bis(succinimidyl) fumarate

• 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: bis(succinimidyl) fumarate
• 英文别名: bis(2,5-dioxopyrrolidin-1-yl) fumarate；fumaric acid disuccinimidyl ester；bis(2,5-dioxopyrrolidin-1-yl) (E)-but-2-enedioate
• 化学式: C₁₂H₁₀N₂O₈
• 分子量: 310.22
• InChiKey: YDGMGVCDKKUWDQ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis(succinimidyl) fumarate 、 盐酸多柔比星 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  使用双功能NHS活化的丙烯酰胺对肽和蛋白质进行有效的氨基巯基吻合

  摘要：

  肽功能化工具箱中广泛使用的试剂，Michael受体和N-羟基琥珀酰亚胺（NHS）活化的酯结合在NHS活化的丙烯酰胺中，可对天然肽和蛋白质进行有效的化学选择性氨基巯基吻合。NHS活化的丙烯酰胺可在稀水条件下快速官能化N端半胱氨酸（k 2 = 1.54±0.18×10 3  M -1  s -1），从而实现对其他亲核氨基酸的选择性。此外，这些新的生物偶联手柄的多功能性在链内或C链交联中得到了证明。末端半胱氨酸与附近的赖氨酸残基。NHS活化的丙烯酰胺与其他半胱氨酸选择性试剂兼容，可进行正交双重修饰。该策略已成功应用于具有PEG单元，荧光探针和细胞毒性剂的肽和蛋白质的后期功能化。NHS活化的丙烯酰胺提供的分子控制水平有望促进氨基巯基吻合技术的发展，这是设计功能性生物缀合物的有力策略。

  DOI：

  10.1002/anie.202016936
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 富马酸 在 吡啶 、 三氟乙酸酐 作用下， 以 氯苯 为溶剂， 反应 2.17h， 以66%的产率得到bis(succinimidyl) fumarate
  参考文献：
  名称：

  Synthesis of a Neamine Dimer Targeting the Dimerization Initiation Site of HIV-1 RNA

  摘要：

  [GRAPHICS]A neamine dimer designed to bind to a specific sequence of HIV-1 RNA has been synthesized. Starting from neomycin B (1), a five-step synthesis efficiently provided a key protected neamine monomer 6 (28%). From the latter, coupling reactions with activated diacids gave dimers. After deprotection, a neamine dimer was obtained as the hexachlorohydrate salt 15 with 13% overall yield over nine steps.

  DOI：

  10.1021/ol701760k

文献信息

• Towards Selective Delivery of a Ruthenium(II) Polypyridyl Complex‐Containing Bombesin Conjugate into Cancer Cells
  作者：Maria J. S. A. Silva、Robin Vinck、Youchao Wang、Bruno Saubaméa、Mickaël Tharaud、Elena Dominguez‐Jurado、Johannes Karges、Pedro M. P. Gois、Gilles Gasser

  DOI：10.1002/cbic.202200647

  日期：2023.2.14

  is relevant for increased photodynamic therapy (PDT) efficiency. In this article, we explore the site-selective bioconjugation of a promising Ru(II) polypyridyl complex to an N-terminally Cys-modified bombesin peptide for improved PDT towards cancer cells.

  改善您的目标：降低新的潜在光敏剂在黑暗中的脱靶和一般细胞毒性与提高光动力疗法 (PDT) 效率相关。在这篇文章中，我们探索了一种有前途的 Ru(II) 多吡啶复合物与N末端 Cys 修饰的铃蟾肽的位点选择性生物偶联，以改善对癌细胞的 PDT。
• In Situ Formation of <i>N</i>-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, <i>N</i>-Trifluoroacetyl Amino Acid Succinimidyl Esters, and <i>N</i>-Maleoyl Amino Acid Succinimidyl Esters
  作者：Nicholas M. Leonard、Jarmila Brunckova

  DOI：10.1021/jo201686e

  日期：2011.11.4

  A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.
• Dynamic Combinatorial Chemistry with Novel Dithiol Building Blocks: Towards New Structurally Diverse and Adaptive Screening Collections
  作者：David Spring、Tobias Postma、Warren Galloway、Fabien Cougnon、G. Pantoş、Jamie Stokes

  DOI：10.1055/s-0032-1318407

  日期：——

  We describe the synthesis of a range of novel dithiol-functionalized building blocks and demonstrate how they can be used to generate new structurally diverse dynamic combinatorial libraries. A proof-of-principle experiment using the catecholamine dopamine revealed that molecular recognition changed the library composition under biocompatible conditions and identified new promising candidate receptors of this biologically important neurotransmitter.
• Molecules which Bind to the Dimerization Initiation Site (DIS) of HIV RNA, Their Synthesis and Their Applications as Drugs
  申请人：Pale Patrick

  公开号：US20110118202A1

  公开（公告）日：2011-05-19

  The dimerization of HIV RNA is a key step in the virus replication cycle. Based on RNA DIS crystal structures, a novel kind of compounds, dimeric or not, based on neamine was designed and synthesized. Biological studies showed that such compounds bind and interfere with the targeted RNA sequence, opening a new anti-HIV approach. The crystal structures and bio-chemical experiments showed that the DIS of HIV-1 genomic RNA is a target for new anti-HIV drugs and that those drugs could be derived from aminoglycosides. The results revealed that binding of aminoglycosides to the DIS is specific regarding both the aminoglycoside family and the RNA subtype.
• [EN] MOLECULES WHICH BIND TO THE DIMERIZATION INITIATION SITE (DIS) OF HIV RNA, THEIR SYNTHESIS AND THEIR APPLICATIONS AS DRUGS<br/>[FR] MOLÉCULES QUI SE LIENT AU SITE D'INITIATION DE LA DIMÉRISATION (SID) DE L'ARN DU VIH, LEUR SYNTHÈSE ET LEURS APPLICATIONS COMME MÉDICAMENTS
  申请人：PALE PATRICK

  公开号：WO2007125423A2

  公开（公告）日：2007-11-08

  (EN) The dimerization of HIV RNA is a key step in the virus replication cycle. Based on RNA DIS crystal structures, a novel kind of compounds, dimeric or not, based on neamine was designed and synthesized. Biological studies showed that such compounds bind and interfere with the targeted RNA sequence, opening a new anti-HIV approach. The crystal structures and biochemical experiments showed that the DIS of HIV-I genomic RNA is a target for new anti-HIV drugs and that those drugs could be derived from aminoglycosides. The results revealed that binding of aminoglycosides to the DIS is specific regarding both the aminoglycoside family and the RNA subtype.(FR) La dimérisation de l'ARN du VIH est une étape clé dans le cycle de réplication du virus. En se basant sur des structures cristallines de SID d'ARN, un nouveau type de composés, dimères ou non, à base de néamine a été conçu et synthétisé. Des études biologiques ont montré que ces composés se lient et interfèrent avec la séquence d'ARN ciblée, ouvrant une nouvelle approche anti-VIH. Les structures cristallines et les expériences biochimiques ont montré que le SID de l'ARN génomique du VIH-1 est une cible pour de nouveaux médicaments anti-VIH et que ces médicaments peuvent être dérivés d'aminoglycosides. Les résultats ont révélé que la liaison des aminoglycosides au SID est spécifique à la fois à la famille des aminoglycosides et au sous-type d'ARN.