Rapamycin

Pricing Availability Delivery Time Qty
Cat.No. 1292 - Rapamycin | C51H79NO13 | CAS No. 53123-88-9
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)
Datasheet
Citations (30)
Literature
Pathways

Biological Activity

Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase. Induces autophagy in yeast and mammalian cell lines. Drives hPSC differentiation to mesendoderm and blood progenitor cells. Also used as a chemical dimerizer; rapamycin and GA3-AM (Cat. No. 5407) chemically inducible dimerization systems are orthogonal.

External Portal Information

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

M. Wt 914.18
Formula C51H79NO13
Storage Desiccate 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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 45.71 50
ethanol 18.28 20

Preparing Stock Solutions

The following data is based on the product molecular weight 914.18. 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 1.09 mL 5.47 mL 10.94 mL
5 mM 0.22 mL 1.09 mL 2.19 mL
10 mM 0.11 mL 0.55 mL 1.09 mL
50 mM 0.02 mL 0.11 mL 0.22 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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: 8529316


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Keywords: Rapamycin, supplier, mTOR, inhibitors, immunosuppressant, kinases, FKBP-12, antifungal, inhibits, mammalian, target, of, Rapamycin, antibiotics, dimerizer, mTOR, Tocris Bioscience

30 Citations for Rapamycin

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

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

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

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

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

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

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

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) Insulin-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

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

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

Zhong et al (2009) BC1 regulation of metabotropic glutamate receptor-mediated neuronal excitability. J Neurosci 29 9977 PMID: 19675232

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


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Pathways for Rapamycin

mTOR

mTOR Signaling Pathway

mTOR is a serine/threonine kinase that nucleates at multiprotein complexes mTORC1 and mTORC2. Signaling by these complexes regulates cell growth, proliferation and survival.

Protocols

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