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Ascomycin CAS: 104987-12-4

Category: Inhibitors
Product Name: Ascomycin
Cat No: I000277
CAS No: 104987-12-4
Synonyms: None
Molecular Formula: C43H69NO12
Molecular Weight: 792.0
SMILES: O=C(C(N1[C@H](C(O[C@@H]([C@@H]([C@@H](O)CC([C@H](CC)/C=C(C[C@H](C)C[C@@H]2OC)\C)=O)C)/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)=O)CCCC1)=O)[C@]4(O)O[C@H]2[C@@H](OC)C[C@H]4C
InChI: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,
InChIKey: ZDQSOHOQTUFQEM-NURRSENYSA-N
Solubility: DMSO: ≥ 39 mg/mL
Target: Antibiotic
IC50: 0.55 nM [1]
Storage: Store at -20°C
CAS 104987-12-4,Ascomycin
  • Description

Ascomycin(Immunomycin, FR-900520, FK520) is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties.
IC50 Value: 0.55 nM [1]
Target:
in vitro: When we used either CD4+CD8+ thymocytes or peripheral T cells activated by phorbol ester and ionomycin, the cell surface induction of CD5 was also partially blocked by CsA, FK-520 and rapamycin [2]. Ascomycinalso had a 3-fold lower immunosuppressive potency in a popliteal lymph node hyperplasia assay, resulting in an equivalent therapeutic index consistent with a common mechanistic dependence on calcineurin inhibition [3].
in vivo: In 14-day studies, nephrotoxicity was not induced by continuous i.p. infusion of ascomycin at 10 mg/kg/day or daily oral administration (up to 50 mg/kg/day) in rats on a normal diet, nor by continuous i.v. infusion (up to 6 mg/kg/day) in rats on a low salt diet to enhance susceptibility [3].

  • Spec

Appearance:White solid

  • References


1:Engineering of the LysR family transcriptional regulator FkbR1 and its target gene to improve ascomycin production. Song K, Wei L, Liu J, Wang J, Qi H, Wen J.Appl Microbiol Biotechnol. 2017 Mar 27. doi: 10.1007/s00253-017-8242-4. [Epub ahead of print] PMID: 28349163
2:Integration of parallel 13 C-labeling experiments and in silico pathway analysis for enhanced production of ascomycin. Qi H, Lv M, Song K, Wen J.Biotechnol Bioeng. 2017 May;114(5):1036-1044. doi: 10.1002/bit.26223. Epub 2016 Nov 29. PMID: 27869289
3:Enhancement of ascomycin production in Streptomyces hygroscopicus var. ascomyceticus by combining resin HP20 addition and metabolic profiling analysis. Qi H, Zhao S, Fu H, Wen J, Jia X.J Ind Microbiol Biotechnol. 2014 Sep;41(9):1365-74. doi: 10.1007/s10295-014-1473-9. Epub 2014 Jun 26. PMID: 24965502
4:Chemistry of the immunomodulatory macrolide ascomycin and related analogues. Bulusu MA, Baumann K, Stuetz A.Prog Chem Org Nat Prod. 2011;94:59-126. doi: 10.1007/978-3-7091-0748-5_2. Review. No abstract available. PMID: 21833838
5:Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants. Sierra-Paredes G, Sierra-Marcuño G.CNS Neurosci Ther. 2008 Spring;14(1):36-46. doi: 10.1111/j.1527-3458.2008.00036.x. Review. PMID: 18482098
6:Anticonvulsant effect of the calcineurin inhibitor ascomycin on seizures induced by picrotoxin microperfusion in the rat hippocampus. Vázquez-López A, Sierra-Paredes G, Sierra-Marcuño G.Pharmacol Biochem Behav. 2006 Jul;84(3):511-6. Epub 2006 Jul 26. PMID: 16872668
7:Organic solvents compromise performance of internal standard (ascomycin) in proficiency testing of mass spectrometry-based assays for tacrolimus. Napoli KL.Clin Chem. 2006 Apr;52(4):765-6. No abstract available. PMID: 16595827 Free Article
8:Computer-assisted constitutional assignment of large molecules: COCON analysis of ascomycin. Junker J, Maier W, Lindel T, Köck M.Org Lett. 1999 Sep 9;1(5):737-40. PMID: 16118875
9:Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds. Monaghan P, Fardis M, Revill WP, Bell A.J Infect Dis. 2005 Apr 15;191(8):1342-9. Epub 2005 Mar 4. PMID: 15776382
10:Genetically engineered analogs of ascomycin for nerve regeneration. Revill WP, Voda J, Reeves CR, Chung L, Schirmer A, Ashley G, Carney JR, Fardis M, Carreras CW, Zhou Y, Feng L, Tucker E, Robinson D, Gold BG.J Pharmacol Exp Ther. 2002 Sep;302(3):1278-85. PMID: 12183690 Free Article


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