyl]propanoate
  参考文献：
  名称：

  Degradable Self-Assembling Dendrons for Gene Delivery: Experimental and Theoretical Insights into the Barriers to Cellular Uptake

  摘要：

  This paper uses a combined experimental and theoretical approach to gain unique insight into gene delivery. We report the synthesis and investigation of a new family of second-generation dendrons with four triamine surface ligands capable of binding to DNA, degradable aliphatic-ester dendritic scaffolds, and hydrophobic units at their focal points. Dendron self-assembly significantly enhances DNA binding as monitored by a range of experimental methods and confirmed by multiscale modeling. Cellular uptake studies indicate that some of these dendrons are highly effective at transporting DNA into cells (ca. 10 times better than poly(ethyleneimine), PEI). However, levels of transgene expression are relatively low (ca. 10% of PEI). This indicates that these dendrons cannot navigate all of the intracellular barriers to gene delivery. The addition of chloroquine indicates that endosomal escape is not the limiting factor in this case, and it is shown, both experimentally and theoretically, that gene delivery can be correlated with the ability of the dendron assemblies to release DNA. Mass spectrometric assays demonstrate that the dendrons, as intended, do degrade under biologically relevant conditions over a period of hours. Multiscale modeling of degraded dendron structures suggests that complete dendron degradation would be required for DNA release. Importantly, in the presence of the lower pH associated with endosomes, or when bound to DNA, complete degradation of these dendrons becomes ineffective on the transfection time scale we propose this explains the poor transfection performance of these dendrons. As such, this paper demonstrates that taking this kind of multidisciplinary approach can yield a fundamental insight into the way in which dendrons can navigate barriers to cellular uptake. Lessons learned from this work will inform future dendron design for enhanced gene delivery.

  DOI：

  10.1021/ja2070736
• 作为产物：
  描述：

  prop-2-yn-1-yl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate 以91%的产率得到2-methyl-2-((prop-2-yn-1-yloxy)carbonyl)propane-1,3-diyl bis(2,2,5-trimethyl-1,3-dioxane-5-carboxylate)
  参考文献：
  名称：

  Method for making amphiphilic dendrimers

  摘要：

  一系列AB型两性树枝状聚酯已经通过分叉法制备，其中两种杂交物通过铜(1)-催化的三唑形成耦合。

  公开号：

  US20090182151A1

文献信息

• Self-assembling amphiphilic Janus dendrimers: mesomorphic properties and aggregation in water
  作者：Elisabetta Fedeli、Alexandre Lancelot、José Luis Serrano、Pilar Calvo、Teresa Sierra

  DOI：10.1039/c4nj02071e

  日期：——

  article. The designed molecules possess two parts with different polarity; this feature is the key factor that forces their self-assembly in water into supramolecular architectures, due to hydrophobic interactions between the lipophilic fractions of the molecules, and the appearance of mesomorphic order in bulk in response to a variation of temperature (thermotropic liquid crystals). The effects provoked

  基于bis-MPA的两亲性树枝状大分子衍生物在水中和水中的自组装行为是本文的主题。设计的分子具有两个不同极性的部分。此功能是迫使其在水中自组装成超分子体系的关键因素，这归因于分子的亲脂性部分之间的疏水相互作用，以及随着温度的变化而大量出现的同晶顺序（热致液晶） 。研究了由分子的亲水/亲脂平衡引起的效应，改变了相应树突的生成并通过CuAAC单击化学，以获得对称和不对称的最终Janus树状聚合物。还研究了在水中形成的聚集体包封疏水性药物的能力。
• Multivalent, bifunctional dendrimers prepared by click chemistry
  作者：Peng Wu、Michael Malkoch、Jasmine N. Hunt、Robert Vestberg、Eiton Kaltgrad、M. G. Finn、Valery V. Fokin、K. Barry Sharpless、Craig J. Hawker

  DOI：10.1039/b512021g

  日期：——

  Unsymmetrical dendrimers, containing both mannose binding units and coumarin fluorescent units, have been prepared using click chemistry and shown to be highly efficient, dual-purpose recognition/detection agents for the inhibition of hemagglutination.

  含有甘露糖结合单元和香豆素荧光单元的非对称树枝状大分子，已通过点击化学方法制备，并显示出作为高效且多用途的凝集抑制识别/检测剂的潜力。
• [EN] HYBRID NANOPARTICLES CONTAINING DENDRONS, METHODS OF PRODUCING SUCH HYBRID NANOPARTICLES, AND USES THEREOF<br/>[FR] NANOPARTICULES HYBRIDES CONTENANT DES DENDRONS, PROCÉDÉS DE PRODUCTION DE CES NANOPARTICULES HYBRIDES, ET LEURS UTILISATIONS
  申请人：RHODIA OPERATIONS

  公开号：WO2016201310A1

  公开（公告）日：2016-12-15

  The present disclosure relates to a hybrid nanoparticle comprising a metallic core and at least one lipophilic dendron attached to the surface of the metallic core, and methods of producing such hybrid nanoparticles. The present disclosure also relates to films containing the hybrid nanoparticles described herein.

  本公开涉及一种混合纳米颗粒，包括金属核和至少一个附着在金属核表面的亲脂性树状分子，以及制备这种混合纳米颗粒的方法。本公开还涉及包含所述混合纳米颗粒的薄膜。
• Modular Construction of Dynamic Nucleodendrimers
  作者：Valentina Abet、Robert Evans、Florian Guibbal、Stefano Caldarelli、Raphaël Rodriguez

  DOI：10.1002/anie.201402400

  日期：2014.5.5

  Isoguanosine‐containing dendritic small molecules self‐assemble into decameric nucleodendrimers as observed by 1D NMR spectroscopy, 2D DOSY, and mass spectrometry. In particular, apolar building blocks readily form pentameric structures in acetonitrile while the presence of alkali metals promotes the formation of stable decameric assemblies with a preference for cesium ions. Remarkably, co‐incubation

  通过1D NMR光谱，2D DOSY和质谱法观察到，含有异鸟苷的树枝状小分子会自组装成十聚体的核树枝状大分子。特别是，非极性结构单元很容易在乙腈中形成五聚体结构，而碱金属的存在促进了稳定的十聚体组装的形成，偏爱铯离子。值得注意的是，鸟苷和含异鸟苷的核糖核酸的共孵育会导致在不添加盐的情况下形成十聚体结构。对该混合物的进一步分析表明鸟苷衍生物有助于形成，但不参与十聚体结构。一个让人想起分子拥挤的过程。该分子系统为多功能树突状大分子的快速模块化组装提供了强大的平台。
• Convergent Synthesis of Glycodendropeptides by Click Chemistry Approaches
  作者：Wioleta Kowalczyk、Ainhoa Mascaraque、Macarena Sánchez-Navarro、Javier Rojo、David Andreu

  DOI：10.1002/ejoc.201200428

  日期：2012.8

  We thank the Spanish Ministry of Science and Innovation (MICINN) for financial support (BIO2008-04487-CO3-02 and SAF2009-24899 to D. A. and CTQ2008-01694/BQU and CTQ2011-23410 to J. R). W. K., and A. M. thank MICINN for Juan de la Cierva and FPI fellowships, respectively.

  我们感谢西班牙科学与创新部 (MICINN) 的财政支持 (BIO2008-04487-CO3-02 和 SAF2009-24899 到 DA 和 CTQ2008-01694/BQU 和 CTQ2011-23410 到 J. R)。WK 和 AM 分别感谢 MICINN 为 Juan de la Cierva 和 FPI 奖学金。