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AdipoGen Life Sciences
Ascomycin (high purity)
30
CHF
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
| 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
- Ascomycin, an antifungal antibiotic: T. Arai, et al.; J. Antibiot. 15, 231 (1962)
- Identity of immunosuppressant FR-900520 with ascomycin: M. Morisaki, et al.; J. Antibiot. 45, 126 (1992)
- 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)
- 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)
- Ascomycins: promising agents for the treatment of inflammatory skin diseases: C. Paul, et al.; Expert Opin. Investig. Drugs 9, 69 (2000)
- Ascomycin: an advance in the management of atopic dermatitis: C.E. Griffiths; Br. J. Dermatol. 144, 679 (2001)
- 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)
- 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)
- 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)
- 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)
- Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants: G. Sierra-Paredes & G. Sierra-Marcuno; CNS Neurosci. Ther. 14, 36 (2008)
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