Ascomycin

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Cat.No. 4210 - Ascomycin | C43H69NO12 | CAS No. 104987-12-4
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
Datasheet
Citations
Reviews (1)
Literature (1)

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.

Select a batch to recalculate based on the batch molecular weight:
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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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

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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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Literature in this Area

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