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KI1383GRISEOFULVIN1 g$5560

Chemical Characteristic

Product NameGRISEOFULVIN
SynonymsMicrocrystalline
CAS No.126-07-8
Molecular Weight 352.77
FormulaC17H17ClO6
Chemical NameSpiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S,6'R)-
SmilesO1[C@]2(C(=O)c3c1c(c(cc3OC)OC)Cl)C(=CC(=O)C[C@H]2C)OC
Chemical Structure

Biological activities

Griseofulvin is a metabolic product of several species of Penicillium. Griseofulvin, as an antifungal antibiotic, accumulates in the keratin layers of the epidermis and inhibits the fungal growth. In mammalian cells, griseofulvin binds to tubulinin in vitro with a weak affinity (Kd=300 µM), interfering with microtubule function, and inhibits mitosis with an IC50 of 20 µM.[1] Griseofulvin (5 µM) reduces the rates of growing and shortening by 50 and 70%, respectively.[2] Griseofulvin at a concentration of 50 µM destroies cytoplasmic microtubules in mouse 3T3 cells. Griseofulvin at a concentration of 10 µM allows 3T3 cells to accumulate in c-mitotic (??olchicin-mitotic?? arrest.[3] Griseofulvin inhibits the aggregation of multiple centrioles in SCC114 and N115 mouse neuroblastoma cell lines.[4] Griseofulvin (50 mg/kg) in combination with nocodazole enhances the effect of nocodazole against the colon cancer cells in vivo and leads to cessation of tumor growth.[5]

Protocols

Molecular levels: In vitro: Griseofulvin is dissolved in 0.1%DMSO.[2]

References

[1] Wehland J, et al. Interaction of griseofulvin with microtubules, microtubule protein and tubulin. J Mol Biol. 1977, 111(3): 329-342.
[2] Panda D, et al. Kinetic suppression of microtubule dynamic instability by griseofulvin: implications for its possible use in the treatment of cancer. Proc Natl Acad Sci U S A. 2005, 102(28): 9878-9883.
[3] Weber K, et al. Griseofulvin interacts with microtubules both in vivo and in vitro. J Mol Biol. 1976, 102(4): 817-829.
[4] Rebacz B, et al. Identification of griseofulvin as an inhibitor of centrosomal clustering in a phenotype-based screen. Cancer Res. 2007, 67(13): 6342-6350.
[5] Ho YS, et al. Griseofulvin potentiates antitumorigenesis effects of nocodazole through induction of apoptosis and G2/M cell cycle arrest in human colorectal cancer cells. Int J Cancer. 2001, 91(3): 393-401.

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