IUPAC/Chemical Name
N-((1R,2R)-1-hydroxy-3-morpholino-1-phenylpropan-2-yl)palmitamide
InChi Key
OFBANDBMHLEMFA-XRKRLSELSA-N
InChi Code
InChI=1S/C29H50N2O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-28(32)30-27(25-31-21-23-34-24-22-31)29(33)26-18-15-14-16-19-26/h14-16,18-19,27,29,33H,2-13,17,20-25H2,1H3,(H,30,32)/t27-,29-/m1/s1
SMILES Code
O[C@H](C1=CC=CC=C1)[C@H](NC(CCCCCCCCCCCCCCC)=O)CN2CCOCC2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
D-threo-PPMP is a potent inhibitor of glucosylceramide (GlcCer) synthase.
In vitro activity:
On the other hand, D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP), an inhibitor of glucosylceramide synthesis, blocked karyokinesis and reduced cyst production in culture. PPMP also altered the expression of cyst wall protein transcripts in encysting cells.
Reference: Infect Immun. 2008 Jul;76(7):2939-49. https://pubmed.ncbi.nlm.nih.gov/18426892/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
474.73
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hernandez Y, Shpak M, Duarte TT, Mendez TL, Maldonado RA, Roychowdhury S, Rodrigues ML, Das S. Novel role of sphingolipid synthesis genes in regulating giardial encystation. Infect Immun. 2008 Jul;76(7):2939-49. doi: 10.1128/IAI.00116-08. Epub 2008 Apr 21. PMID: 18426892; PMCID: PMC2446683.
2. Gouazé V, Liu YY, Prickett CS, Yu JY, Giuliano AE, Cabot MC. Glucosylceramide synthase blockade down-regulates P-glycoprotein and resensitizes multidrug-resistant breast cancer cells to anticancer drugs. Cancer Res. 2005 May 1;65(9):3861-7. doi: 10.1158/0008-5472.CAN-04-2329. PMID: 15867385.
In vitro protocol:
1. Hernandez Y, Shpak M, Duarte TT, Mendez TL, Maldonado RA, Roychowdhury S, Rodrigues ML, Das S. Novel role of sphingolipid synthesis genes in regulating giardial encystation. Infect Immun. 2008 Jul;76(7):2939-49. doi: 10.1128/IAI.00116-08. Epub 2008 Apr 21. PMID: 18426892; PMCID: PMC2446683.
2. Gouazé V, Liu YY, Prickett CS, Yu JY, Giuliano AE, Cabot MC. Glucosylceramide synthase blockade down-regulates P-glycoprotein and resensitizes multidrug-resistant breast cancer cells to anticancer drugs. Cancer Res. 2005 May 1;65(9):3861-7. doi: 10.1158/0008-5472.CAN-04-2329. PMID: 15867385.
1. Atilla-Gokcumen GE, Bedigian AV, Sasse S, Eggert US. Inhibition of glycosphingolipid biosynthesis induces cytokinesis failure. J Am Chem Soc. 2011 Jul 6;133(26):10010-3. doi: 10.1021/ja202804b. Epub 2011 Jun 14. PMID: 21668028; PMCID: PMC3131740.
PubMed ID: 21668028
2. Wu X, Kim Y, Sun BC, Moore JD, Shaw WA, Maurer BJ. Liquid chromatography method for quantifying D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (D-threo-PPMP) in mouse plasma and liver. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jun 6;837(1-2):44-8. doi: 10.1016/j.jchromb.2006.03.060. Epub 2006 May 22. PMID: 16716770.
PubMed ID: 16716770
3. Gouazé V, Liu YY, Prickett CS, Yu JY, Giuliano AE, Cabot MC. Glucosylceramide synthase blockade down-regulates P-glycoprotein and resensitizes multidrug-resistant breast cancer cells to anticancer drugs. Cancer Res. 2005 May 1;65(9):3861-7. doi: 10.1158/0008-5472.CAN-04-2329. PMID: 15867385.
PubMed ID: 15867385
4. O'Donnell PH, Guo WX, Reynolds CP, Maurer BJ. N-(4-hydroxyphenyl)retinamide increases ceramide and is cytotoxic to acute lymphoblastic leukemia cell lines, but not to non-malignant lymphocytes. Leukemia. 2002 May;16(5):902-10. doi: 10.1038/sj.leu.2402485. PMID: 11986953.
PubMed ID: 11986953
5. Maurer BJ, Melton L, Billups C, Cabot MC, Reynolds CP. Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. J Natl Cancer Inst. 2000 Dec 6;92(23):1897-909. doi: 10.1093/jnci/92.23.1897. PMID: 11106681.
PubMed ID: 11106681
6. de Chaves EI, Bussière M, Vance DE, Campenot RB, Vance JE. Elevation of ceramide within distal neurites inhibits neurite growth in cultured rat sympathetic neurons. J Biol Chem. 1997 Jan 31;272(5):3028-35. doi: 10.1074/jbc.272.5.3028. PMID: 9006952.
PubMed ID: 9006952
