C1832

Sigma-Aldrich

Cyclosporin A

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

Synonym(s):
Antibiotic S 7481F1, Cyclosporine
Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
Molecular Weight:
1202.61
Beilstein/REAXYS Number:
3647785
MDL number:
PubChem Substance ID:
NACRES:
NA.52

Quality Level

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)

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General description

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.
Chemical structure: peptide

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

R A Nichols et al.
The Journal of biological chemistry, 269(38), 23817-23823 (1994-09-23)
In response to Ca2+ entry, several prominent brain nerve terminal phosphoproteins undergo dephosphorylation, but the relation between dephosphorylation and neurotransmitter release is unknown. Using the immunosuppressants cyclosporin A (CsA) and L-683,590 (FK-520) to inhibit specifically the Ca2+/calmodulin-dependent protein phosphatase calcineurin...
Mi-Ok Lee et al.
Arteriosclerosis, thrombosis, and vascular biology, 32(2), 343-352 (2011-11-15)
A number of studies have revealed that stress signaling and subsequent stress responses in stem/progenitor cells are responsible for attenuated regeneration or degenerative disease. Because ionizing radiation (IR), which sensitizes diverse types of stem cells, reportedly induces cardio-circulatory diseases, we...
E A Emmel et al.
Science (New York, N.Y.), 246(4937), 1617-1620 (1989-12-22)
One action of cyclosporin A thought to be central to many of its immunosuppressive effects is its ability to inhibit the early events of T lymphocyte activation such as lymphokine gene transcription in response to signals initiated at the antigen...
N A Clipstone et al.
The Journal of biological chemistry, 269(42), 26431-26437 (1994-10-21)
The calcium/calmodulin-regulated phosphatase calcineurin (CN) is the site of action of the immunosuppressive drugs cyclosporin A (CsA) and FK506. CN has recently been established as a key signaling enzyme in the T cell signal transduction cascade and an important regulator...
Koichi Watashi et al.
Hepatology (Baltimore, Md.), 38(5), 1282-1288 (2003-10-28)
Persistent infection of hepatitis C virus (HCV) is a major cause of liver diseases such as chronic hepatitis, liver cirrhosis, and hepatocellular carcinoma. Searching for a substance with anti-HCV potential, we examined the effects of a variety of compounds on...

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