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G4753

Sigma-Aldrich

Griseofulvin

from Penicillium griseofulvum, 97.0-102.0%

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Synonym(s):
(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione
Empirical Formula (Hill Notation):
C17H17ClO6
CAS Number:
126-07-8
Molecular Weight:
352.77
Beilstein:
95226
EC Number:
204-767-4
MDL number:
MFCD00082343
UNSPSC Code:
12352200
PubChem Substance ID:
24895185
NACRES:
NA.77

biological source

Penicillium griseofulvum

Quality Level

100

Assay

97.0-102.0%

form

powder

antibiotic activity spectrum

fungi

Mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

ClC1=C(O[C@@]2(C(OC)=CC(C[C@H]2C)=O)C3=O)C3=C(OC)C=C1OC

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

InChI key

DDUHZTYCFQRHIY-RBHXEPJQSA-N

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Biochem/physiol Actions

Antifungal. Mode of action: Disrupts the mitotic spindle structure and inhibits nuclear division. Induces apoptosis in human tumor cell lines.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H317,H351,H360FD

Hazard Classifications

Carc. 2 - Repr. 1B - Skin Sens. 1

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Griseofulvin inhibits fungal mitosis.
K Gull et al.
Nature, 244(5414), 292-294 (1973-07-27)
Xing Wang et al.
Molecular cancer therapeutics, 22(4), 519-528 (2023-02-09)
Extra copies of centrosomes are frequently observed in cancer cells. To survive and proliferate, cancer cells have developed strategies to cluster extra-centrosomes to form bipolar mitotic spindles. The aim of this study was to investigate whether centrosome clustering (CC) inhibition
Dulal Panda et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(28), 9878-9883 (2005-06-30)
The antifungal drug griseofulvin inhibits mitosis strongly in fungal cells and weakly in mammalian cells by affecting mitotic spindle microtubule (MT) function. Griseofulvin also blocks cell-cycle progression at G(2)/M and induces apoptosis in human tumor cell lines. Despite extensive study
Konstantinos Drosopoulos et al.
Methods in molecular biology (Clifton, N.J.), 1953, 33-42 (2019-03-27)
Cellular models for siRNA and small molecule high-throughput screening have been widely used in the last decade to identify targets for drug discovery. As an example, we present a twofold readout approach based on cell viability and multipolar phenotype. To
Marc S Raab et al.
Cancer research, 72(20), 5374-5385 (2012-09-04)
In contrast to normal cells, malignant cells are frequently aneuploid and contain multiple centrosomes. To allow for bipolar mitotic division, supernumerary centrosomes are clustered into two functional spindle poles in many cancer cells. Recently, we have shown that griseofulvin forces
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