Ascomycin
Ascomycin Basic information
- Product Name:
- Ascomycin
- Synonyms:
-
- ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS
- ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS VAR ASCOMYCETICUS
- FR-900520
- FK-520
- IMMUNOMYCIN
- AAG
- ASCOMYCIN (IMMUNOMYCIN, FR-900520) \ INH IBITS CALCINEURIN (PP2B)
- (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
- CAS:
- 11011-38-4
- MF:
- C43H69NO12
- MW:
- 792.01
- EINECS:
- 658-052-0
- Product Categories:
-
- API
- Immunosuppressant
- Mol File:
- 11011-38-4.mol
Ascomycin Chemical Properties
- Melting point:
- 158 - 161°C
- storage temp.
- -20°C
- solubility
- Soluble in DMSO (up to 50 mg/ml), or in Ethanol (up to 50 mg/ml with warming).
- form
- White crystalline solid
- color
- White
- biological source
- goat
- Stability:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
Ascomycin Usage And Synthesis
Description
Ascomycin (11011-38-4) is an analog of FK-506 (Cat.# 10-1103). Potent immunosuppressant1. Binds to FKBP122 and inhibits calcineurin and NFAT. Ascomycin displays anti-inflammatory effects in skin diseases3. Cell permeable and active in vivo.
Chemical Properties
White powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from biological fermentation.
Uses
A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases.
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.
Biochem/physiol Actions
Product does not compete with ATP.
Enzyme inhibitor
This antifungal antibiotic (FW = 792.02 g/mol; CAS 104987-12-4; Solubility: 50 mM in DMSO), also known as FK520, isolated from Streptomyces hygroscopicus, is also a powerful immunosuppressant. Note that ascomycin is a structural analogue of tacrolimus (or FK506) and, as such, operates by a similar mechanism of action (See Tacrolimus). Ascomycin inhibits allogenic T-lymphocyte proliferation and calcineurin phosphatase activity.
References
[1] H HATANAKA. FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics.[J]. Journal of Antibiotics, 1988, 41 11: 1592-1601. DOI:10.7164/antibiotics.41.1592
[2] A. M. PETROS. NMR studies of an FK-506 analog [U-13C]ascomycin, bound to FKBP: conformation and regions of ascomycin involved in binding[J]. Journal of Medicinal Chemistry, 1991, 34 9: 2925-2928. DOI:10.1021/jm00113a037
[3] KARL W. MOLLISON. A Macrolactam Inhibitor of T Helper Type 1 and T Helper Type 2 Cytokine Biosynthesis for Topical Treatment of Inflammatory Skin Diseases1[J]. Journal of Investigative Dermatology, 1999, 112 5: Pages 729-738. DOI:10.1046/j.1523-1747.1999.00567.x
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