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F5807

Sigma-Aldrich

FIPI hydrochloride hydrate

≥98% (HPLC), powder

Synonym(s):

4-Fluoro-N-(2-(4-(5-fluoro-1H-indol-1-yl)piperidin-1-yl)ethyl)benzamide, 5-Fluoro-2-indolyl des-chlorohalopemide hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C23H24FN5O2·HCl · xH2O
CAS Number:
2329374-20-9
Molecular Weight:
457.93 (anhydrous basis)
MDL number:
MFCD12912411
UNSPSC Code:
12352204
PubChem Substance ID:
329799747
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

off-white

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

O.Cl.Fc1ccc2[nH]c(cc2c1)C(=O)NCCN3CCC(CC3)N4C(=O)Nc5ccccc45

InChI

1S/C23H24FN5O2.ClH.H2O/c24-16-5-6-18-15(13-16)14-20(26-18)22(30)25-9-12-28-10-7-17(8-11-28)29-21-4-2-1-3-19(21)27-23(29)31;;/h1-6,13-14,17,26H,7-12H2,(H,25,30)(H,27,31);1H;1H2

InChI key

ZORDQKCXPCXYKL-UHFFFAOYSA-N

Application

FIPI (4-Fluoro-N-(2-(4-(5-fluoro-1H-indol-1-yl)piperidin-1-yl)ethyl)benzamide, 5-Fluoro-2-indolyl des-chlorohalopemide) is used to study the cell signaling pathways, cell processes and cell dysregulations that depend upon phospholipase D1 (PLD1) and phospholipase D2 (PLD2) activities. FIPI may be used to help identify and characterized phospholipase D enzymes.

Biochem/physiol Actions

FIPI is a potent Phospholipase D (PLD) inhibitor. The signaling enzyme Phospholipase D (PLD) and the lipid second messenger phosphatidic acid (PA) generated by PLD are implicated in many cell biological processes including Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. FIPI is a potent in vivo inhibitor of both PLD1 and PLD2, setting the stage for a new era of exploration and validation of cell biological roles for mammalian PLD. It rapidly blocks in vivo PA production with sub-nM potency. FIPI inhibits PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis, indicating potential utility for it as a therapeutic for autoimmunity and cancer metastasis. It does not affect PLD subcellular localization, PIP2 availability, the actin stress fiber network in resting CHO cells, or selected signaling events proximal to PLD activation.
FIPI is a potent phospholipase D (PLD) inhibitor effective at sub-nM levels. Phospholipase D (PLD) and the lipid second messenger phosphatidic acid (PA) generated by PLD are implicated in many cell biological processes including Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. FIPI inhibits both PLD1 and PLD2, rapidly blocking in vivo PA production. FIPI inhibits PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis, suggesting potential as a therapeutic for autoimmune diseases and cancer metastasis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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My career as a cardiologist and the developmental history of coronary intervention in Japan.
Masakiyo Nobuyoshi
Cardiovascular intervention and therapeutics, 25(2), 51-52 (2010-07-01)
David Stegner et al.
Arteriosclerosis, thrombosis, and vascular biology, 33(9), 2212-2217 (2013-07-23)
We recently showed that mice lacking the lipid signaling enzyme phospholipase (PL) D1 or both PLD isoforms (PLD1 and PLD2) were protected from pathological thrombus formation and ischemic stroke, whereas hemostasis was not impaired in these animals. We sought to
Han Han et al.
Molecular cell, 72(2), 328-340 (2018-10-09)
The Hippo pathway plays a crucial role in organ size control and tumor suppression, but its precise regulation is not fully understood. In this study, we discovered that phosphatidic acid (PA)-related lipid signaling is a key regulator of the Hippo
Xiao Tang et al.
Journal of immunology (Baltimore, Md. : 1950), 195(3), 1191-1201 (2015-06-28)
Bioactive peptide LL-37/hCAP18, the only human member of the cathelicidin family, plays important roles in killing various pathogens, as well as in immune modulation. We demonstrate that LL-37 is internalized by human macrophages in a time-, dose-, temperature-, and peptide

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