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Submit ReviewAscomycin
Description: Calcineurin phosphatase inhibitor; analog of FK 506 (Cat. No. 3631)
Alternative Names: FK 520, FR 900520
Chemical Name: (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
Biological Activity
Analog of FK 506 (Cat. No. 3631); binds to FK 506-binding protein 12 (FKBP12) in order to inhibit calcineurin phosphatase activity (IC50 = 49 nM) and activation of nuclear factor of activated T cells (NFAT). Displays antifungal and immunosuppressive activities.
Technical Data
| M. Wt | 792.01 |
| Formula | C43H69NO12 |
| Storage | Store at -20°C |
| CAS Number | 104987-12-4 |
| PubChem ID | 5282071 |
| InChI Key | ZDQSOHOQTUFQEM-NURRSENYSA-N |
| Smiles | O[C@H]1[C@H](OC)C[C@H](/C=C(C)/[C@@H](O4)[C@H](C)[C@@H](O)CC([C@H](CC)/C=C(C)/C[C@H](C)C[C@H](OC)[C@@]2([H])O[C@](C(C(N3[C@@](C4=O)([H])CCCC3)=O)=O)(O)[C@H](C)C[C@@H]2OC)=O)CC1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 39.6 | 50 | |
| ethanol | 39.6 | 50 |
Preparing Stock Solutions
The following data is based on the product molecular weight 792.01. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 2.53 mL | 12.63 mL | 25.25 mL |
| 2.5 mM | 0.51 mL | 2.53 mL | 5.05 mL |
| 5 mM | 0.25 mL | 1.26 mL | 2.53 mL |
| 25 mM | 0.05 mL | 0.25 mL | 0.51 mL |
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Product Datasheets
References
References are publications that support the biological activity of the product.
Motamedi et al (1996) Characterization of methyltransferase and hydroxylase genes involved in the biosynthesis of the immunosuppressants FK506 and FK520. J.Bacteriol. 178 5243 PMID: 8752344
Arndt et al (1999) Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans. Microbiology 145 1989 PMID: 10463165
Revill et al (2002) Genetically engineered analogs of ascomycin for nerve regeneration. J.Pharmacol.Exp.Ther. 302 1278 PMID: 12183690
Hatanaka et al (1988) FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physicochemical and biological characteristics. J.Antibiot (Tokyo). 41 1593
If you know of a relevant reference for Ascomycin, please let us know.
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Keywords: Ascomycin, Ascomycin supplier, FK520, FR900520, Ascomycin, calcineurin, phosphatase, inhibitors, inhibits, analogs, FK, 506, fkbp12, immunosuppressives, antifungals, antibiotics, 520, FR, 900520, Protein, Ser/Thr, Phosphatases, Antibiotics, NFAT, 4210, Tocris Bioscience
Citations for Ascomycin
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Reviews for Ascomycin
Average Rating: 5 (Based on 1 Review.)
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The immunosuppressant activity of Ascomycin was studied.
By
Anonymous on 12/15/2019
Species: Human
The immunosuppressant activity of Ascomycin was studied. Analysis of the proteins in iMK1208 against Streptomyces species conducted.
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