476300

Myriocin, Mycelia sterilia

A potent immunosuppressant.

• Synonym(s): Myriocin, Mycelia sterilia, ISP-1, Thermozymocidin, [2S,3R,4R]-(E)-2-Amino-3,4-dihydroxy-2-[hydroxymethyl]-14-oxo-6-eicosenoic Acid
• Empirical Formula (Hill Notation): C₂₁H₃₉NO₆
• CAS Number: 35891-70-4
• Molecular Weight: 401.54
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD01632772
• Assay: ≥95% (TLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• description: RTECS - JX3890000
• assay: ≥95% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 25 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: N[C@]([C@@H](O)[C@H](O)C\C=C\CCCCCCC(=O)CCCCCC)(CO)C(=O)O
• InChI: 1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
• InChI key: ZZIKIHCNFWXKDY-GNTQXERDSA-N

Description

General description

A potent immunosuppressant. Displays 10- to 100-fold more potent immunosuppressant activity than cyclosporin A. Potently inhibits serine palmitoyltransferase (SPT; K_i = 280 pM) thereby blocking the synthesis of ceramide. Disrupts substratum adhesion of melanoma cells. Inhibits cell proliferation and induces apoptosis in IL-2 dependent murine cytotoxic T lymphocyte cell line CTLL-2.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Serine palmitoyltransferase

Product does not compete with ATP.

Reversible: no

Target K_i: 280 pM against serine palmitoyltransferase

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Hanada, K., et al. 2000. Biochem. Pharmacol.59, 1211.
Chen, J.K., et al. 1999. Chem. Biol. 6, 221.
Hidari, K.I.P.J., et al. 1996. J. Biol. Chem. 271, 14636.
Nakamura, S., et al. 1996. J. Biol. Chem. 271, 1255.
Mikaye, Y., et al. 1995. Biochem. Biophys. Res. Commun. 211, 396.
Fujita, T., et al. 1994. J. Antibiot. 47, 208.

Legal Information

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

Disclaimer

Toxicity: Harmful (C)

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable