试剂3-Mercaptopropanyl-N-hydroxysuccinimideester | 117235-10-6

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 试剂3-Mercaptopropanyl-N-hydroxysuccinimideester
• 英文名称: 3-Mercapropropanoyl-N-hydroxysuccinimide ester
• 英文别名: 2,5-dioxopyrrolidine-1-yl 3-mercaptopropionate；2,5-Pyrrolidinedione, 1-(3-mercapto-1-oxopropoxy)-；(2,5-dioxopyrrolidin-1-yl) 3-sulfanylpropanoate
• CAS: 117235-10-6
• 化学式: C₇H₉NO₄S
• 分子量: 203.219
• InChiKey: UTBOEPMMEANMPS-UHFFFAOYSA-N

物化性质

• 沸点：
  318.4±44.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P201,P202,P264,P270,P273,P280,P301+P312+P330,P308+P313,P391,P405,P501
• 危险品运输编号：
  3082
• 危险性描述：
  H302,H350,H411
• 储存条件：
  -20°C，惰性气体，密封

制备方法与用途

3- Mercaptopropanyl-N-hydroxysuccinimide ester 是一种 PROTEOLYSIS-TARGETING CHEMISTRY (PROTAC) 连接子，属于烷基/醚类化合物。它可以用于合成 PROTAC 分子。

反应信息

• 作为反应物：
  描述：

  1-叔丁氧羰基-1,7-二氨基庚烷 、 试剂3-Mercaptopropanyl-N-hydroxysuccinimideester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以65%的产率得到tert-Butyl-N-(7-((3-sulfanylpropanoyl)amino)heptyl)carbamate
  参考文献：
  名称：

  Characterization of Protein Aggregated Gold Nanocrystals

  摘要：

  This paper describes the preparation of an aqueous dispersion of electrostatically stabilized gold nanocrystals. It also describes the characterization of these nanocrystals by NMR, SAXS, SLS, and TEM prior to and following their modification by chemisorption of 3-mecaptopropanoic acid. Using the insights gained, these nanocrystals were subsequently modified by chemisorption and appropriate surface concentration of a disulfide biotin analogue (DSBA). Addition of streptavidin to the DSBA-modified gold dispersion results in the binding of gold nanocrystals to opposite faces of the protein and in the aggregation of the dispersion. The growth kinetics and structure of the resulting aggregates were characterized by W-visible spectroscopy, DLS, SAXS, and TEM. Some implications of these findings for the assembly of complex nanocrystal architectures in solution are considered.

  DOI：

  10.1021/jp992842u
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 3-巯基丙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 试剂3-Mercaptopropanyl-N-hydroxysuccinimideester
  参考文献：
  名称：

  通过增强光声-影像引导的光热疗法和超声疗法相结合的方法有效地根除肿瘤

  摘要：

  为了消除肿瘤，需要开发一种处理诊断和治疗功能的综合策略。在这项研究中，我们介绍了两种通用的纳米颗粒：一种是聚乙二醇和聚乙烯亚胺改性的金纳米棒（mPEG–PEI–AuNRs），另一种是通过mPEG–PEI和碳酸钙纳米颗粒（mPEG–PEI / CaNPs）。这两种纳米颗粒具有以下有利特性：1）mPEG–PEI–AuNRs和mPEG–PEI / CaNPs不仅在酸性肿瘤pH值下具有高细胞摄取能力，而且在循环时间长的肿瘤中也能有效蓄积。2）mPEG–PEI / CaNPs可以在酸性肿瘤环境中产生二氧化碳（CO 2）气泡，并且通过产生CO 2可以增强mPEG–PEI–AuNRs的光声（PA）信号气泡。3）可以通过在近红外（NIR）激光下结合光热疗法（PTT）和超声疗法（UST）以及存在mPEG–PEI–AuNRs和来自mPEG–PEI /的CO 2气泡的超声照射来根除肿瘤CaNPs。在体外或体内对

  DOI：

  10.1002/adfm.202009314

文献信息

• A multifunctional PEG–PLL drug conjugate forming redox-responsive nanoparticles for intracellular drug delivery
  作者：Zhuxian Zhou、Jianbin Tang、Qihang Sun、William J. Murdoch、Youqing Shen

  DOI：10.1039/c5tb01027f

  日期：——

  Tumor-targeting camptothecin (CPT)-conjugated nanoparticles with high stability and GSH-triggered drug release were developed for cancer targeting drug delivery.

  肿瘤靶向紫杉醇（CPT）共轭纳米颗粒具有高稳定性和谷胱甘肽（GSH）诱导的药物释放，用于癌症靶向药物输送。
• [EN] POLYOXAZOLINE ANTIBODY DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT DE POLYOXAZOLINE
  申请人：SERINA THERAPEUTICS INC

  公开号：WO2016019340A1

  公开（公告）日：2016-02-04

  In the present disclosure, polymer conjugates, including polymer-antibody-drug conjugates (polymer ADCs) are described, as well as the use of such conjugates to treat human disease. The polymer conjugates can contain a large number of polymer-bound agents, thus effectively increasing the drug antibody ration (DAR) of the antibody significantly beyond the currently available technology. This may be of particular importance when antibodies to low density antigens are used as target antibodies. The described polymer-ADCs have improved pharmacokinetics and solubility relative to traditional ADCs. The linker between agent and the polymer can be tailored to provide release of toxin at the desired site and under the desired conditions within the tumor. An additional feature of the polymer-ADCs of the current disclosure is that a purification moiety can be attached to the polymer backbone to provide ease of purification of the polymer-ADCs.

  本公开描述了聚合物偶联物，包括聚合物-抗体-药物偶联物（聚合物ADCs），以及使用这些偶联物治疗人类疾病。该聚合物偶联物可以含有大量的聚合物结合剂，从而有效提高抗体的药物抗体比率（DAR），显著超过目前现有技术。当使用针对低密度抗原的抗体作为靶点抗体时，这一点可能尤为重要。与传统的ADC相比，所述聚合物ADC具有改善的药代动力学和溶解性。毒素与聚合物之间的连接器可以根据需要在肿瘤内特定部位和特定条件下释放毒素进行定制。当前公开的聚合物ADC的另一个特点是，可以在聚合物主链上附着一个纯化部分，以提供聚合物ADC的纯化便利。
• Immobilised Biological Entities
  申请人：Vestberg Robert

  公开号：US20160228572A9

  公开（公告）日：2016-08-11

  There is described inter alia a medical device having a surface which comprises a coating layer, said coating layer being a biocompatible composition comprising an anti-coagulant entity capable of interacting with mammalian blood to prevent coagulation or thrombus formation, which anti-coagulant entity is covalently attached to said surface through a linker comprising a thioether.

  描述了一种医疗设备，其表面包括一层涂层，所述涂层是一种生物相容性组合物，包括一种抗凝剂实体，能够与哺乳动物的血液相互作用，以防止凝血或血栓形成，该抗凝剂实体通过含有硫醚的连接物共价地连接到所述表面。
• DEGRADABLE THIOL-ENE POLYMERS AND METHODS OF MAKING THEREOF
  申请人：MOSAIC BIOSCIENCES, INC.

  公开号：US20180043030A1

  公开（公告）日：2018-02-15

  Provided are methods for linking polypeptides (including peptides and proteins) to other moieties using radical imitated thiol-ene chemistries, for example, modifying a polypeptide by introducing reactive thiol groups and reacting the thiol groups with olefin-containing reagents or alkyne-containing reagents under conditions that support radical thiol-ene or thiol-yne reactions. The reactive thiol groups have greater activity for radical thiol-ene reactions that a cysteine thiol group, including thiol groups that are separated from the peptide backbone by at least two carbon atoms, for example, the thiol group of a homocysteine residue. Also provided are compositions and biomaterials containing the linked polypeptides, for example, peptide and protein conjugates, and thiol-ene based biocompatible hydrogel polymers, and their uses in the medical field.

  提供了一种使用自由基模拟硫醇-烯化学方法将多肽（包括肽和蛋白质）与其他基团连接的方法，例如，通过引入反应性硫醇基团修饰多肽，并在支持自由基硫醇-烯或硫醇-炔反应的条件下将硫醇基团与含有烯烃或炔烃的试剂反应。反应性硫醇基团对于自由基硫醇-烯反应具有比半胱氨酸硫醇基团更高的活性，包括与肽骨架至少相隔两个碳原子的硫醇基团，例如，同型半胱氨酸残基的硫醇基团。还提供了含有连接的多肽的组合物和生物材料，例如，肽和蛋白质共轭物，以及基于硫醇-烯的生物相容性水凝胶聚合物，以及它们在医学领域中的用途。
• INSULIN ANALOG DIMERS
  申请人：INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION

  公开号：US20150274802A1

  公开（公告）日：2015-10-01

  Disclosed herein are insulin analog dimers having unique insulin receptor agonist activity based on insulin polypeptide sequences, the site of dimerization and the length of the dimerization linker that connects the two insulin polypeptides. In accordance with one embodiment the first and second insulin polypeptide are independently a two chain insulin analog or a single chain analog and the first and second insulin polypeptides are linked to one another via a B29-B29′, B1-C8, B1-B1 or C8-C8 linkage.

  本文披露了胰岛素类似物二聚体的独特胰岛素受体激动剂活性，基于胰岛素多肽序列，二聚化位点和连接两个胰岛素多肽的二聚化连接器的长度。根据一种实施例，第一和第二胰岛素多肽分别是双链胰岛素类似物或单链类似物，第一和第二胰岛素多肽通过B29-B29′、B1-C8、B1-B1或C8-C8连接彼此链接。