F2929
6-Fluoromevalonate
≥90% (GC), viscous liquid
Synonym(s):
Tetrahydro-4-fluoromethyl-4-hydroxy-2H-pyran-2-one, ZR 3516
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About This Item
Empirical Formula (Hill Notation):
C6H9FO3
CAS Number:
Molecular Weight:
148.13
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
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 Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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.
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
Ari Hashimoto et al.
The Journal of cell biology, 213(1), 81-95 (2016-04-06)
Drug resistance, metastasis, and a mesenchymal transcriptional program are central features of aggressive breast tumors. The GTPase Arf6, often overexpressed in tumors, is critical to promote epithelial-mesenchymal transition and invasiveness. The metabolic mevalonate pathway (MVP) is associated with tumor invasiveness
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