A PAD inhibitor
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Cl-Amidine (hydrochloride)

Item No. 10599

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S)-1-(aminocarbonyl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-benzamide, monohydrochloride
CAS Number
1373232-26-8
Molecular Formula
C14H19ClN4O2 • HCl
Formula Weight
347.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 50 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 3 mg/ml
SMILES
O=C(N[C@@H](CCCNC(CCl)=N)C(N)=O)C1=CC=CC=C1.Cl
InChi Code
InChI=1S/C14H19ClN4O2.ClH/c15-9-12(16)18-8-4-7-11(13(17)20)19-14(21)10-5-2-1-3-6-10;/h1-3,5-6,11H,4,7-9H2,(H2,16,18)(H2,17,20)(H,19,21);1H/t11-;/m0./s1
InChi Key
OPFMEGSAOZAJIV-MERQFXBCSA-N
License
Sold under license from the University of South Carolina under U.S. Patent No. 7,964,636
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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    Cayman Chemical
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    Product Description

    Cl-Amidine is an irreversible inhibitor of protein arginine deiminases (PADs; IC50s = 0.8, 6.2, and 5.9 µM for PAD1, PAD3, and PAD4, respectively).1,2,3 It is cytotoxic to HL-60, MCF-7, and HT-29 cancer cells (IC50s = 0.25, 0.05, and 1 μM, respectively).4 Cl-amidine (50 mg/kg) reduces ex vivo extracellular neutrophil extracellular trap (NET) formation and increases survival in a mouse model of sepsis induced by cecal ligation and puncture (CLP).5 It also decreases the citrulline content in serum and joints and reduces the development of IgG autoantibodies in a mouse model of collagen-induced arthritis in a dose-dependent manner.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Knuckley, B., Causey, C.P., Jones, J.E., et al. Substrate specificity and kinetic studies of PADs 1, 3, and 4 identify potent and selective inhibitors of protein arginine deiminase 3. Biochem. 49(23), 1-28 (2010).

    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. Slack, J.L., Causey, C.P., and Thompson, P.R. Protein arginine deiminase 4: A target for an epigenetic cancer therapy. Cell Mol. Life Sci. 68(4), 709-720 (2011).

    5. Biron, B.M., Chung, C.-S., O'Brien, X.M., et al. Cl-Amidine prevents histone 3 citrullination and neutrophil extracellular trap formation, and improves survival in a murine sepsis modep. J. Innate Immun. 9(1), 22-32 (2017).

    6. Willis, V.C., Gizinski, A.M., Banda, N.K., et al. N-α-benzoyl-N5-(2-chloro-1-iminoethyl)-L-orninthine amide, a protein arginine deiminase inhibitor, reduces the severity of murine collagen-induced arthritis. J. Immunol. 186(7), 4396-4404 (2011).

    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).

    Vaibhav, K., Braun, M., Alverson, K., et al. Neutrophil extracellular traps exacerbate neurological deficits after traumatic brain injury. Sci. Adv. 6(22), eaax8847 (2020).

    Li, M., Lin, C., Deng, H., et al. A novel peptidylarginine deiminase 4 (PAD4) inhibitor BMS-P5 blocks formation of neutrophil extracellular traps and delays progression of multiple myeloma. Mol. Cancer Ther. 19(7), 1530-1538 (2020).

    Krishnamurthy, A., Ytterberg, A.J., M., S., et al. Citrullination contols dendritic cell transdifferentiation into osteoclasts. J. Immunol. 204(1), 1-8 (2020).

    Nakabo, S., Ohmura, K., Akizuki, S., et al. Activated neutrophil carbamylates albumin via the release of myeloperoxidase and reactive oxygen species regardless of NETosis. Mod. Rheumatol. 30(2), 345-349 (2019).

    Falcão, A.M., Meijer, M.K., Scaglione, A., et al. PAD2-mediated citrullination contributes to efficient oligodendrocyte differentiation and myelination. Cell Rep. 27(4), 1090-1102 (2019).

    Sun, M., Rethi, B., Krishnamurthy, A., et al. Anticitrullinated protein antibodies facilitate migration of synovial tissue-derived fibroblasts. Ann. Rheum. Dis. 78(12), 1621-1631 (2019).