(4S,7S,10S,13S,16S,19S)-4-(((S)-1-amino-6-(6-hydrazineyl-6-oxohexanamido)-1-oxohexan-2-yl)carbamoyl)-7-(2-carboxyethyl)-16,19-diisopropyl-10,13-dimethyl-6,9,12,15,18,21-hexaoxo-5,8,11,14,17,20-hexaazahexatriacontanoic acid | 1321803-61-5

• 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: (4S,7S,10S,13S,16S,19S)-4-(((S)-1-amino-6-(6-hydrazineyl-6-oxohexanamido)-1-oxohexan-2-yl)carbamoyl)-7-(2-carboxyethyl)-16,19-diisopropyl-10,13-dimethyl-6,9,12,15,18,21-hexaoxo-5,8,11,14,17,20-hexaazahexatriacontanoic acid
• CAS: 1321803-61-5
• 化学式: C₅₄H₉₇N₁₁O₁₄
• 分子量: 1124.43
• InChiKey: JLIIKHATGMMPKO-ZUUNZGCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  79.0
• 可旋转键数：
  46.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  405.61
• 氢给体数：
  13.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  萘丁美酮 、 (4S,7S,10S,13S,16S,19S)-4-(((S)-1-amino-6-(6-hydrazineyl-6-oxohexanamido)-1-oxohexan-2-yl)carbamoyl)-7-(2-carboxyethyl)-16,19-diisopropyl-10,13-dimethyl-6,9,12,15,18,21-hexaoxo-5,8,11,14,17,20-hexaazahexatriacontanoic acid 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Drug release from hydrazone-containing peptide amphiphiles

  摘要：

  在肽表面活性剂中研究了水解性可降解的肼酮，作为从纳米纤维凝胶中释放药物纳布美特的可降解连接物。将新化合物三-Boc-肼基癸二酸加入到赖氨酸ε-氨基上，可以精确地在肽序列中放置肼基。

  DOI：

  10.1039/c1cc12570b

文献信息

• Nanostructure-templated control of drug release from peptide amphiphile nanofiber gels
  作者：John B. Matson、Christina J. Newcomb、Ronit Bitton、Samuel I. Stupp

  DOI：10.1039/c2sm07420f

  日期：——

  High aspect ratio peptide nanofibers have potential as biodegradable vehicles for drug delivery. We report here the synthesis of four self-assembling peptide amphiphiles (PAs) containing a lysine ε-amine-derivatized hydrazide that was systematically placed at different positions along the backbone of the peptide sequence C16V2A2E2 (where C16 = palmitic acid). Hydrazones were formed from each hydrazide by condensation with the solvatochromic dye 6-propionyl-2-dimethylaminonaphthalene (Prodan), which is typically used to probe cell membranes. All four compounds were found to self-assemble into nanofibers, and Prodan release was measured from filamentous gels prepared by screening PA charges with divalent cations. Near zero-order release kinetics were observed for all nanofibers, but release half-lives differed depending on the position of the fluorophore in the PA sequence. Dye release kinetics were rationalized through the use of cryogenic transmission electron microscopy, small-angle X-ray scattering, fluorescence spectroscopy, fluorescence anisotropy, circular dichroism, and partition coefficient calculations. Relative release rates were found to correlate directly with fluorophore mobility, which varied inversely with packing density, degree of order in the hydrophobic PA core, and the β-sheet character of the peptide.

  高长径比肽纳米纤维具有作为药物输送的生物可降解载体的潜力。我们在此报告了四种自组装肽两亲物 (PA) 的合成，其中含有赖氨酸 ε-胺衍生的酰肼，该酰肼被系统地放置在肽序列 C16V2A2E2（其中 C16 = 棕榈酸）主链的不同位置。每种酰肼通过与溶剂化显色染料 6-丙酰基-2-二甲氨基萘 (Prodan) 缩合形成腙，该染料通常用于探测细胞膜。所有四种化合物都被发现自组装成纳米纤维，并且通过用二价阳离子筛选 PA 电荷制备的丝状凝胶测量了 Prodan 的释放。所有纳米纤维均观察到接近零级的释放动力学，但释放半衰期因荧光团在 PA 序列中的位置而异。通过使用低温透射电子显微镜、小角 X 射线散射、荧光光谱、荧光各向异性、圆二色性和分配系数计算，染料释放动力学合理化。研究发现相对释放速率与荧光团迁移率直接相关，而荧光团迁移率与堆积密度、疏水性 PA 核心的有序程度以及肽的 β 片层特征成反比。