Palmostatin B | CAS#1233365-12-2 | Ras-signaling modulator

MedKoo Cat#: 562905 | Name: Palmostatin B

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Description:

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

Palmostatin B is a Ras-signaling modulator and PPT1 inhibitor. It acts by targeting acyl protein thioesterase 1 (APT1) and 2 (APT2) in cells.

Chemical Structure

Palmostatin B

CAS#1233365-12-2

Theoretical Analysis

MedKoo Cat#: 562905

Name: Palmostatin B

CAS#: 1233365-12-2

Chemical Formula: C23H36O4

Exact Mass: 376.2614

Molecular Weight: 376.54

Elemental Analysis: C, 73.37; H, 9.64; O, 17.00

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 650.00	2 Weeks

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Synonym

Palmostatin B; Palmostatin-B;

IUPAC/Chemical Name

(3S,4S)-3-Decyl-4-[2-(3,4-dimethoxyphenyl)ethyl]oxetan-2-one

InChi Key

ASVWFAVGLYUDFD-PMACEKPBSA-N

InChi Code

InChI=1S/C23H36O4/c1-4-5-6-7-8-9-10-11-12-19-20(27-23(19)24)15-13-18-14-16-21(25-2)22(17-18)26-3/h14,16-17,19-20H,4-13,15H2,1-3H3/t19-,20-/m0/s1

SMILES Code

O=C1O[C@@H](CCC2=CC=C(OC)C(OC)=C2)[C@@H]1CCCCCCCCCC

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

>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).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Palmostatin B is a Ras-signaling modulator.

In vitro activity:

In contrast to ML348 and ML349, palmostatin B led to a dose dependent cell viability decrease in most NRAS mutant cell lines, while no significant cell viability decrease was observed in the BRAF mutant cell line SK-MEL-28 (Figure 4). The GI50 values (concentrations of drugs resulting in 50% decrease in cell viability relative to DMSO treated controls) ranged from 9.93 μM for the cell line WM3670 to >100 μM for MM415 and the BRAF mutant SK-MEL-28 (Supplementary Table S1). Reference: Oncotarget. 2016 Feb 9;7(6):7297-306. https://pubmed.ncbi.nlm.nih.gov/26771141/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 376.54 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. Vujic I, Sanlorenzo M, Esteve-Puig R, Vujic M, Kwong A, Tsumura A, Murphy R, Moy A, Posch C, Monshi B, Rappersberger K, Ortiz-Urda S. Acyl protein thioesterase 1 and 2 (APT-1, APT-2) inhibitors palmostatin B, ML348 and ML349 have different effects on NRAS mutant melanoma cells. Oncotarget. 2016 Feb 9;7(6):7297-306. doi: 10.18632/oncotarget.6907. PMID: 26771141; PMCID: PMC4872786. 2. Dekker FJ, Hedberg C. Small molecule inhibition of protein depalmitoylation as a new approach towards downregulation of oncogenic Ras signalling. Bioorg Med Chem. 2011 Feb 15;19(4):1376-80. doi: 10.1016/j.bmc.2010.11.025. Epub 2010 Nov 11. PMID: 21129981.

In vitro protocol:

In vivo protocol:

TBD

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Glutathione-dependent depalmitoylation of phospholemman by peroxiredoxin 6. Cell Rep. 2024 Feb 27;43(2):113679. doi: 10.1016/j.celrep.2024.113679. Epub 2024 Jan 17. PMID: 38236777. 5: Liu Y, Zhang H, Liu Y, Zhang S, Su P, Wang L, Li Y, Liang Y, Wang X, Zhao W, Chen B, Luo D, Zhang N, Yang Q. Hypoxia-induced GPCPD1 depalmitoylation triggers mitophagy via regulating PRKN-mediated ubiquitination of VDAC1. Autophagy. 2023 Sep;19(9):2443-2463. doi: 10.1080/15548627.2023.2182482. Epub 2023 Mar 1. PMID: 36803235; PMCID: PMC10392732. 6: Brown RWB, Sharma AI, Villanueva MR, Li X, Onguka O, Zilbermintz L, Nguyen H, Falk BA, Olson CL, Taylor JM, Epting CL, Kathayat RS, Amara N, Dickinson BC, Bogyo M, Engman DM. Trypanosoma brucei Acyl-Protein Thioesterase-like (TbAPT-L) Is a Lipase with Esterase Activity for Short and Medium-Chain Fatty Acids but Has No Depalmitoylation Activity. Pathogens. 2022 Oct 27;11(11):1245. doi: 10.3390/pathogens11111245. PMID: 36364996; PMCID: PMC9693859. 7: Song J, Gao T, Li W, Yuan C, Hao J, Xia X. The Palmitoylation/Depalmitoylation Cycle is Involved in the Inhibition of AMPA Receptor Trafficking Induced by Aluminum In Vitro. Biol Trace Elem Res. 2023 Mar;201(3):1398-1406. doi: 10.1007/s12011-022-03234-2. Epub 2022 Apr 13. PMID: 35415819. 8: Dore K, Carrico Z, Alfonso S, Marino M, Koymans K, Kessels HW, Malinow R. PSD-95 protects synapses from β-amyloid. Cell Rep. 2021 Jun 1;35(9):109194. doi: 10.1016/j.celrep.2021.109194. PMID: 34077732; PMCID: PMC8237704. 9: Turcotte C, Dumais É, Archambault AS, Martin C, Blanchet MR, Bissonnette É, Boulet LP, Laviolette M, Di Marzo V, Flamand N. Human leukocytes differentially express endocannabinoid-glycerol lipases and hydrolyze 2-arachidonoyl-glycerol and its metabolites from the 15-lipoxygenase and cyclooxygenase pathways. J Leukoc Biol. 2019 Dec;106(6):1337-1347. doi: 10.1002/JLB.3A0919-049RRR. Epub 2019 Sep 26. PMID: 31556464. 10: Zhang J, Huang Y, Chen J, Zhu H, Whiteheart SW. Dynamic cycling of t-SNARE acylation regulates platelet exocytosis. J Biol Chem. 2018 Mar 9;293(10):3593-3606. doi: 10.1074/jbc.RA117.000140. Epub 2018 Jan 19. PMID: 29352103; PMCID: PMC5846156. 11: Qiu T, Kathayat RS, Cao Y, Beck MW, Dickinson BC. A Fluorescent Probe with Improved Water Solubility Permits the Analysis of Protein S-Depalmitoylation Activity in Live Cells. Biochemistry. 2018 Jan 16;57(2):221-225. doi: 10.1021/acs.biochem.7b00835. Epub 2017 Oct 18. PMID: 29023093; PMCID: PMC5823605. 12: Lin DTS, Davis NG, Conibear E. Targeting the Ras palmitoylation/depalmitoylation cycle in cancer. Biochem Soc Trans. 2017 Aug 15;45(4):913-921. doi: 10.1042/BST20160303. Epub 2017 Jun 19. PMID: 28630138. 13: Turcotte C, Zarini S, Jean S, Martin C, Murphy RC, Marsolais D, Laviolette M, Blanchet MR, Flamand N. The Endocannabinoid Metabolite Prostaglandin E2 (PGE2)-Glycerol Inhibits Human Neutrophil Functions: Involvement of Its Hydrolysis into PGE2 and EP Receptors. J Immunol. 2017 Apr 15;198(8):3255-3263. doi: 10.4049/jimmunol.1601767. Epub 2017 Mar 3. PMID: 28258202. 14: Vujic I, Sanlorenzo M, Esteve-Puig R, Vujic M, Kwong A, Tsumura A, Murphy R, Moy A, Posch C, Monshi B, Rappersberger K, Ortiz-Urda S. Acyl protein thioesterase 1 and 2 (APT-1, APT-2) inhibitors palmostatin B, ML348 and ML349 have different effects on NRAS mutant melanoma cells. Oncotarget. 2016 Feb 9;7(6):7297-306. doi: 10.18632/oncotarget.6907. PMID: 26771141; PMCID: PMC4872786. 15: Lin DT, Conibear E. ABHD17 proteins are novel protein depalmitoylases that regulate N-Ras palmitate turnover and subcellular localization. Elife. 2015 Dec 23;4:e11306. doi: 10.7554/eLife.11306. PMID: 26701913; PMCID: PMC4755737. 16: Klaus C, Schneider U, Hedberg C, Schütz AK, Bernhagen J, Waldmann H, Gassler N, Kaemmerer E. Modulating effects of acyl-CoA synthetase 5-derived mitochondrial Wnt2B palmitoylation on intestinal Wnt activity. World J Gastroenterol. 2014 Oct 28;20(40):14855-64. doi: 10.3748/wjg.v20.i40.14855. PMID: 25356045; PMCID: PMC4209548. 17: Savinainen JR, Patel JZ, Parkkari T, Navia-Paldanius D, Marjamaa JJ, Laitinen T, Nevalainen T, Laitinen JT. Biochemical and pharmacological characterization of the human lymphocyte antigen B-associated transcript 5 (BAT5/ABHD16A). PLoS One. 2014 Oct 7;9(10):e109869. doi: 10.1371/journal.pone.0109869. PMID: 25290914; PMCID: PMC4188605. 18: Milde S, Coleman MP. Identification of palmitoyltransferase and thioesterase enzymes that control the subcellular localization of axon survival factor nicotinamide mononucleotide adenylyltransferase 2 (NMNAT2). J Biol Chem. 2014 Nov 21;289(47):32858-70. doi: 10.1074/jbc.M114.582338. Epub 2014 Sep 30. PMID: 25271157; PMCID: PMC4239634. 19: Wang CH, Shyu RY, Wu CC, Tsai TC, Wang LK, Chen ML, Jiang SY, Tsai FM. Phospholipase A/Acyltransferase enzyme activity of H-rev107 inhibits the H-RAS signaling pathway. J Biomed Sci. 2014 May 1;21(1):36. doi: 10.1186/1423-0127-21-36. PMID: 24884338; PMCID: PMC4012743. 20: Koyama K, Ogura Y, Nakai D, Watanabe M, Munemasa T, Oofune Y, Kubota K, Shinagawa A, Izumi T. Identification of bioactivating enzymes involved in the hydrolysis of laninamivir octanoate, a long-acting neuraminidase inhibitor, in human pulmonary tissue. Drug Metab Dispos. 2014 Jun;42(6):1031-8. doi: 10.1124/dmd.114.057620. Epub 2014 Mar 28. PMID: 24682756.