An antagonist of C3aR
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SB 290157 (trifluoroacetate salt)

Item No. 15783

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N2-[2-(2,2-diphenylethoxy)acetyl]-L-arginine, 2,2,2-trifluoroacetate
CAS Number
1140525-25-2
Molecular Formula
C22H28N4O4 • CF3COOH
Formula Weight
526.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
O=C(N[C@H](C(O)=O)CCCNC(N)=N)COCC(C1=CC=CC=C1)C2=CC=CC=C2.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C22H28N4O4.C2HF3O2/c23-22(24)25-13-7-12-19(21(28)29)26-20(27)15-30-14-18(16-8-3-1-4-9-16)17-10-5-2-6-11-17;3-2(4,5)1(6)7/h1-6,8-11,18-19H,7,12-15H2,(H,26,27)(H,28,29)(H4,23,24,25);(H,6,7)/t19-;/m0./s1
InChi Key
ZJRMPPVJAQWGEG-FYZYNONXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    25 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    The anaphylatoxin C3a induces a range of responses by activating its G protein-coupled receptor, C3aR, resulting in calcium mobilization.1 SB 290157 is a non-peptide antagonist of C3aR, competitively blocking C3a binding with an IC50 value of 200 nM.2 It potently inhibits a wide variety of C3a-induced responses in cells, including calcium increase in human neutrophils (IC50 = 28 nM) and ATP release from guinea pig platelets (IC50 = 30 nM).2 SB 290157 is also effective in vivo, reducing inflammation in a variety of animal models.2,3,4 It also significantly reduces or reverses diet-induced obesity in rats and accelerates the mobilization of hematopoietic progenitor cells to the peripheral blood in mice.5,6 Notably, SB 290157 has C3aR agonist activity in some cell systems.7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ames, R.S., Li, Y., Sarau, H.M., et al. Molecular cloning and characterization of the human anaphylatoxin C3a receptor. The Journal of Biological Chemisty 271(34), 20231-20234 (1996).

    2. Ames, R.S., Lee, D., Foley, J.J., et al. Identification of a selective nonpeptide antagonist of the anaphylatoxin C3a receptor that demonstrates antiinflammatory activity in animal models. J. Immunol. 166(10), 6341-6348 (2001).

    3. Proctor, L.M., Arumugam, T.V., Shiels, I., et al. Comparative anti-inflammatory activities of antagonists to C3a and C5a receptors in a rat model of intestinal ischaemia/reperfusion injury. Br. J. Pharmacol. 142(4), 756-764 (2004).

    4. Hutamekalin, P., Takeda, K., Tani, M., et al. Effect of the C3a-receptor antagonist SB 290157 on anti-OVA polyclonal antibody-induced arthritis. J. Pharmacol. Sci. 112(1), 56-63 (2010).

    5. Lim, J., Iyer, A., Suen, J.Y., et al. C5aR and C3aR antagonists each inhibit diet-induced obesity, metabolic dysfunction, and adipocyte and macrophage signaling. The FASEB Journal 27(2), 822-831 (2013).

    6. Ratajczak, J., Reca, R., Kucia, M., et al. Mobilization studies in mice deficient in either C3 or C3a receptor (C3aR) reveal a novel role for complement in retention of hematopoietic stem/progenitor cells in bone marrow. Blood 103(6), 2071-2078 (2004).

    7. Mathieu, M.C., Sawyer, N., Greig, G.M., et al. The C3a receptor antagonist SB 290157 has agonist activity. Immunol. Lett. 100(2), 139-145 (2005).

    8. Therien, A.G. Agonist activity of the small molecule C3aR ligand SB 290157. J. Immunol. 174(12), 7479-7490 (2005).