Rapamycin

Pricing Availability   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 (45)
Reviews (1)
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.

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

Solubility Data

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

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 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
0.5 mM 2.19 mL 10.94 mL 21.88 mL
2.5 mM 0.44 mL 2.19 mL 4.38 mL
5 mM 0.22 mL 1.09 mL 2.19 mL
25 mM 0.04 mL 0.22 mL 0.44 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.

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


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

View Related Products by Product Action

View all mTOR Inhibitors

Keywords: Rapamycin, Rapamycin supplier, mTOR, inhibitors, immunosuppressant, kinases, FKBP-12, antifungal, inhibits, mammalian, target, of, Rapamycin, antibiotics, dimerizer, RSK, Autophagy, Immunosuppressants, Antibiotics, ESCs, and, iPSC, Biochemicals, Molecular, Biology, Protein, Dimerizers, 1292, Tocris Bioscience

45 Citations for Rapamycin

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

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

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

Li et al (2018) Upregulation of IRS1 Enhances IGF1 Response in Y537S and D538G ESR1 Mutant Breast Cancer Cells. Endocrinology 159 285 PMID: 29029116

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

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

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

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

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

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

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

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


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

Reviews for Rapamycin

Average Rating: 5 (Based on 1 Review.)

5 Star
100%
4 Star
0%
3 Star
0%
2 Star
0%
1 Star
0%

Have you used Rapamycin?

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:


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.

review image

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download 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
Kinases

Kinases Product Listing

A collection of over 400 products for kinase research, the listing includes inhibitors of:

  • Receptor Tyrosine Kinases
  • Protein Kinases A, C, D and G
  • PI-3 Kinase, Akt and mTOR
  • MAPK Signaling
  • Receptor Serine/Threonine Kinases
Pain

Pain Research Product Guide

A collection of over 250 products for pain research, the guide includes research tools for the study of:

  • Nociception
  • Ion Channels
  • G-Protein-Coupled Receptors
  • Intracellular Signaling

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.