Ascomycin An immunosuppressive antibiotic FK506 analog

Ascomycin (CAS 11011-38-4)

Ascomycin | CAS 11011-38-4 is rated 5.0 out of 5 by 1.
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Synonym: FK-520; Immunomycin; FR-900520
Application: An immunosuppressive antibiotic FK506 analog
CAS Number: 11011-38-4
Purity: >95%
Molecular Weight: 792.0
Molecular Formula: C43H69NO12
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ascomycin is a macrolide immunosuppressant antibiotic and an analog of the well-known antibiotic FK506 (sc-24649, an ethyl group substituted for the exocyclic allyl group of FK506). Ascomycin binds to the FK-506-binding protein FKBP12 and blocks the peptidyl-prolyl cis-trans isomerase activity of the protein. This binded complex also inhibits the activity of calcineurin, consequently suppressing the presentation of Th1 and Th2-type cytokines in cells and reducing production of interleukins IL-2, 4, and 10, leading to immunosuppression. Pimecrolimus (sc-208172), a derivative of the Ascomycin macrolide, has been shown to block the release of allergic response mediators from mast cells.


References

1. Pahl, A. and Keller, U. 1992. J. Bacteriol. 174: 5888-5894. PMID: 1381710
2. Mollison, K.W., et al. 1993. Ann. N.Y. Acad. Sci. 685: 55-57. PMID: 7689812
3. Meadows, R.P., et al. 1993. Biochemistry. 32: 754-765. PMID: 7678499
4. Kawai, M., et al. 1993. FEBS Lett. 316: 107-113. PMID: 7678400
5. Paul, C., et al. 2000. Expert Opin Investig Drugs. 9: 69-77. PMID: 11060661
6. Zuberbier, T., et al. 2001. J. Allergy Clin. Immunol. 108: 275-280. PMID: 11496246
7. Sierra-Paredes, G., et al. 2008. CNS Neurosci Ther. 14: 36-46. PMID: 18482098

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml), and ethanol (50 mM).
Storage :
Store at -20° C
Boiling Point :
~868.3° C at 760 mmHg (Predicted)
Density :
~1.20 g/cm3 (Predicted)
Refractive Index :
n20D 1.55
IC50 :
Calcineurin phosphatase: IC50 = 49 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
CI7570000
PubChem CID :
2241
MDL Number :
MFCD06198665
SMILES :
CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C

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Ascomycin  Product Citations

See how others have used Ascomycin. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 15546853  Shuttleworth, TJ. et al. 2004. Physiology (Bethesda). 19: 355-361.

PMID: # 12438168  Hamelink, C. et al. 2002. Ann. N. Y. Acad. Sci. 971: 474-490.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Shuttleworth et al Shuttleworth et al. (PubMed ID 15546853) used Ascomycin, an immunosuppressive antibiotic analog, to reverse calcium-dependent inhibition of ARC channels by blocking calcineurin activity. -SCBT Publication Review
Date published: 2015-01-21
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