Rapamycin

Cat. No. 1292

Rapamycin C51H79NO13 [53123-88-9]

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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

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
Solubility:
Soluble to 20 mM in ethanol and to 50 mM in DMSO
Purity:
>98 %
Storage:
Desiccate at -20°C
CAS No:
53123-88-9

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.

Certificate of Analysis / Product Datasheet / Safety Datasheet

Certificate of Analysis / Product Datasheet
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References are publications that support the products' biological activity.

Galluzzi et al (2017) Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov. . PMID: 28529316 .

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.

Fleming et al (2011) Chemical modulators of autophagy as biological probes and potential therapeutics. 7 9. PMID: 21164513.

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.

Huang et al (2003) Rapamycins: mechanism of action and cellular resistance. Cancer Biol.Ther. 2 221. PMID: 12878853.

Kuo et al (1992) Rapamycin selectively inhibits interleukin-2 activation of p70 S6 kinase. Nature 358 70. PMID: 1614535.

If you know of a relevant reference for Rapamycin please let us know.

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

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.

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.

Kamekura et al (2015) Inflammation-induced desmoglein-2 ectodomain shedding compromises the mucosal barrier. Biochem J 26 3165. PMID: 26224314.

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.

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.

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.

Stretton et al (2015) GSK3-mediated raptor phosphorylation supports amino-acid-dependent mTORC1-directed signalling. Front Neurosci 470 207. PMID: 26348909.

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.

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.

Dai et al (2014) Interaction of mTOR and Erk1/2 signaling to regulate oligodendrocyte differentiation. Glia 62 2096. PMID: 25060812.

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.

Han et al (2014) Parallel measurement of dynamic changes in translation rates in single cells. Nat Methods 11 86. PMID: 24213167.

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.

Mohseni et al (2014) A genetic screen identifies an LKB1-MARK signalling axis controlling the Hippo-YAP pathway. J Virol 16 108. PMID: 24362629.

Wang et al (2014) SynGAP regulates protein synthesis and homeostatic synaptic plasticity in developing cortical networks. PLoS One 8 e83941. PMID: 24391850.

Murthy et al (2013) Post-transcriptional regulation of GABAB receptor and GIRK1 channels by Nogo receptor 1. Cereb Cortex 6 30. PMID: 23829864.

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.

Xia et al (2013) Identification of repurposed small molecule drugs for chordoma therapy. Cancer Biol Ther 14 638. PMID: 23792643.

Gangoiti et al (2012) Ceramide 1-phosphate stimulates proliferation of C2C12 myoblasts. Biochimie 94 597. PMID: 21945811.

Ladoire et al (2012) Immunohistochemical detection of cytoplasmic LC3 puncta in human cancer specimens. Autophagy 8 1175. PMID: 22647537.

Lainey et al (2012) Erlotinib antagonizes ABC transporters in acute myeloid leukemia. Cell Cycle 11 4079. PMID: 23095522.

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.

Muller et al (2012) Passenger deletions generate therapeutic vulnerabilities in cancer. Nature 488 337. PMID: 22895339.

Piecewicz et al (2012) Insulin-like growth factors promote vasculogenesis in embryonic stem cells. PLoS One 7 e32191. PMID: 22363814.

Pietrocola et al (2012) Pro-autophagic polyphenols reduce the acetylation of cytoplasmic proteins. Cell Cycle 11 3851. PMID: 23070521.

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.

Do you know of a great paper that uses Rapamycin from Tocris? If so please let us know.show all ▼show less ▲

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

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