F5807
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:
Molecular Weight:
457.93 (anhydrous basis)
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Rebecca Elizabeth Kattan et al.
Molecular & cellular proteomics : MCP, 21(2), 100195-100195 (2022-01-11)
Mammalian phospholipase D (PLD) enzyme family consists of six members. Among them, PLD1/2/6 catalyzes phosphatidic acid (PA) production, while PLD3/4/5 has no catalytic activities. Deregulation of the PLD-PA lipid signaling has been associated with various human diseases including cancer. However
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Inositol is an essential metabolite that serves as a precursor for structural and signaling molecules. Although perturbation of inositol homeostasis has been implicated in numerous human disorders, surprisingly little is known about how inositol levels are regulated in mammalian cells.
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
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