N-Hexacosanoyl-D-erythro-sphingosylphosphorylcholine-d4/N-六十碳酚酰基-D-红- 鞘氨苷磷酰胆碱

Specifications

• Catalog #:2213

• Scientific Name:N-Hexacosanoyl-D-erythro-sphingosylphosphorylcholine-d₄

• Common Name:N-C26:0-sphingomyelin-d₄; N-C26:0-SM-d₄

• Empirical Formula:C₄₉H₉₅D₄N₂O₆P

• SDS:View Safety Data Sheet

• Data Sheet:View Data Sheet

• Formula Weight:847

• Unit:500 µg

• Solvent:none

• Source:semisynthetic

• Purity:98+%

• Analytical Methods:TLC; identity confirmed by MS

• Natural Source:bovine buttermilk

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

• Physical Appearance:solid

• Storage:-20℃

• Dry Ice:No

• Hazardous:No

Description

Incorporation purity: ≥99% deuterated forms (d₁-d₄)

Application Notes:

鞘磷脂存在于哺乳动物的细胞膜中，尤其是髓鞘的细胞膜中。它是哺乳动物中最丰富的鞘磷脂，被认为主要存在于膜的外质小叶中，尽管也有证据表明膜的内层小叶中有鞘磷脂池。它参与信号转导和细胞凋亡。神经鞘磷脂与神经酰胺的不适当比例已被证明是尼曼-皮克病和新生儿呼吸窘迫综合征的一个因素，神经鞘磷脂与神经酰胺的比值因细胞类型的不同而不同当血浆脂蛋白库因大量脂质负荷或代谢异常而扩大时，鞘磷脂是一种重要的两亲性成分n -己酰-鞘氨酰磷酰胆碱已被用来增强癌细胞对抗肿瘤药物的摄取，从而增加对这些癌细胞的细胞毒性.

Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis.¹ An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease² and neonatal respiratory distress syndrome.³ However, the ratio of sphingomyelin to ceramide is different for different cell types.⁴ Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.⁵ N-hexanoyl-sphingosylphosphorylcholine has been used to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.⁶

Selected References:
1. R. N. Kolesnick, A. Haimovitz-Friedman, Z. Fuks “The sphingomyelin signal transduction pathway mediates apoptosis for tumor necrosis factor, Fas, and ionizing radiation” Biochem Cell Biol., Vol. 72(11-12) pp. 471-474, 1994
2. M. Schmuth, et al. “Permeability barrier disorder in Niemann-Pick disease: sphingomyelin-ceramide processing required for normal barrier homeostasis” J Invest Dermatol., Vol. 115(3) pp. 459-466, 2000
3. C. St Clair et al. “The probability of neonatal respiratory distress syndrome as a function of gestational age and lecithin/sphingomyelin ratio” Am J Perinatol., Vol. 25(8) pp. 473-480, 2008,
4. J. Kilkus et al. “Differential regulation of sphingomyelin synthesis and catabolism in oligodendrocytes and neurons” J Neurochem. Vol. 106(4) pp. 1745- 1757, 2008
5. N. Duan RD. “Absorption and lipoprotein transport of sphingomyelin” J Lipid Res., Vol. 47(1) pp. 154-171, 2006
6. R. Veldman et al. “N-hexanoyl-sphingomyelin potentiates in vitro doxorubicin cytotoxicity by enhancing its cellular influx” Nature, vol. 90 pp. 917-925, 2004