甘氨酰精氨酰甘氨酰天门冬氨酰丝氨酸 | 96426-21-0

• 物质功能分类: 生物化工 - 多肽
• 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
• 中文名称: 甘氨酰精氨酰甘氨酰天门冬氨酰丝氨酸
• 英文名称: (S)-3-{2-[(S)-2-(2-Amino-acetylamino)-5-guanidino-pentanoylamino]-acetylamino}-N-((S)-1-carboxy-2-hydroxy-ethyl)-succinamic acid
• 英文别名: H-Gly-Arg-Gly-Asp-Ser-OH；Gly-Arg-Gly-Asp-Ser-OH；Gly-Arg-Gly-Asp-Ser；GRGDS；(3S)-3-[[2-[[(2S)-2-[(2-aminoacetyl)amino]-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-4-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-4-oxobutanoic acid
• CAS: 96426-21-0
• 化学式: C₁₇H₃₀N₈O₉
• 分子量: 490.473
• InChiKey: RGNVSYKVCGAEHK-GUBZILKMSA-N

物化性质

• 密度：
  1.66±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：100 mg/mL (203.89 mM)；水：33.33 mg/mL (67.96 mM)
• 碰撞截面：
  205.9 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]
• 稳定性/保质期：
  常温常压下稳定，应避免与强酸和强碱接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -7.9
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  302
• 氢给体数：
  10
• 氢受体数：
  11

制备方法与用途

生物活性

Gly-Arg-Gly-Asp-Ser 是一种五肽，构成了糖蛋白，并与骨桥蛋白的细胞结合域相关。

靶点

• IC50: αvβ3: 5 μM, αvβ5: 6.5 μM

体外研究

Gly-Arg-Gly-Asp-Ser 能够与整合素受体 αvβ3 结合，其 IC50 值为 5 μM。将 Gly-Arg-Gly-Asp-Ser 固定在二氧化钛纳米管上可以增强类似成骨细胞 (MG-63) 的黏附性，并显著增加细胞扩展和增殖。

参考质量标准

• 外观：白色粉末
• 纯度（HPLC）≥98.0%
• 醋酸根含量≤12.0%
• 水分含量≤8.0%
• 肽含量≥80.0%
• 内毒素≤50EU/mg
• 氨基酸组成分析偏差≤±10%

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	H-Gly-DL-Arg-Gly-DL-Asp-OH	——	C14H25N7O7	403.39

反应信息

• 作为反应物：
  描述：

  、 甘氨酰精氨酰甘氨酰天门冬氨酰丝氨酸 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  RGD-conjugated triarylmethyl radical as probe for electron paramagnetic imaging

  摘要：

  A stable RGD-conjugated triarylmethyl (TAM) radical 3 has been synthesized in a straightforward three-step sequence. CT-03 'the Finland trityl' which is a very popular contrast agent for electron paramagnetic resonance imaging has been covalently bound to the NH2-ending of a pentapeptide commonly used to target integrins and confers tissue selectivity. Moreover, this new TAM radical is stable and sensitive to molecular oxygen. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.120
• 作为产物：
  描述：

  H-Gly-Arg(Mts)-Gly-Asp(OChx)-Ser(Bzl)-OH*TFA 在 三氟甲磺酸 、 茴香硫醚 、 间甲酚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到甘氨酰精氨酰甘氨酰天门冬氨酰丝氨酸
  参考文献：
  名称：

  Kalashnikov, V. V.; Troshkov, M. L.; Samukov, V. V., Journal of general chemistry of the USSR, 1990, vol. 60, # 8.2., p. 1707 - 1713

  摘要：

  DOI：

文献信息

• Peptide microarrays for the discovery of bioactive surfaces that guide cellular processes: a single step azide–alkyne “click” chemistry approach
  作者：Douglas Zhang、Kristopher A. Kilian

  DOI：10.1039/c4tb00375f

  日期：——

  Mixed peptide microarrays were formed in a single step using copper-catalyzed “click” chemistry for exploring cell adhesion and differentiation.

  使用铜催化的“点击”化学，单步形成了混合肽微阵列，用于探索细胞粘附和分化。

• Surfaces having desirable cell adhesive effects
  申请人：Board of Regents, The University of Texas System

  公开号：US05330911A1

  公开（公告）日：1994-07-19

  An absorbed protein-independent cell-adhesive surface is disclosed. The treated surface comprises a chemically derivatized material to which small peptides, having less than 12 amino acid residues and including YIGSR, RGD or REDV amino acid sequence are covalently linked to. The peptides of the present invention include a terminal glycine amino acid. Tresyl chloride activation of surface hydroxyl moieties provides the active surface sites by which a terminal glycine arm of a selected peptide attaches to form covalent bonds between the substrate and peptide. Peptides high with cell adhesive properties are bound in high efficiency. By way of example, surfaces which may be used in conjunction with the present invention include polymer, metal, and ceramic surfaces. The most preferred polymer surfaces include PHEMA and PET polymer surfaces, with the most preferred glass surfaces being glycophase glass. The present methods also include a pretreatment method which provides hydroxyl moieties to surfaces devoid of readily available hydroxyl moieties. The pretreatment, by way of example, comprises immersion of the surface in a mixture of formaldehyde and acetic acid. Methods of preparing the treated surfaces are also included in the present invention. Also included are surface-treated biomedical implant devices and cell culturing devices. The treated surface promotes an enhanced rate and an enhanced amount of cell adhesion to the surface, independent of media serum concentrations or other absorbed proteins. The treated surfaces of the present invention are thermally stable, reusable, peptide efficient (attached to surface only) and resistant to cell proteolysis. The invention further concerns polymeric substrates with a surface having physically interpenetrating water-soluble polymer chains, and methods for production thereof.

  本发明涉及一种吸附蛋白独立的细胞粘附表面。处理后的表面包括一种化学衍生材料，小肽通过共价键连接到其中，这些小肽具有少于12个氨基酸残基，包括YIGSR，RGD或REDV氨基酸序列。本发明的肽包括一个末端甘氨酸氨基酸。通过三氯化砜活化表面羟基官能团，使得所选肽的末端甘氨酸臂连接到基质和肽之间形成共价键的活性表面位点。具有细胞粘附性能的肽以高效率结合。例如，可以与本发明一起使用的表面包括聚合物、金属和陶瓷表面。最优选的聚合物表面包括PHEMA和PET聚合物表面，最优选的玻璃表面为糖基玻璃。本发明还包括一种预处理方法，用于为缺乏易于获取的羟基官能团的表面提供羟基官能团。例如，预处理包括将表面浸泡在甲醛和醋酸的混合物中。本发明还包括制备处理后表面的方法。还包括经处理的生物医学植入物装置和细胞培养装置。处理后的表面促进细胞与表面的粘附速率和粘附量增强，不受培养基血清浓度或其他吸附蛋白的影响。本发明的处理后表面具有热稳定性，可重复使用，肽效率高（仅附着于表面），并且抗细胞蛋白酶解。本发明还涉及具有物理相互穿插的水溶性聚合物链表面的聚合物基材料，以及其生产方法。
• Electrospun PNIPAAm/PCL fiber mats for aligned cell sheets
  申请人：Board of Regents, The University of Texas System

  公开号：US11111611B2

  公开（公告）日：2021-09-07

  The present invention provides compositions comprising aligned fibers of electrospun PNIPAAm and poly (ε-caprolactone) (PCL) (denoted PNIPAAm/PCL fibers). The PNIPAAm/PCL compositions enable enhanced growth and detachment of intact anisotropic cell sheets. The compositions do not require chemical modification or resource-intensive techniques, thus saving time and expense, and have the potential to generate tissue-specific, aligned cell sheets for transplant studies.

  本发明提供了由电纺 PNIPAAm 和聚（ε-己内酯）（PCL）的排列纤维（简称 PNIPAAm/PCL 纤维）组成的组合物。PNIPAAm/PCL 组合物能增强完整的各向异性细胞片的生长和分离。这种组合物不需要化学修饰或资源密集型技术，因此节省了时间和费用，并有可能为移植研究生成组织特异、排列整齐的细胞薄片。
• Valve translocation device and method for the treatment of functional valve regurgitation
  申请人：University of Maryland, Baltimore

  公开号：US11259925B2

  公开（公告）日：2022-03-01

  The present invention provides devices for treating functional mitral regurgitation and methods of use thereof. The devices translocate a subject's mitral valve in an apical direction. The devices thereby treat mitral regurgitation while preserving a subject's original mitral valve and chordae tendinae.

  本发明提供了治疗功能性二尖瓣反流的装置及其使用方法。 这些装置可将受试者的二尖瓣向心尖方向移位。 这些装置可治疗二尖瓣反流，同时保留受试者原有的二尖瓣和腱索。
• RGD-conjugated triarylmethyl radical as probe for electron paramagnetic imaging
  作者：Benoît Driesschaert、Philippe Levêque、Bernard Gallez、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.tetlet.2013.08.120

  日期：2013.10

  A stable RGD-conjugated triarylmethyl (TAM) radical 3 has been synthesized in a straightforward three-step sequence. CT-03 'the Finland trityl' which is a very popular contrast agent for electron paramagnetic resonance imaging has been covalently bound to the NH2-ending of a pentapeptide commonly used to target integrins and confers tissue selectivity. Moreover, this new TAM radical is stable and sensitive to molecular oxygen. (C) 2013 Elsevier Ltd. All rights reserved.