4-(2-吡啶基二硫代)-1-丁醇 | 892402-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-(2-吡啶基二硫代)-1-丁醇
• 英文名称: 4-((2-pyridyl)dithio)butan-1-ol
• 英文别名: 4-(Pridin-2-yldisulfanyl)butan-1-ol；4-(pyridin-2-yldisulfanyl)butan-1-ol
• CAS: 892402-95-8
• 化学式: C₉H₁₃NOS₂
• 分子量: 215.34
• InChiKey: INLLFOARRZWRSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-吡啶基二硫代)-1-丁醇 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 三乙胺 作用下， 以 吡啶 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Solid-Phase Synthesis of Thermolytic DNA Oligonucleotides Functionalized with a Single 4-Hydroxy-1-butyl or 4-Phosphato-/Thiophosphato-1-butyl Thiophosphate Protecting Group

  摘要：

  Several thermolytic CpG-containing DNA oligonucleotides analogous to 1 have been synthesized to serve as potential immunotherapeutic oligonucleotide prodrug formulations for the treatment of infectious diseases in animal models. Specifically, the CpG motif (GACGTT) of each DNA oligonucleotide has been functionalized with either the thermolabile 4-hydroxy-1-butyl or the 4-phosphato-/thiophosphato-1-butyl thiophosphate protecting group. This functionalization was achieved through incorporation of activated deoxyribonucleoside phosphoramidite 8b into the oligonucleotide chain during solid-phase synthesis and, optionally, through subsequent phosphorylation effected by phosphoramidite 9. Complete conversion of CpG ODNs hbu1555, psb1555, and pob1555 to CpG ODN 1555 (homologous to 2) occurred under elevated temperature conditions, thereby validating the function of these diastereomeric oligonucleotides as prodrugs in vitro. Noteworthy is the significant increase in solubility of CpG ODN psb1555 and CpG pob1555 in water when compared to that of neutral CpG ODN fma1555 (homologous to 1).

  DOI：

  10.1021/jo062087y
• 作为产物：
  描述：

  2,2'-二硫二吡啶 、 4-巯基-1-丁醇 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到4-(2-吡啶基二硫代)-1-丁醇
  参考文献：
  名称：

  Glutathione-sensitive nanoplatform for monitored intracellular delivery and controlled release of Camptothecin

  摘要：

  我们报道了一种基于共价连接模式的纳米药物的设计、合成、表征及体外测试，该模式允许药物在细胞内受控释放。通过直接将合成的（吡啶-2-二硫基）烷基碳酸酯类喜树碱（CPT）衍生物与含非多孔核心和介孔壳层的硅基杂化纳米粒子的硫醇基团耦合，实现了新的合成策略。在生理条件下与硫醇反应时，二硫键断裂，通过分子内环化机制释放裸药。在粒子核心中额外引入荧光团有利于亚细胞水平成像，以便监测摄取和递送。在HeLa宫颈癌细胞中进行的共聚焦显微镜实验证实，纳米粒子通过内吞作用进入细胞，但能够逃逸出内溶酶体，进入胞质溶胶释放其内含物。向细胞中加入谷胱甘肽抑制剂L-丁硫氨酸亚砜亚胺，可以得出结论，细胞内释放机制主要由该三肽的还原活性驱动。这种喜树碱纳米平台显示出与自由药物相同的细胞毒性活性，并且在依赖酶解释放的系统中明显优越（通过计算IC50比值确定）。

  DOI：

  10.1039/c3ra41404c

文献信息

• [EN] POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS<br/>[FR] CONSTRUCTIONS POLYNUCLÉOTIDIQUES CONTENANT DES GROUPES DISULFURE
  申请人：SOLSTICE BIOLOG LTD

  公开号：WO2015069932A1

  公开（公告）日：2015-05-14

  The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internudeotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.

  该发明涉及包含一个或多个组分（i）的聚核苷酸构造，其中每个一个或多个组分连接到聚核苷酸构造的一个核苷酸桥连基团或末端基团上，每个一个或多个组分（i）包含靠近二硫键的一个或多个臃肿基团。该发明还涉及包含一个或多个组分（i）的聚核苷酸构造，其中每个一个或多个组分（i）连接到聚核苷酸构造的一个核苷酸桥连基团或末端基团上，每个一个或多个组分（i）在二硫键和核苷酸桥连基团或末端基团的磷原子之间的链中至少包含4个原子；并且该链不包含磷酸酯、酰胺、酯或烯基烃。该发明还涉及使用该发明的聚核苷酸构造将聚核苷酸传递到细胞的方法。
• COMPOSITIONS AND METHODS FOR TRANSPORT OF MOLECULES WITH ENHANCED RELEASE PROPERTIES ACROSS BIOLOGICAL BARRIERS
  申请人：Wender Paul A

  公开号：US20100255499A1

  公开（公告）日：2010-10-07

  Conjugates of a cargo molecule with a transporter molecule are disclosed, where the cargo molecule and the transporter molecule are linked covalently by a releasable linker. The cargo of the conjugate can be a biologically active agent or a reporter molecule. The transporter modulates the transport of the cargo across a biological barrier (e.g., a cell membrane) compared to the transport of the unconjugated cargo. Releasable linkers suitable for rapid and facile conjugation to various types of cargo and transporters are also disclosed, along with methods for using the linkers in the synthesis of conjugates.

  本发明公开了一种货物分子与运输蛋白分子的共轭体，其中货物分子和运输蛋白分子通过可释放的连接剂共价连接。共轭体的货物可以是生物活性剂或报告分子。与未共轭货物的运输相比，运输蛋白调节货物通过生物屏障（例如细胞膜）的运输。还公开了适用于快速和容易地与各种类型的货物和运输蛋白共轭的可释放连接剂，以及使用连接剂合成共轭体的方法。
• POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS
  申请人：BRADSHAW Curt W.

  公开号：US20160257961A1

  公开（公告）日：2016-09-08

  The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internucleotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internucleotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internucleotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.

  本发明涉及一种聚核苷酸构建物，其包含一个或多个组分（i），该组分包含一个二硫键，其中每个组分中的一个或多个组分连接到聚核苷酸构建物的核苷酸桥接基团或末端基团上，并且每个组分（i）在二硫键附近包含一个或多个笨重基团。本发明还涉及一种聚核苷酸构建物，其包含一个或多个组分（i），该组分包含一个二硫键，其中每个组分中的一个或多个组分连接到聚核苷酸构建物的核苷酸桥接基团或末端基团上，并且每个组分（i）在二硫键和核苷酸桥接基团或末端基团的磷原子之间的链中至少含有4个原子；并且链中不含有磷酸盐、酰胺、酯或烯基烃。本发明还涉及使用本发明的聚核苷酸构建物向细胞传递聚核苷酸的方法。
• [EN] POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS<br/>[FR] CONSTRUCTIONS DE POLYNUCLÉOTIDES POSSÉDANT DES GROUPES BIORÉVERSIBLES ET NON BIORÉVERSIBLES
  申请人：SOLSTICE BIOLOG LTD

  公开号：WO2015188197A3

  公开（公告）日：2016-02-25
• Releasable Luciferin−Transporter Conjugates:  Tools for the Real-Time Analysis of Cellular Uptake and Release
  作者：Lisa R. Jones、Elena A. Goun、Rajesh Shinde、Jonathan B. Rothbard、Christopher H. Contag、Paul A. Wender

  DOI：10.1021/ja0586283

  日期：2006.5.1

  The design, synthesis, and evaluation of conjugates of arginine-rich transporters and luciferin are described that release luciferin only after entry into cells that are stably transfected with luciferase. Each molecule of free luciferin that is released after entry generates a photon that can be measured allowing for real-time quantification of uptake and release in cells. The process provides a method to assay uptake and release of free luciferin as a function of variations in the releasable linker and in the transporter.