linoleic acid succinimidyl ester | 69888-88-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: linoleic acid succinimidyl ester
• 英文别名: N-hydroxysuccinimide ester of linoleic acid；2,5-dioxo-tetrahydropyrrole-1-linoleate；N-succinimidyl cis,cis-9,12-octadecadienoate；linoleic acid NHS ester；2,5-Pyrrolidinedione, 1-[[(9Z,12Z)-1-oxo-9,12-octadecadienyl]oxy]-；(2,5-dioxopyrrolidin-1-yl) (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 69888-88-6
• 化学式: C₂₂H₃₅NO₄
• 分子量: 377.524
• InChiKey: DXXZWPDPHMIAHP-HZJYTTRNSA-N

物化性质

• 沸点：
  485.5±48.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DL-Threonine 、 linoleic acid succinimidyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以52.87%的产率得到linoleoyl threonine
  参考文献：
  名称：

  一种抗β淀粉样蛋白活性的化合物的制备方法 和应用

  摘要：

  本发明提供了式I所示化合物、或其药学上可接受的盐。本发明还提供了该化合物的制备方法。实验结果表明，发明提供的化合物能够显著抑制Aβ诱导的细胞毒性，能够显著降低患有AD的APP/PS1转基因小鼠的Aβ水平，改善患有AD的APP/PS1转基因小鼠的学习记忆能力，在制备β淀粉样蛋白抑制剂、预防或治疗阿尔茨海默氏病的药物中具有良好的应用前景。

  公开号：

  CN110577480B
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 linoleic acid succinimidyl ester
  参考文献：
  名称：

  Unsaturated acyl chains dramatically enhanced cellular uptake by direct translocation of a minimalist oligo-arginine lipopeptide

  摘要：

  不饱和脂肪酰链有利于短阳离子NBD标记肽的直接转位。

  DOI：

  10.1039/c5cc06116d

文献信息

• 4,5-Cis Unsaturated α-GalCer Analogues Distinctly Lead to CD1d-Mediated Th1-Biased NKT Cell Responses
  作者：Yanli Cui、Zhiyuan Li、Zhaodong Cheng、Chengfeng Xia、Yongmin Zhang

  DOI：10.1021/acs.chemrestox.5b00047

  日期：2015.6.15

  The total synthesis of 4,5-cis unsaturated α-GalCer analogues was achieved, and their immune-response altering activity was assessed in vitro as well as in vivo in mice. Using glycosyl iodide as a glycosyl donor, construction of the sphingosine unit was shortened by four steps and single α-stereoselectivity was achieved in good yield (67%). With regard to the therapeutic use of α-GalCer, the novel analogues (1b and 1c) distinctly induced a Th1-biased cytokine response, avoiding induction of a contradictory response and overstimulation.

  4,5-顺式不饱和α-GalCer类似物的全合成得以实现，并评估了它们在体外及小鼠体内的免疫应答改变活性。利用糖基碘作为糖基供体，缩短了鞘氨醇单元的构建步骤，并通过高产率（67%）实现了单一的α-立体选择性。针对α-GalCer的治疗用途，新型类似物（1b和1c）显著诱导了偏向Th1的细胞因子反应，避免了矛盾反应和过度刺激的诱导。
• Chemoselective Acylation of Fully Deprotected Hydrazino Acetyl Peptides. Application to the Synthesis of Lipopeptides
  作者：Dominique Bonnet、Nathalie Ollivier、Hélène Gras-Masse、Oleg Melnyk

  DOI：10.1021/jo0010577

  日期：2001.1.1

  N-terminal alpha-hydrazino acetyl peptides were synthesized and chemoselectively acylated on the hydrazine moiety with various fatty acid succinimidyl esters or N-(cholesterylcarbonyloxy) succinimide to give lipopeptides of high purity. The buffer and pH were adjusted in order to minimize the oxidation of the hydrazine moiety and to achieve the best conversion and selectivity. The acylation was performed

  合成了完全脱保护的N-末端α-肼基乙酰基肽，并在肼部分上用各种脂肪酸琥珀酰亚胺酯或N-（胆固醇基羰基氧基）琥珀酰亚胺化学选择性地酰化，以得到高纯度的脂肽。调节缓冲液和pH以使肼部分的氧化最小化并获得最佳的转化率和选择性。酰化在pH 5.1的柠檬酸盐-磷酸盐缓冲液/ 2-甲基丙烷-2-醇混合物中进行。发现我们的模型肽上的α-肼基乙酰基的pKa为6.45，即比甘氨酰残基的pKa低约2个单位。随后将该反应用于由棕榈酰基衍生的38AA肽的合成。
• <i>N</i>-Linoleyltyrosine Protects against Transient Cerebral Ischemia in Gerbil <i>via</i> CB2 Receptor Involvement in PI3K/Akt Signaling Pathway
  作者：Lin Cheng、Jinsi Li、Yi Zhou、Qixue Zheng、Xin Ming、Sha Liu

  DOI：10.1248/bpb.b19-00394

  日期：2019.11.1

  Anandamide (AEA) played potent neuroprotective activities via cannabinoid type 1 (CB1) and 2 (CB2) receptor. N-Linoleyltyrosine (NITyr), as an AEA analogue, was synthesized in our laboratory and evaluated the neuroprotective effects and mechanisms for the first time. NITyr was synthesized via substitution reaction. The neuroprotective effects of NITyr were evaluated in a gerbil model of transient cerebral ischemia. Each gerbil was subjected to open field test (OFT), Rotard rod test (RRT), Morris water maze (MWM) successively and executed after animal behaviors. Part of the brain was stained with hematoxylin and eosin (HE) and Nissl staining, and the rest for biochemical analysis. NITyr could not increase spontaneous locomotor activity and ameliorate the anxiety behavior in the OFT but could improve the motor coordination in the RRT and the spatial memory impairment in the MWM. Immunohistochemically, NITyr could attenuate the ischemia-induced neural loss in the hippocampus. The Enzyme-linked immunosorbent assay (ELISA) suggested that NITyr ameliorated the inflammation and oxidative stress. Consistently, NITyr could up-regulate the expressions of p-phosphadylinositol 3-kinase (PI3K) and p-Akt but not PI3K and Akt in the hippocampus. In addition to oxidative stress, CB2 receptor antagonist AM630 but not CB1 receptor antagonist AM251 could reverse the above phenomena. However, CB1 receptor antagonist AM251 could reverse oxidative stress. Accordingly, NITyr could up-regulate the expressions of CB2 but not CB1. NITyr could improve the motor coordination, learning and memory impairments, neural loss in the hippocampus and the inflammation of the mice via CB2 receptor involvement of PI3K/Akt signaling pathway.

  阿南酰胺（AEA）通过大麻素类型1（CB1）和2（CB2）受体发挥强效的神经保护活性。我们的实验室合成了作为AEA类似物的N-亚麻酰酪氨酸（NITyr），并首次评估了其神经保护效果及机制。NITyr是通过取代反应合成的。在一项暂时性脑缺血的沙鼠模型中评估了NITyr的神经保护效果。每只沙鼠依次接受了开放场测试（OFT）、旋转杆测试（RRT）和莫里斯水迷宫（MWM）测试，随后进行了行为观察。部分脑组织用苏木素-伊红（HE）和尼氏染色进行染色，余下部分用于生化分析。NITyr并未增加自发运动活动，也未改善OFT中的焦虑行为，但能够改善RRT中的运动协调性和MWM中的空间记忆损伤。在免疫组织化学上，NITyr能够减轻缺血引起的海马神经损失。酶联免疫吸附测定（ELISA）显示，NITyr改善了炎症和氧化应激。一致地，NITyr能够上调海马中磷酸化的磷脂酰肌醇3-激酶（PI3K）和磷酸化的Akt的表达，但对PI3K和Akt本身没有影响。除了氧化应激外，CB2受体拮抗剂AM630可以逆转上述现象，而CB1受体拮抗剂AM251则无法。尽管如此，CB1受体拮抗剂AM251能够逆转氧化应激。因此，NITyr可以上调CB2的表达，而不影响CB1。NITyr可通过CB2受体介入PI3K/Akt信号通路，改善运动协调性、学习和记忆损伤、海马神经损失及小鼠的炎症。
• The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid L-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells
  作者：Li Yun Grace Lim、Yingying Su、Filip Braet、Pall Thordarson

  DOI：10.1071/ch09211

  日期：——

  A series of saturated and unsaturated fatty acid l-serines 3 were synthesized and their ability to form self-assembled gels was investigated. The saturated (lauroyl 3a and steraoyl 3b) and monounsaturated (oleoyl 3c) fatty acid l-serines form gels in both water and organic solvent, whereas the diunsaturated linoleyl-l-serine 3d does not form gels in these solvents, indicating that unsaturation adversely affects the gelation process. Cytotoxicity studies on these compounds with Caco-2 cancer cells in vitro show that these gels are only moderately cytotoxic at concentrations up to 0.5 mM, making them a promising candidate for applications such as drug delivery.

  研究人员合成了一系列饱和和不饱和脂肪酸 l-丝氨酸 3，并考察了它们形成自组装凝胶的能力。饱和（月桂酰基 3a 和链烷基 3b）和单不饱和（油酰基 3c）脂肪酸 l-丝氨酸在水和有机溶剂中都能形成凝胶，而二不饱和亚油酰基 l-丝氨酸 3d 在这些溶剂中不能形成凝胶，这表明不饱和会对凝胶过程产生不利影响。用 Caco-2 癌细胞对这些化合物进行的体外细胞毒性研究表明，当浓度达到 0.5 毫摩尔时，这些凝胶仅具有适度的细胞毒性，使它们成为药物递送等应用的理想候选物质。
• [EN] CARRIERS FOR EFFICIENT NUCLEIC ACID DELIVERY<br/>[FR] VECTEURS DESTINÉS À L'ADMINISTRATION EFFICACE D'ACIDES NUCLÉIQUES
  申请人：TIBA BIOTECH LLC

  公开号：WO2021207020A1

  公开（公告）日：2021-10-14

  Nanoparticle compositions for delivery of nucleic acids to subjects including carriers comprising polyester (PE) dendrimers or dendrons, and therapeutic or immunogenic nucleic acid agents enclosed within the PE are described. Methods for treating or preventing diseases or conditions in a subject by administering the nanoparticle compositions that provide immune responses and synergistic therapeutic or preventive effects are provided.

  描述了用于将核酸传递给受试者的纳米颗粒组合物，其中包括包含聚酯（PE）树状聚合物或树状分子的载体，以及包含在PE内部的治疗性或免疫原性核酸药剂。提供了通过给予提供免疫反应和协同治疗或预防效果的纳米颗粒组合物来治疗或预防受试者疾病或状况的方法。