4-(1-芘基)丁酰-phe-oh | 199612-75-4

• 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
• 中文名称: 4-(1-芘基)丁酰-phe-oh
• 英文名称: N-[4(1-pyrene)butyroyl]-L-phenylalanine
• 英文别名: N-(1-Oxo-4-(1-pyrenyl)butyl)-L-phenylalanine；(2S)-3-phenyl-2-(4-pyren-1-ylbutanoylamino)propanoic acid
• CAS: 199612-75-4
• 化学式: C₂₉H₂₅NO₃
• 分子量: 435.522
• InChiKey: DPTMGBIKSPWCNS-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-芘基)丁酰-phe-oh 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine
  参考文献：
  名称：

  Delivery of Floxuridine Derivatives to Cancer Cells by Water-Soluble Organometallic Cages

  摘要：

  The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene (pPr(i)C(6)H(4)Me) ruthenium building blocks and 2,5-dioxydo-1,4-benzoquinonato (dobq) or 5,8-dioxydo-1,4-naphthoquinonato (donq) bridges, in the presence of a pyrenyl-nucleoside derivatives (pyreneR),. affords the triangular prismatic host guest compounds [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(dobq)(3)](6+) ([(pyrene-R)C1](6+)) and [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(donq)(3)](6+) ([(pyrene-R)C2](6+)), respectively. The inclusion of six monosubstituted pyrenyl-nucleosides (pyrene-R1 = 5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R2 = 5-fluoro-5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R3 = 5'-{N-[1-oxo-4-(1-pyrenyl)butyl]glycyl}-2'-deoxyuridine, pyrene-R4 = 5-fluoro-5'-{N[1-oxo-4-(1-pyrenyl)butyl]-glycyl}2'-deoxyuridine, pyrene-R5 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyvuridine, pyrene-R6 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine) has been accomplished. The carceplex nature of [(pyrene-R)C1](6+) with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)C2](6+) was studied in solution by NMR techniques. In contrast to the floxuridine compounds used in the clinic, the host-guest complexes are highly water-soluble. Consequently, the cytotoxicities of these water-soluble compounds have been established using human ovarian A2780 and A2780cisR cancer cells. All the host guest systems are more cytotoxic than the empty cages alone [1][CF3SO3](6) (IC50 = 23 mu M) and [2][CF3SO3](6) (IC50 = 10 mu M), the most active compound [pyrene-R4C1][CF3SO3](6) being 2 orders of magnitude more cytotoxic (IC50 = 0.3 mu M) on these human ovarian cancer cell lines (A2780 and A2780cisR).

  DOI：

  10.1021/bc200472n
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-(1-芘基)丁酰-phe-oh
  参考文献：
  名称：

  Delivery of Floxuridine Derivatives to Cancer Cells by Water-Soluble Organometallic Cages

  摘要：

  The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene (pPr(i)C(6)H(4)Me) ruthenium building blocks and 2,5-dioxydo-1,4-benzoquinonato (dobq) or 5,8-dioxydo-1,4-naphthoquinonato (donq) bridges, in the presence of a pyrenyl-nucleoside derivatives (pyreneR),. affords the triangular prismatic host guest compounds [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(dobq)(3)](6+) ([(pyrene-R)C1](6+)) and [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(donq)(3)](6+) ([(pyrene-R)C2](6+)), respectively. The inclusion of six monosubstituted pyrenyl-nucleosides (pyrene-R1 = 5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R2 = 5-fluoro-5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R3 = 5'-{N-[1-oxo-4-(1-pyrenyl)butyl]glycyl}-2'-deoxyuridine, pyrene-R4 = 5-fluoro-5'-{N[1-oxo-4-(1-pyrenyl)butyl]-glycyl}2'-deoxyuridine, pyrene-R5 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyvuridine, pyrene-R6 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine) has been accomplished. The carceplex nature of [(pyrene-R)C1](6+) with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)C2](6+) was studied in solution by NMR techniques. In contrast to the floxuridine compounds used in the clinic, the host-guest complexes are highly water-soluble. Consequently, the cytotoxicities of these water-soluble compounds have been established using human ovarian A2780 and A2780cisR cancer cells. All the host guest systems are more cytotoxic than the empty cages alone [1][CF3SO3](6) (IC50 = 23 mu M) and [2][CF3SO3](6) (IC50 = 10 mu M), the most active compound [pyrene-R4C1][CF3SO3](6) being 2 orders of magnitude more cytotoxic (IC50 = 0.3 mu M) on these human ovarian cancer cell lines (A2780 and A2780cisR).

  DOI：

  10.1021/bc200472n

文献信息

• Pyrene-Based Fluorescent Ambidextrous Gelators: Scaffolds for Mechanically Robust SWNT-Gel Nanocomposites
  作者：Deep Mandal、Tanmoy Kar、Prasanta Kumar Das

  DOI：10.1002/chem.201303401

  日期：2014.1.27

  successful integration of the SWNTs within the gel. The prepared hydro‐ and organogels along with their SWNT‐integrated nanocomposites are thermoreversible in nature. The supramolecular morphologies of the dried gels and SWNT–gel nanocomposites have been studied by transmission electron microscopy, fluorescence microscopy and polarising optical microscopy, which confirmed the presence of three‐dimensional

  随着超分子软材料的发展迅速，能够通过同一结构支架固定水和有机溶剂的低分子量胶凝剂（LMWG）的例子非常有限。在本文中，我们报告了基于of的基于肽的灵巧胶凝剂（AGs）的开发，该胶凝剂具有有效胶凝有机和水性溶剂的能力。在某些酸性pH值（pH 2.0-4.0）下，这些胶凝剂的有机和水凝胶效率在各种有机溶剂中为0.7-1.1％w / v，在水中为0.5-5％w / v。此外，首次将AG用于制备在水凝胶和有机凝胶基质中包含单壁碳纳米管（SWNT）的软纳米复合材料。不同的非共价相互作用的影响，例如氢键，自组装凝胶中的疏水，π-π和范德华相互作用已通过圆二色性，FTIR，可变温度NMR，二维NOESY和发光光谱进行了详细研究。有趣的是，结构中of部分的存在使这些AG具有固有的荧光性，将SWNT成功整合到凝胶中后将其淬灭。制备的水凝胶和有机凝胶以及与SWNT集成的纳米复合材料本质上是可热逆的。已通过透射
• Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3‐Based Whole‐Cell Biocatalyst
  作者：Masayuki Karasawa、Kai Yonemura、Joshua Kyle Stanfield、Kazuto Suzuki、Osami Shoji

  DOI：10.1002/anie.202111612

  日期：2022.2.7

  cellular uptake of amino acid derivatives as decoy molecules has been developed. Co-expression of the OmpF mutant with wild-type P450BM3 enabled the Escherichia coli-based whole-cell biocatalyst to efficiently oxidise benzene with the assistance of decoy molecules. Moreover, whole-cell-catalysed stereoselective hydroxylation was achieved by changing the decoy molecule.

  已经开发了一种外膜蛋白 F (OmpF) 的工程变体，它有助于细胞摄取氨基酸衍生物作为诱饵分子。OmpF 突变体与野生型 P450BM3 的共表达使基于大肠杆菌的全细胞生物催化剂能够在诱饵分子的帮助下有效地氧化苯。此外，通过改变诱饵分子实现了全细胞催化的立体选择性羟基化。
• Single amino acid based thixotropic hydrogel formation and pH-dependent morphological change of gel nanofibers
  作者：Jayanta Nanda、Abhijit Biswas、Arindam Banerjee

  DOI：10.1039/c3sm27050e

  日期：——

  A single amino acid (phenylalanine) based pyrene conjugated low molecular weight hydrogelator has been discovered. This amino acid derivative has been found to form hydrogels in a wide range of aqueous solutions of pH 7.46–14 and the estimated minimum gelation concentration (MGC) in phosphate buffer solution at physiological pH 7.46 is 0.037% (w/v) i.e. 0.85 mM. A transparent hydrogel has been produced in the pH range (7.46–10.5), while a translucent hydrogel has been formed at higher pH. The hydrogel has been characterized by field emission scanning electron microscopy (FE-SEM), fluorescence microscopy, differential scanning calorimetry (DSC), circular dichroism (CD), X-ray diffraction (XRD) and rheological studies. A distinct morphological change of the gel nanofibers from helical to tape-like morphology has been noticed in the FE-SEM studies with an increase in pH. These observations have been supported by a significant decrease of the CD signals and different XRD patterns found with the increase in pH. Interestingly, this hydrogel shows a pH dependent thixotropic property. The thixotropic property of the hydrogel has been examined using rheological experiments. This thixotropic property of the hydrogel has been utilized for the encapsulation of vitamin B12 and an anticancer drug, doxorubicin, in the hydrogel matrix without any heating–cooling cycle and sustained release of these bioactive molecules has been studied at physiological temperature (37 °C) and pH (7.46) over a period of about 3 days.

  我们发现了一种基于单一氨基酸（苯丙氨酸）的芘共轭低分子量水凝胶剂。这种氨基酸衍生物可在 pH 值为 7.46-14 的各种水溶液中形成水凝胶，在生理 pH 值为 7.46 的磷酸盐缓冲溶液中的最小凝胶浓度（MGC）估计为 0.037%（w/v），即 0.85 mM。在 pH 值（7.46-10.5）范围内产生了透明的水凝胶，而在较高的 pH 值范围内则形成了半透明的水凝胶。通过场发射扫描电子显微镜（FE-SEM）、荧光显微镜、差示扫描量热仪（DSC）、圆二色仪（CD）、X 射线衍射（XRD）和流变学研究对该水凝胶进行了表征。在 FE-SEM 研究中发现，随着 pH 值的增加，凝胶纳米纤维的形态发生了明显的变化，从螺旋状变为胶带状。随着 pH 值的升高，CD 信号明显减弱，XRD 图谱也发生了变化，这也证实了上述观察结果。有趣的是，这种水凝胶显示出与 pH 值相关的触变性能。水凝胶的触变性能已通过流变实验进行了检测。利用水凝胶的这种触变性能，在水凝胶基质中封装了维生素 B12 和抗癌药物多柔比星，无需任何加热-冷却循环，并研究了这些生物活性分子在生理温度（37 °C）和 pH 值（7.46）下持续释放约 3 天的情况。
• A tryptophan-containing fluoroionophore sensor with high sensitivity to and selectivity for lead ion in water
  作者：Li-Jun Ma、Yi-Fu Liu、Yuqing Wu

  DOI：10.1039/b604623a

  日期：——

  We report herein a fluoroionophore sensor derivated from tryptophan that shows high sensitivity (detection limit up to 0.15 microM) and specific selectivity for lead ion (Pb2+) over Ca2+, Cd2+, Co2+, Cr3+, Cu2+, K+, Mg2+, Na+, Fe2+, Mn2+, Ni2+ and Zn2+ in aqueous solution.

  我们在此报告了一种色氨酸衍生的氟离子传感器，该传感器在Ca2 +，Cd2 +，Co2 +，Cr3 +，Cu2 +，K +，Mg2 +，Na +，Fe2 +，Mn2 +上显示出高灵敏度（检测限高达0.15 microM）和铅离子（Pb2 +）的特异性选择性，Ni2 +和Zn2 +的水溶液。
• Phenylboronic Acid Appended Pyrene-Based Low-Molecular-Weight Injectable Hydrogel: Glucose-Stimulated Insulin Release
  作者：Deep Mandal、Subhra Kanti Mandal、Moumita Ghosh、Prasanta Kumar Das

  DOI：10.1002/chem.201501170

  日期：2015.8.17

  glucose‐responsive swelling of the hydrogel. A rheological study indicated the loss of the rigidity of the native gel in the presence of glucose. Hence, the glucose‐induced swelling of the hydrogel was exploited in the controlled release of insulin from the hydrogel. The insulin‐loaded hydrogel showed thixotropic self‐recovery property, which hoisted it as an injectable soft composite. Encouragingly, the

  合成了含pyr的苯基硼酸（PBA）功能化的低分子量水凝胶剂，旨在开发葡萄糖敏感的胰岛素释放。胶凝剂在pH值为8–12的缓冲水溶液中显示出吸收溶剂的能力，而胶凝剂的钠盐在生理pH 7.4时形成了水凝胶，最小胶凝浓度（MGC）为5 mg mL -1。通过使用显微镜和光谱技术，包括透射电子显微镜，FTIR，UV / Vis，发光和CD光谱，研究了这种热可逆水凝胶的聚集行为。这些研究表明，氢键，π-π堆积和范德华相互作用是自组装凝胶化的关键因素。明智地将胶凝剂中对二醇敏感的PBA部分和the单元用于在生理pH值下微量荧光的荧光检测。通过扫描电子显微镜研究了由于添加葡萄糖而引起的凝胶的形态变化，这表明水凝胶对葡萄糖的响应性溶胀。流变学研究表明在葡萄糖存在下天然凝胶的刚性丧失。因此，葡萄糖诱导的水凝胶溶胀被用于胰岛素从水凝胶中的受控释放。装有胰岛素的水凝胶显示出触变性的自我恢复特性，将其提升为可注射的