999995P
Avanti
Edelfosine
Avanti Research™ - A Croda Brand 999995P, powder
Synonyme(s) :
1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine
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About This Item
Formule empirique (notation de Hill):
C27H58NO6P
Numéro CAS:
Poids moléculaire :
523.73
Code UNSPSC :
51191904
Nomenclature NACRES :
NA.25
Produits recommandés
Forme
powder
Conditionnement
pkg of 1 × 5 mg (999995P-5mg)
Fabricant/nom de marque
Avanti Research™ - A Croda Brand 999995P
Type de lipide
cardiolipins
phospholipids
Conditions d'expédition
dry ice
Température de stockage
−20°C
Chaîne SMILES
[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
Clé InChI
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
Actions biochimiques/physiologiques
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).
Conditionnement
5 mL Clear Glass Sealed Ampule (999995P-5mg)
Informations légales
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Certificats d'analyse (COA)
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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
Nicolas M B Brancucci et al.
Cell, 171(7), 1532-1544 (2017-11-14)
Transmission represents a population bottleneck in the Plasmodium life cycle and a key intervention target of ongoing efforts to eradicate malaria. Sexual differentiation is essential for this process, as only sexual parasites, called gametocytes, are infective to the mosquito vector. Gametocyte production
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