naproxen-D-Phe-D-Phe-D-Lys-D-Tyr phosphate | 1411591-36-0

• 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-D-Tyr phosphate
• 英文别名: (2R)-2-[[(2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
• CAS: 1411591-36-0
• 化学式: C₄₇H₅₄N₅O₁₁P
• 分子量: 895.946
• InChiKey: DUIJYMOSTNDXCV-VAAOUYGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  256
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  naproxen-D-Phe-D-Phe-D-Lys-D-Tyr phosphate 在 phosphatase 作用下， 生成 naproxen-D-Phe-D-Phe-D-Lys-D-Tyr
  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
• 作为产物：
  描述：

  萘普生 在 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 naproxen-D-Phe-D-Phe-D-Lys-D-Tyr phosphate
  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

• <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.