AdipoGen Life Sciences

Ascomycin (high purity)

CHF 30.00
In stock
AG-CN2-0420-M0011 mgCHF 30.00
AG-CN2-0420-M0055 mgCHF 60.00
AG-CN2-0420-M02525 mgCHF 160.00
More Information
Product Details
Synonyms Immunomycin; FK520; Analog of FK-506; FR-900520; L-683590; NSC 106410; WS 7238A
Product Type Chemical
Properties
Formula

C43H69NO12

MW 792.0
CAS 104987-12-4
RTECS CI7570000; KD4185000
Source/Host Chemicals Isolated from Streptomyces sp..
Purity Chemicals ≥98%
Appearance White to off-white solid.
Solubility Soluble in DMSO or ethanol.
Identity Determined by MS and IR.
InChi Key ZDQSOHOQTUFQEM-VZQNCADUSA-N
Smiles [H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@H]1C(=O)O[C@@H]([C@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)\C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@@H](O)[C@@H](C1)OC
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Working aliquots are stable for up to 3 months when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Macrolide antibiotic. Ethyl analog of FK506 [1, 2].
  • Strong immunosuppressant. Binds to the FK-506-binding protein FKBP12. This complex inhibits calcineurin (protein phosphatase 2B (PP2B)) [2-4, 8].
  • Suppresses the production of T helper type 1 (Th1) (interferon and IL-2) and Th2 (IL-4 and IL-10) cytokines in T lymphocytes and preferentially inhibits the activation of mast cells [5-7].
  • Anti-inflammatory. Used for topical treatment of inflammatory skin diseases [5, 6].
  • Potently inhibits anti-IgE-induced histamine and cytokine release and reduces IgE-dependent p38 MAPK activation in human basophils. Inhibits basophil degranulation at the initial phase of allergic skin reactions [7, 8].
  • Antifungal [1].
  • Antimalaria compound [9].
  • Anticonvulsant (antiepileptic) [10, 11].
Product References
  1. Ascomycin, an antifungal antibiotic: T. Arai, et al.; J. Antibiot. 15, 231 (1962)
  2. Identity of immunosuppressant FR-900520 with ascomycin: M. Morisaki, et al.; J. Antibiot. 45, 126 (1992)
  3. Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation: K.W. Mollison, et al.; Ann. N. Y. Acad. Sci. 685, 55 (1993)
  4. FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics: H. Hatanaka, et al.; J. Antibiot. (Tokyo) 41, 1592 (1988)
  5. Ascomycins: promising agents for the treatment of inflammatory skin diseases: C. Paul, et al.; Expert Opin. Investig. Drugs 9, 69 (2000)
  6. Ascomycin: an advance in the management of atopic dermatitis: C.E. Griffiths; Br. J. Dermatol. 144, 679 (2001)
  7. The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils: T. Zuberbier, et al.; J. Allergy Clin. Immunol. 108, 275 (2001)
  8. Calcineurin antagonists differentially affect mediator secretion, p38 mitogen-activated protein kinase and extracellular signal-regulated kinases from immunologically activated human basophils: K.E. Plath, et al.; Clin. Exp. Allergy 33, 342 (2003)
  9. Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds: P. Monaghan, et al.; J. Infect. Dis. 191, 1342 (2005)
  10. Anticonvulsant effect of the calcineurin inhibitor ascomycin on seizures induced by picrotoxin microperfusion in the rat hippocampus: A. Vazquez-Lopez, et al.; Pharmacol. Biochem. Behav. 84, 511 (2006)
  11. Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants: G. Sierra-Paredes & G. Sierra-Marcuno; CNS Neurosci. Ther. 14, 36 (2008)
© 2017 Adipogen Life Sciences. Pictures: © 2012 Martin Oeggerli. All Rights Reserved.