FIPI

Phospholipase D inhibitor CAS# 939055-18-2

FIPI

Catalog No. BCC7721----Order now to get a substantial discount!

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Quality Control of FIPI

Number of papers citing our products

Chemical structure

FIPI

3D structure

Chemical Properties of FIPI

Cas No. 939055-18-2 SDF Download SDF
PubChem ID 16739265 Appearance Powder
Formula C23H24FN5O2 M.Wt 421.5
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 5-Fluoro-2-indolyl deschlorohalopemide
Solubility DMSO : 14.67 mg/mL (34.81 mM; Need ultrasonic and warming)
Chemical Name 5-fluoro-N-[2-[4-(2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]ethyl]-1H-indole-2-carboxamide
SMILES C1CN(CCC1N2C3=CC=CC=C3NC2=O)CCNC(=O)C4=CC5=C(N4)C=CC(=C5)F
Standard InChIKey LHABRXRGDLASIH-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H24FN5O2/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)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of FIPI

DescriptionPotent phosholipase D (PLD) inhibitor (IC50 values are 20 and 25 nM for PLD2 and PLD1 respectively). Ameliorates PLD2-driven suppression of membrane ruffling and cell spreading. Orally available.

FIPI Dilution Calculator

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FIPI Molarity Calculator

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Preparing Stock Solutions of FIPI

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3725 mL 11.8624 mL 23.7248 mL 47.4496 mL 59.312 mL
5 mM 0.4745 mL 2.3725 mL 4.745 mL 9.4899 mL 11.8624 mL
10 mM 0.2372 mL 1.1862 mL 2.3725 mL 4.745 mL 5.9312 mL
50 mM 0.0474 mL 0.2372 mL 0.4745 mL 0.949 mL 1.1862 mL
100 mM 0.0237 mL 0.1186 mL 0.2372 mL 0.4745 mL 0.5931 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on FIPI

FIPI is a derivative of halopemide which potently inhibits both PLD1 and PLD2 with IC50s of 25 nM and 20 nM, respectively.

In Vitro:Despite the high clearance of greater than 2 L/h/kg, FIPI shows a half-life of greater than 5 h, a Cmax of greater than 10-fold the 50 versus PLD2, and moderate bioavailability of 18%[1]. FIPI inhibits both PLD1 and PLD2 in a dose-dependent manner, with 50% loss of activity observed at approximately 25 nM. FIPI is not an irreversible suicide inhibitor but neither is it rapidly and completely reverses upon removal of the drug. IPI does not alter PLD subcellular localization, access to PIP2, actin stress fibers, or upstream signaling events. FIPI rescues PLD2-suppressed membrane ruffling and cell spreading[2]. FIPI attenuats the thimerosal-induced PLD activation, and the Hg-induced PLD activation in MAECs in a dose-dependent manner, and the agonist- and oxidant-induced PLD activation in a dose-dependent manner in MAECs[3].

References:
[1]. Monovich L, et al. Optimization of halopemide for phospholipase D2 inhibition. Bioorg Med Chem Lett. 2007 Apr 15;17(8):2310-1. [2]. Su W, et al. 5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis. Mol Pharmacol. 2009 Mar;75(3):437-46. [3]. Secor JD, et al. Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid si

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References on FIPI

5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis.[Pubmed:19064628]

Mol Pharmacol. 2009 Mar;75(3):437-46.

The signaling enzyme phospholipase D (PLD) and the lipid second messenger it generates, phosphatidic acid (PA), are implicated in many cell biological processes, including Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. PLD production of PA is inhibited by the primary alcohol 1-butanol, which has thus been widely employed to identify PLD/PA-driven processes. However, 1-butanol does not always effectively reduce PA accumulation, and its use may result in PLD-independent deleterious effects. Consequently, identification of potent specific small-molecule PLD inhibitors would be an important advance for the field. We examine one such here, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI), which was identified recently in an in vitro chemical screen for PLD2 inhibitors, and show that it rapidly blocks in vivo PA production with subnanomolar potency. We were surprised to find that several biological processes blocked by 1-butanol are not affected by FIPI, suggesting the need for re-evaluation of proposed roles for PLD. However, FIPI does inhibit PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis, indicating potential utility for it as a therapeutic for autoimmunity and cancer metastasis.

Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells.[Pubmed:21994240]

Int J Toxicol. 2011 Dec;30(6):619-38.

Here, we investigated thiol-redox-mediated phospholipase D (PLD) signaling as a mechanism of mercury cytotoxicity in mouse aortic endothelial cell (MAEC) in vitro model utilizing the novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and the novel PLD-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI). Our results demonstrated (i) mercury in the form of mercury(II) chloride, methylmercury, and thimerosal induced PLD activation in a dose- and time-dependent manner; (ii) NBMI and FIPI completely attenuated mercury- and oxidant-induced PLD activation; (iii) mercury induced upstream phosphorylation of extracellular-regulated kinase 1/2 (ERK1/2) leading to downstream threonine phosphorylation of PLD(1) which was attenuated by NBMI; (iv) mercury caused loss of intracellular glutathione which was restored by NBMI; and (v) NBMI and FIPI attenuated mercury- and oxidant-induced cytotoxicity in MAECs. For the first time, this study demonstrated that redox-dependent and PLD-mediated bioactive lipid signaling was involved in mercury-induced vascular EC cytotoxicity which was protected by NBMI and FIPI.

Optimization of halopemide for phospholipase D2 inhibition.[Pubmed:17317170]

Bioorg Med Chem Lett. 2007 Apr 15;17(8):2310-1.

Halopemide, which was identified by HTS to inhibit phospholipase D2 (PLD2), provided the basis for an exploratory effort to identify potent inhibitors of PLD2 for use as inflammatory mediators. Parallel synthesis and purification were utilized to rapidly identify orally available amide analogs derived from indole 2-carboxylic acids with superior potency versus PLD2.

Description

FIPI is a derivative of halopemide which potently inhibits both PLD1 and PLD2 with IC50s of 25 nM and 20 nM, respectively.

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