A 286982

LFA-1/ICAM-1 interaction inhibitor CAS# 280749-17-9

A 286982

Catalog No. BCC3946----Order now to get a substantial discount!

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Chemical structure

A 286982

3D structure

Chemical Properties of A 286982

Cas No. 280749-17-9 SDF Download SDF
PubChem ID 9846729 Appearance Powder
Formula C24H27N3O4S M.Wt 453.55
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 50 mM in ethanol
Chemical Name (E)-1-(4-acetylpiperazin-1-yl)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-en-1-one
SMILES CC(C)C1=CC=CC=C1SC2=C(C=C(C=C2)C=CC(=O)N3CCN(CC3)C(=O)C)[N+](=O)[O-]
Standard InChIKey HTGGAYLWTDOFDK-PKNBQFBNSA-N
Standard InChI InChI=1S/C24H27N3O4S/c1-17(2)20-6-4-5-7-22(20)32-23-10-8-19(16-21(23)27(30)31)9-11-24(29)26-14-12-25(13-15-26)18(3)28/h4-11,16-17H,12-15H2,1-3H3/b11-9+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of A 286982

DescriptionPotent inhibitor of the LFA-1/ICAM-1 interaction (IC50 values are 44 and 35 nM in LFA-1/ICAM-1 binding and LFA-1-mediated cell adhesion assays respectively).

A 286982 Dilution Calculator

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Preparing Stock Solutions of A 286982

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2048 mL 11.0241 mL 22.0483 mL 44.0966 mL 55.1207 mL
5 mM 0.441 mL 2.2048 mL 4.4097 mL 8.8193 mL 11.0241 mL
10 mM 0.2205 mL 1.1024 mL 2.2048 mL 4.4097 mL 5.5121 mL
50 mM 0.0441 mL 0.2205 mL 0.441 mL 0.8819 mL 1.1024 mL
100 mM 0.022 mL 0.1102 mL 0.2205 mL 0.441 mL 0.5512 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on A 286982

A 286982 is a selective inhibitor of LFA-1/ICAM-1 binding and LFA-1 with IC50 value of 44 nM and 35 nM, respectively [1].

Lymphocyte function-associated antigen-1 (LFA-1) is a member of leukocyte intergrins family and involves in T cells binding to antigen presenting cells. Intracellular adhension molecule-1 (ICAM-1) is a type of intercellular adhesion molecule and plays a pivotal role in cell-cell interactions. LFA-1/ICAM-1 interaction plays an important role in the pathogenesis of inflammatory disease [2].

A 286982 is a potent LFA-1/ICAM-1 inhibitor and has a different effect on the binding of compound 2B. When tested with LFA-1/ICAM-1 binding assay and LFA-1-mediated cellular adhesion assays, A-286982 treatment for 28h exhibited inhibition on LFA-1/ICAM-1interaction [1]. Using the LFA-1/ICAM-1 ELISA assay, it was shown that A 286982 exhibited inhibition on the binding of ICAM-1-Ig to LFA-1 by reducing both ligands affinity and binding capacity [3].

References:
[1].  Liu, G., et al., Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 1. Identification of an additional binding pocket based on an anilino diaryl sulfide lead. J Med Chem, 2000. 43(21): p. 4025-40.
[2].  Katakai, T., K. Habiro, and T. Kinashi, Dendritic cells regulate high-speed interstitial T cell migration in the lymph node via LFA-1/ICAM-1. J Immunol, 2013. 191(3): p. 1188-99.
[3].  Keating, S.M., et al., Competition between intercellular adhesion molecule-1 and a small-molecule antagonist for a common binding site on the alphal subunit of lymphocyte function-associated antigen-1. Protein Sci, 2006. 15(2): p. 290-303.

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References on A 286982

Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 1. Identification of an additional binding pocket based on an anilino diaryl sulfide lead.[Pubmed:11052808]

J Med Chem. 2000 Oct 19;43(21):4025-40.

The interaction between leukocyte function-associated antigen-1 (LFA-1), a member of the beta(2)-integrin family of adhesion molecules, and intracellular adhesion molecule ICAM-1 (cd54) is thought to play a critical role in the inflammatory process. On the basis of an anilino diaryl sulfide screening lead 1, in combination with pharmacophore analysis of other screening hits, we have identified an adjacent binding pocket. Subsequently, a p-ethenylcarbonyl linker was discovered to be optimal for accessing this binding site. Solution-phase parallel synthesis enabled rapid optimization of the cinnamides for this pocket. In conjunction with fine-tuning of the diaryl substituents, we discovered a novel series of potent, nonpeptide inhibitors of LFA-1/ICAM-1 interaction, exemplified by A-286982 (28h), which has IC(50) values of 44 and 35 nM in an LFA-1/ICAM-1 binding assay and LFA-1-mediated cellular adhesion assay, respectively.

Competition between intercellular adhesion molecule-1 and a small-molecule antagonist for a common binding site on the alphal subunit of lymphocyte function-associated antigen-1.[Pubmed:16384997]

Protein Sci. 2006 Feb;15(2):290-303.

The lymphocyte function-associated antigen-1 (LFA-1) binding of a unique class of small-molecule antagonists as represented by compound 3 was analyzed in comparison to that of soluble intercellular adhesion molecule-1 (sICAM-1) and A-286982, which respectively define direct and allosteric competitive binding sites within LFA-1's inserted (I) domain. All three molecules antagonized LFA-1 binding to ICAM-1-Immunoglobulin G fusion (ICAM-1-Ig) in a competition ELISA, but only compound 3 and sICAM-1 inhibited the binding of a fluorescein-labeled analog of compound 3 to LFA-1. Compound 3 and sICAM-1 displayed classical direct competitive binding behavior with ICAM-1. Their antagonism of LFA-1 was surmountable by both ICAM-1-Ig and a fluorescein-labeled compound 3 analog. The competition of both sICAM-1 and compound 3 with ICAM-1-Ig for LFA-1 resulted in equivalent and linear Schild plots with slopes of 1.24 and 1.26, respectively. Cross-linking studies with a photoactivated analog of compound 3 localized the high-affinity small-molecule binding site to the N-terminal 507 amino acid segment of the alpha chain of LFA-1, a region that includes the I domain. In addition, cells transfected with a variant of LFA-1 lacking this I domain showed no significant binding of a fluorescein-labeled analog of compound 3 or ICAM-1-Ig. These results demonstrate that compound 3 inhibits the LFA-1/ICAM-1 binding interaction in a directly competitive manner by binding to a high-affinity site on LFA-1. This binding site overlaps with the ICAM-1 binding site on the alpha subunit of LFA-1, which has previously been localized to the I domain.

Description

Potent inhibitor of the LFA-1/ICAM-1 interaction

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