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    Griseofulvin (Grifulvin)
    Griseofulvin (Grifulvin)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1623
    CAS #: 126-07-8 Purity ≥98%

    Description: Griseofulvin (Gris-PEG; Grifulvin; Fulvicin, Grisactin, Amudane), a naturally occurring spirocyclic compound isolated from some strains of the mold Penicillium griseofulvumam, is an oral antifungal medication approved for use in the treatment of various dermatophytoses (ringworm) such as fungal infections of the nails and skin when antifungal creams did not work. Griseofulvin is a tubulin/microtubule inhibitor that acts by inhibiting cell mitosis via interfering with microtubule function. Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. It is reserved for cases with nail, hair, or large body surface involvement.

    References: Mutat Res. 1988 Mar;195(2):91-126; Int J Cancer. 2001 Feb 1;91(3):393-401. 

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    Molecular Weight (MW)352.77 
    FormulaC17H17ClO6 
    CAS No.126-07-8 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 50 mg/mL (141.7 mM) 
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Other info

    Chemical Name: (2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

    InChi Key: DDUHZTYCFQRHIY-RBHXEPJQSA-N

    InChi Code: InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

    SMILES Code: O=C1[[email protected]]2(C(OC)=CC(C[[email protected]]2C)=O)OC3=C(Cl)C(OC)=CC(OC)=C13           

    Synonyms

    Gris PEG, Griseofulvin, Fulvicin, Grisactin, GrisPEG, Gris-PEG, Amudane


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    In Vitro

    In vitro activity: Griseofulvin is active against dermatophytes of different species in the genera Microsporum, Trichophyton and Epidermophyton. Other fungi such as Scopulariopsis brevicaulis and Hendersomula toruloidea are insensitive. Griseofulvin has little or no effect against yeasts and bacteria. The minimum inhibitory concentration of Griseofulvin tested in vitro against various dermatophytes ranges between 0.14 and 0.6 μg/mL. Main effect of Griseofulvin on cell mitosis is disorganization of the spindle microtubules. Griseofulvin is also able to induce structural chromosomal aberrations in mammalian cells. Griseofulvin inhibits the viability of human colon adenocarcinoma cells COLO 205 and HT 29, hepatoma cells Hep G2 and Hep 3B, leukemia cells HL 60, and normal keratinocytes (#76 KhGH) with IC50s of ~1 and ~5 μM, 5 and 5 μM, 1 μM, and 50 μM, respectively after a 30 hr incubation,. Griseofulvin (20 μM) induces a marked presence of abnormal mitotic spindle formation with mono-, bi-, and tripolar spindles of varying lengths in HT 29 cells, and causes G2/M cell cycle arrest at 24h through elevation of cyclin B1/cdc2 kinase activity and down-regulation of myt-1 protein expression. Griseofulvin is able to induce apoptosis of HT 29 cells via caspase3 activation, Bcl-2 hyperphosphorylation and inhibition of the normal function of Bcl-2 associated with Bax.


    Cell Assay: The cells (5× 103/mL) are incubated in triplicate in a 96-well plate in the presence or absence of indicated concentration of Griseofulvin in a final volume of 0.2 mL for different time intervals at 37 ℃. Thereafter, 20 μL MTT solution (5 mg/mL in PBS) is added to each well. After a 2-hour incubation at 37 ℃, 0.1 mL lysis buffer (20% SDS, 50% dimethylformamide) is added, incubation is continued overnight at 37 ℃, and then the optical density at 570 nm is measured by plate reader.

    In VivoGriseofulvin displays potent anti-infection activity in vivo. The minimum effective dose of Griseofulvin given daily per os is 250 mg/kg (6 days) in mice with a cutaneous infection of Trichophyton quinckeanum and 25 mg/kg (12 days) in guinea pigs with a cutaneous infection of Trichophyton mentagrophytes. Griseofulvin (50 mg/kg) is able to suppress COLO 205 tumor xenografts growth. Treatment with Griseofulvin and nocodazole (5 mg/kg) together significantly enhances the efficacy of nocodazole, leading to cessation of tumor growth. 
    Animal modelHuman colon adenocarcinoma xenografts COLO 205 
    Formulation & DosageDissolved in DMSO; 50 mg/kg; i.p. injection  
    References

    Mutat Res. 1988 Mar;195(2):91-126; Int J Cancer. 2001 Feb 1;91(3):393-401.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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