PACOCF3 | CAS# 141022-99-3 | Phospholipase A2 inhibitor

MedKoo Cat#: 574838 | Name: PACOCF3

Description:

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

PACOCF3 is a Phospholipase A2 inhibitor. PACOCF3 reduced the phagocytosis induced by MT-II and MT-III.

Chemical Structure

PACOCF3

CAS#141022-99-3

Theoretical Analysis

MedKoo Cat#: 574838

Name: PACOCF3

CAS#: 141022-99-3

Chemical Formula: C17H31F3O

Exact Mass: 308.2327

Molecular Weight: 308.43

Elemental Analysis: C, 66.20; H, 10.13; F, 18.48; O, 5.19

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,450.00	2 Weeks
1g	USD 3,250.00	2 Weeks
2g	USD 5,850.00	2 Weeks

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Related CAS #

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Synonym

PACOCF3; Palmityl trifluoromethyl ketone

IUPAC/Chemical Name

1,1,1-Trifluoro-2-heptadecanone

InChi Key

MAHYXYTYTLCTQD-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(21)17(18,19)20/h2-15H2,1H3

SMILES Code

CCCCCCCCCCCCCCCC(C(F)(F)F)=O

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

Shelf Life

>3 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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

PACOCF3 (Palmityltrifluoromethylketone) is a selective phospholipase A2 inhibitor with an IC50 of 3.8 μM.

In vitro activity:

A novel Ca(2+)-independent phospholipase A2 (PLA2) has recently been purified from the murine macrophage-like cell line P388D1. This enzyme is now shown to be inhibited by palmitoyl trifluoromethyl ketone (PACOCF3), arachidonyl trifluoromethyl ketone (AACOCF3), and a bromoenol lactone (BEL). Both PACOCF3 and AACOCF3 were found to inhibit the macrophage PLA2 in a concentration-dependent manner. PACOCF3 was found to be approximately 4-fold more potent than AACOCF3, with IC50 values of 3.8 microM (0.0075 mol fraction) and 15 microM (0.028 mol fraction) Reference: J Biol Chem. 1995 Jan 6;270(1):445-50. https://pubmed.ncbi.nlm.nih.gov/7814408/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	33.3	108.06

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 308.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jan CR, Chou KJ, Lee KC, Wang JL, Tseng LL, Cheng JS, Chen WC. Dual action of palmitoyl trifluoromethyl ketone (PACOCF3) on Ca2+ signaling: activation of extracellular Ca2+ influx and alteration of ATP- and bradykinin-induced Ca2+ responses in Madin Darby canine kidney cells. Arch Toxicol. 2000 Oct;74(8):447-51. doi: 10.1007/s002040000130. PMID: 11097381. 2. Ackermann EJ, Conde-Frieboes K, Dennis EA. Inhibition of macrophage Ca(2+)-independent phospholipase A2 by bromoenol lactone and trifluoromethyl ketones. J Biol Chem. 1995 Jan 6;270(1):445-50. doi: 10.1074/jbc.270.1.445. PMID: 7814408.

In vitro protocol:

In vivo protocol:

TBD

1: Kopper TJ, Zhang B, Bailey WM, Bethel KE, Gensel JC. The effects of myelin on macrophage activation are phenotypic specific via cPLA2 in the context of spinal cord injury inflammation. Sci Rep. 2021 Mar 18;11(1):6341. doi: 10.1038/s41598-021-85863-6. PMID: 33737707; PMCID: PMC7973514. 2: Zuliani JP, Gutiérrez JM, Teixeira C. Signaling pathways involved in zymosan phagocytosis induced by two secreted phospholipases A2 isolated from Bothrops asper snake venom in macrophages. Int J Biol Macromol. 2018 Jul 1;113:575-582. doi: 10.1016/j.ijbiomac.2018.02.158. Epub 2018 Mar 6. PMID: 29501751. 3: Dias RG, Sampaio SC, Sant'Anna MB, Cunha FQ, Gutiérrez JM, Lomonte B, Cury Y, Picolo G. Articular inflammation induced by an enzymatically-inactive Lys49 phospholipase A2: activation of endogenous phospholipases contributes to the pronociceptive effect. J Venom Anim Toxins Incl Trop Dis. 2017 Mar 23;23:18. doi: 10.1186/s40409-017-0104-0. PMID: 28344594; PMCID: PMC5364601. 4: Barbour SE, Ramanadham S. Analyses of Calcium-Independent Phospholipase A2beta (iPLA2β) in Biological Systems. Methods Enzymol. 2017;583:119-141. doi: 10.1016/bs.mie.2016.09.001. Epub 2016 Oct 18. PMID: 28063488; PMCID: PMC5771648. 5: Dubinin MV, Astashev ME, Penkov NV, Gudkov SV, Dyachenko IA, Samartsev VN, Belosludtsev KN. Effects of Phospholipase A2 Inhibitors on Bilayer Lipid Membranes. J Membr Biol. 2016 Jun;249(3):339-47. doi: 10.1007/s00232-016-9872-7. Epub 2016 Jan 13. PMID: 26762382. 6: Nguyen CT, Shetty V, Maresso AW. Global metabolomic analysis of a mammalian host infected with Bacillus anthracis. Infect Immun. 2015 Dec;83(12):4811-25. doi: 10.1128/IAI.00947-15. Epub 2015 Oct 5. PMID: 26438791; PMCID: PMC4645395. 7: Belosludtsev KN, Belosludtseva NV, Kondratyev MS, Agafonov AV, Purtov YA. Interaction of phospholipase A of the E. coli outer membrane with the inhibitors of eucaryotic phospholipases A₂ and their effect on the Ca²⁺-induced permeabilization of the bacterial membrane. J Membr Biol. 2014 Mar;247(3):281-8. doi: 10.1007/s00232-014-9633-4. Epub 2014 Jan 30. PMID: 24477786. 8: Anwar MA, Ford WR, Herbert AA, Broadley KJ. Signal transduction and modulating pathways in tryptamine-evoked vasopressor responses of the rat isolated perfused mesenteric bed. Vascul Pharmacol. 2013 Jan;58(1-2):140-9. doi: 10.1016/j.vph.2012.10.007. Epub 2012 Oct 30. PMID: 23117109; PMCID: PMC3884126. 9: Last V, Williams A, Werling D. Inhibition of cytosolic Phospholipase A2 prevents prion peptide-induced neuronal damage and co-localisation with Beta III Tubulin. BMC Neurosci. 2012 Aug 28;13:106. doi: 10.1186/1471-2202-13-106. PMID: 22928663; PMCID: PMC3496594. 10: Damas JE, Cake MH. An albumin-associated PLA2-like activity inactivates surfactant phosphatidylcholine secreted from fetal type II pneumocytes. Am J Physiol Lung Cell Mol Physiol. 2011 Dec;301(6):L966-74. doi: 10.1152/ajplung.00103.2011. Epub 2011 Sep 9. PMID: 21908590. 11: Han MS, Lim YM, Quan W, Kim JR, Chung KW, Kang M, Kim S, Park SY, Han JS, Park SY, Cheon HG, Dal Rhee S, Park TS, Lee MS. Lysophosphatidylcholine as an effector of fatty acid-induced insulin resistance. J Lipid Res. 2011 Jun;52(6):1234-1246. doi: 10.1194/jlr.M014787. Epub 2011 Mar 28. PMID: 21447485; PMCID: PMC3090244. 12: Manjavachi MN, Motta EM, Marotta DM, Leite DFP, Calixto JB. Mechanisms involved in IL-6-induced muscular mechanical hyperalgesia in mice. Pain. 2010 Nov;151(2):345-355. doi: 10.1016/j.pain.2010.07.018. Epub 2010 Aug 14. PMID: 20709454. 13: Cinque B, Fanini D, Di Marzio L, Palumbo P, La Torre C, Donato V, Velardi E, Bruscoli S, Riccardi C, Cifone MG. Involvement of cPLA2 inhibition in dexamethasone-induced thymocyte apoptosis. Int J Immunopathol Pharmacol. 2008 Jul-Sep;21(3):539-51. doi: 10.1177/039463200802100307. PMID: 18831921. 14: Moreira V, Gutiérrez JM, Soares AM, Zamunér SR, Purgatto E, Teixeira Cde F. Secretory phospholipases A(2) isolated from Bothrops asper and from Crotalus durissus terrificus snake venoms induce distinct mechanisms for biosynthesis of prostaglandins E2 and D2 and expression of cyclooxygenases. Toxicon. 2008 Sep 1;52(3):428-39. doi: 10.1016/j.toxicon.2008.06.012. Epub 2008 Jun 21. PMID: 18619987. 15: Kanoo S, Deshpande SB. Involvement of phospholipase A2 pathway for the Indian red scorpion venom-induced augmentation of cardiopulmonary reflexes elicited by phenyldiguanide. Neurosci Lett. 2008 Aug 8;440(3):242-5. doi: 10.1016/j.neulet.2008.05.088. Epub 2008 Jun 19. PMID: 18571849. 16: Marrelli SP, O'neil RG, Brown RC, Bryan RM Jr. PLA2 and TRPV4 channels regulate endothelial calcium in cerebral arteries. Am J Physiol Heart Circ Physiol. 2007 Mar;292(3):H1390-7. doi: 10.1152/ajpheart.01006.2006. Epub 2006 Oct 27. PMID: 17071727. 17: Schaeffer EL, Gattaz WF. Requirement of hippocampal phospholipase A2 activity for long-term memory retrieval in rats. J Neural Transm (Vienna). 2007 Mar;114(3):379-85. doi: 10.1007/s00702-006-0585-4. Epub 2006 Oct 27. PMID: 17066253. 18: Motta EM, Calixto JB, Rae GA. Mechanical hyperalgesia induced by endothelin-1 in rats is mediated via phospholipase C, protein kinase C, and MAP kinases. Exp Biol Med (Maywood). 2006 Jun;231(6):1141-5. PMID: 16741065. 19: Schaeffer EL, Gattaz WF. Inhibition of calcium-independent phospholipase A2 activity in rat hippocampus impairs acquisition of short- and long-term memory. Psychopharmacology (Berl). 2005 Sep;181(2):392-400. doi: 10.1007/s00213-005-2256-9. Epub 2005 Oct 14. PMID: 15830227. 20: Schaeffer EL, Bassi F Jr, Gattaz WF. Inhibition of phospholipase A2 activity reduces membrane fluidity in rat hippocampus. J Neural Transm (Vienna). 2005 May;112(5):641-7. doi: 10.1007/s00702-005-0301-9. PMID: 15830123.