• Cyclosporin D, EvoPure packaged and labeled.

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SKU: C045

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Description

Cyclosporin D is a hydroxylated metabolite of cyclosporin A.  Cyclosporin D and other cyclosporin metabolites have been found to have lower (<10%) immunosuppressant activity than cyclosporin A.  Cyclosporin D has been found to reverse daunorubicin resistance in some resistant leukemia cells by possibly inhibiting the efflux functions of P-glycoprotein.

For more cyclosporin products, click here.

    CAS Number

    63775-96-2

    Molecular Formula

    C63H113N11O12

    Molecular Weight

    1216.63 g/mol

    Mechanism of Action

    Cyclosporin B (and other cyclosporin A metabolites) have lower immunosuppressive activity but likely operate under the same mechanism as cyclosporin A described below.

    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).

Specifications

    Form

    Powder

    Appearance

    White crystal powder

    Source

    Tolypocladium inflatum

    Water Content (Karl Fischer)

    ≤3.0%

    Melting Point

    148 -151 °C

    Assay

    ≥95.0% (as is)

    Heavy Metals

    ≤0.02%

    Impurities

    Total: ≤5.0%

Technical Data

Spectral Data - Cyclosporin D, 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: 0.1 mg/mL
Instrument: Agilent
References

    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

    Matsuda, 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

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