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239835

Sigma-Aldrich

Cyclosporin A, Tolypocladium inflatum

Cyclosporin A, CAS 59865-13-3, is an immunosuppressant that induces apoptosis in rat thymocytes and in the murine B cell lymphoma cell line, WEH1-231. Induces cardiomyocytes formation from ESCs.

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Synonym(s):
Cyclosporin A, Tolypocladium inflatum
Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
MDL number:
MFCD00274558

Quality Level

200

Assay

≥97% dry basis

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white to off-white

solubility

DMSO: 25 mg/mL
chloroform: soluble
ethanol: soluble
methanol: soluble

shipped in

ambient

storage temp.

2-8°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+

InChI key

PMATZTZNYRCHOR-IMVLJIQESA-N

General description

Cyclic oligopeptide with immunosuppressant properties. Induces apoptosis in rat thymocytes and in the murine B cell lymphoma cell line, WEH1-231. However, prevents anti-IgM and ionomycin-induced apoptosis in BLB cell lines. The complex of cyclosporin A with cyclophilin inhibits protein phosphatase 2B with nanomolar affinity. Inhibits nitric oxide synthesis induced by interleukin-1α, lipopolysaccharides, and TNF-α. Induces cardiomyocytes from embryonic stem cells.
Material is a nonpolar cyclic oligopeptide with immunosuppressant activity. Appears to act via interaction with the intracellular protein cyclophilin. The cyclophilin-cyclosporin A complex is a potent inhibitor of the protein phosphatase activity of calcineurin (protein phosphatase 2B, PP2B). Induces apoptosis in rat thymocytes and in the murine B-cell lymphoma cell line, WEHI-231; however, it prevents anti-IgM and ionomycin-induced apoptosis in BLB cell lines. Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides, and TNFα. Induces cardiomyocytes from embryonic stem cells.

Biochem/physiol Actions

Cell permeable: no
Primary Target
NOS induced by interlukin-1-α
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Yan, P., et al. 2008. Biochem. Biophys. Res. Commun.in press.
Hattori, Y., and Naranishi, N. 1995. Cell Immunol.165, 7.
Marumo, T., et al. 1995. Hypertension25, 764.
Crabtree, G.R., and Clipstone, N.A. 1994. Annu. Rev. Biochem.63, 1045.
Gottschalk, A.R., et al. 1994. Proc. Natl. Acad. Sci. USA91, 7350.
Montague, J.W., et al. 1994. J. Biol. Chem.269, 18877.
Fast, D.J., et al. 1993. J.Interferon Res. 13, 235.
Liu, J. 1993. Trends Pharmacol. Sci. 14, 182.
Fruman, D.A., et al. 1992. Proc. Natl. Acad. Sci. USA89, 3686.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

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Zoë Steier et al.
Nature immunology, 24(9), 1579-1590 (2023-08-15)
The development of CD4+ T cells and CD8+ T cells in the thymus is critical to adaptive immunity and is widely studied as a model of lineage commitment. Recognition of self-peptide major histocompatibility complex (MHC) class I or II by
Sabrina Giampaolo et al.
iScience, 26(3), 106234-106234 (2023-03-18)
In thymus, the ablation of T cell receptor (TCR)-activated transcription factor NFATc1 or its inducible isoforms during the double-negative (DN) stages of thymocyte development leads to a marked increase in γδ thymocytes whereas the development of αβ thymocytes remains mostly unaffected.
Yunqing Li et al.
Pharmaceutics, 13(8) (2021-08-29)
Hypoxia is a complex microenvironmental condition known to regulate choline kinase α (CHKA) activity and choline transport through transcription factor hypoxia-inducible factor-1α (HIF-1α) and, therefore, may confound the uptake of choline radiotracer [18F]fluoromethyl-[1,2-2H4]-choline ([18F]-D4-FCH). The aim of this study was
Magda N Hernández Vásquez et al.
The EMBO journal, 40(12), e107192-e107192 (2021-05-03)
The lymphatic system is composed of a hierarchical network of fluid absorbing lymphatic capillaries and transporting collecting vessels. Despite distinct functions and morphologies, molecular mechanisms that regulate the identity of the different vessel types are poorly understood. Through transcriptional analysis
Vânia Vilas-Boas et al.
International journal of molecular sciences, 22(20) (2021-10-24)
Drug-induced liver injury, including cholestasis, is an important clinical issue and economic burden for pharmaceutical industry and healthcare systems. However, human-relevant in vitro information on the ability of other types of chemicals to induce cholestatic hepatotoxicity is lacking. This work

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