FIPI HCl
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522718

CAS#: 1781834-93-2 (HCl)

Description: FIPI is a potent and selective phospholipase D inhibitor. FIPI attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. FIPI 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 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.


Price and Availability

Size
Price

1g
USD 2950
Size
Price

2g
USD 5250
Size
Price

5g
USD 7650

FIPI hydrochloride, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522718
Name: FIPI HCl
CAS#: 1781834-93-2 (HCl)
Chemical Formula: C23H25ClFN5O2
Exact Mass:
Molecular Weight: 457.9344
Elemental Analysis: C, 60.33; H, 5.50; Cl, 7.74; F, 4.15; N, 15.29; O, 6.99


Related CAS #: 1781834-93-2 (HCl)   939055-18-2 (free base)    

Synonym: FIPI; FIPI HCl; FIPI hydrochloride

IUPAC/Chemical Name: 5-fluoro-N-(2-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)ethyl)-1H-indole-2-carboxamide hydrochloride

InChi Key: BNMQCDOCYPGJJD-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H24FN5O2.ClH/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

SMILES Code: O=C(C(N1)=CC2=C1C=CC(F)=C2)NCCN3CCC(N4C5=CC=CC=C5NC4=O)CC3.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934990300


References

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2: Ganesan R, Mahankali M, Alter G, Gomez-Cambronero J. Two sites of action for PLD2 inhibitors: The enzyme catalytic center and an allosteric, phosphoinositide biding pocket. Biochim Biophys Acta. 2015 Mar;1851(3):261-72. doi: 10.1016/j.bbalip.2014.12.007. Epub 2014 Dec 20. PubMed PMID: 25532944; PubMed Central PMCID: PMC4312721.

3: McDavid S, Bauer MB, Brindley RL, Jewell ML, Currie KP. Butanol isomers exert distinct effects on voltage-gated calcium channel currents and thus catecholamine secretion in adrenal chromaffin cells. PLoS One. 2014 Oct 2;9(10):e109203. doi: 10.1371/journal.pone.0109203. eCollection 2014. PubMed PMID: 25275439; PubMed Central PMCID: PMC4183593.

4: Björnström K, Turina D, Strid T, Sundqvist T, Eintrei C. Orexin A inhibits propofol-induced neurite retraction by a phospholipase D/protein kinase Cε-dependent mechanism in neurons. PLoS One. 2014 May 14;9(5):e97129. doi: 10.1371/journal.pone.0097129. eCollection 2014. PubMed PMID: 24828410; PubMed Central PMCID: PMC4020800.

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6: Bates RC, Fees CP, Holland WL, Winger CC, Batbayar K, Ancar R, Bergren T, Petcoff D, Stith BJ. Activation of Src and release of intracellular calcium by phosphatidic acid during Xenopus laevis fertilization. Dev Biol. 2014 Feb 1;386(1):165-80. doi: 10.1016/j.ydbio.2013.11.006. Epub 2013 Nov 21. PubMed PMID: 24269904; PubMed Central PMCID: PMC3922219.

7: El Osta M, Liu M, Adada M, Senkal CE, Idkowiak-Baldys J, Obeid LM, Clarke CJ, Hannun YA. Sustained PKCβII activity confers oncogenic properties in a phospholipase D- and mTOR-dependent manner. FASEB J. 2014 Jan;28(1):495-505. doi: 10.1096/fj.13-230557. Epub 2013 Oct 11. PubMed PMID: 24121461; PubMed Central PMCID: PMC3868841.

8: Stegner D, Thielmann I, Kraft P, Frohman MA, Stoll G, Nieswandt B. Pharmacological inhibition of phospholipase D protects mice from occlusive thrombus formation and ischemic stroke--brief report. Arterioscler Thromb Vasc Biol. 2013 Sep;33(9):2212-7. doi: 10.1161/ATVBAHA.113.302030. Epub 2013 Jul 18. PubMed PMID: 23868933.

9: Kim BJ, Kwon YK, Kim E, So I. Effects of histamine on cultured interstitial cells of cajal in murine small intestine. Korean J Physiol Pharmacol. 2013 Apr;17(2):149-56. doi: 10.4196/kjpp.2013.17.2.149. Epub 2013 Apr 10. PubMed PMID: 23626477; PubMed Central PMCID: PMC3634092.

10: Ye Q, Kantonen S, Gomez-Cambronero J. Serum deprivation confers the MDA-MB-231 breast cancer line with an EGFR/JAK3/PLD2 system that maximizes cancer cell invasion. J Mol Biol. 2013 Feb 22;425(4):755-66. doi: 10.1016/j.jmb.2012.11.035. Epub 2012 Dec 10. PubMed PMID: 23238254; PubMed Central PMCID: PMC3568238.

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12: Elvers M, Grenegård M, Khoshjabinzadeh H, Münzer P, Borst O, Tian H, Di Paolo G, Lang F, Gawaz M, Lindahl TL, Fälker K. A novel role for phospholipase D as an endogenous negative regulator of platelet sensitivity. Cell Signal. 2012 Sep;24(9):1743-52. doi: 10.1016/j.cellsig.2012.04.018. Epub 2012 May 3. PubMed PMID: 22579635.

13: Hughes DA, Malmenäs M, Deegan PB, Elliott PM, Ginsberg L, Hajioff D, Ioannidis AS, Orteu CH, Ramaswami U, West M, Pastores GM, Jenkinson C; FOS Investigators. Fabry International Prognostic Index: a predictive severity score for Anderson-Fabry disease. J Med Genet. 2012 Mar;49(3):212-20. doi: 10.1136/jmedgenet-2011-100407. Epub 2012 Feb 7. PubMed PMID: 22315436.

14: Secor JD, Kotha SR, Gurney TO, Patel RB, Kefauver NR, Gupta N, Morris AJ, Haley BE, Parinandi NL. 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. Int J Toxicol. 2011 Dec;30(6):619-38. doi: 10.1177/1091581811422413. Epub 2011 Oct 12. PubMed PMID: 21994240; PubMed Central PMCID: PMC3503146.

15: Patel RB, Kotha SR, Sherwani SI, Sliman SM, Gurney TO, Loar B, Butler SO, Morris AJ, Marsh CB, Parinandi NL. Pulmonary fibrosis inducer, bleomycin, causes redox-sensitive activation of phospholipase D and cytotoxicity through formation of bioactive lipid signal mediator, phosphatidic acid, in lung microvascular endothelial cells. Int J Toxicol. 2011 Feb;30(1):69-90. doi: 10.1177/1091581810388850. Epub 2010 Dec 3. PubMed PMID: 21131602; PubMed Central PMCID: PMC3503147.

16: Huang H, He X, Deng X, Li G, Ying G, Sun Y, Shi L, Benovic JL, Zhou N. Bombyx adipokinetic hormone receptor activates extracellular signal-regulated kinase 1 and 2 via G protein-dependent PKA and PKC but β-arrestin-independent pathways. Biochemistry. 2010 Dec 28;49(51):10862-72. doi: 10.1021/bi1014425. Epub 2010 Dec 2. PubMed PMID: 21126059.

17: Chang LC, Huang TH, Chang CS, Tsai YR, Lin RH, Lee PW, Hsu MF, Huang LJ, Wang JP. Signaling mechanisms of inhibition of phospholipase D activation by CHS-111 in formyl peptide-stimulated neutrophils. Biochem Pharmacol. 2011 Jan 15;81(2):269-78. doi: 10.1016/j.bcp.2010.10.007. Epub 2010 Oct 20. PubMed PMID: 20965153.

18: Faugaret D, Chouinard FC, Harbour D, El azreq MA, Bourgoin SG. An essential role for phospholipase D in the recruitment of vesicle amine transport protein-1 to membranes in human neutrophils. Biochem Pharmacol. 2011 Jan 1;81(1):144-56. doi: 10.1016/j.bcp.2010.09.014. Epub 2010 Sep 19. PubMed PMID: 20858461.

19: Yanase Y, Carvou N, Frohman MA, Cockcroft S. Reversible bleb formation in mast cells stimulated with antigen is Ca2+/calmodulin-dependent and bleb size is regulated by ARF6. Biochem J. 2009 Dec 14;425(1):179-93. doi: 10.1042/BJ20091122. PubMed PMID: 19845506.

20: Su W, Yeku O, Olepu S, Genna A, Park JS, Ren H, Du G, Gelb MH, Morris AJ, Frohman MA. 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. doi: 10.1124/mol.108.053298. Epub 2008 Dec 8. PubMed PMID: 19064628; PubMed Central PMCID: PMC2684902.
(last updated: 4/20/2016)