N-生物素-3,6,9-三氧杂十一烷-1,11-二胺 | 359860-27-8

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: N-生物素-3,6,9-三氧杂十一烷-1,11-二胺
• 中文别名: 生物素-PEG₃-胺
• 英文名称: N-(2-(2-(2-(2-amidoethoxy)ethoxy)ethoxy)ethoxy)biotinamide
• 英文别名: biotin-PEG3-amine；N-biotinyl-3,6,9-trioxaundecane-1,11-diamine；N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide；amine-PEG₃-biotin；EZ-link amine PEG₃-biotin；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]pentanamide
• CAS: 359860-27-8
• 化学式: C₁₈H₃₄N₄O₅S
• 分子量: 418.558
• InChiKey: KIJSBKNJFAUJFV-ZOBUZTSGSA-N

物化性质

• 熔点：
  101-103°C
• 沸点：
  705.8±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)
• 溶解度：
  少许溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335
• 储存条件：
  -20°C

制备方法与用途

生物活性分子 Amine-PEG3-Biotin 作为一种信号放大标记物，兼具生物素基团和末端伯胺基。

反应信息

• 作为反应物：
  描述：

  N-生物素-3,6,9-三氧杂十一烷-1,11-二胺 在 吡啶 、 pyridine hydrofluoride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-(4-{[(4-nitrophenoxy)carbonyloxy]methyl}benzoyl)benzyl 13-oxo-17-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-3,6,9-trioxa-12-azaheptadecylcarbamate
  参考文献：
  名称：

  Design and synthesis of biotin- or alkyne-conjugated photoaffinity probes for studying the target molecules of PD 404182

  摘要：

  To investigate the mechanism of action of the potent antiviral compound PD 404182, three novel photo-affinity probes equipped with a biotin or alkyne indicator were designed and synthesized based on previous structure-activity relationship studies. These probes retained the potent anti-HIV activity of the original pyrimidobenzothiazine derivatives. In photoaffinity labeling studies using HIV-1-infected H9 cells (H9IIIB), eight potential proteins were observed to bind PD 404182. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.016
• 作为产物：
  描述：

  3,6,9-三氧杂十一烷-1,11-二胺 在 4-二甲氨基吡啶 、 TEA 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 N-生物素-3,6,9-三氧杂十一烷-1,11-二胺
  参考文献：
  名称：

  Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120

  摘要：

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00325-x

文献信息

• [EN] THERAPEUTIC AGENT FOR TREATING TUMORS<br/>[FR] AGENT THÉRAPEUTIQUE POUR LE TRAITEMENT DE TUMEURS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2015143092A1

  公开（公告）日：2015-09-24

  The present disclosure relates to a therapeutic agent of the formula: Z-C(=O)-(CH2)n-ϕ-S-S-(CRR')m-(CH2)p-C(=O)- NH-(CH2)q-NH-Y[NH-(CH2)r-X-T-W][NH-(CH2-CH-O)t (CH2)s-NH-V] Formula I or a pharmaceutically acceptable salt thereof, useful for treating tumors, including cancers. Where the compound of Formula I also contains a radionuclide or an imaging agent or both, the compound of formula I is a theranostic agent useful for treating and diagnosing tumors, including cancers.

  本公开涉及一种治疗剂，其化学式为：Z-C(=O)-(CH2)n-ϕ-S-S-(CRR')m-( )p-C(=O)- NH-( )q-NH-Y[NH-( )r-X-T-W][NH-( -CH-O)t ( )s-NH-V] 化学式I或其药学上可接受的盐，用于治疗肿瘤，包括癌症。化合物I的化学式还包含放射性核素或成像剂或两者的情况下，化合物I是一种治疗和诊断肿瘤，包括癌症的治疗剂。
• The Ras Pathway Modulator Melophlin A Targets Dynamins
  作者：Tanja Knoth、Karin Warburg、Catherine Katzka、Amrita Rai、Alexander Wolf、Andreas Brockmeyer、Petra Janning、Thomas F. Reubold、Susanne Eschenburg、Dietmar J. Manstein、Katja Hübel、Markus Kaiser、Herbert Waldmann

  DOI：10.1002/anie.200902023

  日期：2009.9.14

  combination of organic synthesis, chemical proteomics, biophysics, and cell and molecular biology investigations reveals that the natural product melophlin A (purple) influences signal propagation through the Ras network by interfering with the function of dynamins (green) in endocytosis.

  天然原因：有机合成，化学蛋白质组学，生物物理学以及细胞和分子生物学研究的结合表明，天然产物melophlin A（紫色）通过干扰细胞活力（绿色）在胞吞作用中影响通过Ras网络传播的信号。
• [EN] SYNTHESIS OF NOVEL ASYMMETRIC BOW-TIE PAMAM DENDRIMER-BASED CONJUGATES FOR TUMOR-TARGETING DRUG DELIVERY<br/>[FR] SYNTHÈSE DE NOUVEAUX CONJUGUÉS ASYMÉTRIQUES À BASE D'UN DENDRIMÈRE PAMAM EN NŒUD PAPILLON POUR ADMINISTRATION DE MÉDICAMENTS CIBLÉE VERS UNE TUMEUR
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2015038493A1

  公开（公告）日：2015-03-19

  The present disclosure relates to a dendrimer-based conjugate of the formula Vm-D-C-D'-(T-F)n, which is useful for tumor targeting drug delivery. The use of asymmetric dendrimers allow for specific targeting as well as synthetic reproducibility.

  本公开涉及一种公式为Vm-D-C-D'-(T-F)n的基于树状聚合物的结合物，该结合物对于肿瘤靶向药物传递很有用。不对称树状聚合物的使用可以实现特定的靶向以及合成的可重复性。
• A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation
  作者：Partha Sarathi Addy、Sarah B. Erickson、James S. Italia、Abhishek Chatterjee

  DOI：10.1021/jacs.7b05125

  日期：2017.8.30

  diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling

  复杂生物分子的化学选择性修饰已成为化学生物学的基石。尽管过去二十年取得了令人振奋的发展，但对具有独特能力的新化学选择性反应以及与现有化学物质兼容的并发多位点定向标记的需求仍然很高。在这里，我们表明 5-羟基吲哚对芳香重氮离子表现出非常高的反应性，并且该反应可用于化学选择性标记蛋白质。我们之前已经在大肠杆菌和真核生物中对非规范氨基酸 5-羟色氨酸进行了遗传编码，从而能够将 5-羟​​基吲哚有效地定点掺入到几乎任何蛋白质中。5-羟色氨酸残基显示允许使用偶氮偶联反应进行快速的化学选择性蛋白质修饰，并且通过产生功能性抗体-荧光团缀合物进一步说明了这种生物缀合策略的效用。尽管由此产生的偶氮键在其他方面是稳定的，但我们表明它可以在用连二亚硫酸盐处理后有效地裂解。我们的工作建立了一种独特的化学选择性“不可点击”生物偶联策略，以对在细菌和真核生物中表达的蛋白质进行位点特异性修饰。
• Chemoselective Rapid Azo-Coupling Reaction for Bioconjugation
  申请人：Trustees of Boston College

  公开号：US20180360984A1

  公开（公告）日：2018-12-20

  Novel biomolecular conjugates containing non-natural aromatic chemical moieties covalently coupled to a diazonium compound and methods of their use are disclosed.

  揭示了含有非天然芳香化学基团的新型生物分子共轭物，其与重氮化合物共价耦合，并公开了它们的使用方法。