γ-N-{2-[2-(2-aminoethoxy)ethoxy]ethylcarbamate}folic acid | 1135617-24-1

• 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: γ-N-{2-[2-(2-aminoethoxy)ethoxy]ethylcarbamate}folic acid
• 英文别名: (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethylamino]-5-oxopentanoic acid
• CAS: 1135617-24-1
• 化学式: C₃₀H₄₁N₉O₉
• 分子量: 671.71
• InChiKey: AQCMZVQWEROCHG-NRFANRHFSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  258
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  γ-N-{2-[2-(2-aminoethoxy)ethoxy]ethylcarbamate}folic acid 在 三氟乙酸 作用下， 反应 2.0h， 生成 Folate-PEG2-amine
  参考文献：
  名称：

  Novel ^99mTc radiolabeled folate complexes with PEG linkers for FR-positive tumor imaging: synthesis and biological evaluation

  摘要：

  这种新型复合物^99mTc(FA-PEG2-HYNIC)(tricine/TPPTS)在靶向叶酸受体阳性肿瘤120分钟后明显可视化，突显其作为有效的叶酸受体肿瘤成像剂的潜力。

  DOI：

  10.1039/c4ra03564j
• 作为产物：
  描述：

  folate 、 2-(2-(2-氨基乙氧基)乙氧基)乙基氨基甲酸叔丁酯 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 γ-N-{2-[2-(2-aminoethoxy)ethoxy]ethylcarbamate}folic acid
  参考文献：
  名称：

  Novel ^99mTc radiolabeled folate complexes with PEG linkers for FR-positive tumor imaging: synthesis and biological evaluation

  摘要：

  这种新型复合物^99mTc(FA-PEG2-HYNIC)(tricine/TPPTS)在靶向叶酸受体阳性肿瘤120分钟后明显可视化，突显其作为有效的叶酸受体肿瘤成像剂的潜力。

  DOI：

  10.1039/c4ra03564j

文献信息

• NOVEL CHLORIN E6-FOLIC ACID CONJUGATE, PREPARATION METHOD THEREOF, AND A PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF CANCER COMPRISING THE SAME
  申请人：Park Kye Shin

  公开号：US20120059018A1

  公开（公告）日：2012-03-08

  The present invention relates to a novel chlorin e6-folic acid conjugate, a preparation method thereof, and a pharmaceutical composition for the treatment of cancer comprising the same, and more particularly, to a novel compound prepared by linking chlorin e6 to folic acid, which effectively produces singlet oxygen in various media and has much better tumor selectivity than the known porphyrin-based photosensitizers, thereby being used effectively in photodynamic therapy for malignant tumors, a preparation method thereof, and a pharmaceutical composition for photodynamic treatment of solid tumors comprising the compound.

  本发明涉及一种新型的氯原卟啉E6-叶酸共轭物，其制备方法以及包含该共轭物的用于治疗癌症的药物组合物。更具体地说，本发明涉及一种由氯原卟啉E6与叶酸连接而成的新化合物，该化合物在各种介质中能够有效产生单线态氧，并且比已知的基于卟啉的光敏剂具有更好的肿瘤选择性，因此在恶性肿瘤的光动力治疗中能够有效使用，同时还涉及该化合物的制备方法以及用于光动力治疗实体肿瘤的药物组合物。
• Modular Integration of Upconverting Nanocrystal-Dendrimer Composites for Folate Receptor-Specific NIR Imaging and Light-Triggered Drug Release
  作者：Pamela T. Wong、Dexin Chen、Shengzhuang Tang、Sean Yanik、Michael Payne、Jhindan Mukherjee、Alexa Coulter、Kenny Tang、Ke Tao、Kang Sun、James R. Baker、Seok Ki Choi

  DOI：10.1002/smll.201501575

  日期：2015.12

  nanocrystals (UCNs) display near‐infrared (NIR)‐responsive photoluminescent properties for NIR imaging and drug delivery. The development of effective strategies for UCN integration with other complementary nanostructures for targeting and drug conjugation is highly desirable. This study reports on a core/shell‐based theranostic system designed by UCN integration with a folate (FA)‐conjugated dendrimer for tumor

  上转换纳米晶体（UCN）显示用于近红外（NIR）成像和药物递送的近红外（NIR）响应光致发光特性。非常需要开发有效的策略，以将UCN与其他互补纳米结构整合以靶向和药物结合。这项研究报告了一种通过UCN与叶酸（FA）缀合的树枝状大分子结合以靶向肿瘤并以光笼阿霉素为细胞毒剂而设计的基于核/壳的治疗方法。描述了两种类型的UCN（NaYF 4：Yb / Er（或Yb / Tm）；直径=≈50至54 nm），每种类型在NIR（980 nm）激发时显示出不同的发射特性。通过将光笼中的阿霉素（ONB‐Dox）和多价FA共轭聚酰胺型聚酰胺（PAMAM）树状大分子G5（FA）共价连接，可以对UCN进行表面修饰。6准备UCN @（ONB-Dox）（G5FA）。仅使用G5（FA）6树状聚合物进行的表面等离子体共振实验显示出与叶酸结合蛋白的纳摩尔结合亲和力（K D = 5.9×10 -9 m）。这种树状大分子的结合与FAR阳性KB癌细胞在体外对UCN
• Suppressing Unspecific Cell Uptake for Targeted Delivery Using Hydroxyethyl Starch Nanocapsules
  作者：Grit Baier、Daniela Baumann、Jörg Max Siebert、Anna Musyanovych、Volker Mailänder、Katharina Landfester

  DOI：10.1021/bm300653v

  日期：2012.9.10

  Synthesizing nanocarriers with stealth properties and delivering a "payload" to the particular organ remains a big challenge but is the prime prerequisite for any in vivo application. As a nontoxic alternative to the modification by poly(ethylene glycol) PEG, we describe the synthesis of cross-linked hydroxyethyl starch (HES, M-w 200,000 g/mol) nanocapsules with a size range of 170-300 nm, which do not show nonspecific uptake into cells. The specific uptake was shown by coupling a folic acid conjugate as a model targeting agent onto the surface of the nanocapsules, because folic acid has a high affinity to a variety of human carcinoma cell lines which overexpress the folate receptor on the cell surface. The covalent binding of the folic acid conjugate onto HES capsules was confirmed by FTIR and NMR spectroscopy. The coupling efficiency was determined using fluorescence spectroscopy. The specific cellular uptake of the HES nanocapsules after folic acid coupling into the folate-receptor presenting cells was studied by confocal laser scanning microscopy (CLSM) and flow cytometry.