1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine 

1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine is a polyunsaturated phospholipid that serves as a component of lipid monolayers and small unilamellar vesicles. 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine can be used to prepare endoplasmic reticulum-targeted liposomes (PERLs), which are composed of 1,2-didocosahexaenoyl-sn-glycero-3-phosphoethanolamine, l-α-phosphatidylinositol and l-α-phosphatidylserine at a molar ratio of 1.5:1.5:1:1. PERLs reduce cholesterol levels in human peripheral blood mononuclear cells (PBMCs) and decrease HIV-1 particle secretion from HIV-1-infected PBMCs. Liposomes formed from 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine exhibit cytotoxicity against leukemia cells. 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine is applicable to studies related to hepatitis C virus infection, HIV infection, hepatitis B virus infection and leukemia^[1][2].

PERLs containing 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine (1-50 μM; 4 d) cause a significant concentration-dependent reduction in free and/or esterified cellular cholesterol levels in Huh7.5, PBMC, CD4⁺ T and HepG2.2.2.15 cells, with the greatest reduction mediated by 50 μM PERLs (a 53% decrease in free cholesterol in Huh7.5 cells)^[1].
PERLs containing 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine (1-50 μM; 4 d) significantly reduce the infectivity of HCV and HIV in a concentration-dependent manner after 4 days of pretreatment of uninfected Huh7.5 cells and PBMCs^[1].
1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine liposomes (lipid concentration 2-14 mg lipid/mL; incubation for 2 h) exert dose-dependent direct cytotoxicity against T27A mouse leukemia cells^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

878.17

C₅₂H₈₀NO₈P

99296-81-8

Liquid

Colorless to light yellow

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O[C@H](COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COP(OCC[N+](C)(C)C)([O-])=O)=O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Pollock S, et al. Polyunsaturated liposomes are antiviral against hepatitis B and C viruses and HIV by decreasing cholesterol levels in infected cells. Proc Natl Acad Sci U S A. 2010;107(40):17176-17181.  [Content Brief]

  [2]. Kafrawy O, et al. Docosahexaenoic acid in phosphatidylcholine mediates cytotoxicity more effectively than other omega-3 and omega-6 fatty acids. Cancer Lett. 1998 Oct 23;132(1-2):23-9.  [Content Brief]