An internal standard for the quantification of griseofulvin
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Unlabeled Version(s)
19461Griseofulvin
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Griseofulvin-d3

Item No. 33366

Technical Information
Formal Name
7-chloro-4,6-dimethoxy-2′-(methoxy-d3)-6′R-methyl-spiro[benzofuran-2(3H),1′S-[2]cyclohexene]-3,4′-dione
CAS Number
1279033-22-5
Molecular Formula
C17H14ClD3O6
Formula Weight
Purity
≥99% deuterated forms (d1-d3)
A solid
Acetonitrile: solubleDMF: solubleDMSO: solubleMethanol: soluble
SMILES
C[C@H](C1)[C@](C(C2=C3OC)=O)(OC2=C(C(OC)=C3)Cl)C(OC([2H])([2H])[2H])=CC1=O
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/i4D3
InChi Key
DDUHZTYCFQRHIY-BCBJJHLGSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    Product Description

    Griseofulvin-d3 is intended for use as an internal standard for the quantification of griseofulvin (Item No. 19461) by GC- or LC-MS. Griseofulvin is a fungal metabolite that has been found in Penicillium and has diverse biological activities.1 It is active against clinical isolates of the dermatophytes T. rubrum, T. tonsurans, and M. canis (MICs = 0.0078-0.0156, 1-4, and 0.5-2 µg/ml, respectively).2 Griseofulvin binds to tubulin (Kd = 300 µM) and reduces the growth rate and shortening rate of isolated bovine brain microtubulin, indicating stabilization of microtubule dynamics, when used at concentrations ranging from 0.5 to 20 µM.3 It induces abnormal microtubule polymerization and cell cycle arrest at the G2/M phase in HT-29 cells when used at a concentration of 20 µM.4 Griseofulvin (30 mg/kg), alone or in combination with nocodazole (Item No. 13857), reduces tumor growth in a COLO 205 mouse xenograft model. Formulations containing griseofulvin have been used in the treatment of fungal infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Singh, P., Rathinasamy, K., Mohan, R., et alMicrotubule assembly dynamics: An attractive target for anticancer drugs. IUBMB Life 60(6), 368-375 (2008).

    2. Brilhante, R.S.N., Correia, E.E.M., Guedes, G.M.M., et alIn vitro activity of azole derivatives and griseofulvin against planktonic and biofilm growth of clinical isolates of dermatophytes. Mycoses 61(7), 449-454 (2018).

    3. Panda, D., Rathinasamy, K., Santra, M.K., et alKinetic suppression of microtubule dynamic instability by griseofulvin: Implications for its possible use in the treatment of cancer. Proc. Natl. Acad. Sci. USA 102(28), 9878-9883 (2005).

    4. Ho, Y.-S., Duh, J.-S., Jeng, J.-H., et alGriseofulvin potentiates antitumorigenesis effects of nocodazole through induction of apoptosis and G2/M cell cycle arrest in human colorectal cancer cells. Int. J. Cancer 91(3), 393-401 (2001).