Catalog Number: 3631
Alternate Names: Tacrolimus, Fujimycin
Chemical Name: (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-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-8-(2-propen-1-yl)-15,19-e
Biological Activity
Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC50 = 1 nM), IL-3, IL-4, IL-6 (IC50 = 35 nM), GM-CSF, TNFα (IC50 = 10 nM), IFNγ and Myc from activated T cells in vitro. Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo.

Analog also available.

Technical Data
  • M.Wt:
    804.02
  • Formula:
    C44H69NO12
  • Solubility:
    Soluble to 100 mM in DMSO and to 100 mM in ethanol
  • Purity:
    >99%
  • Storage:
    Store at -20°C
  • CAS No:
    104987-11-3
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Other Product-Specific Information:
Background References
  1. The complex of FK506-binding protein 12 and FK506 inhibits calcineurin phosphatase activity and IgE activation-induced cytokine transcripts, but not exocytosis, in mouse mast cells.
    Fruman et al.
    J.Immunol., 1995;154:1846
  2. Tissue distribution and abundance of human FKBP51, and FK506-binding protein that can mediate calcineurin inhibition.
    Baughman et al.
    Biochem.Biophys.Res.Commun., 1997;232:437
  3. Ascomycin and FK506: Pharmacology and therapeutic potential as anticonvulsants and neuroprotectants.
    Sierra-Paredes and Sierra-Marcuno
    CNS Neurosci.Ther., 2008;14:36
Citations:

The citations listed below are publications that use Tocris products. Selected citations for FK 506 include:

11 Citations: Showing 1 - 10
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  1. Increasing the Receptor Tyrosine Kinase EphB2 Prevents Amyloid-β-induced Depletion of Cell Surface Glutamate Receptors by a Mechanism That Requires the PDZ-binding Motif of EphB2 and Neuronal Activity.
    Authors: Miyamoto Et al.
    Cell Rep 2016;291:1719
  2. Transcriptome Profiling of Patient-Specific Human iPSC-Cardiomyocytes Predicts Individual Drug Safety and Efficacy Responses In Vitro.
    Authors: Matsa Et al.
    Cell Stem Cell. 2016;19:311
  3. Intra-CA1 administration of FK-506 (tacrolimus) in rat impairs learning and memory in an inhibitory avoidance paradigm.
    Authors: Hadjiasgary Et al.
    J Neurosci 2015;18:130
  4. Heterosynaptic structural plasticity on local dendritic segments of hippocampal CA1 neurons.
    Authors: Oh Et al.
    Iran J Basic Med Sci 2015;10:162
  5. Interleukin-6 secretion by astrocytes is dynamically regulated by PI3K-mTOR-calcium signaling.
    Authors: Codeluppi Et al.
    PLoS One 2014;9:e92649
  6. Distinct molecular components for thalamic- and cortical-dependent plasticity in the lateral amygdala.
    Authors: Mirante Et al.
    J Biol Chem 2014;7:62
  7. Cocaine-induced changes of synaptic transmission in the striatum are modulated by adenosine A2A receptors and involve the tyrosine phosphatase STEP.
    Authors: Chiodi Et al.
    Neuropsychopharmacology 2014;39:569
  8. Upregulation of nuclear factor of activated T-cells by nerve injury contributes to development of neuropathic pain.
    Authors: Cai Et al.
    J Pharmacol Exp Ther 2013;345:161
  9. Human T cell activation results in extracellular signal-regulated kinase (ERK)-calcineurin-dependent exposure of Tn antigen on the cell surface and binding of the macrophage galactose-type lectin (MGL).
    Authors: Vliet Et al.
    J Biol Chem 2013;288:27519
  10. Oxytocin-stimulated NFAT transcriptional activation in human myometrial cells.
    Authors: Pont Et al.
    Mol.Endocrinol. 2012;26:1743
  11. AKAP79/150 impacts intrinsic excitability of hippocampal neurons through phospho-regulation of A-type K+ channel trafficking.
    Authors: Lin Et al.
    Br J Pharmacol 2011;31:1323
Expand to show all 11 Citations
Tocris Small Molecules
Description Application Cat# Citations Images  

Ascomycin

4210  
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