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Myriocin (Synonyms: ISP-1; Thermozymocidin)

Catalog No.GC14278

immunosuppressant and specific serine palmitoyltransferase inhibitor

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Myriocin Chemical Structure

Cas No.: 35891-70-4

Size Price Stock Qty
1mg
$38.00
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5mg
$95.00
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10mg
$156.00
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25mg
$271.00
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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 3 publications

Product Documents

Quality Control & SDS

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Background

Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A.[1] Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. [2] It disrupts substratum adhesion of melanoma cells.[3] It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis.[2],[4] Myriocin suppresses replication of the hepatitis C virus in a murine model.[5]

Reference:
[1]. Fujita, T., Inoue, K., Yamamoto, S., et al. Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. Journal of Antibiotics 47, 208-215 (1994).
[2]. Miyake, Y., Kozutsumi, Y., Nakamura, S., et al. Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin. Biochemical and Biophysical Research Communications 211(2), 396-403 (1995).
[3]. Hidari, K.I.P.J., Ichikawa, S., Fujita, T., et al. Complete removal of sphingolipids from the plasma membrane disrupts cell to substratum adhesion of mouse melanoma cells. The Journal of Biological Chemisty 271(24), 14636-14641 (1996).
[4]. Nakamura, S., Kozutsumi, Y., Sun, Y., et al. Dual roles of sphingolipids in signaling of the escape from and onset of apoptosis in a mouse cytotoxic T-cell line, CTLL-2. The Journal of Biological Chemisty 271, 1255-1257 (1996).
[5]. Umehara, T., Sudoh, M., Yasui, F., et al. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model. Biochemical and Biophysical Research Communications 346, 67-73 (2006).

Chemical Properties

Cas No. 35891-70-4 SDF
Synonyms ISP-1; Thermozymocidin
Chemical Name (2S,3R,4R,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Canonical SMILES CCCCCCC(CCCCCC/C([H])=C([H])/C[C@](O)([H])[C@@](O)([H])[C@@](C(O)=O)(N)CO)=O
Formula C21H39NO6 M.Wt 401.54
Solubility Methanol: 2 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.4904 mL 12.4521 mL 24.9041 mL
5 mM 0.4981 mL 2.4904 mL 4.9808 mL
10 mM 0.249 mL 1.2452 mL 2.4904 mL
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Reviews

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Average Rating: 5 ★★★★★ (Based on Reviews and 12 reference(s) in Google Scholar.)

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