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Cyclosporin A, EvoPure^®

SKU: C042

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Description

Cyclosporin A, EvoPure^® is a neutral, cyclic oligopeptide with immunosuppressive activity. Cyclosporin A has the most potent immunosuppressive activity of all the metabolites (Cyclosporin B, C, D, E, and H). Cyclosporin A has been used to prevent organ transplant rejection. Cyclosporin A is soluble in ethanol (50 mM) and DMSO (100 mM).

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CAS Number

59865-13-3

Molecular Formula

C₆₂H₁₁₁N₁₁O₁₂

Molecular Weight

1202.6 g/mol

Mechanism of Action

After entering a T-cell, Cyclosporin A associates with the cytosolic protein cyclophilin which helps in protein folding. Cyclosporin A binds to cyclophilins and this complex binds another cytosolic protein phosphatase called Calcineurin (protein phosphatase 2B) that dephosphorylates a transcription factor (nuclear factor of activated T-cells, or NF-AT) needed for expression of interleukin 2 (IL-2.). It also blocks the pathway to nitric oxide synthesis via tumor necrosis factor (TNFa) and Interleukin 1a.

Storage Conditions

-20°C

Tariff Code

2933.79.8500

Applications

Cancer Applications

Cyclosporin’s immunosuppressive properties and potential toxicity can be studied during in vitro assays. Other metabolites of Cyclosporin A (AM1, AM1c, DihydroAM1, AM19, and AM4N) can also be studied (Vollenbroeker B et al, 2005).

Eukaryotic Cell Culture Applications

Cyclosporins have used as tools to study complex biological networks and pathways, involving protein function, and protein-protein interactions. Cyclosporin A had a suppressive effect on the Hepatitis C virus (HCV) replicon at the RNA level and HCV protein expression in cultured hepatocytes. Cyclosporin A also inhibited multiplication of the HCV genome in a human hepatocyte cell line infected with HCV using HCV-positive plasma (Watashi et al, 2003). Cyclosporin A has been used to establish Epstein-Barr virus-transformed human lymphoblastoid cell lines (Anderson and Gusella 1984).

Specifications

Form

Powder

Appearance

White powder

Source

Tolypocladium inflatum

Assay

≥99.0% (HPLC, as is)

Technical Data

Spectral Data - Cyclosporin A, EvoPure^®

HNMR Spectra

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Solvent:	cdc13
Instrument:	Mercury 300
Frequency:	300 MHz

FTIR Spectra

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Mass Spectra

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Polarity/Scan Type:	Positive
Solvent:	MeOH
Solution Concentration:	10 mg/mL
Instrument:	Agilent

References

Anderson MA and Gusella JF (1984) Use of Cyclosporin A in establishing Epstein-Barr virus-transformed human lymphoblastoid cell lines. In Vitro 20(11):856-858. PMID 6519667

Copelan KR, Yatscoff RW and McKenna RM (1990) Immunosuppressive activity of Cyclosporine metabolites compared and characterized by mass spectrometry and nuclear magnetic resonance. Clin. Chem. 36(2): 225-229. PMID 2137384

Dreyfuss, M et al (1976) Cyclosporin A and C. Eur. J. Appl Microbiol. 3(2): 125-133

Laupacis A et al. PA (1982) Cyclosporin A: A powerful immunosuppressant. Can. Med Assoc. J 126(9):1041-1046 PMID 7074504 Matsuda S and Koyasu S (2000) Mechanisms of Action of Cyclosporine. Immunopharmacol. 47(2-3): 119-125. PMID 10878286

Oliyai R. & Stella V. J. (1992) Kinetics and mechanism of isomerization of cyclosporin A. Pharm. Res. 9(5):617-622

Stiller, CR and Ulan RA (1981) Cyclosporin A: A Powerful Immunosuppressant."Can. Med. Assn. 126 (1981): 1041-046.

Vollenbroeker B et al (2005) Determination of cyclosporine and its metabolites in blood via HPLC-MS and correlation to clinically important parameters. Transplant Proc. 37(4):1741-1744 PMID 15919451

Wang, PC et al. (1989) Isolation of 10 Cyclosporine Metabolites from Human Bile. Drug Metab. Dispos. 17(3): 292-296 PMID 2568911

Watashi K, Hijikata M, Hosaka M, Yamaji M, Shimotohno K (2003) Cyclosporin A suppresses replication of hepatitis C virus genome in cultured hepatocytes. Hepatol. 38(5):1282-1288. PMID 14578868

Zheng XS, Chan T, and Zhou HH (2004) Genetic and genomic approaches to identify and study the targets of bioactive small molecules. Chem and Biol 11(5):609-618 PMID 15157872