FK 506

Pricing Availability   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 (19)
Reviews (2)
Literature (1)

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. Identified as targeting human host cell proteins that interact with SARS-CoV-2.

Analog 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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

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 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
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:

References

References are publications that support the biological activity of the product.

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

Gordon et al (2020) A SARS-CoV-2-human protein-protein interaction map reveals drug targets and potential drug-repurposing. Nature 583 PMID: 32353859


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: FK 506, FK 506 supplier, Potent, calcineurin, inhibitors, inhibits, protein, phosphatases, 2B, Protein, Ser/Thr, FK506, antibiotics, COVID-19, SARS-CoV-2, severe, acute, respiratory, syndrome, Tacrolimus, Fujimycin, Phosphatases, Immunosuppressants, Antibiotics, NFAT, Coronavirus, 3631, Tocris Bioscience

19 Citations for FK 506

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

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

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

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

Chiu et al (2019) NMDAR-Activated PP1 Dephosphorylates GluN2B to Modulate NMDAR Synaptic Content. Cell Rep 28 332 PMID: 31291571

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

Palmqvist et al (2016) A human and animal model-based approach to investigating the anti-inflammatory profile and potential of the 5-HT2B receptor antagonist AM1030. J Inflamm (Lond) 13 20 PMID: 27340371

Sharma et al (2016) Protein Phosphatase 1-α Regulates AS160 Ser588 and Thr642 Dephosphorylation in Skeletal Muscle. Diabetes 65 2606 PMID: 27246912

Sharanek et al (2014) Different dose-dependent mechanisms are involved in early cyclosp. a-induced cholestatic effects in hepaRG cells. Toxicol Sci 141 244 PMID: 24973091

Henson et al (2017) Long-term depression-associated signaling is required for an in vitro model of NMDA receptor-dependent synapse pruning. Neurobiol Learn Mem 138 39 PMID: 27794462

Neustadtl et al (2017) Reduced cortical excitatory synapse number in APOE4 mice is associated with increased calcineurin activity. Neuroreport 28 618 PMID: 28542068

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

Marra et al (2012) A preferentially segregated recycling vesicle pool of limited size supports neurotransmission in native central synapses. Neuron 76 579 PMID: 23141069

Torres et al (2018) FK506 Attenuates the MRP1-Mediated Chemoresistant Phenotype in Glioblastoma Stem-Like Cells. Int J Mol Sci 19 PMID: 30208561

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

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

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


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

Reviews for FK 506

Average Rating: 4.5 (Based on 2 Reviews.)

5 Star
50%
4 Star
50%
3 Star
0%
2 Star
0%
1 Star
0%

Have you used FK 506?

Submit a review and receive an Amazon gift card.

$50/€35/£30/$50CAN/¥300 Yuan/¥5000 Yen for first to review with an image

$25/€18/£15/$25CAN/¥75 Yuan/¥1250 Yen for a review with an image

$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image

Submit a Review

Filter by:


Works as intended..
By Anonymous on 04/04/2020
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Sprague-Dawley rats primary neuronal

FK506 for PP2B (FK, 1 μM)

PMID: 31291571 Reference
review image

FK 506, a treatment for primary sclerosing cholangitis.
By Anonymous on 12/25/2019
Species: Human

FK 506 was tested for its antibiotic properties. FK 506, a treatment for primary sclerosing cholangitis: results of an open-label preliminary trial.

review image

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


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