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F2929

Sigma-Aldrich

6-Fluoromevalonate

≥90% (GC), viscous liquid

Sinónimos:

Tetrahydro-4-fluoromethyl-4-hydroxy-2H-pyran-2-one, ZR 3516

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About This Item

Fórmula empírica (notación de Hill):
C6H9FO3
Número de CAS:
2822-77-7
Peso molecular:
148.13
MDL number:
MFCD08276919
UNSPSC Code:
51111800
PubChem Substance ID:
24724480
NACRES:
NA.77

Quality Level

100

assay

≥90% (GC)

form

viscous liquid

color

yellow tint

solubility

DMSO: ≥3 mg/mL

storage temp.

2-8°C

SMILES string

OC1(CF)CCOC(=O)C1

InChI

1S/C6H9FO3/c7-4-6(9)1-2-10-5(8)3-6/h9H,1-4H2

InChI key

DPPMVKMESJJAJZ-UHFFFAOYSA-N

Application

6-Fluoromevalonate has been used as a mevalonate pyrophosphate decarboxylase inhibitor:
  • to study the effect of mevalonate pathway inhibition on patient-derived brain tumor-initiating cells (BTICs) growth and self-renewal
  • to study its effect on induction of trained immunity by β-glucan in monocytes
  • to determine the effect of the mevalonate pathway (MVP) on ADP-ribosylation factor 6 (ARF6) activation

Biochem/physiol Actions

Mevalonate-pyrophosphate decarboxylase inhibitor

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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J A Cuthbert et al.
Cancer research, 55(8), 1732-1740 (1995-04-15)
Mevalonate is the precursor of a number of different products potentially required for the growth of cells, including the prenylated oncoprotein Ras. To determine whether inhibition of mevalonate metabolism would selectively block proliferation of Ras-transformed cells, 6-fluoromevalonate (Fmev), an inhibitor
J A Cuthbert et al.
The Journal of biological chemistry, 265(30), 18568-18575 (1990-10-25)
The sterol synthesis inhibitor 6-fluoromevalonate (Fmev) was used to explore the role of mevalonate products in lymphocyte proliferation. Fmev blocks the synthesis of isopentenyl pyrophosphate and all more distal products in the sterol pathway. When cells were cultured in lipoprotein-deficient
J F Nave et al.
The Biochemical journal, 227(1), 247-254 (1985-04-01)
6-Fluoromevalonate blocks the incorporation of mevalonic acid, but not that of isopentenyl pyrophosphate, into non-saponifiable lipids in a rat liver multienzyme system. With 3H-labelled 6-fluoromevalonate, it was found that 6-fluoromevalonate is converted to its phospho and pyrophospho derivatives in this
A Corsini et al.
Comptes rendus des seances de la Societe de biologie et de ses filiales, 191(2), 169-194 (1997-01-01)
The role of mevalonic acid (MVA) and its products (isoprenoids) in cell proliferation prompted us to investigate the effect of drugs affecting diverse enzymatic steps of the MVA pathway on rat aorta smooth muscle cell (SMC) proliferation. Competitive inhibitors of
Linda Henneman et al.
Biochimica et biophysica acta, 1811(4), 227-233 (2011-01-18)
The isoprenoid biosynthesis pathway provides the cell with a variety of compounds which are involved in multiple cellular processes. Inhibition of this pathway with statins and bisphosphonates is widely applied in the treatment of hypercholesterolemia and metabolic bone disease, respectively.
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