ChemicalBook > CAS DataBase List > BB-Cl-Amidine

BB-Cl-Amidine

Product Name: BB-Cl-Amidine
CAS No.: 1802637-39-3
Chemical Name: BB-Cl-Amidine
Synonyms: CS-2826;BB-Cl-Amidine;N-{(1S)-1-(1H-Benzimidazol-2-yl)-4-[(2-chloroethanimidoyl)amino]butyl}-4-biphenylcarboxamide;(S)-N-(1-(1H-Benzo[d]imidazol-2-yl)-4-(2-chloroacetimidamido)butyl)-[1,1'-biphenyl]-4-carboxamide;Peptidylarginine Deiminase,Inhibitor,BBClAmidine,BB Cl Amidine,Protein Arginine Deiminase,inhibit;N-[(1S)-1-(1H-1,3-benzodiazol-2-yl)-4-(2-chloroethanimidamido)butyl]-[1,1'-biphenyl]-4-carboxamide;[1,1'-Biphenyl]-4-carboxamide, N-[(1S)-1-(1H-benzimidazol-2-yl)-4-[(2-chloro-1-iminoethyl)amino]butyl]-;BB-CI-Amidine N1-[1,4’-phenyl]benzoyl-N5-(2-chloro-1-iminoethyl)-1-(1H-benzo[d]imidazol-2-yl)-L-ornithine
CBNumber: CB63152560
Molecular Formula: C26H26ClN5O
Formula Weight: 459.971
MOL File: 1802637-39-3.mol

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BB-Cl-Amidine Property

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
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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 17079
Product name: BB-Cl-Amidine
Purity: ≥95%
Packaging: 1mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 17079
Product name: BB-Cl-Amidine
Purity: ≥95%
Packaging: 10mg
Price: $302
Updated: 2024/03/01

Cayman Chemical

Product number: 17079
Product name: BB-Cl-Amidine
Purity: ≥95%
Packaging: 500μg
Price: $99
Updated: 2021/12/16

Cayman Chemical

Product number: 17079
Product name: BB-Cl-Amidine
Purity: ≥95%
Packaging: 5mg
Price: $169
Updated: 2024/03/01

AK Scientific

Product number: 6591EJ
Product name: BB-Cl-Amidine
Packaging: 1mg
Price: $313
Updated: 2021/12/16

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BB-Cl-Amidine Chemical Properties,Usage,Production

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 (k_inact/K_I = 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

Raw materials

Preparation Products

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1802637-39-3, BB-Cl-AmidineRelated Search:

CS-2826

BB-Cl-Amidine

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

1802637-39-3