1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine
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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.
For research use only. We do not sell to patients.
- Purity : 97.3%
- CAS No.: 99296-81-8
- Formula: C52H80NO8P
- Molecular Weight:878.17
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Storage:
Solution, -20°C, 2 years
Biological Activity
Description
IC50 & Target
[1]|
HIV-1 |
In Vitro
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.
Chemical Information
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CAS No. 99296-81-8
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Appearance Liquid
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Molecular Weight 878.17
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Formula C52H80NO8P
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Color Colorless to light yellow
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SMILES
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
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Solution, -20°C, 2 years
Purity & Documentation
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Data Sheet (267 KB)
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SDS (644 KB)
- English - EN (644 KB)
- Français - FR (644 KB)
- Deutsch - DE (644 KB)
- Norwegian - NO (644 KB)
- Español - ES (644 KB)
- Swedish - SV (644 KB)
- Italian - IT (644 KB)
- Korean - KR (644 KB)
- Portuguese - PT (644 KB)
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Handling Instructions (2659 KB)
References
[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]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)