Boc-Arg(NO)_2-Gly | 90600-39-8

• 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: Boc-Arg(NO)_2-Gly
• 英文别名: Boc-Arg(NO2)-Gly-OH；2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]acetic acid
• CAS: 90600-39-8
• 化学式: C₁₃H₂₄N₆O₇
• 分子量: 376.37
• InChiKey: XTKGWBJWVFKZPY-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  201
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-Arg(NO)_2-Gly 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-3-(2-((S)-2-amino-5-guanidinopentanamido)acetamido)-4-(octadecyloxy)-4-oxobutanoic acid
  参考文献：
  名称：

  RGD-fatty alcohol-modified docetaxel liposomes improve tumor selectivity in vivo

  摘要：

  The tripeptide arginine-glycine-aspartate (RGD) was conjugated with various fatty alcohols to obtain RGDOC(n)H(2n) + 1 (n = 8, 10, 12, 14, 16, 18), which were incorporated into the bilayer of docetaxel liposomes to improve their tumor specificity. The fatty alcohols were accepted as linking groups to insert the tetrapeptide RGDX (X = amino acid) into the bilayer of liposomes. RGDX was previously shown to be a potent ligand to target tumor cell-surface integrin receptors, whereas RGD was not shown to have this ability. We hypothesized that RGD-fatty alcohol conjugates lacking the fourth amine X can guide liposomes to tumors without reducing their binding affinity to integrins. Antitumor activity, pharmacokinetics and biodistribution studies were evaluated in mice inoculated with S180 sarcoma. Compared with unmodified liposomes, RGD-fatty alcohol-modified liposomes successfully delivered significantly more docetaxel to tumors, which led to significant tumor weight loss and increased tumor docetaxel concentrations accompanied by reduced liver accumulation. Improved affinity of RGD-fatty alcohols to integrins was also confirmed on A375 cell model. Further comparisons among the tumor-targeting capacities of liposomes containing RGD-fatty alcohols, RGDF-fatty alcohols and RGDV-fatty acids demonstrated that RGD-fatty alcohols were as effective as the other two tetrapeptide derivatives. Therefore, a simplified tumor-targeting delivery system using RGD-fatty alcohols was developed. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2014.04.001
• 作为产物：
  描述：

  N-Boc-N'-硝基-L-精氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Arg(NO)_2-Gly
  参考文献：
  名称：

  新型四肽，RGDF，介导的肿瘤特异性脂质体阿霉素（DOX）制剂

  摘要：

  精氨酸-甘氨酸-天冬氨酸（RGD）已显示出对在肿瘤细胞中过度表达的整联蛋白具有很强的亲和力，尤其是在肿瘤浸润，血管生成和转移过程中。在其他工作的基础上，已设计并研究了一种新颖的四肽精氨酸-甘氨酸-天冬氨酸-苯基苯胺（RGDF）作为将脂质体阿霉素（DOX）导向肿瘤细胞的归巢装置。为了将RGDF掺入脂质体DOX制剂中，将RGDF与三种不同的脂肪醇偶联，以获得RGDF-脂肪醇偶联物。合成甘氨酸-甘氨酸-天冬氨酸-苯基苯胺（GGDF）-月桂醇缀合物作为阴性对照。RGDF-脂肪醇共轭物（RGDFO（CH 2）n CH 3）和GGDF-月桂醇共轭物（L-GGDFC12-DOX）掺入的脂质体制剂，首先使用膜分散法制备脂质体，然后使用跨膜pH梯度法上样DOX。由于两亲性质，RGDF–或GGDF–脂肪醇结合物很容易掺入脂质体，其脂肪烷基链插入脂质体双层脂肪酰基链之间，而亲水肽部分（RGDF或GGDF）锚定在

  DOI：

  10.1021/mp200039s

文献信息

• Novel Tetrapeptide, RGDF, Mediated Tumor Specific Liposomal Doxorubicin (DOX) Preparations
  作者：Huirui Du、Chunying Cui、Lili Wang、Hu Liu、Guohui Cui

  DOI：10.1021/mp200039s

  日期：2011.8.1

  liposomes with their fatty alkanyl chains being intercalated between fatty acyl chains of liposomal bilayers and the hydrophilic peptide moiety (RGDF or GGDF) being anchored on the surface of liposomes. The particle size and zeta potential of liposomal DOX preparations containing RGDF–fatty alcohol conjugate (L-RGDF-DOXs) or L-GGDFC12-DOX were measured, and their morphology was studied using transmission electron

  精氨酸-甘氨酸-天冬氨酸（RGD）已显示出对在肿瘤细胞中过度表达的整联蛋白具有很强的亲和力，尤其是在肿瘤浸润，血管生成和转移过程中。在其他工作的基础上，已设计并研究了一种新颖的四肽精氨酸-甘氨酸-天冬氨酸-苯基苯胺（RGDF）作为将脂质体阿霉素（DOX）导向肿瘤细胞的归巢装置。为了将RGDF掺入脂质体DOX制剂中，将RGDF与三种不同的脂肪醇偶联，以获得RGDF-脂肪醇偶联物。合成甘氨酸-甘氨酸-天冬氨酸-苯基苯胺（GGDF）-月桂醇缀合物作为阴性对照。RGDF-脂肪醇共轭物（RGDFO（CH 2）n CH 3）和GGDF-月桂醇共轭物（L-GGDFC12-DOX）掺入的脂质体制剂，首先使用膜分散法制备脂质体，然后使用跨膜pH梯度法上样DOX。由于两亲性质，RGDF–或GGDF–脂肪醇结合物很容易掺入脂质体，其脂肪烷基链插入脂质体双层脂肪酰基链之间，而亲水肽部分（RGDF或GGDF）锚定在
• Synthesis, evaluation and 3D QSAR analysis of novel estradiol–RGD octapeptide conjugates with oral anti-osteoporosis activity
  作者：Jiangyuan Liu、Xiaoyi Zhang、Ming Zhao、Shiqi Peng

  DOI：10.1016/j.ejmech.2008.09.036

  日期：2009.4

  To enhance the potency, reduce the side effects and improve oral property of estradiol in estrogen replacement therapy (ERT), 6 novel estradiol–RGD octapeptide conjugates have been prepared. In an ovariectomized mouse osteoporotic model, at an oral dosage of 110.3 nmol/kg per day, their anti-osteoporosis activity was significantly higher than that of estradiol and estradiol–RGD tetrapeptide conjugates

  为了增强雌激素替代疗法（ERT）的效力，降低副作用并改善雌二醇的口服特性，已制备了6种新型雌二醇-RGD八肽偶联物。在卵巢切除的小鼠骨质疏松模型中，每天口服剂量为110.3 nmol / kg，它们的抗骨质疏松活性显着高于雌二醇和雌二醇-RGD四肽偶联物，它们的血栓形成和子宫内膜增生的风险明显低于雌二醇和雌二醇-RGD四肽共轭物的结合力。使用Cerius2的QSAR模块，对接受小鼠的雌二醇-RGD肽结合物的股骨重量和股骨灰分重量进行了3D QSAR。的[R 2 高达0.995和0.988的3D QSAR方程式表明，它们能够预测结合物的相对精确的抗骨质疏松活性。
• Design and synthesis of nanoscaled IQCA-TAVV as a delivery system capable of antiplatelet activation, targeting arterial thrombus and releasing IQCA
  作者：Jianhui Wu、Haimei Zhu、Guodong Yang、Jianhong He、Yuji Wang、Shurui Zhao、Xiaoyi Zhang、Lin Gui、Ming Zhao、Shiqi Peng

  DOI：10.2147/ijn.s150205

  日期：——

  aggregators. In vivo IQCA-TAVV targeted arterial thrombus, dose dependently inhibited arterial thrombosis with a 1 nmol/kg of minimal effective dose, and the activity waŝ1670 folds of that of aspirin. CONCLUSION IQCA-TAVV represented the design, preparation and application of nanomedicine capable of adhering on the surface of activated platelets, attenuating platelet activation, targeting arterial thrombus and

  背景技术动脉血栓形成与一系列病理状况有关，动脉血栓形成抑制剂的发现具有临床意义。方法通过分析抗血小板药物、血栓靶向肽和抗血栓纳米系统3S-1,2,3,4-四氢异喹啉-3-羰基-Thr-Ala-Arg-Gly-Asp(Val)的药效团)-Val (IQCA-TAVV) 被设计和制备为纳米级动脉血栓形成抑制剂。结果 IQCA-TAVV纳米粒在体外能够粘附在活化血小板表面，减弱活化血小板以延长伪足，抑制活化血小板形成聚集体。体内IQCA-TAVV靶向动脉血栓，以1 nmol/kg的最小有效剂量剂量依赖性抑制动脉血栓形成，活性是阿司匹林的1670倍。
• IQCA-TASS: a nano-scaled P-selectin inhibitor capable of targeting thrombus and releasing IQCA/TARGD(S)S in vivo
  作者：Jianhui Wu、Haimei Zhu、Ming Zhao、Yuji Wang、Guodong Yang、Yaonan Wang、Shurui Zhao、Lin Gui、Xiaoyi Zhang、Shiqi Peng

  DOI：10.1039/c6tb02705a

  日期：——

  Thrombosis is a serious threat to human health worldwide. Tetrahydroisoquinoline-3-carboxylic acid (IQCA) is an antithrombotic agent, while Thr-Ala-Arg-Gly-Asp(Ser)-Ser (TASS) can target thrombus.

  血栓形成是全球人类健康的严重威胁。四氢异喹啉-3-羧酸（IQCA）是一种抗血栓药物，而苏氨酸-丙氨酸-精氨酸-甘氨酸-天冬氨酸（丝）-丝氨酸（TASS）可以靶向血栓。
• Studies of Bitter Peptides from Casein Hydrolyzate. IX. Syntheses and Bitter Taste of Bitter Peptide BPIa Dimer, (Arg–Gly–Pro–Pro–Phe–Ile–Val)₂, and Gly–Gly BPIa Derivatives
  作者：Ichizo Miyake、Katsushige Kouge、Hidenori Kanehisa、Hideo Okai

  DOI：10.1246/bcsj.57.815

  日期：1984.3

  In order to elucidate the relationship between taste exhibition and chemical structure of bitter peptide BPIa, di–BPIa, Gly–Gly–BPIa, BPIa–Gly–Gly, and Gly–Gly–BPIa–Gly–Gly were synthesized. All of the peptides possessed a strong bitter taste of the same level as that of BPIa. In addition, the CD curves of the peptides were similar to that of BPIa. The results suggested that their spatial structures are essentially similar and that the whole molecular shape of BPIa contributes to its bitterness.

  为了阐明苦味肽BPIa的味道展示与化学结构之间的关系，合成了di-BPIa、Gly-Gly-BPIa、BPIa-Gly-Gly和Gly-Gly-BPIa-Gly-Gly。所有这些肽都具有与 BPIa 相同的强烈苦味。此外，多肽的 CD 曲线与 BPIa 相似。这些结果表明，它们的空间结构基本相似，而 BPIa 的整个分子形状是造成其苦味的原因。