SB-297006 | CAS#58816-69-6 | CCR3 antagonist

MedKoo Cat#: 555605 | Name: SB-297006

Description:

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

SB-297006 is an antagonist of C-C chemokine receptor 3 (CCR3; IC50 = 39 nM).

Chemical Structure

SB-297006

CAS#58816-69-6

Theoretical Analysis

MedKoo Cat#: 555605

Name: SB-297006

CAS#: 58816-69-6

Chemical Formula: C18H18N2O5

Exact Mass: 342.1216

Molecular Weight: 342.35

Elemental Analysis: C, 63.15; H, 5.30; N, 8.18; O, 23.37

Price and Availability

Size	Price	Availability
100mg	USD 450.00	2 Weeks
200mg	USD 750.00	2 Weeks
500mg	USD 1,450.00	2 Weeks
1g	USD 2,150.00	2 Weeks
2g	USD 3,950.00	2 Weeks
5g	USD 5,650.00	2 Weeks

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Related CAS #

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Synonym

SB-297006; SB 297006; SB297006;

IUPAC/Chemical Name

N-benzoyl-4-nitro-L-phenylalanine, ethyl ester

InChi Key

BEZXGSZPWXRHIN-INIZCTEOSA-N

InChi Code

InChI=1S/C18H18N2O5/c1-2-25-18(22)16(19-17(21)14-6-4-3-5-7-14)12-13-8-10-15(11-9-13)20(23)24/h3-11,16H,2,12H2,1H3,(H,19,21)/t16-/m0/s1

SMILES Code

O=C(OCC)[C@H](CC1=CC=C([N+]([O-])=O)C=C1)NC(C2=CC=CC=C2)=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:

SB-297006 is a potent and selective CCR3 antagonist (IC50 = 39 nM). SB-297006 displays 250-fold selectivity for CCR3 over other chemokine receptors, including CXCR1, CXCR2, CCR1 and CCR7 (IC50 >27 μM). It inhibits calcium mobilization induced by MCP-4, eotaxin-2 and eotaxin in RBL-2H3 cells transfected with CCR3 (IC50 values are 80, 90 and 210 nM respectively).

In vitro activity:

SB-297006 effectively inhibited the migration and proliferation of 4T1 mammary tumor cells induced by recCCL11, indicating its potential as a modulator of CCL11-CCR3 signaling. SB-297006 has potential for mitigating allergic inflammation-triggered metastasis, particularly in the context of breast cancer dissemination to the lungs. Reference: Respir Res. 2021 Feb 19;22(1):61. https://pubmed.ncbi.nlm.nih.gov/33608009/

In vivo activity:

In this study, SB-297006 showed dual effects in stroke conditions. In adolescent mice, CCL11 promoted gliogenesis and neurogenesis, while in adult mice, CCL11 aggravated acute brain injury and hindered neurological recovery. SB-297006 significantly reversed these effects, suggesting its potential for future stroke treatments by targeting the CCL11 pathway. Reference: Cells. 2019 Dec 26;9(1):66. https://pubmed.ncbi.nlm.nih.gov/31888056/

	Solvent	mg/mL	mM
Solubility
	DMSO	150.0	438.15

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 342.35 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. Bekaert S, Rocks N, Vanwinge C, Noel A, Cataldo D. Asthma-related inflammation promotes lung metastasis of breast cancer cells through CCL11-CCR3 pathway. Respir Res. 2021 Feb 19;22(1):61. doi: 10.1186/s12931-021-01652-9. PMID: 33608009; PMCID: PMC7893955. 2. 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. 3. Lieschke S, Zechmeister B, Haupt M, Zheng X, Jin F, Hein K, Weber MS, Hermann DM, Bähr M, Kilic E, Doeppner TR. CCL11 Differentially Affects Post-Stroke Brain Injury and Neuroregeneration in Mice Depending on Age. Cells. 2019 Dec 26;9(1):66. doi: 10.3390/cells9010066. PMID: 31888056; PMCID: PMC7017112. 4. 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.

In vitro protocol:

In vivo protocol:

1. Lieschke S, Zechmeister B, Haupt M, Zheng X, Jin F, Hein K, Weber MS, Hermann DM, Bähr M, Kilic E, Doeppner TR. CCL11 Differentially Affects Post-Stroke Brain Injury and Neuroregeneration in Mice Depending on Age. Cells. 2019 Dec 26;9(1):66. doi: 10.3390/cells9010066. PMID: 31888056; PMCID: PMC7017112. 2. 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.

1: 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. eCollection 2017. PubMed PMID: 28458639; PubMed Central PMCID: PMC5394117. 2: Wang F, Baba N, Shen Y, Yamashita T, Tsuru E, Tsuda M, Maeda N, Sagara Y. CCL11 promotes migration and proliferation of mouse neural progenitor cells. Stem Cell Res Ther. 2017 Feb 7;8(1):26. doi: 10.1186/s13287-017-0474-9. PubMed PMID: 28173860; PubMed Central PMCID: PMC5297016. 3: 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. PubMed PMID: 23532518. 4: 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. PubMed PMID: 17804691. 5: 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. PubMed PMID: 10969084.