454863

D-erythro-MAPP

A synthetic analog of ceramide.

• Synonym(s): D-erythro-MAPP, (1S,2R)-D- erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol, AC Inhibitor II, Acid Ceramidase Inhibitor II, D-e-MAPP, (1S,2R)-D-erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol, AC Inhibitor II, Acid Ceramidase Inhibitor II, D-e-MAPP
• Empirical Formula (Hill Notation): C₂₃H₃₉NO₂
• CAS Number: 143492-38-0
• Molecular Weight: 361.56
• UNSPSC Code: 12352211

Properties

• Quality Level: 100
• Assay: ≥98% (NMR)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• solubility: ethanol: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-16-19-22(25)24-20(2)23(26)21-17-14-13-15-18-21/h13-15,17-18,20,23,26H,3-12,16,19H2,1-2H3,(H,24,25)/t20-,23-/m1/s1
• InChI key: YLAZEWZHIRBZDA-NFBKMPQASA-N

Description

General description

A synthetic analog of ceramide. Shown to selectively inhibit alkaline ceramidase both in vitro and in HL-60 cells (IC₅₀ = 1-5 µM for alkaline ceramidase versus IC₅₀ >500 µM for acid ceramidase). This inhibition results in over 3-fold increase in endogenous ceramide in treated cells due to lack of breakdown of ceramide to sphingosine.

A synthetic analog of ceramide. Shown to selectively inhibit alkaline ceraminidase both in vitro and in HL-60 cells (IC₅₀ = 1-5 µM for alkaline ceramides versus IC₅₀ >500 µM for acid ceraminidase). This inhibition results in and over 3-fold increase in endogenous ceramide in treated cells due to a lack of breakdown of ceramide to sphingosine.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Alkaline ceramidase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 1-5 µM for alkaline ceramidase versus >500 µM for acid ceramidase

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Bielawska, A., et al. 1996. J. Biol. Chem. 271, 12646.
Hannun, Y.A. 1996. Science274, 1855.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable