(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]-5-(3-azidopropylamino)-5-oxopentanoic acid

• 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: (2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]-5-(3-azidopropylamino)-5-oxopentanoic acid
• 化学式: C₂₂H₂₅N₁₁O₅
• 分子量: 523.511
• InChiKey: VQCBYAXTKCZLQI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  215
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-叠氮基丙胺 、 folate 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]-5-(3-azidopropylamino)-5-oxopentanoic acid
  参考文献：
  名称：

  Asati, Atul; Santra, Santimukul; Kaittanis, Charalambos, Angewandte Chemie - International Edition, 2009, vol. 48, p. 2308 - 2312

  摘要：

  DOI：

文献信息

• The facile synthesis of multifunctional PAMAM dendrimer conjugates through copper-free click chemistry
  作者：Baohua Huang、Jolanta F. Kukowska-Latallo、Shengzhuang Tang、Hong Zong、Kali B. Johnson、Ankur Desai、Chris L. Gordon、Pascale R. Leroueil、James R. Baker

  DOI：10.1016/j.bmcl.2012.03.052

  日期：2012.5

  The facile conjugation of three azido modified functionalities, namely a therapeutic drug (methotrexate), a targeting moiety (folic acid), and an imaging agent (fluorescein) with a G5 PAMAM dendrimer scaffold with cyclooctyne molecules at the surface through copper-free click chemistry is reported. Mono-, di-, and tri-functional PAMAM dendrimer conjugates can be obtained via combinatorial mixing of

  通过无铜点击化学，将三种叠氮基修饰功能（即治疗药物（甲氨蝶呤）、靶向部分（叶酸）和显像剂（荧光素））与表面具有环辛炔分子的 G5 PAMAM 树枝状聚合物支架轻松缀合被报道。单、二和三官能的 PAMAM 树枝状聚合物缀合物可以通过同时或顺序地与树枝状聚合物平台组合混合不同的叠氮基修饰官能团来获得。初步流式细胞术结果表明叶酸靶向纳米颗粒与 KB 细胞有效结合。
• Folate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery
  作者：Zhigang Yang、Jae Hong Lee、Hyun Mi Jeon、Ji Hye Han、Nayoung Park、Yanxia He、Hyunseung Lee、Kwan Soo Hong、Chulhun Kang、Jong Seung Kim

  DOI：10.1021/ja405372k

  日期：2013.8.7

  A series of heptamethine cyanine (1-3) derivatives bearing a carbamate ethyl disulfide group and gemcitabine, an anticancer drug, have been newly synthesized. Their disulfide bonds are readily cleaved by various thiols including glutathione, to result in a subsequent decomposition of the carbamate into amine followed by release of the active gemcitabine, which can be monitored by the fluorescence changes. In the biological experiment, prodrug 1 is preferentially up-taken by folate-positive KB cells over folate-negative A549 cells via receptor-mediated endocytosis to release gemcitabine causing cell death and to emit fluorescence in endoplasmic reticulum. Moreover, it is selectively accumulated in the KB cells which were treated to mice by dorsal subcutaneous injection. This drug delivery system is a new theranostic agent, wherein both therapeutic effect and drug uptake can be easily monitored at the subcellular level, by in vivo and in vitro fluorescence imaging.
• MODIFICATION OF BIOLOGICAL TARGETING GROUPS FOR THE TREATMENT OF CANCER
  申请人：Breitenkamp Kurt

  公开号：US20090110662A1

  公开（公告）日：2009-04-30

  The present invention relates to the field of polymer chemistry and more particularly to click-functionalized targeting compounds and methods for using the same.
• [EN] MODIFICATION OF BIOLOGICAL TARGETING GROUPS FOR THE TREATMENT OF CANCER<br/>[FR] MODIFICATION DES GROUPES DE CIBLAGE BIOLOGIQUES POUR LE TRAITEMENT DU CANCER
  申请人：INTEZYNE TECHNOLOGIES INC

  公开号：WO2008134761A2

  公开（公告）日：2008-11-06

  [EN] The present invention relates to the field of polymer chemistry and more particularly to click- functionalized targeting compounds and methods for using the same.
  [FR] La présente invention concerne le domaine de la chimie des polymères et, plus particulièrement, les composés de ciblage fonctionnalisés par clic et des procédés pour les utiliser.