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R0395

Sigma-Aldrich

Rapamycin

from Streptomyces hygroscopicus, ≥95% (HPLC), powder, mTOR inhibitor

Synonym(s):

23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus

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About This Item

Empirical Formula (Hill Notation):
C51H79NO13
CAS Number:
Molecular Weight:
914.17
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

Rapamycin from Streptomyces hygroscopicus, ≥95% (HPLC), powder

Quality Level

Assay

≥95% (HPLC)

form

powder

color

off-white

solubility

ethanol: 2 mM
DMSO: soluble

antibiotic activity spectrum

fungi
yeast

Mode of action

enzyme | inhibits
protein synthesis | interferes

storage temp.

−20°C

SMILES string

CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC

InChI

1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

InChI key

QFJCIRLUMZQUOT-HPLJOQBZSA-N

Gene Information

human ... FKBP1A(2280)

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General description

Chemical structure: macrolide
Rapamycin is derived from Streptomyces hygroscopicus . It can inhibit viral replication. This natural anti-fungal antibiotic is a proven anti-aging agent. Rapamycin significantly inhibits mTORC1 regardless of age. It suppresses protein kinase C activity and enhances ion transport in A6 cells. It also suppresses the immune response in membrane and cytosolic preparations. Additionally, it has specific effects on the translation of endogenous mRNAs and inhibits the translation of 5′TOP mRNAs by blocking p70s6k activation in the signaling pathway. Rapamycin exhibits antineoplastic properties.

Application

Rapamycin from Streptomyces hygroscopicus has been used:
  •  to treat BV2 cells or BV2-LC3 cells for autophagy assay
  • as an autophagy activator in the bone marrow mesenchymal stem cells (BM-MSCs) transfected with lentivirus carrier of small interfering RNA for FOXO3 (siFOXO3) to study the effects of Forkhead Box O3 (FOXO3) on the autophagy of BM-MSCs
  • to pre-incubate villi to inhibit the mammalian target of rapamycin complex 1 (mTORC1) signaling

Biochem/physiol Actions

A macrocyclic triene antibiotic that binds to and inhibits the molecular target of rapamycin (mTOR). It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). Rapamycin is a potent immunosuppressant and has anticancer activity.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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