F6892

Farnesyl pyrophosphate ammonium salt

Name: Farnesyl pyrophosphate ammonium salt
Brand: SIGMA

methanol:ammonia solution, ≥95% (TLC)

Synonyme(s) :

3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, FPP

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About This Item

Formule empirique (notation de Hill) :

C₁₅H₃₇N₃O₇P₂

Numéro CAS:

13058-04-3

Poids moléculaire :

433.42

NACRES:

NA.83

PubChem Substance ID:

24894923

UNSPSC Code:

12352204

MDL number:

MFCD00189688

Nom du produit

Farnesyl pyrophosphate ammonium salt, methanol:ammonia solution, ≥95% (TLC)

InChI

1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+

SMILES string

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI key

VWFJDQUYCIWHTN-YFVJMOTDSA-N

assay

≥95% (TLC)

form

methanol:ammonia solution

packaging

vial of 200 μg

storage temp.

−20°C

Application

Farnesyl pyrophosphate ammonium salt has been used:

as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays
in the prenylation of the hepatocyte growth factor (HGF) in human umbilical vein endothelial cells (HUVECs)
as a substrate in prenyltransferases assay in diatom Haslea ostrearia

Biochem/physiol Actions

Farnesyl pyrophosphate (FPP) is the precursor for the biosynthesis of cholesterol, ubiquinone and dolicol. It is part of the intracellular mevalonate pathway. FPP is essential for cell survival and is used for prenylation of several low molecular mass G proteins, including Ras. Inhibition of prenylation results in loss of oncogenic potential of Ras proteins. Inhibition of prenylation may serve as therapeutic potential for management of synaptic plasticity and Alzheimer′s disease.

General description

Farnesyl pyrophosphate is a 15-carbon isoprenoid synthesized from geranyl pyrophosphate (GPP) by the action of enzyme farnesyl pyrophosphate synthase (FPPS).

Physical form

Solution in methanol: 10mM aqueous NH₄OH (7:3)
Actual concentration given on label

pictograms

GHS02,GHS06,GHS08

signalword

Danger

hcodes

H225,H301 + H311 + H331,H315,H319,H370,H412

pcodes

P210 - P273 - P280 - P301 + P310 - P303 + P361 + P353 - P304 + P340 + P311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 1

target_organs

Eyes,Central nervous system

Classe de stockage

3 - Flammable liquids

wgk

WGK 2

flash_point_f

60.8 °F

flash_point_c

16 °C

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Consulter la Bibliothèque de documents

Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption.

John M Sanders et al.

Journal of medicinal chemistry, 48(8), 2957-2963 (2005-04-15)

We report the design, synthesis and testing of a series of novel bisphosphonates, pyridinium-1-yl-hydroxy-bisphosphonates, based on the results of comparative molecular similarity indices analysis and pharmacophore modeling studies of farnesyl diphosphate synthase (FPPS) inhibition, human Vgamma2Vdelta2 T cell activation and

Protein prenylation: enzymes, therapeutics, and biotechnology applications

Palsuledesai CC and Distefano MD

ACS Chemical Biology, 10(1), 51-62 (2014)

Matrix metalloproteinase-1 contribution to sarcoma cell invasion

Garamszegi N, et al.

Journal of Cellular and Molecular Medicine, 16(6), 1331-1341 (2012)

Structural characterization of substrate and inhibitor binding to farnesyl pyrophosphate synthase from Pseudomonas aeruginosa

Schmidberger JW, et al.

Acta Crystallographica Section D, Biological Crystallography, 71(3), 721-731 (2015)

Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative.

Petra M Bleeker et al.

Proceedings of the National Academy of Sciences of the United States of America, 109(49), 20124-20129 (2012-11-22)

Tomato breeding has been tremendously efficient in increasing fruit quality and quantity but did not focus on improving herbivore resistance. The biosynthetic pathway for the production of 7-epizingiberene in a wild tomato was introduced into a cultivated greenhouse variety with

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