Rapamycin from Streptomyces hygroscopicus

SIGMA/R0395 - ≥95% (HPLC), powder

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

CAS Number: 53123-88-9
Empirical Formula (Hill Notation): C₅₁H₇₉NO₁₃
Molecular Weight: 914.17
MDL Number: MFCD00867594
Linear Formula: C₅₁H₇₉NO₁₃
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-R0395-1MG	1 mg	$360.00 1/EA	Add To Favorites

Rapamycin inhibits mTOR (the mammalian target of rapamycin) by associating with its intracellular receptor FKBP12. The FKBP12–rapamycin complex binds directly to the FKBP12-Rapamycin Binding (FRB) domain of mTOR, inhibiting its activity (affecting protein synthesis, cell cycle progression, immune responses and autophagy).

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Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	fungi
	yeast
assay	≥95% (HPLC)
color	off-white
form	powder
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
mode of action	enzyme \| inhibits
	protein synthesis \| interferes
Quality Level	300
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=CC=CC=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
solubility	DMSO: soluble
	ethanol: 2 mM
storage temp.	−20°C

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 .
General description:	Chemical structure: macrolide
General description:	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.
Other Notes:	Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place
Packaging:	1 mg in glass bottle

Symbol	GHS08
Signal word	Warning
Hazard statements	H351 - H361fd
Precautionary statements	P201 - P202 - P280 - P308 + P313 - P405 - P501
RIDADR	NONH for all modes of transport
WGK Germany	WGK 2

Purity	≥95% (HPLC)
Storage Temp.	−20°C
UNSPSC	12352200

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