• Cyclosporin H, EvoPure packaged and labeled.

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SKU: C046

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Description

Cyclosporin H is a hydroxylated metabolite of cyclosporin A (CsA). Cyclosporin H (M-1) and other cyclosporin metabolites have been found to have lower (<10%) immunosuppressant activity than cyclosporin A (CsA). Cyclosporin H has been found to be a potent inhibitor of superoxide anion (O2-) formation by FMLP (N-Formylmethionyl-leucyl-phenylalanine) in human neutrophils.

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    CAS Number

    83602-39-5

    Molecular Formula

    C62H111N11O12

    Molecular Weight

    1202.6 g/mol

    Mechanism of Action

    Cyclosporin H (and other cyclosporin A (CsA) metabolites) have lower immunosuppressant activity but most likely operate under the same mechanism as cyclosporin A (CsA) described below.

    Cyclosporin A (CsA) immunosuppressant activity stems from its ability to prevent T-cell activation by blocking specific cytokine transcription genes. After entering a T-cell, cyclosporin A (CsA) associates with ubiquitous cytosolic proteins called cyclophilins which aid in protein folding. Cyclosporin A (CsA) : cyclophilin complexes together bind calcineurin, (another cytosolic protein) effectively blocking the pathway to IL-2 gene transcription and T-cell activation.

    Storage Conditions

    -20°C

    Tariff Code

    2933.79.8500

Applications

    Cancer Applications

    Cyclosporin metabolites can be used to study toxicity and immunosuppressant activity in various in vitro assays and experiments.

Specifications

    Form

    Powder

    Appearance

    White crystal powder

    Source

    Tolypocladium Inflatum

    Water Content (Karl Fisher)

    3.0%

    Melting Point

    162-165°C

    Assay

    ≥ 95.0%

    Heavy Metals

    ≤0.02%

    Impurities

    Total:≤5.0%

Technical Data

Spectral Data - Cyclosporin H, 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

    Stiller, C. R., MD, and R. A. Ulan, MD. "Cyclosporin A: A Powerful Immunosuppressant."Canadian Medical Association 126 (1981): 1041-046. www.ncbi.gov. Web. 27 Aug. 2012.

    Crabtree, G. R., J. Nourse, and L. Timmermann. "The Mechanism of Action of Cyclosporin A and FK506." Clinical Immunology and Immunotherapy (1996): 40-45.www.ncbi.gov. Web. 27 Aug. 2012.

    Wang, Paul C. et. al. "Isolation of 10 Cyclosporine Metabolites from Human Bile." Drug Metabolism and Disposition 17.3 (1989): 292-96. Nih.gov. Web. 28 Oct. 2013.

    Copeland, Kenneth R. "Immunosuppressive Activity of Cyclosporine Metabolites Compared and Characterized by Mass Spectrometry and Nuclear Magnetic Resonance."Clinical Chemistry 36.2 (1990): 225-29. Web. 28 Oct. 2013.

    Matsuda, Staoshi. "Mechanisms of Action of Cyclosporine." Immunopharmacology 47 (2000): 119-25. Elsevier. Web. 28 Oct. 2013.

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