naproxen-D-Phe-D-Phe-D-Lys | 1411587-09-1

• 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: naproxen-D-Phe-D-Phe-D-Lys
• 英文别名: (2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoic acid
• CAS: 1411587-09-1
• 化学式: C₃₈H₄₄N₄O₆
• 分子量: 652.791
• InChiKey: HFPOILKIZVZFQS-AVGVBVFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Fmoc-D-苯丙氨酸 在 2-chlorotrityl chloride polystyrene resin 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 naproxen-D-Phe-D-Phe-D-Lys
  参考文献：
  名称：

  d-Amino Acids Boost the Selectivity and Confer Supramolecular Hydrogels of a Nonsteroidal Anti-Inflammatory Drug (NSAID)

  摘要：

  As systemically used therapeutics for treating acute or chronic pains or inflammations, nonsteroidal anti-inflammatory drugs (NSAIDs) also associate with the adverse gastrointestinal and renal effects and cardiovascular risks. Thus, it is beneficial to develop topical gels that selectively inhibit cyclooxygenase-2 (COX-2) for the management of local inflammation. In this work, we demonstrate that the covalent conjugation of D-amino acids to naproxen (i.e., a NSAID) not only affords supramolecular hydrogelators for the topical gels but also unexpectedly and significantly elevates the selectivity toward COX-2 about 20X at little expense of the activity of naproxen. This work illustrates a previously unexplored approach that employs D-amino acids for the development of functional molecules that have dual or multiple roles and exceptional biostability, which offers a new class of molecular hydrogels of therapeutic agents.

  DOI：

  10.1021/ja310019x

文献信息

• [EN] HYDROGELATORS COMPRISING D-AMINO ACIDS<br/>[FR] COMPOSÉS FORMANT DES HYDROGELS COMPRENANT DES ACIDES AMINÉS D
  申请人：UNIV BRANDEIS

  公开号：WO2014074789A1

  公开（公告）日：2014-05-15

  Described herein are compounds comprising an oligopeptide and a non-steroidal antiinflammatory agent. The compounds self-assemble into supramolecular hydrogels and can be used as topical treatments for inflammatory conditions, such as osteoarthritis. Also described herein are oligopeptides compounds made from D-amino acid residues that form supramolecular hydrogels. The compounds may be functionalized with active agents, such as anticancer therapeutic agents, antiinflammatory agents, or imaging agents, therefore providing new mechanisms for delivery of active agents.

  本文描述了包含寡肽和非甾体抗炎药物的化合物。这些化合物自组装成超分子水凝胶，可用作治疗炎症病症，如骨关节炎的局部治疗。本文还描述了由D-氨基酸残基制成的寡肽化合物，形成超分子水凝胶。这些化合物可以与活性剂（如抗癌治疗剂、抗炎药物或成像剂）功能化，从而提供了传递活性剂的新机制。
• HYDROGELATORS COMPRISING D-AMINO ACIDS
  申请人：BRANDEIS UNIVERSITY

  公开号：US20150306232A1

  公开（公告）日：2015-10-29

  Described herein are compounds comprising an oligopeptide and a non-steroidal antiinflammatory agent. The compounds self-assemble into supramolecular hydrogels and can be used as topical treatments for inflammatory conditions, such as osteoarthritis. Also described herein are oligopeptides compounds made from D-amino acid residues that form supramolecular hydrogels. The compounds may be functionalized with active agents, such as anticancer therapeutic agents, antiinflammatory agents, or imaging agents, therefore providing new mechanisms for delivery of active agents.

  本文描述了包含寡肽和非甾体抗炎药物的化合物。这些化合物自组装成超分子水凝胶，并可用作局部治疗炎症疾病，如骨关节炎。本文还描述了由D-氨基酸残基制成的寡肽化合物，形成超分子水凝胶。这些化合物可与活性剂（如抗癌治疗剂、抗炎剂或成像剂）功能化，因此提供了新的活性剂传递机制。
• <scp>d</scp>-Amino Acids Boost the Selectivity and Confer Supramolecular Hydrogels of a Nonsteroidal Anti-Inflammatory Drug (NSAID)
  作者：Jiayang Li、Yi Kuang、Yuan Gao、Xuewen Du、Junfeng Shi、Bing Xu

  DOI：10.1021/ja310019x

  日期：2013.1.16

  As systemically used therapeutics for treating acute or chronic pains or inflammations, nonsteroidal anti-inflammatory drugs (NSAIDs) also associate with the adverse gastrointestinal and renal effects and cardiovascular risks. Thus, it is beneficial to develop topical gels that selectively inhibit cyclooxygenase-2 (COX-2) for the management of local inflammation. In this work, we demonstrate that the covalent conjugation of D-amino acids to naproxen (i.e., a NSAID) not only affords supramolecular hydrogelators for the topical gels but also unexpectedly and significantly elevates the selectivity toward COX-2 about 20X at little expense of the activity of naproxen. This work illustrates a previously unexplored approach that employs D-amino acids for the development of functional molecules that have dual or multiple roles and exceptional biostability, which offers a new class of molecular hydrogels of therapeutic agents.