PDN01791 | CAS# 149301-79-1 | Arachidonic Acid Analog

MedKoo Cat#: 574544 | Name: PDN01791

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Description:

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

PDN01791, also known as Arachidonyl Trifluoromethyl Ketone is an analog of arachidonic acid in which the carboxyl group is replaced by a trifluoromethyl ketone group. It inhibits the activity of the 85 kDa cPLA2 and the 80 kDa macrophage iPLA2 without altering the activity of the 14 kDa sPLA2s. ATK is useful for differentiating the effects of cPLA2 and iPLA2 from sPLA2. This product has no formal name at the moment. For the convenience of communication, a temporary code name was therefore proposed according to MedKoo Chemical Nomenclature (see web page: https://www.medkoo.com/page/naming).

Chemical Structure

PDN01791

CAS#149301-79-1

Theoretical Analysis

MedKoo Cat#: 574544

Name: PDN01791

CAS#: 149301-79-1

Chemical Formula: C21H31F3O

Exact Mass: 356.2327

Molecular Weight: 356.47

Elemental Analysis: C, 70.76; H, 8.77; F, 15.99; O, 4.49

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Synonym

Arachidonyl Trifluoromethyl Ketone; AACOCF3; Arach-CF3; ATK; AATFMK; PDN 01791; PDN-01791; PDN01791

IUPAC/Chemical Name

1,1,1-trifluoro-6Z,9Z,12Z,15Z-heneicosatetraen-2-one

InChi Key

PLWROONZUDKYKG-DOFZRALJSA-N

InChi Code

InChI=1S/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-

SMILES Code

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(C(F)(F)F)=O

Appearance

A solution in ethanol

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:

AACOCF3 is a potent and selective slow binding inhibitor of the 85-kDa cytosolic phospholipase A2 (cPLA2).

In vitro activity:

AACOCF3 inhibited the release of AA from calcium ionophore-challenged U937 cells (IC50 = 8 microM, 2 x 10(6) cells ml-1) and from platelets (IC50 = 2 microM, 4 x 10(7) cells ml-1). In addition to the release of AA, AACOCF3 also inhibited the production of 12-hydroxyeicosatetraenoic acid (12-HETE) and thromboxane B2, two of the major metabolites of AA produced by platelets. AACOCF3 blocked thromboxane B2 formation by both calcium ionophore- and AA-challenged platelets, indicating that the compound affects the cyclooxygenase pathway in addition to AA release. Reference: J Biol Chem. 1994 Jun 3;269(22):15619-24. https://pubmed.ncbi.nlm.nih.gov/8195210/

In vivo activity:

These effects were paralleled by inhibition of aortic osteogenic/chondrogenic signaling by AACOCF3. As shown in Figure 4, cholecalciferol overload significantly upregulated mRNA expression of osteogenic transcription factors Msx2 and Cbfa1 and of osteogenic enzyme tissue-nonspecific alkaline phosphatase (Alpl), markers of increased osteogenic/chondrogenic transdifferentiation in the aortic tissue, effects again significantly ameliorated by AACOCF3 treatment. Thus, AACOCF3 inhibited aortic osteoinductive signaling and vascular calcification in the cholecalciferol-overload mouse model. Reference: JCI Insight. 2019 May 16;4(10):e125638. https://pubmed.ncbi.nlm.nih.gov/31092728/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	715.34

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 356.47 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. Loweth AC, Scarpello JH, Morgan NG. A specific inhibitor of cytosolic phospholipase A2 activity, AACOCF3, inhibits glucose-induced insulin secretion from isolated rat islets. Biochem Biophys Res Commun. 1996 Jan 17;218(2):423-7. doi: 10.1006/bbrc.1996.0075. PMID: 8561771. 2. Riendeau D, Guay J, Weech PK, Laliberté F, Yergey J, Li C, Desmarais S, Perrier H, Liu S, Nicoll-Griffith D, et al. Arachidonyl trifluoromethyl ketone, a potent inhibitor of 85-kDa phospholipase A2, blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. J Biol Chem. 1994 Jun 3;269(22):15619-24. PMID: 8195210. 3. Schanstra JP, Luong TT, Makridakis M, Van Linthout S, Lygirou V, Latosinska A, Alesutan I, Boehme B, Schelski N, Von Lewinski D, Mullen W, Nicklin S, Delles C, Feuillet G, Denis C, Lang F, Pieske B, Bascands JL, Mischak H, Saulnier-Blache JS, Voelkl J, Vlahou A, Klein J. Systems biology identifies cytosolic PLA2 as a target in vascular calcification treatment. JCI Insight. 2019 May 16;4(10):e125638. doi: 10.1172/jci.insight.125638. PMID: 31092728; PMCID: PMC6542631.

In vitro protocol:

In vivo protocol:

1. Schanstra JP, Luong TT, Makridakis M, Van Linthout S, Lygirou V, Latosinska A, Alesutan I, Boehme B, Schelski N, Von Lewinski D, Mullen W, Nicklin S, Delles C, Feuillet G, Denis C, Lang F, Pieske B, Bascands JL, Mischak H, Saulnier-Blache JS, Voelkl J, Vlahou A, Klein J. Systems biology identifies cytosolic PLA2 as a target in vascular calcification treatment. JCI Insight. 2019 May 16;4(10):e125638. doi: 10.1172/jci.insight.125638. PMID: 31092728; PMCID: PMC6542631.

1: Zhou X, Ling Y, Cui J, Wang X, Long N, Teng W, Liu J, Xiang X, Yang H, Chu L. Mitochondrial RNA modification-based signature to predict prognosis of lower grade glioma: a multi-omics exploration and verification study. Sci Rep. 2024 Jun 1;14(1):12602. doi: 10.1038/s41598-024-63592-w. PMID: 38824202; PMCID: PMC11144219. 2: Huang Y, Wang S, Zhang X, Yang C, Wang S, Cheng H, Ke A, Gao C, Guo K. Identification of Fasudil as a collaborator to promote the anti-tumor effect of lenvatinib in hepatocellular carcinoma by inhibiting GLI2-mediated hedgehog signaling pathway. Pharmacol Res. 2024 Feb;200:107082. doi: 10.1016/j.phrs.2024.107082. Epub 2024 Jan 26. PMID: 38280440. 3: Yan WH, Tan MS, Huang C, Ma NS, Tang XS. [Neuroprotective effect and mechanism of cPLA2 inhibitor increases autophagic flux on spinal cord injury]. Zhongguo Gu Shang. 2023 Sep 25;36(9):873-9. Chinese. doi: 10.12200/j.issn.1003-0034.2023.09.015. PMID: 37735081. 4: Yao HH, Min YJ, Hong DY, Wang L, Lu XY, Yang YH. [Electroacupuncture improves limb motor function by down-regulating cytosolic phospholi-pase A2 and reducing apoptosis of nerve cells in rats with spinal cord injury]. Zhen Ci Yan Jiu. 2023 Aug 25;48(8):782-90. Chinese. doi: 10.13702/j.1000-0607.20220513. PMID: 37614136. 5: Wang M, Xiong D, Wang X, Gu D, Meng C, Jiao X, Pan Z. The DNA adenine methylase of Salmonella Enteritidis promotes their intracellular replication by inhibiting arachidonic acid metabolism pathway in macrophages. Front Microbiol. 2023 Mar 2;14:1080851. doi: 10.3389/fmicb.2023.1080851. PMID: 36937256; PMCID: PMC10018194. 6: Lai Y, Lin H, Chen M, Lin X, Wu L, Zhao Y, Lin F, Lin C. Integration of bulk RNA sequencing and single-cell analysis reveals a global landscape of DNA damage response in the immune environment of Alzheimer's disease. Front Immunol. 2023 Feb 21;14:1115202. doi: 10.3389/fimmu.2023.1115202. PMID: 36895559; PMCID: PMC9989175. 7: Lai Y, Lin P, Lin F, Chen M, Lin C, Lin X, Wu L, Zheng M, Chen J. Identification of immune microenvironment subtypes and signature genes for Alzheimer's disease diagnosis and risk prediction based on explainable machine learning. Front Immunol. 2022 Dec 8;13:1046410. doi: 10.3389/fimmu.2022.1046410. PMID: 36569892; PMCID: PMC9773397. 8: Yang S, Zhao J, Cui X, Zhan Q, Yi K, Wang Q, Xiao M, Tan Y, Hong B, Fang C, Kang C. TCA-phospholipid-glycolysis targeted triple therapy effectively suppresses ATP production and tumor growth in glioblastoma. Theranostics. 2022 Oct 3;12(16):7032-7050. doi: 10.7150/thno.74197. PMID: 36276638; PMCID: PMC9576613. 9: Chen P, Liu H, Xin H, Cheng B, Sun C, Liu Y, Liu T, Wen Z, Cheng Y. Inhibiting the Cytosolic Phospholipase A2-Arachidonic Acid Pathway With Arachidonyl Trifluoromethyl Ketone Attenuates Radiation-Induced Lung Fibrosis. Int J Radiat Oncol Biol Phys. 2023 Feb 1;115(2):476-489. doi: 10.1016/j.ijrobp.2022.03.008. Epub 2022 Apr 19. PMID: 35450754. 10: Hassan JJ, Lieske A, Dörpmund N, Klatt D, Hoffmann D, Kleppa MJ, Kustikova OS, Stahlhut M, Schwarzer A, Schambach A, Maetzig T. A Multiplex CRISPR-Screen Identifies PLA2G4A as Prognostic Marker and Druggable Target for HOXA9 and MEIS1 Dependent AML. Int J Mol Sci. 2021 Aug 30;22(17):9411. doi: 10.3390/ijms22179411. PMID: 34502319; PMCID: PMC8431012. 11: Yang H, Sun W, Fan YN, Li SY, Yuan JQ, Zhang ZQ, Li XY, Lin MB, Hou Q. Perilla Leaf Extract Attenuates Asthma Airway Inflammation by Blocking the Syk Pathway. Mediators Inflamm. 2021 May 10;2021:6611219. doi: 10.1155/2021/6611219. PMID: 34045925; PMCID: PMC8128618. 12: Gwak YS, Chen G, Abdi S, Kim HK. Calcium-independent phospholipase A2 inhibitor produces an analgesic effect in a rat model of neuropathic pain by reducing central sensitization in the dorsal horn. Neurol Res. 2021 Aug;43(8):683-692. doi: 10.1080/01616412.2021.1915079. Epub 2021 Apr 18. PMID: 33866950. 13: Giurdanella G, Lupo G, Gennuso F, Conti F, Furno DL, Mannino G, Anfuso CD, Drago F, Salomone S, Bucolo C. Activation of the VEGF-A/ERK/PLA2 Axis Mediates Early Retinal Endothelial Cell Damage Induced by High Glucose: New Insight from an In Vitro Model of Diabetic Retinopathy. Int J Mol Sci. 2020 Oct 13;21(20):7528. doi: 10.3390/ijms21207528. PMID: 33065984; PMCID: PMC7589177. 14: Sarkar C, Jones JW, Hegdekar N, Thayer JA, Kumar A, Faden AI, Kane MA, Lipinski MM. PLA2G4A/cPLA2-mediated lysosomal membrane damage leads to inhibition of autophagy and neurodegeneration after brain trauma. Autophagy. 2020 Mar;16(3):466-485. doi: 10.1080/15548627.2019.1628538. Epub 2019 Jun 25. PMID: 31238788; PMCID: PMC6999646. 15: Schanstra JP, Luong TT, Makridakis M, Van Linthout S, Lygirou V, Latosinska A, Alesutan I, Boehme B, Schelski N, Von Lewinski D, Mullen W, Nicklin S, Delles C, Feuillet G, Denis C, Lang F, Pieske B, Bascands JL, Mischak H, Saulnier- Blache JS, Voelkl J, Vlahou A, Klein J. Systems biology identifies cytosolic PLA2 as a target in vascular calcification treatment. JCI Insight. 2019 May 16;4(10):e125638. doi: 10.1172/jci.insight.125638. PMID: 31092728; PMCID: PMC6542631. 16: Vandenberghe LTM, Heindryckx B, Smits K, Popovic M, Szymanska K, Bonte D, Peelman L, Deforce D, De Sutter P, Van Soom A, De Schauwer C. Intracellular localisation of platelet-activating factor during mammalian embryo development in vitro: a comparison of cattle, mouse and human. Reprod Fertil Dev. 2019 Apr;31(4):658-670. doi: 10.1071/RD18146. PMID: 30458920. 17: Zhang W, Wang X, Zhang L, Geng D, Wang Y, Sun D, Sui P, Zhao X, Xin C, Jiang J, Sui M. Inhibition of PLA2G4A Reduces the Expression of Lung Cancer-Related Cytokines. DNA Cell Biol. 2018 Oct 16. doi: 10.1089/dna.2018.4286. Epub ahead of print. PMID: 30328712. 18: Kumar S, Sharma SK, Kaushik G, Avti PK, Pandey SK, Sarma P, Medhi B, Khanduja KL. Therapeutic potential of arachidonyl trifluromethyl ketone, a cytosolic phospholipaseA2 IVA specific inhibitor, in cigarette smoke condensate-induced pathological conditions in alveolar type I & II epithelial cells. Toxicol In Vitro. 2019 Feb;54:215-223. doi: 10.1016/j.tiv.2018.09.013. Epub 2018 Sep 22. PMID: 30253184. 19: Zhang G, Gui S, Wang W, Meng D, Meng Q, Luan H, Zhao R, Zhang J, Sui H. Acute stimulatory effect of tumor necrosis factor on the basolateral 50 pS K channels in the thick ascending limb of the rat kidney. Mol Med Rep. 2018 Nov;18(5):4733-4738. doi: 10.3892/mmr.2018.9475. Epub 2018 Sep 10. PMID: 30221721. 20: Arthur S, Singh S, Sundaram U. Cyclooxygenase pathway mediates the inhibition of Na-glutamine co-transporter B0AT1 in rabbit villus cells during chronic intestinal inflammation. PLoS One. 2018 Sep 7;13(9):e0203552. doi: 10.1371/journal.pone.0203552. Erratum in: PLoS One. 2023 Nov 9;18(11):e0294387. doi: 10.1371/journal.pone.0294387. PMID: 30192835; PMCID: PMC6128596.