methyl (2S)-2,7-diaminoheptanoate

• 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: methyl (2S)-2,7-diaminoheptanoate
• 化学式: C₂₆H₂₃ClNO₄Pol
• 分子量: 174.24
• InChiKey: SGIVSYZIYSEDKA-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2,7-diaminoheptanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-Ac-D-Ala-Arg{Nω-(N-methylcarbamoyl)}-N-methyl-Phe-Asp(OAllyl)-OH
  参考文献：
  名称：

  Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide

  摘要：

  An effective solid phase synthesis of Argifin, providing subsequent access to effective synthesis of analogues, was developed in 13% overall yield, as well as elucidating structure-activity relationships. The novel acyclic peptide 18b, prepared from a synthetic intermediate of Argifin, was found to be 70 times more potent as an inhibitor of Serratia marcescens chitinases B than Argifin itself (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.047
• 作为产物：
  描述：

  2-chlorotrityl chloride polystyrene resin 、 Fmoc-L-天冬氨酸 4-烯丙酯 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl (2S)-2,7-diaminoheptanoate
  参考文献：
  名称：

  ANTICANCER PRODRUG ACTIVATED BY RADIATION OR ULTRAVIOLET TREATMENT AND USE THEREOF

  摘要：

  本发明涉及一种抗癌前药，由乙酰-SEQ ID NO:1肽-连接体-抗癌药物组成。该抗癌前药有效地提供了一种在酸性或碱性环境中不稳定的抗癌药物，例如多柔比星，以前药的形式存在。因此，当在体内注射时，抗癌前药以无毒的不活性形式存在，但在注射后，当存在由辐射或紫外线处理后激活的半胱氨酸蛋白酶时，在目标区域中有效地释放抗癌药物作为活性成分。因此，该抗癌药物对癌细胞表现出选择性抗癌作用，从而最大化治疗效果并最小化化疗的副作用。

  公开号：

  US20130338422A1

文献信息

• ANTICANCER PRODRUG ACTIVATED BY RADIATION OR ULTRAVIOLET TREATMENT AND USE THEREOF
  申请人：Ryu Ju-Hee

  公开号：US20130338422A1

  公开（公告）日：2013-12-19

  The present invention relates to an anticancer prodrug consisting of peptide of acetyl-SEQ ID NO: 1-linker-anticancer drug. The anticancer prodrug effectively provides an anticancer drug unstable in acid or base, such as doxorubicin, in a form of prodrug. Thus, the anticancer prodrug exists as a non-toxic inactive form when administered into the body, but effectively releases the anticancer drug as an active ingredient in the target area in the presence of caspase activated by radiation or UV treatment after administered into the body. Accordingly, the anticancer drug exhibits selective anticancer effects on cancer cells, thereby maximizing the therapeutic effect and minimizing the side-effects of chemotherapy.

  本发明涉及一种抗癌前药，由乙酰-SEQ ID NO:1肽-连接体-抗癌药物组成。该抗癌前药有效地提供了一种在酸性或碱性环境中不稳定的抗癌药物，例如多柔比星，以前药的形式存在。因此，当在体内注射时，抗癌前药以无毒的不活性形式存在，但在注射后，当存在由辐射或紫外线处理后激活的半胱氨酸蛋白酶时，在目标区域中有效地释放抗癌药物作为活性成分。因此，该抗癌药物对癌细胞表现出选择性抗癌作用，从而最大化治疗效果并最小化化疗的副作用。
• Computer-aided rational molecular design of argifin-derivatives with increased inhibitory activity against chitinase B from Serratia marcescens
  作者：Hiroaki Gouda、Toshiaki Sunazuka、Kanami Iguchi、Akihiro Sugawara、Tomoyasu Hirose、Yoshihiko Noguchi、Yoshifumi Saito、Yuichi Yanai、Tsuyoshi Yamamoto、Takeshi Watanabe、Kazuro Shiomi、Satoshi Ōmura、Shuichi Hirono

  DOI：10.1016/j.bmcl.2009.04.013

  日期：2009.5

  Argifin, a novel pentapeptide chitinase inhibitor isolated from Gliocladium fungal culture, is a promising candidate for the development of new fungicides, insecticides, and anti-asthma medications. In this study, we undertook rational molecular design of argifin-derivatives and tested them against chitinase B from Serratia marcescens (SmChiB). The work involved molecular dynamics simulation with explicit water molecules, the molecular docking calculation, and free-energy analysis using the molecular mechanics Poisson-Boltzmann surface area method. The custom-designed derivatives were synthesized via effective solid phase synthesis, developed recently in our laboratory, and their inhibitory activities were measured against SmChiB. Finally, we identified and obtained a derivative which exhibited 28-fold more inhibition than argifin itself, a compound in which the D-Ala(5) of argifin was replaced with D-Leu and the 4-benzylpiperdine was attached to L-Asp(4). (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of myxochelin analogues as antimetastatic agents
  作者：Satoshi Miyanaga、Hiroaki Sakurai、Ikuo Saiki、Hiroyasu Onaka、Yasuhiro Igarashi

  DOI：10.1016/j.bmc.2009.02.040

  日期：2009.4

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.
• Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide
  作者：Toshiaki Sunazuka、Akihiro Sugawara、Kanami Iguchi、Tomoyasu Hirose、Kenichiro Nagai、Yoshihiko Noguchi、Yoshifumi Saito、Tsuyoshi Yamamoto、Hideaki Ui、Hiroaki Gouda、Kazuro Shiomi、Takeshi Watanabe、Satoshi Ōmura

  DOI：10.1016/j.bmc.2009.02.047

  日期：2009.4

  An effective solid phase synthesis of Argifin, providing subsequent access to effective synthesis of analogues, was developed in 13% overall yield, as well as elucidating structure-activity relationships. The novel acyclic peptide 18b, prepared from a synthetic intermediate of Argifin, was found to be 70 times more potent as an inhibitor of Serratia marcescens chitinases B than Argifin itself (c) 2009 Elsevier Ltd. All rights reserved.
• Supramolecular Probes for Assessing Glutamine Uptake Enable Semi-Quantitative Metabolic Models in Single Cells
  作者：Min Xue、Wei Wei、Yapeng Su、Dazy Johnson、James R. Heath

  DOI：10.1021/jacs.5b12187

  日期：2016.3.9

  We describe a supramolecular surface competition assay for quantifying glutamine uptake from single cells. Cy3-labeled cyclodextrins were immobilized on a glass surface as a supramolecular host/FRET donor, and adamantane-BHQ2 conjugates were employed as the guest/quencher. An adamantane-labeled glutamine analog was selected through screening a library of compounds and validated by cell uptake experiments. When integrated onto a single cell barcode chip with a multiplex panel of 15 other metabolites, associated metabolic enzymes, and phosphoproteins, the resultant data provided input for a steady-state model that describes energy potential in single cells and correlates that potential with receptor tyrosine kinase signaling. We utilize this integrated assay to interrogate a dose-dependent response of model brain cancer cells to EGFR inhibition. We find that low-dose (1 mu M erlotinib) drugging actually increases cellular energy potential even as glucose uptake and phosphoprotein signaling is repressed. We also identify new interactions between phosphoprotein signaling and cellular energy processes that may help explain the facile resistance exhibited by certain cancer patients to EGFR inhibitors.