| Identification | Back Directory | [Name]
Ascomycin | [CAS]
11011-38-4 | [Synonyms]
AAG
FK-520
CS-740
CGTHBA
Nsc106410
Ascomycin
FR-900520
Aids093221
Aids-093221
IMMUNOMYCIN
Ascomycin 1
RP23-177M10.6
Ascomycin (FK520)
Ascomycin, >=98.5%
Ascomycin (Immunomycin
Ascomycin (Immunomycin,FK-520)
Anti-Nprl3 antibody produced in goat
ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS
nitrogen permease regulator-like 3 (S. cerevisiae)
ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS VAR ASCOMYCETICUS
ASCOMYCIN (IMMUNOMYCIN, FR-900520) \ INH IBITS CALCINEURIN (PP2B)
Ascomycin, Streptomyces hygroscopicus - CAS 11011-38-4 - Calbiochem
(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
15,19-Epoxy-3H-pyrido[2,1-C][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 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-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26as)- | [EINECS(EC#)]
658-052-0 | [Molecular Formula]
C43H69NO12 | [MDL Number]
MFCD06198665 | [MOL File]
11011-38-4.mol | [Molecular Weight]
792.01 |
| Chemical Properties | Back Directory | [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 | [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. |
| Hazard Information | Back Directory | [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. | [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) Hatanaka et al. (1988), FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physio-chemical and biological characteristics; J. Antibiot. (Tokyo), 41 1592
2) Petros et al. (1991), NMR studies of an FK506 analogue [U-13C]ascomycin, bound to FKBP: conformation and regions of ascomycin involved in binding; J. Med. Chem., 34 2925
3) Mollison et al. (1999), A macrolactam inhibitor of T helper type 1 and T helper type 2 cytokine biosynthesis for topical treatment of inflammatory skin diseases; J. Invest. Dermatol., 112 729 |
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