A pan PAD inhibitor
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BB-Cl-Amidine (trifluoroacetate salt)

Item No. 17079

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S)-1-(1H-benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-[1,1'-biphenyl]-4-carboxamide, trifluoroacetate salt
Molecular Formula
C26H26ClN5O • XCF3COOH
Formula Weight
460.0
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 25 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
274, 281 nm
SMILES
O=C(N[C@@H](CCCNC(CCl)=N)C1=NC2=C(C=CC=C2)N1)C(C=C3)=CC=C3C4=CC=CC=C4.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C26H26ClN5O.C2HF3O2/c27-17-24(28)29-16-6-11-23(25-30-21-9-4-5-10-22(21)31-25)32-26(33)20-14-12-19(13-15-20)18-7-2-1-3-8-18;3-2(4,5)1(6)7/h1-5,7-10,12-15,23H,6,11,16-17H2,(H2,28,29)(H,30,31)(H,32,33);(H,6,7)/t23-;/m0./s1
InChi Key
GVJRBPSKBWIJOF-BQAIUKQQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

    $186

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    10 mg

    $333

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    NET Formation Screening & Analysis Services
    Our experts are here to help.
    • Detection of NET formation ex vivo and screening for modulators using:
      • High-content imaging
      • Enzymatic detection
      • Citrullination/carbamylation detection
    • Experienced scientists skilled in neutrophil biology, isolation, and handling
    LEARN MORE
    Product Description

    BB-Cl-amidine is a pan inhibitor of peptidyl arginine deiminases (PADs) and a proteolysis-resistant derivative of Cl-amidine (Item No. 10599).1 It irreversibly inhibits PAD1-4 (kinact/KI = 16,100, 4,100, 6,800, and 13,300 M-1min-1, respectively).2,3 BB-Cl-amidine (20 and 200 µM) inhibits the formation of neutrophil extracellular traps (NETs) induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) without altering hydrogen peroxide (H2O2) production in bone marrow-derived neutrophils.1 It inhibits IFN-β production induced by the DNA virus herpes simplex virus 1 (HSV-1) but not the RNA virus Sendai virus in mouse bone marrow-derived macrophages (BMDMs) when used at a concentration of 1 µM.4 Ex vivo, BB-Cl-amidine (10 mg/kg) reduces BMDM IFN-β and TNF-α production induced by diABZI STING agonist-1 (Item No. 28054) in wild-type, Pad2-/-, and Pad4-/- mice. BB-Cl-amidine (20 mg/kg per day) increases survival, as well as reduces splenomegaly, myocarditis, and cardiac fibrosis in a Trex1D18N/D18N mouse model of Aicardi-Goutières syndrome (AGS).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Knight, J.S., Subramanian, V., O'Dell, A.A., et al. Peptidylarginine deiminase inhibition disrupts NET formation and protects against kidney, skin and vascular disease in lupus-prone MRL/lpr mice. Ann. Rheum. Dis. 74(12), 2199-2206 (2015).

    2. Luo, Y., Arita, K., Bhatia, M., et al. Inhibitors and inactivators of protein arginine deiminase 4: Functional and structural characterization. Biochemistry 45(39), 11727-11736 (2006).

    3. Muth, A., Subramanian, V., Beaumont, E., et al. Development of a selective inhibitor of protein arginine deiminase 2. J. Med. Chem. 60(7), 3198-3211 (2017).

    4. Humphries, F., Shmuel-Galia, L., Jiang, Z., et al. Targeting STING oligomerization with small-molecule inhibitors. Proc. Natl. Acad. Sci. USA 120(33), e2305420120 (2023).

    Product Citations

    Pasquero, S., Gugliesi, F., Griffante, G., et al. Novel antiviral activity of PAD inhibitors against human beta-coronaviruses HCoV-OC43 and SARS-CoV-2. Antiviral Res. 200, 105278 (2022).

    Zhou, Y., An, L.-L., Chaerkady, R., et al. Evidence for a direct link between PAD4-mediated citrullination and the oxidative burst in human neutrophils. Sci. Rep. 8(1), 15228 (2018).