182800

Ascomycin, Streptomyces hygroscopicus

An ethyl analog of FK506 with similar immunosuppressant properties.

• Synonym(s): Ascomycin, Streptomyces hygroscopicus, Immunomycin, FR-900520
• Empirical Formula (Hill Notation): C₄₃H₆₉NO₁₂
• CAS Number: 104987-12-4
• Molecular Weight: 792.01
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥90% (HPLC)
• form: crystalline solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 1 mg/mL; ethanol: 1 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29+,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
• InChI key: ZDQSOHOQTUFQEM-BFFCMSJVSA-N

Description

General description

An ethyl analog of FK506 with similar immunosuppressant properties. Acts by binding to immunophilins. Inhibits the synthesis of Th-1 and Th-2 type cytokines in target cells.

Ethyl analog of FK-506 that possesses the same potent immunosuppressive properties as the parent compound. Inhibition of the Ca2⁺/calmodulin activated phosphatase calcineurin (IC₅₀ = 10 nM) by the ascomycin/FK-506 binding protein complex is believed to be important in the mechanism of immunosuppression. Acts by binding immumophilins.

Biochem/physiol Actions

Cell permeable: no

Fully active via yeast rotamase (FK 506 binding protein) inhibition

Primary Target
Immunophilins

Product does not compete with ATP.

Reversible: no

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Ethanol stock solutions are stable for up to 3 days at -20°C. Anhydrous DMSO stock solutions are stable for up to 1 month -20°C.

Other Notes

Paul, C., et al. 2000. Expert Opin. Invest. Drugs9, 69.
Kawai, M., et al. 1993. FEBS Lett.316, 107.
Pilot-Matias, T.J., et al. 1993. Gene128, 219.
Shafiee, A., et al. 1993. J. Antibiot.46, 1397.
Petros, A.M., et al. 1992. J. Med. Chem. 35, 2467.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3