R0395

Rapamycin from Streptomyces hygroscopicus

≥95% (HPLC), powder

• Synonym(s): 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus
• Empirical Formula (Hill Notation): C₅₁H₇₉NO₁₃
• CAS Number: 53123-88-9
• Molecular Weight: 914.17
• MDL number: MFCD00867594
• UNSPSC Code: 12352200
• PubChem Substance ID: 57654583
• NACRES: NA.77

Properties

• Quality Level: 300
• 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)

Description

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

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H351 - H361fd
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• 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