SKF86002 | CAS#72873-74-6 | p38 MAP kinase inhibitor

MedKoo Cat#: 530341 | Name: SKF86002

Description:

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

SKF86002 is a p38 MAP kinase inhibitor. SKF86002 inhibits IL-1 beta production by affecting at least two distinct steps in the biosynthesis of this cytokine.

Chemical Structure

SKF86002

CAS#72873-74-6

Theoretical Analysis

MedKoo Cat#: 530341

Name: SKF86002

CAS#: 72873-74-6

Chemical Formula: C16H12FN3S

Exact Mass: 297.0736

Molecular Weight: 297.35

Elemental Analysis: C, 64.63; H, 4.07; F, 6.39; N, 14.13; S, 10.78

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 650.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,850.00	2 Weeks
2g	USD 3,950.00	2 Weeks
5g	USD 6,950.00	2 Weeks

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Related CAS #

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Synonym

SKF-86002; SKF 86002; SKF86002.

IUPAC/Chemical Name

6-(4-Fluorophenyl)-5-(4-pyridyl)-2,3-dihydroimidazo[2,1-b]-thiazole

InChi Key

YOELZIQOLWZLQC-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H12FN3S/c17-13-3-1-11(2-4-13)14-15(12-5-7-18-8-6-12)20-9-10-21-16(20)19-14/h1-8H,9-10H2

SMILES Code

FC1=CC=C(C2=C(C3=CC=NC=C3)N4C(SCC4)=N2)C=C1

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SKF-86002 inhibits lipopolysaccharide (LPS)-stimulate human monocyte IL-1 and TNF-α production (IC50 = 1 μM). SKF-86002 inhibits lipoxygenase- and cyclooxygenase-mediated metabolism of arachidonic acid.

In vitro activity:

This study demonstrates that SKF86002 was a potent inhibitor of IL-1 production by LPS-stimulated human monocytes and inhibited cell-associated IL-1 activity. SKF86002 did not exert general inhibitory effects on such parameters as adherence, cytotoxic function and protein synthesis of the monocytes. The inhibition of IL-1 production by SKF86002 may be dissociated from its inhibition of fatty acid oxygenases. Reference: Int J Immunopharmacol. 1988;10(7):835-43. https://pubmed.ncbi.nlm.nih.gov/3148560/

In vivo activity:

SKF86002 restored neuronal p38γ MAPK and ameliorated synaptic degeneration in a mouse model of dementia with Lewy bodies/ Parkinson's disease. SKF86002 reduced neuroinflammation and ameliorated synaptic, neurodegenerative, and motor behavioral deficits in transgenic mice overexpressing human α-synuclein. SKF86002 promoted the redistribution of p38γ to synapses and reduced the accumulation of α-synuclein in mice overexpressing human α-synuclein. Reference: Sci Transl Med. 2023 May 10;15(695):eabq6089. https://pubmed.ncbi.nlm.nih.gov/37163617/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	33.3	112.09

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 297.35 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. Poulsen JN, Larsen F, Duroux M, Gazerani P. Primary culture of trigeminal satellite glial cells: a cell-based platform to study morphology and function of peripheral glia. Int J Physiol Pathophysiol Pharmacol. 2014 Mar 13;6(1):1-12. PMID: 24665354; PMCID: PMC3961097. 2. Lee JC, Griswold DE, Votta B, Hanna N. Inhibition of monocyte IL-1 production by the anti-inflammatory compound, SK&F 86002. Int J Immunopharmacol. 1988;10(7):835-43. doi: 10.1016/0192-0561(88)90007-0. PMID: 3148560. 3. Iba M, Kim C, Kwon S, Szabo M, Horan-Portelance L, Peer CJ, Figg WD, Reed X, Ding J, Lee SJ, Rissman RA, Cookson MR, Overk C, Wrasidlo W, Masliah E. Inhibition of p38α MAPK restores neuronal p38γ MAPK and ameliorates synaptic degeneration in a mouse model of DLB/PD. Sci Transl Med. 2023 May 10;15(695):eabq6089. doi: 10.1126/scitranslmed.abq6089. Epub 2023 May 10. PMID: 37163617. 4. Santén S, Mihaescu A, Laschke MW, Menger MD, Wang Y, Jeppsson B, Thorlacius H. p38 MAPK regulates ischemia-reperfusion-induced recruitment of leukocytes in the colon. Surgery. 2009 Mar;145(3):303-12. doi: 10.1016/j.surg.2008.10.011. Epub 2009 Feb 1. PMID: 19231583.

In vitro protocol:

In vivo protocol:

1. Iba M, Kim C, Kwon S, Szabo M, Horan-Portelance L, Peer CJ, Figg WD, Reed X, Ding J, Lee SJ, Rissman RA, Cookson MR, Overk C, Wrasidlo W, Masliah E. Inhibition of p38α MAPK restores neuronal p38γ MAPK and ameliorates synaptic degeneration in a mouse model of DLB/PD. Sci Transl Med. 2023 May 10;15(695):eabq6089. doi: 10.1126/scitranslmed.abq6089. Epub 2023 May 10. PMID: 37163617. 2. Santén S, Mihaescu A, Laschke MW, Menger MD, Wang Y, Jeppsson B, Thorlacius H. p38 MAPK regulates ischemia-reperfusion-induced recruitment of leukocytes in the colon. Surgery. 2009 Mar;145(3):303-12. doi: 10.1016/j.surg.2008.10.011. Epub 2009 Feb 1. PMID: 19231583.

1: Chen W, Wu Z, Yin M, Zhang Y, Qin Y, Liu X, Tu J. Blockage of p38MAPK in astrocytes alleviates brain damage in a mouse model of embolic stroke through the CX43/AQP4 axis. J Stroke Cerebrovasc Dis. 2024 Oct 10;33(12):108085. doi: 10.1016/j.jstrokecerebrovasdis.2024.108085. Epub ahead of print. PMID: 39393507. 2: Ye Q, Zhao Y, Zhao J, Ouyang Z, Feng Y, Hu J, Su X, Chen N, Chen Y, Tan L, Feng Y, Guo Y. Prevotella, a dominant bacterium in young people with stage Ⅲ periodontitis, related to the arachidonic acid metabolism pathway. Microbes Infect. 2024 May-Jun;26(4):105316. doi: 10.1016/j.micinf.2024.105316. Epub 2024 Feb 27. PMID: 38423169. 3: Iba M, Kim C, Kwon S, Szabo M, Horan-Portelance L, Peer CJ, Figg WD, Reed X, Ding J, Lee SJ, Rissman RA, Cookson MR, Overk C, Wrasidlo W, Masliah E. Inhibition of p38α MAPK restores neuronal p38γ MAPK and ameliorates synaptic degeneration in a mouse model of DLB/PD. Sci Transl Med. 2023 May 10;15(695):eabq6089. doi: 10.1126/scitranslmed.abq6089. Epub 2023 May 10. PMID: 37163617. 4: Uwada J, Nakazawa H, Mikami D, Islam MS, Muramatsu I, Taniguchi T, Yazawa T. PNU-120596, a positive allosteric modulator of α7 nicotinic acetylcholine receptor, directly inhibits p38 MAPK. Biochem Pharmacol. 2020 Dec;182:114297. doi: 10.1016/j.bcp.2020.114297. Epub 2020 Oct 22. PMID: 33132165. 5: Kitanaka N, Nakano R, Sugiura K, Kitanaka T, Namba S, Konno T, Nakayama T, Sugiya H. Interleukin-1β promotes interleulin-6 expression via ERK1/2 signaling pathway in canine dermal fibroblasts. PLoS One. 2019 Jul 25;14(7):e0220262. doi: 10.1371/journal.pone.0220262. PMID: 31344106; PMCID: PMC6658082. 6: Khattab M, Van Dongen M, Wang F, Clayton AH. Solvatochromism and linear solvation energy relationship of the kinase inhibitor SKF86002. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Jan 5;170:226-33. doi: 10.1016/j.saa.2016.07.027. Epub 2016 Jul 17. PMID: 27450120. 7: Dai HL, Hu WY, Jiang LH, Li L, Gaung XF, Xiao ZC. p38 MAPK Inhibition Improves Synaptic Plasticity and Memory in Angiotensin II-dependent Hypertensive Mice. Sci Rep. 2016 Jun 10;6:27600. doi: 10.1038/srep27600. PMID: 27283322; PMCID: PMC4901328. 8: Mizukoshi Y, Takeuchi K, Arutaki M, Takizawa T, Hanzawa H, Takahashi H, Shimada I. Suppression of problematic compound oligomerization by cosolubilization of nondetergent sulfobetaines. ChemMedChem. 2015 Apr;10(4):736-41. doi: 10.1002/cmdc.201500057. Epub 2015 Mar 11. PMID: 25760302; PMCID: PMC4471626. 9: Poulsen JN, Larsen F, Duroux M, Gazerani P. Primary culture of trigeminal satellite glial cells: a cell-based platform to study morphology and function of peripheral glia. Int J Physiol Pathophysiol Pharmacol. 2014 Mar 13;6(1):1-12. PMID: 24665354; PMCID: PMC3961097. 10: Parker LJ, Taruya S, Tsuganezawa K, Ogawa N, Mikuni J, Honda K, Tomabechi Y, Handa N, Shirouzu M, Yokoyama S, Tanaka A. Kinase crystal identification and ATP-competitive inhibitor screening using the fluorescent ligand SKF86002. Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):392-404. doi: 10.1107/S1399004713028654. Epub 2014 Jan 29. PMID: 24531473. 11: Yokoyama K, Hiyama A, Arai F, Nukaga T, Sakai D, Mochida J. C-Fos regulation by the MAPK and PKC pathways in intervertebral disc cells. PLoS One. 2013 Sep 2;8(9):e73210. doi: 10.1371/journal.pone.0073210. PMID: 24023832; PMCID: PMC3759433. 12: Falck D, de Vlieger JS, Giera M, Honing M, Irth H, Niessen WM, Kool J. On- line electrochemistry-bioaffinity screening with parallel HR-LC-MS for the generation and characterization of modified p38α kinase inhibitors. Anal Bioanal Chem. 2012 Apr;403(2):367-75. doi: 10.1007/s00216-011-5663-2. Epub 2012 Jan 8. PMID: 22227812; PMCID: PMC3314180. 13: Oh PS, Lim KT. Anti-inflammatory effect of glycoprotein isolated from Cudrania tricuspidata Bureau: involvement of MAPK/NF-κB signaling. Immunol Invest. 2011;40(1):76-91. doi: 10.3109/08820139.2010.516049. Epub 2010 Oct 5. PMID: 20923328. 14: Oh PS, Lim KT. IgE, COX-2, and IL-4 are expressed by DEHP through p38 MAPK and suppressed by plant glycoprotein (75 kDa) in ICR mice. Inflammation. 2011 Oct;34(5):326-34. doi: 10.1007/s10753-010-9238-8. PMID: 20686831. 15: Yoo BK, Choi JW, Shin CY, Jeon SJ, Park SJ, Cheong JH, Han SY, Ryu JR, Song MR, Ko KH. Activation of p38 MAPK induced peroxynitrite generation in LPS plus IFN-gamma-stimulated rat primary astrocytes via activation of iNOS and NADPH oxidase. Neurochem Int. 2008 May;52(6):1188-97. doi: 10.1016/j.neuint.2007.12.009. Epub 2007 Dec 27. PMID: 18289732. 16: Lee SJ, Lim KT. Phytoglycoprotein inhibits interleukin-1beta and interleukin-6 via p38 mitogen-activated protein kinase in lipopolysaccharide- stimulated RAW 264.7 cells. Naunyn Schmiedebergs Arch Pharmacol. 2008 Mar;377(1):45-54. doi: 10.1007/s00210-007-0253-8. Epub 2008 Jan 18. PMID: 18204996. 17: Gomez-Lazaro M, Galindo MF, Concannon CG, Segura MF, Fernandez-Gomez FJ, Llecha N, Comella JX, Prehn JH, Jordan J. 6-Hydroxydopamine activates the mitochondrial apoptosis pathway through p38 MAPK-mediated, p53-independent activation of Bax and PUMA. J Neurochem. 2008 Mar;104(6):1599-612. doi: 10.1111/j.1471-4159.2007.05115.x. Epub 2007 Nov 6. PMID: 17996028. 18: Gomez-Lazaro M, Galindo MF, Melero-Fernandez de Mera RM, Fernandez-Gómez FJ, Concannon CG, Segura MF, Comella JX, Prehn JH, Jordan J. Reactive oxygen species and p38 mitogen-activated protein kinase activate Bax to induce mitochondrial cytochrome c release and apoptosis in response to malonate. Mol Pharmacol. 2007 Mar;71(3):736-43. doi: 10.1124/mol.106.030718. Epub 2006 Dec 15. PMID: 17172466. 19: Tu Y, Perdue MH. CD23-mediated transport of IgE/immune complexes across human intestinal epithelium: role of p38 MAPK. Am J Physiol Gastrointest Liver Physiol. 2006 Sep;291(3):G532-8. doi: 10.1152/ajpgi.00524.2005. PMID: 16899715. 20: Ateghang B, Wartenberg M, Gassmann M, Sauer H. Regulation of cardiotrophin-1 expression in mouse embryonic stem cells by HIF-1alpha and intracellular reactive oxygen species. J Cell Sci. 2006 Mar 15;119(Pt 6):1043-52. doi: 10.1242/jcs.02798. Epub 2006 Feb 28. PMID: 16507596.