(2S)-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid | 950831-50-2

• 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-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
• CAS: 950831-50-2
• 化学式: C₃₉H₃₈N₃O₉P
• 分子量: 723.719
• InChiKey: XHYHCCUSRPNVAU-IMKBVMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid 在 acid phosphatase 作用下， 以 水 为溶剂， 反应 2.0h， 生成 Nap-Phe-Phe-Tyr-OH
  参考文献：
  名称：

  用于在水中自组装和形成生物功能超分子水凝胶的多功能小分子基序

  摘要：

  这篇专题文章介绍了新的结构基序（称为“samogen”），它们作为水凝胶剂的构建块，用于分子在水中的自组装，从而产生一系列超分子水凝胶。使用由两个苯丙氨酸残基和一个萘基组成的化合物（也缩写为 NapFF ( 1) 在本文中) 作为 samogens 的一个例子，我们展示了 samogens 将生物活性分子转化为分子水凝胶剂的能力，这些分子水凝胶剂在水中自组装以产生纳米纤维。通过简要总结这些衍生自 samogens 的分子水凝胶的特性和应用（例如，伤口愈合、药物输送、控制细胞命运、分型细菌和催化），我们打算说明小分子水凝胶的基本要求和前景用于化学、材料科学和生物医学领域的应用。

  DOI：

  10.1021/la1020324
• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 Fmoc-O-磷酸基-L-酪氨酸 、 2-萘乙酸 在 哌啶 、 N,N-二异丙基乙胺 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
  参考文献：
  名称：

  Alkaline phosphatase-triggered assembly of etoposide enhances its anticancer effect

  摘要：

  在水凝胶前体1P的协助下，酸性磷酸酶诱导下，磷酸依托泊苷（EP）被组装起来，明显增强了其抗癌功效。

  DOI：

  10.1039/c7cc09365a

文献信息

• Versatile Small-Molecule Motifs for Self-Assembly in Water and the Formation of Biofunctional Supramolecular Hydrogels
  作者：Ye Zhang、Yi Kuang、Yuan Gao、Bing Xu

  DOI：10.1021/la1020324

  日期：2011.1.18

  hydrogelators for molecular self-assembly in water to result in a series of supramolecular hydrogels. Using a compound that consists of two phenylalanine residues and a naphthyl group (also abbreviated as NapFF (1) in this text) as an example of the samogens, we demonstrated the ability of the samogens to convert bioactive molecules into molecular hydrogelators that self-assemble in water to result in nanofibers

  这篇专题文章介绍了新的结构基序（称为“samogen”），它们作为水凝胶剂的构建块，用于分子在水中的自组装，从而产生一系列超分子水凝胶。使用由两个苯丙氨酸残基和一个萘基组成的化合物（也缩写为 NapFF ( 1) 在本文中) 作为 samogens 的一个例子，我们展示了 samogens 将生物活性分子转化为分子水凝胶剂的能力，这些分子水凝胶剂在水中自组装以产生纳米纤维。通过简要总结这些衍生自 samogens 的分子水凝胶的特性和应用（例如，伤口愈合、药物输送、控制细胞命运、分型细菌和催化），我们打算说明小分子水凝胶的基本要求和前景用于化学、材料科学和生物医学领域的应用。
• SYNTHETIC PEPTIDES, ENZYMATIC FORMATION OF PERICELLULAR HYDROGELS/NANOFIBRILS, AND METHODS OF USE
  申请人：BRANDEIS UNIVERSITY

  公开号：US20170037082A1

  公开（公告）日：2017-02-09

  Disclosed are peptides that contain up to about 35 amino acids, including a plurality of aromatic amino acid residues and either (i) an amino acid residue that is phosphorylated or sulfated, or (ii) an amino acid comprising an ester-moiety linked via peptide bond, or both (i) and (ii), wherein the peptide is capable of self-assembly to form nanofibrils in the presence of an enzyme that hydrolyzes the phosphate group, the sulfate group, or the ester-moiety. These peptides are enzymatically responsive hydrogelators, and they can be used to form pericellular hydrogels/nanofibrils upon exposure to target cells that secrete or express a surface bound ectoenzyme having hydrolase activity suitable to induce peptide gelation. These materials, and compositions containing the same, can be used for in vitro and in vivo cellular imaging, treating cancerous conditions, collecting a secretome from a cell upon which the pericellular hydrogels/nanofibrils form, and screening the collected secretome.
• Alkaline phosphatase-triggered assembly of etoposide enhances its anticancer effect
  作者：Sonia Kiran、Zijuan Hai、Zhanling Ding、Lin Wang、Yaling Liu、Huafeng Zhang、Gaolin Liang

  DOI：10.1039/c7cc09365a

  日期：——

  With the assistance of a hydrogelator precursor 1P, etoposide phosphate (EP) was subjected to alkaline phosphatase-triggered assembly which obviously enhanced its anticancer efficacy.

  在水凝胶前体1P的协助下，酸性磷酸酶诱导下，磷酸依托泊苷（EP）被组装起来，明显增强了其抗癌功效。
• <scp>d</scp>-Amino Acids Modulate the Cellular Response of Enzymatic-Instructed Supramolecular Nanofibers of Small Peptides
  作者：Junfeng Shi、Xuewen Du、Dan Yuan、Jie Zhou、Ning Zhou、Yibing Huang、Bing Xu

  DOI：10.1021/bm5010355

  日期：2014.10.13

  Peptides made of d-amino acids, as the enantiomer of corresponding l-peptides, are able to resist proteolysis. It is, however, unclear or much less explored whether or how d-amino acids affect the cellular response of supramolecular nanofibers formed by enzyme-triggered self-assembly of d-peptides. In this work, we choose a cell compatible molecule, Nap-l-Phe-l-Phe-l-pTyr (LLL-1P), and systematically replace the l-amino acids in this tripeptidic precursor or its hydrogelator by the corresponding d-amino acid(s). The replacement of even one d-amino acid in this tripeptidic precursor increases its proteolytic resistance. The results of static light scattering and TEM images show the formation of nanostructures upon the addition of alkaline phosphatase, even at concentrations below the minimum gelation concentration (mgc). All these isomers are able to form ordered nanostructures and exhibit different morphologies. According to the cell viability assay on these stereochemical isomers, cells exhibit drastically different responses to the enantiomeric precursors, but almost same responses to the enantiomeric hydrogelators. Furthermore, the different cellular responses of LLL-1P and DDD-1P largely originate from the ecto-phosphatases catalyzed self-assembly of DDD-1 on the surface of cells. Therefore, this report not only illustrates a new way for tailoring the properties of supramolecular assemblies, but also provides new insights to answering the fundamental question of how mammalian cells respond to enzymatic formation of nanoscale supramolecular assemblies (e.g., nanofibers) of d-peptides.