(2S)-2-[[(2S)-2-[[2-[[2-(1-adamantyl)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid | 895167-17-6

• 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: (2S)-2-[[(2S)-2-[[2-[[2-(1-adamantyl)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
• CAS: 895167-17-6
• 化学式: C₄₇H₆₅N₅O₁₁S
• 分子量: 908.126
• InChiKey: PARFIBKLUGNNBD-FNXMPSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  64
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  253
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S)-2-[[2-[[2-(1-adamantyl)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.5h， 生成 (S)-2-[(S)-2-(2-{2-Adamantan-1-yl-2-[(S)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid
  参考文献：
  名称：

  Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity

  摘要：

  A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma ( HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-GlyGly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing CRR-dialkylated glycine (Aaa1, 1) or CR-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.

  DOI：

  10.1021/jm051026+
• 作为产物：
  描述：

  Adamantan-1-yl-[(S)-2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-acetic acid 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成 (2S)-2-[[(2S)-2-[[2-[[2-(1-adamantyl)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
  参考文献：
  名称：

  Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity

  摘要：

  A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma ( HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-GlyGly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing CRR-dialkylated glycine (Aaa1, 1) or CR-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.

  DOI：

  10.1021/jm051026+

文献信息

• Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity
  作者：Štefica Horvat、Kata Mlinarić-Majerski、Ljubica Glavaš-Obrovac、Andreja Jakas、Jelena Veljković、Saška Marczi、Goran Kragol、Maja Roščić、Marija Matković、Andrea Milostić-Srb

  DOI：10.1021/jm051026+

  日期：2006.6.1

  A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma ( HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-GlyGly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing CRR-dialkylated glycine (Aaa1, 1) or CR-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.