N-Heptadecanoyl-lactosylceramide/N-十七玩酰基-乳糖神经酰胺/1354699-26-5

Specifications

• Catalog #:1538

• Scientific Name:N-Heptadecanoyl-lactosylceramide

• Common Name:N-C17:0-Lactosylceramide; Lactosylceramide with C17:0 fatty acid side chain

• Empirical Formula:C₄₇H₈₉NO₁₃

• CAS#:1354699-26-5

• SDS:View Safety Data Sheet

• Data Sheet:View Data Sheet

• Formula Weight:876

• Unit:1 mg

• Source:semisynthetic

• Purity:98+%

• Analytical Methods:TLC, identity confirmed by MS

• Natural Source:bovine, buttermilk

• Solubility:chloroform/methanol/water, 2:1:0.1

• Physical Appearance:solid

• Storage:-20℃

• Dry Ice:No

• Hazardous:No

Description

Application Notes:

该产品是一种定义明确的乳酰神经酰胺，含有一个乙酰化成鞘氨醇胺的十七烷酰基，是理想的内标。乳酰神经酰胺是许多其他鞘糖脂的前体，同时也作为第二信使和蛋白质受体，使其成为非常重要的有机分子。许多细胞过程依赖于乳酰神经酰胺，因为它是中性低糖基神经酰胺、硫酸盐和神经节苷脂的底物，所有这些都有自己的重要功能。乳酰神经酰胺还有助于稳定脂质膜，激活受体分子，并作为某些细菌和毒素的受体。在动物体内，它主要存在于上皮细胞和神经元细胞中，在中性粒细胞和巨噬细胞上表达，在这些细胞中，它与毒素和细菌结合，然后被吞噬和清除。它作为第二信使的作用已经被发现是至关重要的，在其过程中的功能失调可能导致癌症和炎症，因为它是中性粒细胞活动和激活抗炎反应的关键因此，人们正在研究它在癌症治疗和其他疾病治疗中的应用。其他具有乳酰神经酰胺第二信使功能的例子有肿瘤坏死因子
和血小板源性生长因子。1 .乳糖神经酰胺中水解半乳糖的酶的缺乏导致乳糖神经酰胺病，其特征是乳糖神经酰胺的积累导致原发性神经系统疾病乳酰神经酰胺在血小板/内皮细胞粘附分子-1的激活中也起重要作用，从而导致单核细胞/淋巴细胞粘附和衰竭。

This product is a well-defined lactosylceramide containing a heptadecanoyl group acylated to the amine of the sphingosine and is ideal as an internal standard. Lactosylceramide is the precursor of many other glycosphingolipids and also functions as a second messenger and protein receptor, making it a very important organic molecule. Many cellular processes are dependent on lactosylceramide since it is the substrate for neutral oligoglycosylceramides, sulfatides and gangliosides, all of which have their own vital functions. Lactosylceramide also helps to stabilize the lipid membrane, activate receptor molecules and acts as a receptor for certain bacteria and toxins. In animals, where it is found mostly in epithelial and neuronal cells, it is expressed on neutrophils and macrophages where it binds to toxins and bacteria, which are then engulfed and eliminated. Its role as a second messenger has been found to be vital and dysfunctions in its processes can lead to cancer and inflammation since it is critical to neutrophil activity and in activating anti-inflammatory responses.1 Therefore, it is being studied for its use in cancer therapies and as a therapy for other diseases. Other examples of lactosylceramide second messenger functions are tumor necrosis factor
and platelet-derived growth factor. A deficiency in the enzyme responsible for hydrolyzing the galactose of lactosylceramide leads to lactosylceramidosis, which is characterized by an accumulation of lactosylceramide that causes a primary neurological disorder.2 Lactosylceramide is also important in the activation of platelet/endothelial cell adhesion molecule-1 which causes adhesion and diapedesis of monocytes/lymphocytes.3

References:
1. Ravinder Pannu et al. “A Novel Role of Lactosylceramide in the Regulation of Tumor Necrosis Factor alpha-mediated Proliferation of Rat Primary Astrocytes: IMPLICATIONS FOR ASTROGLIOSIS FOLLOWING NEUROTRAUMA” Journal of Biological Chemistry, Vol. 280 pp. 13742-13751, 2005
2. Glyn Dawson “Glycosphingolipid levels in an unusual neurovisceral storage disease characterized by lactosylceramide galactosyl hydrolase deficiency: lactosylceramidosis” Journal of Lipid Research, Vol. 13 pp. 207-219, 1972
3. NanLing Gong “Lactosylceramide recruits PKC and phospholipase A2 to stimulate PECAM-1 expression in human monocytes and adhesion to endothelial cells” Proceedings of the National Academy of Sciences, Vol. 101:17 pp. 6490-6495, 2004