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| | BB-Cl-Amidine Basic information |
| Product Name: | BB-Cl-Amidine | | Synonyms: | BB-Cl-Amidine;CS-2826;N-{(1S)-1-(1H-Benzimidazol-2-yl)-4-[(2-chloroethanimidoyl)amino]butyl}-4-biphenylcarboxamide;[1,1'-Biphenyl]-4-carboxamide, N-[(1S)-1-(1H-benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-;Peptidylarginine Deiminase,Inhibitor,BBClAmidine,BB Cl Amidine,Protein Arginine Deiminase,inhibit;(S)-N-(1-(1H-Benzo[d]imidazol-2-yl)-4-(2-chloroacetimidamido)butyl)-[1,1'-biphenyl]-4-carboxamide;N-[(1S)-1-(1H-1,3-benzodiazol-2-yl)-4-(2-chloroethanimidamido)butyl]-[1,1'-biphenyl]-4-carboxamide;BB-CI-Amidine
N1-[1,4’-phenyl]benzoyl-N5-(2-chloro-1-iminoethyl)-1-(1H-benzo[d]imidazol-2-yl)-L-ornithine | | CAS: | 1802637-39-3 | | MF: | C26H26ClN5O | | MW: | 459.97 | | EINECS: | | | Product Categories: | | | Mol File: | 1802637-39-3.mol |  |
| | BB-Cl-Amidine Chemical Properties |
| density | 1.282±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | DMSO:76.33(Max Conc. mg/mL);165.94(Max Conc. mM)
DMF:20.0(Max Conc. mg/mL);43.48(Max Conc. mM)
Water:70.0(Max Conc. mg/mL);152.18(Max Conc. mM)
Ethanol:54.5(Max Conc. mg/mL);118.48(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.09(Max Conc. mM) | | form | A crystalline solid | | pka | 11.501±0.10(predicted) | | color | white to beige | | InChIKey | YDOAWJHYHGBQFI-QHCPKHFHSA-N | | SMILES | C1(C2=CC=CC=C2)=CC=C(C(N[C@H](C2NC3=CC=CC=C3N=2)CCCNC(=N)CCl)=O)C=C1 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids |
| | BB-Cl-Amidine Usage And Synthesis |
| Description | BB-Cl-Amidine is a modified version of Cl-amidine that retains the functional components but possesses a C-terminal benzimidazole group designed to limit proteolysis of the C-terminal amide. BB-Cl-Amidine irreversibly inactivates all four PAD subtypes (kinact/KI = 16,100, 4,100, 6,800, and 13,300 M-1min-1 for PAD1-4, respectively) by covalently modifying an active site cysteine that is important for its catalytic activity. The cellular potency of BB-Cl-amidine against PAD4 is increased 20-fold over the parent compound (EC50 = 8.8 μM versus >200 μM for Cl-amidine). BB-Cl-Amidine also has a significantly longer in vivo half-life than Cl-amidine (1.75 h versus ~15 min, respectively). Both compounds inhibit the formation of neutrophil extracellular traps without altering H2O2 production by neutrophils. BB-Cl-Amidine is effective in vivo, improving endothelial function while downregulating the expression of type I interferon-regulated genes in MRL/lpr mice. | | Uses | BB-Cl-Amidine is a peptidylarginine deminase (PAD) inhibitor. | | in vivo | Treatment with BB-Cl-amidine subtly reduces splenomegaly in MRL/lpr mice, while there is a trend towards increased circulating levels of anti-NET antibodies with PAD inhibitor treatment. However, neither PAD inhibitor affected body weight or total IgG levels. Indeed, treatment with both Cl-amidine and BB-Cl-amidine significantly improves endothelium-dependent vasorelaxation. The BB-Cl-amidine group also shows a strong trend towards downregulation of IRGs. Treatment with either Cl-amidine or BB-Cl-amidine significantly improves muzzle alopecia, in many cases preventing it entirely[1]. | Animal Model: | MRL/lpr mice[1].
| | Dosage: | 1 mg/kg. | | Administration: | Subcutaneous injection daily from 8 to 14 weeks of age. | | Result: | Significantly improved endothelium-dependent vasorelaxation and showed a strong trend towards downregulation of IRGs. |
| | References | [1] Knight JS, 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. 2015 Dec;74(12):2199-206. DOI:10.1136/annrheumdis-2014-205365 |
| | BB-Cl-Amidine Preparation Products And Raw materials |
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