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Merck
CN

SML2250

BB-Cl-amidine trifluoroacetate salt

≥98% (HPLC)

别名:

N-[(1S)-1-(1H-Benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-[1,1′-biphenyl]-4-carboxamide trifluoroacetate

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关于此项目

经验公式（希尔记法）:
C26H26ClN5O · xC2HF3O2
化学文摘社编号:
1802637-39-3
分子量:
459.97 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

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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

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000152306
0000152306
0000129442
0000051144
0000051143

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Fatemeh Ghari et al.
Science advances, 2(2), e1501257-e1501257 (2016-03-19)
Peptidyl arginine deiminase 4 (PAD4) is a nuclear enzyme that converts arginine residues to citrulline. Although increasingly implicated in inflammatory disease and cancer, the mechanism of action of PAD4 and its functionally relevant pathways remains unclear. E2F transcription factors are
Daniel M Lewallen et al.
ACS chemical biology, 10(11), 2520-2528 (2015-09-12)
Anti-citrullinated protein antibodies (ACPAs) are a hallmark of rheumatoid arthritis (RA) and are routinely used for disease diagnosis. Protein citrullination is also increased in cancer and other autoimmune disorders, suggesting that citrullinated proteins may serve as biomarkers for diseases beyond

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