norbiotinamine trifluoroacetate | 1206708-71-5

• 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
• 英文名称: norbiotinamine trifluoroacetate
• 英文别名: norbiotinamine
• CAS: 1206708-71-5
• 化学式: C₂HF₃O₂*C₉H₁₇N₃OS
• 分子量: 329.343
• InChiKey: RMSMGAWLNGHKHG-WQYNNSOESA-N

物化性质

• 熔点：
  93-94 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  104.45
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  norbiotinamine trifluoroacetate 在 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.25h， 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 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成 norbiotinamine trifluoroacetate
  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

文献信息

• [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。
• Synthesis of labeled meropenem for the analysis of M. tuberculosis transpeptidases
  作者：David B. Kastrinsky、Clifton E. Barry

  DOI：10.1016/j.tetlet.2009.10.124

  日期：2010.1

  A concise synthesis of C-14 labeled meropenem prepared from C-14 dimethylamine hydrochloride is described. Using a similar reaction sequence, the meropenem nucleus was also attached to biotin providing a probe for protein interaction studies. Published by Elsevier Ltd.