FK 506

Pricing Availability Delivery Time Qty
Cat.No. 3631 - FK 506 | C44H69NO12 | CAS No. 104987-11-3
Description: Potent calcineurin inhibitor; immunosuppressant
Alternative 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-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone
Purity: ≥99% (HPLC)
Datasheet
Citations (11)
Literature

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 (ascomycin, Cat. No. 4210) also available.

Technical Data

M. Wt 804.02
Formula C44H69NO12
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 104987-11-3
PubChem ID 445643
InChI Key QJJXYPPXXYFBGM-LFZNUXCKSA-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[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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.4 100
ethanol 80.4 100

Preparing Stock Solutions

The following data is based on the product molecular weight 804.02. Batch specific molecular weights may vary from batch to batch due to solvent 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
1 mM 1.24 mL 6.22 mL 12.44 mL
5 mM 0.25 mL 1.24 mL 2.49 mL
10 mM 0.12 mL 0.62 mL 1.24 mL
50 mM 0.02 mL 0.12 mL 0.25 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

Fruman et al (1995) 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. J.Immunol. 154 1846 PMID: 7530743

Baughman et al (1997) Tissue distribution and abundance of human FKBP51, and FK506-binding protein that can mediate calcineurin inhibition. Biochem.Biophys.Res.Commun. 232 437 PMID: 9125197

Sierra-Paredes and Sierra-Marcuno (2008) Ascomycin and FK506: Pharmacology and therapeutic potential as anticonvulsants and neuroprotectants. CNS Neurosci.Ther. 14 36 PMID: 18482098


If you know of a relevant reference for FK 506, please let us know.

View Related Products by Product Action

View all Protein Ser/Thr Phosphatases Inhibitors

Keywords: Potent calcineurin inhibitors inhibits protein phosphatases 2B Protein Ser/Thr FK506 antibiotics Tacrolimus Fujimycin Protein Ser/Thr Phosphatases

11 Citations for FK 506

Citations are publications that use Tocris products. Selected citations for FK 506 include:

Miyamoto et al (2016) 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. Cell Rep 291 1719 PMID: 26589795

Matsa et al (2016) Transcriptome Profiling of Patient-Specific Human iPSC-Cardiomyocytes Predicts Individual Drug Safety and Efficacy Responses In Vitro. Cell Stem Cell. 19 311 PMID: 27545504

Oh et al (2015) Heterosynaptic structural plasticity on local dendritic segments of hippocampal CA1 neurons. Iran J Basic Med Sci 10 162 PMID: 25558061

Hadjiasgary et al (2015) Intra-CA1 administration of FK-506 (tacrolimus) in rat impairs learning and memory in an inhibitory avoidance paradigm. J Neurosci 18 130 PMID: 25810886

Codeluppi et al (2014) Interleukin-6 secretion by astrocytes is dynamically regulated by PI3K-mTOR-calcium signaling. PLoS One 9 e92649 PMID: 24667246

Chiodi et al (2014) Cocaine-induced changes of synaptic transmission in the striatum are modulated by adenosine A2A receptors and involve the tyrosine phosphatase STEP. Neuropsychopharmacology 39 569 PMID: 23989619

Mirante et al (2014) Distinct molecular components for thalamic- and cortical-dependent plasticity in the lateral amygdala. J Biol Chem 7 62 PMID: 25071439

Vliet et al (2013) 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). J Biol Chem 288 27519 PMID: 23918927

Cai et al (2013) Upregulation of nuclear factor of activated T-cells by nerve injury contributes to development of neuropathic pain. J Pharmacol Exp Ther 345 161 PMID: 23386250

Pont et al (2012) Oxytocin-stimulated NFAT transcriptional activation in human myometrial cells. Mol.Endocrinol. 26 1743 PMID: 22902539

Lin et al (2011) AKAP79/150 impacts intrinsic excitability of hippocampal neurons through phospho-regulation of A-type K+ channel trafficking. Br J Pharmacol 31 1323 PMID: 21273417


Do you know of a great paper that uses FK 506 from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis

Pathways for FK 506

Protocols

TODO: Add Protocols