Accéder au contenu
Merck
Toutes les photos(2)

Documents

C1832

Sigma-Aldrich

Cyclosporin A

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

Synonyme(s) :

Antibiotic S 7481F1, Cyclosporine

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(2)

About This Item

Formule empirique (notation de Hill):
C62H111N11O12
Numéro CAS:
59865-13-3
Poids moléculaire :
1202.61
Numéro Beilstein :
3647785
Numéro MDL:
MFCD00274558
Code UNSPSC :
12352200
ID de substance PubChem :
24892440
Nomenclature NACRES :
NA.52

Source biologique

Tolypocladium inflatum

Niveau de qualité

300

Qualité

for molecular biology

Gamme de produits

BioReagent

Pureté

≥95%

Forme

powder

Technique(s)

drug transporter assay: suitable

Solubilité

dichloromethane: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

Adéquation

corresponds to standard
suitable for molecular biology

Spectre d'activité de l'antibiotique

fungi

Mode d’action

enzyme | inhibits

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

PMATZTZNYRCHOR-CGLBZJNRSA-N

Informations sur le gène

human ... PPIA(5478)

Vous recherchez des produits similaires ? Visite Guide de comparaison des produits

Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H350,H360FD

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
Afficher tous les articles scientifiques apparentés

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique