N-Boc-norbiotinamine | 295322-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并咪唑类化合物
• 英文名称: N-Boc-norbiotinamine
• 英文别名: (3aS,4S,6aR)-4-(4-tert-butoxycarbonylaminobut-1-yl)hexahydro-1H-thieno[3,4-d]imidazolidin-2-one；tert-butyl (4-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)butyl)carbamate；N-(tert-butoxycarbonyl)-norbiotinamine；tert-butyl N-[4-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]butyl]carbamate
• CAS: 295322-49-5
• 化学式: C₁₄H₂₅N₃O₃S
• 分子量: 315.437
• InChiKey: ZDSAUNAOMQWESL-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-norbiotinamine 在 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.25h， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of a cellular stable and detectable biotinylated fumagillin probe and investigation of cell permeability of fumagillin and its analogs to endothelial and cancer cells

  摘要：

  Fumagillin (1), a natural product of fungal origin, and its analogs were discovered to be extremely potent and highly selective inhibitors restraining endothelial cell proliferation in vitro by covalently binding to MetAP2. In order to further understand the unclear biological mechanisms and pharmacological processes of fumagillin and its derivatives, fumagillin-biotin conjugate 8 was designed and synthesized, which is linked with a 27-atom connection chain and by urethane (carbamate) bonds between fumagillol and D-norbiotinamine. The conjugate 8 shows comparable activity and selectivity against HUVEC proliferation as fumagillin. It was demonstrated that the conjugate 8 is stable inside the cell and its linker is of a suitable length for the detection of biotin in native and denatured conditions. Using the conjugate 8, it was determined that the cell permeability of fumagillin (1) and its analogs are not responsible for their inhibitory activity difference against the proliferation of endothelial and cancer cells. Furthermore, we confidently believe that our present strategy is a versatile and convenient method for investigating drug's cell permeability along with other studies regardless of reversible or irreversible interaction between the drug and binding target's. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.033
• 作为产物：
  描述：

  D-生物素 在 二苯基膦叠氮化物 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 N-Boc-norbiotinamine
  参考文献：
  名称：

  [EN] PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS
  [FR] PROFILAGE DE PHOTOPROXIMITÉ D'INTERACTIONS PROTÉINE-PROTÉINE DANS DES CELLULES

  摘要：

  描述了用于检测生物相互作用的光活性探针和探针系统。光活性探针包括同时结合光解和光反应基团的探针。光活性探针系统可以包括第一探针，其中包括光催化基团，以及第二探针，其中包括可作为光催化基团催化反应底物的基团。探针和探针系统还可以包括能够特异性结合到感兴趣生物实体上的结合伙伴的基团，以及可检测的基团或其前体。这些探针和探针系统可以检测蛋白质或细胞的时空相互作用。在某些实施方式中，这些相互作用可以在活细胞中检测到。还描述了检测生物相互作用的方法。

  公开号：

  WO2021055960A1

文献信息

• [EN] NOVEL ANTIBIOTIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBIOTIQUES
  申请人：UNIV ADELAIDE

  公开号：WO2020087122A1

  公开（公告）日：2020-05-07

  Novel antimicrobial inhibitors of Biotin Protein Ligase (BPL), which incorporate biotin, are described. The inhibitors have a structure that inhibit the essential metabolic enzyme BPL of pathogens and have been shown to be stable in whole blood and effective at reducing BPL activity in acceptable concentrations. The described compounds have shown to be effective against, for example, Staphylococcus aureus and compare favourably against erythromycin

  描述了一种新型抗微生物生物素蛋白连接酶（BPL）抑制剂，其中包含生物素。这些抑制剂具有一种结构，可以抑制病原体的关键代谢酶BPL，并且已经证明在全血中稳定，并且在可接受的浓度下能有效降低BPL活性。所描述的化合物已被证明对金黄色葡萄球菌等病原体有效，并且与红霉素相比具有较好的效果。
• [EN] NOVEL ANTIMICROBIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIMICROBIENS
  申请人：ADELAIDE RES & INNOVATION PTY

  公开号：WO2013040647A1

  公开（公告）日：2013-03-28

  A new class of biotin protein ligase (BPL) inhibitors that have antibacterial activity against multiple Staphylococcus aureus isolates, including clinically important methicillin-resistant S. aureus (MRSA) are disclosed that are non-toxic.

  披萨店的招牌菜是各种口味的披萨，包括经典的意大利香肠披萨、夏威夷披萨、墨西哥辣椒披萨等。
• [EN] COMPOUNDS AND METHODS FOR DETECTING EARLY ATHEROSCLEROTIC LESIONS IN BLOOD VESSELS<br/>[FR] COMPOSÉS ET PROCÉDÉS DE DÉTECTION DE LÉSIONS ATHÉROSCLÉREUSES PRÉCOCES DANS DES VAISSEAUX SANGUINS
  申请人：UNIV DEGLI STUDI GENOVA

  公开号：WO2019175019A1

  公开（公告）日：2019-09-19

  A biotin derivative of formula (I) (I) in which R is a peptide with the sequence VHPKQHRGGSKGC, linked to the succinimidyl ring through the -SH group of the C-terminal cysteine, which can be used in a method for detecting early atherosclerotic lesions in the blood vessels of a human subject, which method includes steps of a) forming a complex of this biotin derivative with avidin, neutravidin or streptavidin; b) parenterally administering the complex thus formed; c) subsequently, parenterally administering a chelating agent including a chelating moiety, a biotin moiety and a metal radionuclide, and d) subjecting the human subject to a diagnostic nuclear imaging technique; this biotin derivative can also be used in a method for treating a disease of a human patient characterized by an overexpression of VCAM-1, including inflammatory diseases, atherosclerosis, multiple sclerosis, neurodegenerative diseases and neuroinflammatory diseases.

  一种公式为（I）的生物素衍生物（I），其中R是序列为VHPKQHRGGSKGC的肽链，通过C-末端的半胱氨酸的-SH基团连接到琥珀酰亚胺环上，可用于检测人体主体血管中早期动脉粥样硬化病变的方法，该方法包括以下步骤：a）形成该生物素衍生物与亲和素、中性亲和素或链霉亲和素的复合物；b）经皮给予所形成的复合物；c）随后，经皮给予包括螯合基团、生物素基团和金属放射性核素的螯合剂；d）将人体主体暴露于诊断核成像技术下；该生物素衍生物还可用于治疗人类患者的疾病，其特征为VCAM-1过度表达，包括炎性疾病、动脉粥样硬化、多发性硬化症、神经退行性疾病和神经炎症性疾病。
• Two Novel PET Radiopharmaceuticals for Endothelial Vascular Cell Adhesion Molecule-1 (VCAM-1) Targeting
  作者：Sara Pastorino、Sara Baldassari、Giorgia Ailuno、Guendalina Zuccari、Giuliana Drava、Andrea Petretto、Vanessa Cossu、Cecilia Marini、Silvana Alfei、Tullio Florio、Gianmario Sambuceti、Gabriele Caviglioli

  DOI：10.3390/pharmaceutics13071025

  日期：——

  Atherosclerosis is a chronic progressive disease involving inflammatory events, such as the overexpression of adhesion molecules including the endothelial Vascular Cell Adhesion Molecule-1 (VCAM-1). VCAM-1 is rapidly overexpressed in the first stages of atherosclerosis, thus representing a promising target for early atheroma detection. Two novel Positron Emission Tomography (PET) radiopharmaceuticals (MacroP and NAMP), based on the VCAM-1-binding peptide having sequence VHPKQHRGGSKGC, were synthesized and characterized. MacroP is derived from the direct conjugation of a DOTA derivative with the peptide, while NAMP is a biotin derivative conceived to be employed in a three-step pretargeting system, involving the use of a double-chelating derivative of DOTA. The identity of the newly synthesized radiopharmaceuticals was confirmed by mass spectrometry and, after radiolabeling with 68Ga, both showed high radiochemical purity; in vitro tests on human umbilical vein endothelial cells evidenced their VCAM-1 binding ability, with higher radioactive uptake in the case of NAMP. Moreover, NAMP might also be employed in a theranostic approach in association with functionalized biotinylated nanoparticles.

  动脉粥样硬化是一种慢性进行性疾病，涉及炎症事件，例如过度表达粘附分子，包括内皮细胞血管细胞粘附分子-1（VCAM-1）。 VCAM-1在动脉粥样硬化的早期阶段迅速过度表达，因此代表了早期动脉粥样硬化检测的有希望的靶点。基于VCAM-1结合肽序列VHPKQHRGGSKGC的两种新型正电子发射断层扫描（PET）放射性药物（MacroP和NAMP）已经合成和表征。MacroP是由DOTA衍生物与肽直接共轭而来，而NAMP是一种生物素衍生物，旨在用于三步预先靶向系统，涉及使用DOTA的双螯合衍生物。新合成的放射性药物的身份已经通过质谱确认，在与68Ga标记后，两者都显示出高放射化学纯度;对人脐静脉内皮细胞的体外测试显示它们具有VCAM-1结合能力，在NAMP的情况下放射性摄取率更高。此外，NAMP也可能与功能化生物素化纳米颗粒一起用于治疗和诊断联合应用。
• Chloromethyl-triazole: a new motif for site-selective pseudo-acylation of proteins
  作者：Richard C. Brewster、Georgina C. Gavins、Barbara Günthardt、Sarah Farr、Kimberly M. Webb、Philipp Voigt、Alison N. Hulme

  DOI：10.1039/c6cc06801d

  日期：——

  Chloromethyl triazoles are shown to be cysteine selective alkylation reagents for ‘near-native’ post-translational modification of protein and peptide substrates.

  氯甲基三唑被证明是半胱氨酸选择性烷基化试剂，用于蛋白质和肽基底物的“近似天然”的翻译后修饰。