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C1832 Sigma-Aldrich

Cyclosporin A

from Tolypocladium inflatum, BioReagent, for molecular biology, ≥95%

Synonym: Antibiotic S 7481F1, Cyclosporine

  • CAS Number 59865-13-3

  • Empirical Formula (Hill Notation) C62H111N11O12

  • Molecular Weight 1202.61

  •  Beilstein/REAXYS Number 3647785

  •  MDL number MFCD00274558

  •  PubChem Substance ID 24892440

  •  NACRES NA.52

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Application, Antibiotics by Mechanism of Action, Antibiotics  A-F,
Quality Level   300
biological source   Tolypocladium inflatum
grade   for molecular biology
product line   BioReagent
assay   ≥95%
form   powder
solubility   dichloromethane: 9.80-10.20 mg/mL, clear, colorless to faintly yellow
Mode of action   enzyme | inhibits
antibiotic activity spectrum   fungi
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.
• Measuring the multiple drug resistance transporter activity in putative cancer stem/progenitor cells.
• mRNA transcription studies
• analytical standard

Packaging

5, 10 mg in glass bottle

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. 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. It was found to suppress the replication of hepatitis C virus genome in cultured hepatocytes.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
GZ4120000
Protocols & Articles

Articles

Cyclosporin A from Tolypocladium inflatum

Cyclosporin A is a non-polar cyclic oligopeptide produced by the fungus Tolypocladium inflatum. It is a potent immunosuppressive agent, affecting primarily T-lymphocytes.2 It has been shown to inhibi...
Keywords: Addition reactions, Adsorption, Antibiotics, Cell culture, Centrifugation, Enzyme activity, Enzyme-linked immunosorbent assay, Solvents, Transcription

Peer-Reviewed Papers
15

References

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