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182800

Ascomycin, Streptomyces hygroscopicus

An ethyl analog of FK506 with similar immunosuppressant properties.

Synonym(s):

Ascomycin, Streptomyces hygroscopicus, Immunomycin, FR-900520

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About This Item

Empirical Formula (Hill Notation):
C43H69NO12
CAS Number:
104987-12-4
Molecular Weight:
792.01
UNSPSC Code:
12352200
Assay:
≥90% (HPLC)
Form:
crystalline solid
Quality level:
100
Storage condition:
OK to freeze
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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

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

Preparation Note

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

Disclaimer

Toxicity: Harmful (C)

Storage Class

11 - Combustible Solids

wgk

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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