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Submit ReviewRapamycin
Description: mTOR inhibitor; immunosuppressant
Chemical Name: (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
Purity: ≥98% (HPLC)
Biological Activity for Rapamycin
Rapamycin is an antifungal and immunosuppressant. Rapamycin is a specific inhibitor of mTOR (mammalian target of rapamycin); complexes with FKBP-12 and binds mTOR inhibiting its activity. Rapamycin inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase and induces autophagy in yeast and mammalian cell lines. Rapamycin drives hPSC differentiation to mesendoderm and blood progenitor cells. Also used as a chemical dimerizer; rapamycin and GA3-AM chemically inducible dimerization systems are orthogonal. Inhibits MERS-CoV infection of Huh7 cells in a plaque reduction assay. Enhances lentiviral transduction of hematopoietic stem cells.
External Portal Information for Rapamycin
Chemicalprobes.org is a portal that offers independent guidance on the selection and/or application of small molecules for research. The use of Rapamycin is reviewed on the chemical probes website.
Technical Data for Rapamycin
| M. Wt | 914.18 |
| Formula | C51H79NO13 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 53123-88-9 |
| PubChem ID | 5284616 |
| InChI Key | QFJCIRLUMZQUOT-HPLJOQBZSA-N |
| Smiles | O=C([C@H](C)\C=C([C@@H](O)[C@@H](OC)C([C@@H]4C)=O)/C)C[C@]([C@H](C)C[C@H]2C[C@@H](OC)[C@H](O)CC2)([H])OC([C@@]1([H])N(C(C([C@@]3(O)[C@H](C)CC[C@](C[C@@H](/C(C)=C/C=C/C=C/[C@H](C4)C)OC)([H])O3)=O)=O)CCCC1)=O |
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 Rapamycin
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 18.28 | 20 |
Preparing Stock Solutions for Rapamycin
The following data is based on the product molecular weight 914.18. 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 |
|---|---|---|---|
| 0.2 mM | 5.47 mL | 27.35 mL | 54.69 mL |
| 1 mM | 1.09 mL | 5.47 mL | 10.94 mL |
| 2 mM | 0.55 mL | 2.73 mL | 5.47 mL |
| 10 mM | 0.11 mL | 0.55 mL | 1.09 mL |
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Product Datasheets for Rapamycin
References for Rapamycin
References are publications that support the biological activity of the product.
Huang et al (2003) Rapamycins: mechanism of action and cellular resistance. Cancer Biol.Ther. 2 221 PMID: 12878853
Kobayashi et al (2007) Rapamycin, a specific inhibitor of the mammalian target of rapamycin, suppresses lymphangiogenesis and lymphatic metastasis. Cancer Sci. 98 726 PMID: 17425689
Kuo et al (1992) Rapamycin selectively inhibits interleukin-2 activation of p70 S6 kinase. Nature 358 70 PMID: 1614535
Fleming et al (2011) Chemical modulators of autophagy as biological probes and potential therapeutics. 7 9 PMID: 21164513
Nazareth et al (2016) A multi-lineage screen reveals mTORC1 inhibition enhances human pluripotent stem cell mesendoderm and blood progenitor production. Stem Cell Reports 6 679 PMID: 27132889
Miyamoto et al (2012) Rapid and orthogonal logic gating with a gibberellin-induced dimerization system Nat.Chem.Biol. 8 465 PMID: 22446836
Galluzzi et al (2017) Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov. PMID: 28529316
Kindrachuk et al (2015) Antiviral potential of ERK/MAPK and PI3K/AKT/mTOR signaling modulation for Middle East Respiratory Syndrome coronavirus infection as identified by temporal kinome analysis. Antimicrob.Agents Chemother. 59 1088 PMID: 25487801
Wang et al (2014) Rapamycin relieves lentiviral vector transduction resistance in human and mouse hematopoietic stem cells Blood 124 913 PMID: 24914132
If you know of a relevant reference for Rapamycin, please let us know.
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Keywords: Rapamycin, Rapamycin supplier, mTOR, inhibitors, immunosuppressant, kinases, FKBP-12, antifungal, inhibits, mammalian, target, of, Rapamycin, antibiotics, dimerizer, COVID-19, MERS-CoV, middle, eastern, respiratory, virus, coronavirus, lentiviral, transduction, enhancers, enhances, RSK, Autophagy, Immunosuppressants, Antibiotics, ESCs, and, iPSC, Biochemicals, Molecular, Biology, Protein, Dimerizers, Viral, Transduction, Enhancers, Coronavirus, 1292, Tocris Bioscience
48 Citations for Rapamycin
Citations are publications that use Tocris products. Selected citations for Rapamycin include:
Li et al (2018) Upregulation of IRS1 Enhances IGF1 Response in Y537S and D538G ESR1 Mutant Breast Cancer Cells. Endocrinology 159 285 PMID: 29029116
Villers et al (2014) Long-term potentiation can be induced in the CA1 region of hippocampus in the absence of αCaMKII T286-autophosphorylation. Learn Mem 21 616 PMID: 25322797
Shives et al (2014) West nile virus-induced activation of mammalian target of rapamycin complex 1 supports viral growth and viral protein expression. J Virol 88 9458 PMID: 24920798
Fonseca (2013) Asymmetrical synaptic cooperation between cortical and thalamic inputs to the amygdale. Neuropsychopharmacology 38 2675 PMID: 23884343
Saxena et al (2013) Neuroprotection through excitability and mTOR required in ALS motoneurons to delay disease and extend survival. Neuron 80 80 PMID: 24094105
Pietrocola et al (2012) Pro-autophagic polyphenols reduce the acetylation of cytoplasmic proteins. Cell Cycle 11 3851 PMID: 23070521
Gangoiti et al (2012) Ceramide 1-phosphate stimulates proliferation of C2C12 myoblasts. Biochimie 94 597 PMID: 21945811
Piecewicz et al (2012) Ins-like growth factors promote vasculogenesis in embryonic stem cells. PLoS One 7 e32191 PMID: 22363814
Lainey et al (2012) Erlotinib antagonizes ABC transporters in acute myeloid leukemia. Cell Cycle 11 4079 PMID: 23095522
Muller et al (2012) Passenger deletions generate therapeutic vulnerabilities in cancer. Nature 488 337 PMID: 22895339
Lee et al (2012) Fucoidan from seaweed Fucus vesiculosus inhibits migration and invasion of human lung cancer cell via PI3K-Akt-mTOR pathways. PLoS One 7 e50624 PMID: 23226337
Rosa et al (2010) The angiogenic factor angiopoietin-1 is a proneurogenic peptide on subventricular zone stem/progenitor cells. J Neurosci 30 4573 PMID: 20357108
Lancaster et al (2018) Evidence that TLR4 Is Not a Receptor for Saturated Fatty Acids but Mediates Lipid-Induced Inflammation by Reprogramming Macrophage Metabolism. Cell Metab 27 1096 PMID: 29681442
Alves et al (2015) PAK2 is an effector of TSC1/2 signaling independent of mTOR and a potential therapeutic target for Tuberous Sclerosis Complex. Front Cell Neurosci 5 14534 PMID: 26412398
Springer et al (2015) Modulation of BK channels contributes to activity-dependent increase of excitability through MTORC1 activity in CA1 pyramidal cells of mouse hippocampus. Mol Biol Cell 8 451 PMID: 25628536
Kamekura et al (2015) Inflammation-induced desmoglein-2 ectodomain shedding compromises the mucosal barrier. Biochem J 26 3165 PMID: 26224314
Stretton et al (2015) GSK3-mediated raptor phosphorylation supports amino-acid-dependent mTORC1-directed signalling. Front Neurosci 470 207 PMID: 26348909
Joppé et al (2015) Bone morphogenetic protein dominantly suppresses epidermal growth factor-induced proliferative expansion of adult forebrain neural precursors. Nat Cell Biol 9 407 PMID: 26576147
López-Cotarelo et al (2015) A novel MEK-ERK-AMPK signaling axis controls chemokine receptor CCR7-dependent survival in human mature dendritic cells. Mol Brain 290 827 PMID: 25425646
Ladoire et al (2012) Immunohistochemical detection of cytoplasmic LC3 puncta in human cancer specimens. Autophagy 8 1175 PMID: 22647537
Jing et al (2011) Docosahexaenoic acid induces autophagy through p53/AMPK/mTOR signaling and promotes apoptosis in human cancer cells harboring wild-type p53. Sci Rep 7 1348 PMID: 21811093
Salmond et al (2015) Mechanistic Target of Rapamycin Complex 1/S6 Kinase 1 Signals Influence T Cell Activation Independently of Ribosomal Protein S6 Phosphorylation. J Immunol 195 4615 PMID: 26453749
Kang et al (2015) Anti-Tumor Activity of Yuanhuacine by Regulating AMPK/mTOR Signaling Pathway and Actin Cytoskeleton Organization in Non-Small Cell Lung Cancer Cells. PLoS One 10 e0144368 PMID: 26656173
Gonsalves et al (2014) Angiogenic growth factors augment K-Cl cotransporter expression in erythroid cells via hypoxia-inducible factor-1α. Am J Hematol 89 273 PMID: 24227191
Wang et al (2014) SynGAP regulates protein synthesis and homeostatic synaptic plasticity in developing cortical networks. PLoS One 8 e83941 PMID: 24391850
Dai et al (2014) Interaction of mTOR and Erk1/2 signaling to regulate oligodendrocyte differentiation. Glia 62 2096 PMID: 25060812
Basu et al (2014) Suppression of MAPK/JNK-MTORC1 signaling leads to premature loss of organelles and nuclei by autophagy during terminal differentiation of lens fiber cells. Autophagy 10 1193 PMID: 24813396
Han et al (2014) Parallel measurement of dynamic changes in translation rates in single cells. Nat Methods 11 86 PMID: 24213167
Cope et al (2014) Adaptation to mTOR kinase inhibitors by amplification of eIF4E to maintain cap-dependent translation. J Cell Sci 127 788 PMID: 24363449
Stefanidou et al (2013) Herpes simplex virus 2 (HSV-2) prevents dendritic cell maturation, induces apoptosis, and triggers release of proinflammatory cytokines: potential links to HSV-HIV synergy. J Biol Chem 87 1443 PMID: 23152529
Murthy et al (2013) Post-transcriptional regulation of GABAB receptor and GIRK1 channels by Nogo receptor 1. Cereb Cortex 6 30 PMID: 23829864
Sagrillo-Fagundes et al (2019) Melatonin: The smart molecule that differentially modulates autophagy in tumor and normal placental cells. PLoS One 14 e0202458 PMID: 30629581
Anelli et al (2019) Ras-Induced miR-146a and 193a Target Jmjd6 to Regulate Melanoma Progression. Front Genet 9 675 PMID: 30619488
Mohseni et al (2014) A genetic screen identifies an LKB1-MARK signalling axis controlling the Hippo-YAP pathway. J Virol 16 108 PMID: 24362629
Lefort et al (2014) Inhibition of autophagy as a new means of improving chemotherapy efficiency in high-LC3B triple-negative breast cancers. Autophagy 10 2122 PMID: 25427136
Xia et al (2013) Identification of repurposed small molecule drugs for chordoma therapy. Cancer Biol Ther 14 638 PMID: 23792643
Zhong et al (2009) BC1 regulation of metabotropic glutamate receptor-mediated neuronal excitability. J Neurosci 29 9977 PMID: 19675232
Kim et al (2015) Docosahexaenoic Acid Induces Cell Death in Human Non-Small Cell Lung Cancer Cells by Repressing mTOR via AMPK Activation and PI3K/Akt Inhibition. Biomed Res Int 2015 239764 PMID: 26339598
Hsu et al (2015) Cardiolipin remodeling by TAZ/tafazzin is selectively required for the initiation of mitophagy. Autophagy 11 643 PMID: 25919711
Obakan et al (2015) SILAC-Based Mass Spectrometry Analysis Reveals That Epibrassinolide Induces Apoptosis via Activating Endoplasmic Reticulum Stress in Prostate Cancer Cells. PLoS One 10 e0135788 PMID: 26353013
Zhang (2019) Direct Gαq Gating Is the Sole Mechanism for TRPM8 Inhibition Caused by Bradykinin Receptor Activation. Cell Rep 27 3672 PMID: 31216483
Livingstone et al (2019) Secreted Amyloid Precursor Protein-Alpha Promotes Arc Protein Synthesis in Hippocampal Neurons. Front Mol Neurosci 12 198 PMID: 31474829
Gao et al (2016) Eicosapentaenoic acid attenuates dexamethasome-induced apoptosis by inducing adaptive autophagy via GPR120 in murine bone marrow-derived mesenchymal stem cells. Cell Death Dis 7 e2235 PMID: 27228350
Wang et al (2016) Activation of the Mammalian Target of Rapamycin in the Rostral Ventromedial Medulla Contributes to the Maintenance of Nerve Injury-Induced Neuropathic Pain in Rat. Neural Plast 2015 394820 PMID: 26770837
Jennewein et al (2016) Diagnostic and clinical relevance of the autophago-lysosomal network in human gliomas. Oncotarget 7 20016 PMID: 26956048
Li et al (2016) Vitamin C alleviates aging defects in a stem cell model for Werner syndrome. Protein Cell 7 478 PMID: 27271327
Jiang et al (2013) Activation of mammalian target of rapamycin mediates rat pain-related responses induced by BmK I, a sodium channel-specific modulator. Mol Pain 9 50 PMID: 24099268
Muddashetty et al (2007) Dysregulated metabotropic glutamate receptor-dependent translation of AMPA receptor and postsynaptic density-95 mRNAs at synapses in a mouse model of fragile X syndrome. J Neurosci 27 5338 PMID: 17507556
Do you know of a great paper that uses Rapamycin from Tocris? Please let us know.
Reviews for Rapamycin
Average Rating: 5 (Based on 3 Reviews.)
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Cytotoxicity testing.
By
MARINA KOUTSIOUMPA on 10/18/2022
Assay Type: In Vitro
Species: Human
Studies were performed with rapamycin in chemotherapy-treated cultured cancer cell lines for the evaluation of cytotoxic effects. The product is highly recommended.
The role of mTOR signaling in genotoxics-induced stress..
By
MARINA KOUTSIOUMPA on 06/10/2021
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: MIA PaCa_2
Expected effects. IC50 equals 1nM upon 3 days of treatment of MIA PaCa_2 pancreatic cancer cell line.
rapamycin support human ES cells differentiation.
By
Pinyuan Tian on 05/22/2019
Species: Human
Rapamycin treatment (10nM) on human embryonic stem cells could enhance some cartilage differentiation markers such as SOX9.
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Pathways for Rapamycin
