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C1832

Sigma-Aldrich

Cyclosporin A

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

Synonym(s):

Antibiotic S 7481F1, Cyclosporine

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
Beilstein:
3647785
MDL number:
MFCD00274558
UNSPSC Code:
12352200
PubChem Substance ID:
24892440
NACRES:
NA.52

biological source

Tolypocladium inflatum

Quality Level

300

grade

for 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)

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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

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
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H350 - H360FD

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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
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
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