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

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.

Safety Information

RTECS 

CI7570000

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.

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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