C1832

Cyclosporin A

from Tolypocladium inflatum, BioReagent, Molecular Biology, ≥95%

• Synonym(s): Antibiotic S 7481F1, Cyclosporine
• Empirical Formula (Hill Notation): C₆₂H₁₁₁N₁₁O₁₂
• CAS Number: 59865-13-3
• Molecular Weight: 1202.61
• Beilstein/REAXYS Number: 3647785
• MDL number: MFCD00274558
• UNSPSC Code: 12352200
• PubChem Substance ID: 24892440
• NACRES: NA.52

Properties

• biological source: Tolypocladium inflatum
• Quality Level: 300
• grade: Molecular Biology
• product line: BioReagent
• assay: ≥95%
• form: powder
• technique(s): drug transporter assay: suitable
• solubility: dichloromethane: 9.80-10.20 mg/mL, clear, colorless to faintly yellow
• suitability: corresponds to standard ; suitable for molecular biology
• antibiotic activity spectrum: fungi
• mode of action: enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
• InChI: 1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1
• InChI key: PMATZTZNYRCHOR-CGLBZJNRSA-N
• Gene Information: human ... PPIA(5478)

Description

General description

Chemical structure: peptide

Cyclosporin A is a fungal metabolite with immunosuppressive properties. Cyclosporin A is a non-polar cyclic oligopeptide produced by the fungus Tolypocladium inflatum. It is a potent immunosuppressive agent, affecting primarily T-lymphocytes.

Application

Cyclosporin A was suitable for:

• Using in in vivo Neovascularization Assay, to subcutaneously inject the mice daily for suppressing the immune response.[1]
• Measuring the multiple drug resistance transporter activity in putative cancer stem/progenitor cells.[2]
• mRNA transcription studies
• analytical standard

Biochem/physiol Actions

A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A−cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.

Cyclosporin A has been shown to inhibit the functioning of several nuclear proteins involved in T-cell activation at the level of mRNA transcription.[3] It forms a complex with its intracellular receptor cyclophilin, which can then bind to calcineurin, a Ca2+ - and calmodulin-dependent protein phosphatase, inhibiting its enzymatic activity.[4][5][6] It was found to suppress the replication of hepatitis C virus genome in cultured hepatocytes.[7]

Potent immunosuppressant; inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα; blocks cytochrome c release from mitochondria.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H360FD
• pcodes: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges