Ascomycin (high purity)
Product Code: AG-CN2-0420
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0420-M001 | 1 mg | £40.00 |
Quantity:
| AG-CN2-0420-M005 | 5 mg | £50.00 |
Quantity:
| AG-CN2-0420-M025 | 25 mg | £130.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Immunomycin; FK520; Analog of FK-506; FR-900520; L-683590; NSC 106410; WS 7238A
Appearance:
White to off-white solid.
CAS:
104987-12-4
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light.
Hazards:
H302, H312, H332
InChi:
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
InChiKey:
ZDQSOHOQTUFQEM-VZQNCADUSA-N
Long Description:
Chemical. CAS: 104987-12-4. Formula: C43H69NO12. MW: 792. Isolated from Streptomyces sp. Macrolide antibiotic. Ethyl analog of FK506. Strong immunosuppressant. Binds to the FK-506-binding protein FKBP12. This complex inhibits calcineurin (protein phosphatase 2B (PP2B)). 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. Anti-inflammatory. Used for topical treatment of inflammatory skin diseases. 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. Antifungal. Antimalaria compound. Anticonvulsant (antiepileptic).
MDL:
MFCD06198665
Molecular Formula:
C43H69NO12
Molecular Weight:
792
Package Type:
Vial
Precautions:
P261, P301, P312, P302, P352, P304, P340
Product 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].
Purity:
>98%
Signal word:
Warning
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
Solubility Chemicals:
Soluble in DMSO or ethanol.
Source / Host:
Isolated from Streptomyces sp.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
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.
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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