H2N-Tyr-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Cys-CO-NH2 | 676362-60-0

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: H2N-Tyr-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Cys-CO-NH2
• 英文别名: H₂N-Tyr-(Arg)₉-Cys-NH₂
• CAS: 676362-60-0
• 化学式: C₆₆H₁₂₅N₃₉O₁₂S
• 分子量: 1689.04
• InChiKey: LNUNTRBJWXNOJG-HDKAIKTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.11
• 重原子数：
  118.0
• 可旋转键数：
  60.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  937.44
• 氢给体数：
  41.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  6'-O-(N-maleimido-β-alanyl)-3'-O-butylfluorescein 、 H2N-Tyr-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Cys-CO-NH2 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-酪氨酸 、 Fmoc-S-三苯甲基-L-半胱氨酸 、 Fmoc-Pbf-L-精氨酸 生成 H2N-Tyr-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Cys-CO-NH2
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016

文献信息

• Fluorogenic approach to evaluating prodrug hydrolysis and stability in live cells
  作者：Xin Chen、Yunzhen Xu、Xiaoxu Li、Shiqi Liao

  DOI：10.1016/j.bmc.2019.01.030

  日期：2019.3

  Fluorescein diester which is conjugated with cell membrane permeable Arg9 peptide was proposed as probe for ester prodrug stability and drug release study in living cells. a-Amino protected D-Val and L-Ala which bear differently hindered side chains were used to afford model diesters of 5-maleimide-fluorescein. Such fluorescein diesters were further conjugated with a Cys containing cell membrane permeable Arg9 peptide via thiol-ene crosslink reaction. The resulted conjugates of fluorescein diester and Arg9 peptide were purified with HPLC and characterized with MALDI-TOF MS. Upon incubation with cultured cells, the fluorescein diesters were delivered into the cells, the following hydrolysis of fluorescein diesters and release of fluorescein inside living cells were observed by monitoring the fluorescence accumulation. Fluorescence microscopic imaging studies of HeLa cells treated with fluorescein L-Ala diester show strong fluorescence accumulation in 30 min indicating fast hydrolysis of fluorescein diester and fluorescein release; in contrast D-Val diester remains stable inside cells evidenced by margin fluorescence formation. Further flowcytometry studies on the fluorescein diester-Arg9 conjugate treated cells show that the hydrolysis t1/2 for L-Ala diester is 15 min. The results also show that Arg9 peptide not only transports the ester probes into cell efficiently but also can retain and concentrate hydrolytic product fluorescein inside cells so that the accumulated fluorescence can be accurately quantified. This fluorogenic probe approach provides feasible applications in dynamic studies on ester prodrug hydrolysis and release, facilitating screening and optimization of prodrug structures in living cell settings.