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999995P

Avanti

Edelfosine

Avanti Research™ - A Croda Brand 999995P, powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C27H58NO6P
CAS-Nummer:
77286-66-9
Molekulargewicht:
523.73
UNSPSC-Code:
51191904
NACRES:
NA.25

Form

powder

Verpackung

pkg of 1 × 5 mg (999995P-5mg)

Hersteller/Markenname

Avanti Research™ - A Croda Brand 999995P

Lipid-Typ

cardiolipins
phospholipids

Versandbedingung

dry ice

Lagertemp.

−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

InChIKey

GVMCXWJIRSIWFJ-JTQLQIEISA-N

Anwendung

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. Wirkung

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).

Verpackung

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

Rechtliche Hinweise

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

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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