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999995P

Avanti

Edelfosine

Avanti Research™ - A Croda Brand 999995P, powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C27H58NO6P
Número de CAS:
77286-66-9
Peso molecular:
523.73
Número MDL:
MFCD00063527
Código UNSPSC:
51191904
NACRES:
NA.25

Formulario

powder

envase

pkg of 1 × 5 mg (999995P-5mg)

fabricante / nombre comercial

Avanti Research™ - A Croda Brand 999995P

tipo de lípido

cardiolipins
phospholipids

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

GVMCXWJIRSIWFJ-JTQLQIEISA-N

Categorías relacionadas

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Envase

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

Información legal

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (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

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