SB-328437 | CAS#247580-43-4 | CCR3 antagonist

MedKoo Cat#: 532664 | Name: SB-328437

Description:

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

SB-328437 is a potent and selective CCR3 antagonist (IC50 = 1.6 nM). SB-328437 blocks CCR3 agonist-induced calcium mobilization in CCR3 expressing cells with the following IC50 values: eotaxin, 38 nM; eotaxin-2, 35 nM and MCP4, 20 nM.

Chemical Structure

SB-328437

CAS#247580-43-4

Theoretical Analysis

MedKoo Cat#: 532664

Name: SB-328437

CAS#: 247580-43-4

Chemical Formula: C21H18N2O5

Exact Mass: 378.1216

Molecular Weight: 378.38

Elemental Analysis: C, 66.66; H, 4.80; N, 7.40; O, 21.14

Price and Availability

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

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Related CAS #

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Synonym

SB328437; SB 328437; SB-328437

IUPAC/Chemical Name

methyl (2S)-2-(naphthalene-2-carbonylamino)-3-(4-nitrophenyl)propanoate

InChi Key

KOLBWAVLYDRUOC-IBGZPJMESA-N

InChi Code

InChI=1S/C21H18N2O5/c1-28-21(25)19(12-14-6-10-18(11-7-14)23(26)27)22-20(24)17-9-8-15-4-2-3-5-16(15)13-17/h2-11,13,19H,12H2,1H3,(H,22,24)/t19-/m0/s1

SMILES Code

O=C(OC)[C@@H](NC(C1=CC=C2C=CC=CC2=C1)=O)CC3=CC=C([N+]([O-])=O)C=C3

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:

SB-328437 is a non-peptide CCR3 antagonist with an IC50 of 4.5 nM.

In vitro activity:

SB-328437 and its precursor SB-297006 exhibited high affinity and competitive inhibition of specific chemokine binding to human eosinophils. These compounds effectively blocked Ca(2+) mobilization and chemotaxis induced by various CCR3-activating ligands, demonstrating selectivity for CCR3 over other receptors. Reference: J Biol Chem. 2000 Nov 24;275(47):36626-31. https://pubmed.ncbi.nlm.nih.gov/10969084/

In vivo activity:

In a murine model, SB-328437 diminished neutrophil recruitment in alveolar airspaces and improved LPS-induced acute lung injury and production of IL-8 in bronchoalveolar lavage fluid. Reference: J Cell Physiol. 2011 Sep;226(9):2398-405. https://pubmed.ncbi.nlm.nih.gov/21660963/

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	330.36

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 378.38 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. White JR, Lee JM, Dede K, Imburgia CS, Jurewicz AJ, Chan G, Fornwald JA, Dhanak D, Christmann LT, Darcy MG, Widdowson KL, Foley JJ, Schmidt DB, Sarau HM. Identification of potent, selective non-peptide CC chemokine receptor-3 antagonist that inhibits eotaxin-, eotaxin-2-, and monocyte chemotactic protein-4-induced eosinophil migration. J Biol Chem. 2000 Nov 24;275(47):36626-31. doi: 10.1074/jbc.M006613200. PMID: 10969084. 2. Abonyo BO, Alexander MS, Heiman AS. Autoregulation of CCL26 synthesis and secretion in A549 cells: a possible mechanism by which alveolar epithelial cells modulate airway inflammation. Am J Physiol Lung Cell Mol Physiol. 2005 Sep;289(3):L478-88. doi: 10.1152/ajplung.00032.2005. Epub 2005 Apr 29. PMID: 15863444. 3. Li B, Dong C, Wang G, Zheng H, Wang X, Bai C. Pulmonary epithelial CCR3 promotes LPS-induced lung inflammation by mediating release of IL-8. J Cell Physiol. 2011 Sep;226(9):2398-405. doi: 10.1002/jcp.22577. PMID: 21660963. 4. Li Y, Huang D, Xia X, Wang Z, Luo L, Wen R. CCR3 and choroidal neovascularization. PLoS One. 2011 Feb 15;6(2):e17106. doi: 10.1371/journal.pone.0017106. PMID: 21358803; PMCID: PMC3039674.

In vitro protocol:

In vivo protocol:

1. Li B, Dong C, Wang G, Zheng H, Wang X, Bai C. Pulmonary epithelial CCR3 promotes LPS-induced lung inflammation by mediating release of IL-8. J Cell Physiol. 2011 Sep;226(9):2398-405. doi: 10.1002/jcp.22577. PMID: 21660963. 2. Li Y, Huang D, Xia X, Wang Z, Luo L, Wen R. CCR3 and choroidal neovascularization. PLoS One. 2011 Feb 15;6(2):e17106. doi: 10.1371/journal.pone.0017106. PMID: 21358803; PMCID: PMC3039674.

1: Lopez-Leal F, Cabellos-Avelar T, Correa-Becerril DA, Juarez-Macias B, Cervantes-Diaz R, Reyes-Huerta RF, Juarez-Vega G, Gutierrez-Castaneda D, Castro- Jimenez TK, Bustos-Arriaga J, Maravillas-Montero JL, Perez-Lopez A. Blockade of the CCR3 receptor reduces neutrophil recruitment to the lung during acute inflammation. J Leukoc Biol. 2024 Sep 19:qiae203. doi: 10.1093/jleuko/qiae203. Epub ahead of print. PMID: 39298674. 2: Gutiérrez Á, Reyes ME, Larronde C, Brebi P, Mora-Lagos B. Targeting CCR3 with antagonist SB 328437 sensitizes 5‑fluorouracil‑resistant gastric cancer cells: Experimental evidence and computational insights. Oncol Lett. 2024 May 1;28(1):296. doi: 10.3892/ol.2024.14429. PMID: 38737977; PMCID: PMC11082837. 3: Araújo JMD, Silva LAS, Felix FB, Camargo EA, Grespan R. CCR3 antagonist impairs estradiol-induced eosinophil migration to the uterus in ovariectomized mice. Braz J Med Biol Res. 2019 Dec 20;53(1):e8659. doi: 10.1590/1414-431X20198659. PMID: 31859912; PMCID: PMC6915905. 4: Filippone RT, Robinson AM, Jovanovska V, Stavely R, Apostolopoulos V, Bornstein JC, Nurgali K. Targeting eotaxin-1 and CCR3 receptor alleviates enteric neuropathy and colonic dysfunction in TNBS-induced colitis in guinea pigs. Neurogastroenterol Motil. 2018 Nov;30(11):e13391. doi: 10.1111/nmo.13391. Epub 2018 Jul 3. PMID: 29968270. 5: Kuse Y, Tsuruma K, Kanno Y, Shimazawa M, Hara H. CCR3 Is Associated with the Death of a Photoreceptor Cell-line Induced by Light Exposure. Front Pharmacol. 2017 Apr 18;8:207. doi: 10.3389/fphar.2017.00207. PMID: 28458639; PMCID: PMC5394117. 6: Xing Y, Tian Y, Kurosawa T, Matsui S, Touma M, Yanai T, Wu Q, Sugimoto K. CCL11-induced eosinophils inhibit the formation of blood vessels and cause tumor necrosis. Genes Cells. 2016 Jun;21(6):624-38. doi: 10.1111/gtc.12371. Epub 2016 May 12. PMID: 27169545. 7: Provost V, Larose MC, Langlois A, Rola-Pleszczynski M, Flamand N, Laviolette M. CCL26/eotaxin-3 is more effective to induce the migration of eosinophils of asthmatics than CCL11/eotaxin-1 and CCL24/eotaxin-2. J Leukoc Biol. 2013 Aug;94(2):213-22. doi: 10.1189/jlb.0212074. Epub 2013 Mar 26. PMID: 23532518. 8: Zhou WJ, Liu GQ, Li LB, Zhang XG, Lu PR. Inhibitory effect of CCR3 signal on alkali-induced corneal neovascularization. Int J Ophthalmol. 2012;5(3):251-7. doi: 10.3980/j.issn.2222-3959.2012.03.01. Epub 2012 Jun 18. PMID: 22773968; PMCID: PMC3388388. 9: Dürr C, Follo M, Idzko M, Reichardt W, Zeiser R. Graft-versus-host disease reduces regulatory T-cell migration into the tumour tissue. Immunology. 2012 Sep;137(1):80-8. doi: 10.1111/j.1365-2567.2012.03610.x. PMID: 22681312; PMCID: PMC3449249. 10: Di Prisco S, Summa M, Chellakudam V, Rossi PI, Pittaluga A. RANTES-mediated control of excitatory amino acid release in mouse spinal cord. J Neurochem. 2012 May;121(3):428-37. doi: 10.1111/j.1471-4159.2012.07720.x. Epub 2012 Mar 21. PMID: 22385043. 11: Li Y, Huang D, Xia X, Wang Z, Luo L, Wen R. What is the role of CCR3 in choroidal neovascularization? Adv Exp Med Biol. 2012;723:279-84. doi: 10.1007/978-1-4614-0631-0_36. PMID: 22183343. 12: Li B, Dong C, Wang G, Zheng H, Wang X, Bai C. Pulmonary epithelial CCR3 promotes LPS-induced lung inflammation by mediating release of IL-8. J Cell Physiol. 2011 Sep;226(9):2398-405. doi: 10.1002/jcp.22577. PMID: 21660963. 13: Li Y, Huang D, Xia X, Wang Z, Luo L, Wen R. CCR3 and choroidal neovascularization. PLoS One. 2011 Feb 15;6(2):e17106. doi: 10.1371/journal.pone.0017106. PMID: 21358803; PMCID: PMC3039674. 14: Mori A, Ogawa K, Someya K, Kunori Y, Nagakubo D, Yoshie O, Kitamura F, Hiroi T, Kaminuma O. Selective suppression of Th2-mediated airway eosinophil infiltration by low-molecular weight CCR3 antagonists. Int Immunol. 2007 Aug;19(8):913-21. doi: 10.1093/intimm/dxm049. PMID: 17804691. 15: Abonyo BO, Alexander MS, Heiman AS. Autoregulation of CCL26 synthesis and secretion in A549 cells: a possible mechanism by which alveolar epithelial cells modulate airway inflammation. Am J Physiol Lung Cell Mol Physiol. 2005 Sep;289(3):L478-88. doi: 10.1152/ajplung.00032.2005. Epub 2005 Apr 29. PMID: 15863444. 16: White JR, Lee JM, Dede K, Imburgia CS, Jurewicz AJ, Chan G, Fornwald JA, Dhanak D, Christmann LT, Darcy MG, Widdowson KL, Foley JJ, Schmidt DB, Sarau HM. Identification of potent, selective non-peptide CC chemokine receptor-3 antagonist that inhibits eotaxin-, eotaxin-2-, and monocyte chemotactic protein-4-induced eosinophil migration. J Biol Chem. 2000 Nov 24;275(47):36626-31. doi: 10.1074/jbc.M006613200. PMID: 10969084.