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Submit ReviewFK 506
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)
Biological Activity for FK 506
FK 506 is a 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 for FK 506
| 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 for FK 506
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 80.4 | 100 | |
| ethanol | 80.4 | 100 |
Preparing Stock Solutions for FK 506
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.
| 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 |
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Product Datasheets for FK 506
References for FK 506
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
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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
39 Citations for FK 506
Citations are publications that use Tocris products. Selected citations for FK 506 include:
Jerzy W et al (2022) Integrins Bidirectionally Regulate the Efficacy of Inhibitory Synaptic Transmission and Control GABAergic Plasticity. J Neurosci 42 5830-5842 PMID: 35701161
Armando A et al (2022) Calcineurin Controls Cellular Prion Protein Expression in Mouse Astrocytes. Cells 11 PMID: 35203261
Kevin et al (2022) Mild membrane depolarization in neurons induces immediate early gene transcription and acutely subdues responses to a successive stimulus. J Biol Chem 298 102278 PMID: 35863435
Zhongmei et al (2022) RASA2 ablation in T cells boosts antigen sensitivity and long-term function. Nature 609 174-182 PMID: 36002574
Yan et al (2022) LAMTOR1 inhibition of TRPML1-dependent lysosomal calcium release regulates dendritic lysosome trafficking and hippocampal neuronal function. EMBO J 41 e108119 PMID: 35099830
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
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
Lars et al (2014) Ion channel TRPV1-dependent activation of PTP1B suppresses EGFR-associated intestinal tumorigenesis. J Clin Invest 124 3793-806 PMID: 25083990
Eleonora et al (2020) Calcineurin Controls Expression of EAAT1/GLAST in Mouse and Human Cultured Astrocytes through Dynamic Regulation of Protein Synthesis and Degradation. Int J Mol Sci 21 PMID: 32210081
Douglas et al (2020) Roles of glycogen synthase kinase 3 alpha and calcineurin in regulating the ability of sperm to fertilize eggs. FASEB J 34 1247-1269 PMID: 31914663
Mark L et al (2020) Local miRNA-Dependent Translational Control of GABAAR Synthesis during Inhibitory Long-Term Potentiation. Cell Rep 31 107785 PMID: 32579917
Christopher J et al (2020) BCR-Induced Ca2+ Signals Dynamically Tune Survival, Metabolic Reprogramming, and Proliferation of Naive B Cells. Cell Rep 31 107474 PMID: 32294437
Stuart N et al (2020) TRESK is a key regulator of nocturnal suprachiasmatic nucleus dynamics and light adaptive responses. Nat Commun 11 4614 PMID: 32929069
Bradley J et al (2019) Intracellular Ca2+ Homeostasis and Nuclear Export Mediate Exit from Naive Pluripotency. Cell Stem Cell 25 210-224.e6 PMID: 31104942
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
Pont et al (2012) Oxytocin-stimulated NFAT transcriptional activation in human myometrial cells. Mol.Endocrinol. 26 1743 PMID: 22902539
Hugh P et al (2023) Dynamic physiological α-synuclein S129 phosphorylation is driven by neuronal activity. NPJ Parkinsons Dis 9 4 PMID: 36646701
Torres et al (2018) FK506 Attenuates the MRP1-Mediated Chemoresistant Phenotype in Glioblastoma Stem-Like Cells. Int J Mol Sci 19 PMID: 30208561
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
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
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
Mirante et al (2014) Distinct molecular components for thalamic- and cortical-dependent plasticity in the lateral amygdala. J Biol Chem 7 62 PMID: 25071439
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
Chiu et al (2019) NMDAR-Activated PP1 Dephosphorylates GluN2B to Modulate NMDAR Synaptic Content. Cell Rep 28 332 PMID: 31291571
Marra et al (2012) A preferentially segregated recycling vesicle pool of limited size supports neurotransmission in native central synapses. Neuron 76 579 PMID: 23141069
Timothy S et al (2021) Differential Regulation of ATP- and UTP-Evoked Prostaglandin E2 and IL-6 Production from Human Airway Epithelial Cells. J Immunol 207 1275-1287 PMID: 34389624
Paco S et al (2021) Stepwise disassembly of GABAergic synapses during pathogenic excitotoxicity. Cell Rep 37 110142 PMID: 34936876
Satoe et al (2021) Cell death-inducing cytotoxicity in truncated KCNQ4 variants associated with DFNA2 hearing loss. Dis Model Mech 14 PMID: 34622280
Jing et al (2018) Methods for High-throughput Drug Combination Screening and Synergy Scoring. Methods Mol Biol 1711 351-398 PMID: 29344898
Stephen R et al (2017) Calcineurin Dysregulation Underlies Spinal Cord Injury-Induced K+ Channel Dysfunction in DRG Neurons. J Neurosci 37 8256-8272 PMID: 28751455
Jing et al (2017) The Effects of Tacrolimus on T-Cell Proliferation Are Short-Lived: A Pilot Analysis of Immune Function Testing. Transplant Direct 3 e199 PMID: 28795150
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
Zhen et al (2009) Dopamine D4 receptors regulate AMPA receptor trafficking and glutamatergic transmission in GABAergic interneurons of prefrontal cortex. J Neurosci 29 550-62 PMID: 19144855
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.)
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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)
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.
