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Merck

999995P

Avanti

Edelfosine

Avanti Research - A Croda Brand

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C27H58NO6P
Numéro CAS:
Poids moléculaire :
523.73
MDL number:
UNSPSC Code:
51191904
NACRES:
NA.25
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Nom du produit

Edelfosine, Avanti Research - A Croda Brand 999995P, powder

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (999995P-5mg)

manufacturer/tradename

Avanti Research - A Croda Brand 999995P

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[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 key

GVMCXWJIRSIWFJ-JTQLQIEISA-N

Application

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

Biochem/physiol Actions

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).

Packaging

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

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC


Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Consulter la Bibliothèque de documents



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
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
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