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SML3524

Sigma-Aldrich

EtDO-P4

≥95% (HPLC)

Synonym(s):

D-EtDO-P4, D-threo-1-(3′,4′-Ethylenedioxy)phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol, Ethylenedioxy-P4, N-[(1R,2R)-2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(1-pyrrolidinylmethyl)ethyl]hexadecanamide

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About This Item

Empirical Formula (Hill Notation):
C31H52N2O4
CAS Number:
245329-78-6
Molecular Weight:
516.76
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

InChI

1S/C31H52N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-30(34)32-27(25-33-20-15-16-21-33)31(35)26-18-19-28-29(24-26)37-23-22-36-28/h18-19,24,27,31,35H,2-17,20-23,25H2,1H3,(H,32,34)/t27-,31-/m1/s1

InChI key

BBTZZVJOQCCAOR-DLFZDVPBSA-N

Biochem/physiol Actions

EtDO-P4, a ceramide analog, is a cell penetrant, potent and selective nanomolar inhibitor of UDP-glucose ceramide glucosyltransferase (UGCG). Inhibition of UGCG by EtDO-P4 decreases drug resistance and enhances cytotoxicity of chemotherapeutic drugs such as vincristine, daunorubicin, Lucena-1 and cisplatin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Glucosylceramide synthase inhibitors D-PDMP and D-EtDO-P4 decrease the GM3 ganglioside level, differ in their effects on insulin receptor autophosphorylation but increase Akt1 kinase phosphorylation in human hepatoma HepG2 cells
Acta Biochimica Polonica, 63 (2016)
Globoside promotes activation of ERK by interaction with the epidermal growth factor receptor
Biochimica et Biophysica Acta, 1820 (2012)
Eduardo J Salustiano et al.
The Journal of biological chemistry, 295(19), 6457-6471 (2020-04-02)
Multidrug resistance (MDR) in cancer arises from cross-resistance to structurally- and functionally-divergent chemotherapeutic drugs. In particular, MDR is characterized by increased expression and activity of ATP-binding cassette (ABC) superfamily transporters. Sphingolipids are substrates of ABC proteins in cell signaling, membrane

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