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SML0421

Sigma-Aldrich

SB265610

≥98% (HPLC)

Synonym(s):

1-(2-Bromophenyl)-3-(4-cyano-1H-benzo[d] [1,2,3]triazol-7-yl)urea, N-(2-Bromophenyl)-N′-(7-cyano-1H-benzotriazol-4-yl)urea, SB 265610

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About This Item

Empirical Formula (Hill Notation):
C14H9BrN6O
CAS Number:
211096-49-0
Molecular Weight:
357.16
MDL number:
MFCD09971124
UNSPSC Code:
51111800
PubChem Substance ID:
329825416
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

SMILES string

Brc1ccccc1NC(=O)Nc2ccc(C#N)c3nn[nH]c23

InChI

1S/C14H9BrN6O/c15-9-3-1-2-4-10(9)17-14(22)18-11-6-5-8(7-16)12-13(11)20-21-19-12/h1-6H,(H2,17,18,22)(H,19,20,21)

InChI key

SEDUMQWZEOMXSO-UHFFFAOYSA-N

Application

SB265610 has been used:
  • as a cysteine-amino acid-cysteine (CXC)-chemokine receptor type 2 (CXCR2) antagonist to study its effects on the binding of chemokine with G-protein coupled receptors (GPCR)
  • as a CX-chemokine receptor type 1 (CXCR1) inhibitor to study its effect on the chemotactic activity of chemokines on inflammatory cells
  • as a CXCR2 antagonist to study its effect on migration of neutrophils to the rat brain

Biochem/physiol Actions

SB265610 is a potent and selective CXCR2 chemokine receptor antagonist. It has a Kd = 2.5 nM.

Features and Benefits

This compound is featured on the Chemokine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jing Zhao et al.
Scientific reports, 7(1), 16128-16128 (2017-11-25)
The pulsatile nature of blood flow exposes vascular smooth muscle cells (VSMCs) in the vessel wall to cyclic mechanical stretch (CMS), which evokes VSMC proliferation, cell death, phenotypic switching, and migration, leading to vascular remodeling. These responses have been observed
Meirong Du et al.
PloS one, 8(1), e54572-e54572 (2013-01-30)
Recent evidence indicates that CXCR2 signaling is crucial for cancer progression, and its antagonist SB225002 induces apoptosis in Wilms' tumor cells. Here, we investigated the effect of SB225002 on cell cycle progression and apoptosis induction in vitro, using CDDP-sensitive and
Julia Esser-von Bieren et al.
PLoS pathogens, 11(3), e1004778-e1004778 (2015-03-26)
Helminth parasites can cause considerable damage when migrating through host tissues, thus making rapid tissue repair imperative to prevent bleeding and bacterial dissemination particularly during enteric infection. However, how protective type 2 responses targeted against these tissue-disruptive multicellular parasites might
François Binet et al.
Science (New York, N.Y.), 369(6506) (2020-08-21)
In developed countries, the leading causes of blindness such as diabetic retinopathy are characterized by disorganized vasculature that can become fibrotic. Although many such pathological vessels often naturally regress and spare sight-threatening complications, the underlying mechanisms remain unknown. Here, we
Zongmin Jiang et al.
Scientific reports, 7(1), 14510-14510 (2017-11-08)
Microenvironment (or niche)-providing chemokines regulate many important biological functions of tissue-specific stem cells. However, to what extent chemokines influence human pluripotent stem cells (hPSCs) is not yet completely understood. In this study, we applied protein array to screen chemokines found
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