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Merck

999995P

Avanti

Edelfosine

Avanti Research - A Croda Brand 999995P, powder

别名:

1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine

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About This Item

经验公式(希尔记法):
C27H58NO6P
CAS号:
分子量:
523.73
分類程式碼代碼:
51191904
NACRES:
NA.25

形狀

powder

包裝

pkg of 1 × 5 mg (999995P-5mg)

製造商/商標名

Avanti Research - A Croda Brand 999995P

脂質類型

cardiolipins
phospholipids

運輸包裝

dry ice

儲存溫度

−20°C

SMILES 字串

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC)COCCCCCCCCCCCCCCCCCC)=O

InChI

1S/C10H24NO5P/c1-6-10(14-5)9-16-17(12,13)15-8-7-11(2,3)4/h10H,6-9H2,1-5H3/t10-/m0/s1

InChI 密鑰

GVMCXWJIRSIWFJ-JTQLQIEISA-N

應用

Edelfosine or 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine might be used:
  • as a non-hydrolysable LysoPC (phospholipid) analog for analyzing its ability to block sexual commitment in Plasmodium falciparum
  • in multilamellar vesicle preparation, to study its effect on model membranes
  • in the selection and screening of mutagenized cells, having the ability to inhibit the transport of alkylphosphocholine drugs across the plasma membrane

生化/生理作用

Edelfosine acts as a precursor for alkyl-lysophospholipids. It possesses apoptotic action against several cancer cells such as prostate, leukemia, brain and lung tumors. It is associated with cellular transport system, signaling transducing systems, cytokine synthesis and lipid metabolism. Edelfosine is known to control intracellular calcium levels. It is not mutagenic and its anti-tumor action requires its incorporation into the cell. Edelfosine is also found to block the replication of human immunodeficiency virus type I (HIV-I).

包裝

5 mL Clear Glass Sealed Ampule (999995P-5mg)

法律資訊

Avanti Research is a trademark of Avanti Polar Lipids, LLC

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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Alessio Ausili et al.
The journal of physical chemistry. B, 112(37), 11643-11654 (2008-08-21)
The effect of edelfosine (1- O-octadecyl-2- O-methyl-rac-glycero-3-phosphocholine or ET-18-OCH3) on model membranes containing 1-palmitoyl-2-oleoyl- sn-glycero-3-phosphocholine/sphingomyelin/cholesterol (POPC/SM/cholesterol) was studied by several physical techniques. The sample POPC/SM (1:1 molar ratio) showed a broad phase transition as seen by DSC, X-ray diffraction, and
Pamela K Hanson et al.
The Journal of biological chemistry, 278(38), 36041-36050 (2003-07-05)
The alkylphosphocholine class of drugs, including edelfosine and miltefosine, has recently shown promise in the treatment of protozoal and fungal diseases, most notably, leishmaniasis. One of the major barriers to successful treatment of these infections is the development of drug
Bruno M Castro et al.
The journal of physical chemistry. B, 117(26), 7929-7940 (2013-06-07)
Edelfosine (1-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine) and miltefosine (hexadecylphosphocholine) are synthetic alkylphospholipids (ALPs) that are reported to selectively accumulate in tumor cell membranes, inducing Fas clustering and activation on lipid rafts, triggering apoptosis. However, the exact mechanism by which these lipids elicit these events
Alessio Ausili et al.
Langmuir : the ACS journal of surfaces and colloids, 34(28), 8333-8346 (2018-06-21)
Edelfosine is an anticancer drug with an asymmetric structure because, being a derivative of glycerol, it possesses two hydrophobic substituents of very different lengths. We showed that edelfosine destabilizes liquid-ordered membranes formed by either 1-palmitoyl-2-oleoyl- sn-glycero-3-phosphocholine, sphingomyelin (SM), and cholesterol

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