SML2250
BB-Cl-amidine trifluoroacetate salt
≥98% (HPLC)
Synonym(s):
N-[(1S)-1-(1H-Benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-[1,1′-biphenyl]-4-carboxamide trifluoroacetate
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About This Item
Empirical Formula (Hill Notation):
C26H26ClN5O · xC2HF3O2
CAS Number:
Molecular Weight:
459.97 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
O=C(C1=CC=C(C2=CC=CC=C2)C=C1)N[C@H](C3=NC4=C(N3)C=CC=C4)CCCNC(CCl)=N
Biochem/physiol Actions
BB-Cl-amidine is an irreversible pan-protein-arginine deiminase (PAD) inhibitor (kinact/KI in M-1min-1 = 16100/PAD1, 4100/PAD2, 6800/PAD3, 13300/PAD4) with >20-fold increased potency against U2OS osteosarcoma cutlures (viability assay IC50 = 8.8 μM vs >200 μM with Cl-amidine) and longer in vivo half-life (1.75 hrs vs 15 min for Cl-amidine in plasma post injection in mice) than Cl-amidine. BB-Cl-amidine effectively inhibits PMA-induced neutrophils extracellular trap (NET) formation from lupus-prone MRL/lpr mice-derived bone marrow neutrophils in cultures (by 78% and 34% with 20 μM BB-Cl-amidine or Cl-amidine, respectively), while daily s.c. injection (1 mg/kg) is efficacious in ameliorating lupus symptoms in in MRL/lpr mice in vivo.
Irreversible pan-protein-arginine deiminase (PAD) inhibitor with >10-fold increased potency than Cl-amidine both in vitro and in vivo.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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