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F2929

Sigma-Aldrich

6-Fluoromevalonate

≥90% (GC), viscous liquid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C6H9FO3
Numéro CAS:
2822-77-7
Poids moléculaire :
148.13
Numéro MDL:
MFCD08276919
Code UNSPSC :
51111800
ID de substance PubChem :
24724480
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥90% (GC)

Forme

viscous liquid

Couleur

yellow tint

Solubilité

DMSO: ≥3 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

OC1(CF)CCOC(=O)C1

InChI

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

Clé InChI

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

Actions biochimiques/physiologiques

Mevalonate-pyrophosphate decarboxylase inhibitor

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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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
M Sawamura et al.
Clinical and experimental pharmacology & physiology, 20(7-8), 509-514 (1993-07-01)
1. Recent investigations revealed that isoprenoid compounds serve as key substances for cellular proliferation through post-translational modification. Previously we reported that tissues of spontaneously hypertensive rats (SHR) had a lower activity of isoprenoid biosynthesis when compared with the normotensive control
J A Cuthbert et al.
The Journal of biological chemistry, 266(27), 17966-17971 (1991-09-25)
The role of mevalonate and its products in the regulation of cellular proliferation was examined using 6-fluoromevalonate (Fmev), a compound that blocks the conversion of mevalonate pyrophosphate to isopentenyl pyrophosphate. Fmev suppressed DNA synthesis by a variety of transformed and
J E Carrel et al.
Experientia, 42(7), 853-854 (1986-07-15)
Biosynthesis of cantharidin in a blister beetle, Lytta polita, is effectively inhibited by 6-fluoromevalonate. Inhibition is attributed specifically to the fluorine substituent. Biochemical inhibition has not been demonstrated previously for an arthropod's defensive substance.
A Iwama et al.
Clinical and experimental pharmacology & physiology. Supplement, 22(1), S318-S320 (1995-01-01)
1. Phosphatidylinositol 3-kinase (PI3K) appears to have a crucial role in cellular proliferation induced by platelet-derived growth factor (PDGF). However, the mode of activation of the enzyme has been unclear so far. In the present study, we investigated the effects
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