Cl-amidine TFA - ≥97% , CAS No.1043444-18-3

CAS: 1043444-18-3 Cat. No.: C413918 分子式: C₁₄H₁₉ClN₄O₂.C₂HF₃O₂ 分子量: 424.80

グレード＆純度 ≥97%

Synonyms

(2S)-5-(2-Chloroethanimidamido)-2-(phenylformamido)pentanamide trifluoroacetic acid salt

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

Information

Cl-amidine Cl-amidine is an irreversible pan- peptidylarginine deiminase (PAD) inhibitor with IC50 values of 5.9 ± 0.3 μM, 0.8 ± 0.3 μM, 6.2 ± 1.0 μM for PAD4, PAD1 and PAD3, respectively. Cl-amidine induces apoptosis .

Targets

PAD1 (Cell-free assay); PAD4 (Cell-free assay); PAD3 (Cell-free assay) 0.8 μM; 5.9 μM; 6.2 μM

In vitro

Cl-amidine antagonizes the PAD4-mediated enhancement of the the p300GBD-GRIP1 interaction in a dose-dependent manner. The inhibitory effect of this compound is not a nonspecific one but is targeted at the active PAD4 enzyme. Cl-amidine increases p53 expression in CD45 positive immune cells. It triggers the differentiation and apoptosis of multiple cancer cell lines that are p53+/+ and p53−/− (e.g., HL60, HT29, TK6, and U2-OS cells). Cl-amidine induces the expression of p53 and several downstream target genes including the cyclin dependent kinase inhibitor p21, GADD45, and the proapoptotic protein PUMA in U2-OS osteosarcoma cells.

In vivo

Cl-amidine treatment inhibits NZM(New Zealand mixed 2328) NET(neutrophil extracellular trap) formation in vivo and significantly alters circulating autoantibody profiles and complement levels while reducing glomerular IgG deposition. Further, Cl-amidine increases the differentiation capacity of bone marrow endothelial progenitor cells, improves endothelium-dependent vasorelaxation, and markedly delays time to arterial thrombosis induced by photochemical injury. Cl-amidine delays thrombosis development in NZM mice. It inhibits PADs in mice without significant toxicity and improves disease phenotypes in animal models of inflammatory arthritis and inflammatory bowel disease. And It is shown to reduce disease severity in mouse models of ulcerative colitis and RA.

Cell Research(from reference)

Cell lines：CV-1 cells 

Concentrations：0-200 μM 

Incubation Time：40 h 

仕様

同義語

(2S)-5-(2-Chloroethanimidamido)-2-(phenylformamido)pentanamide trifluoroacetic acid salt

仕様と純度

≥97%

生化学的・生理学的メカニズム

Cl-amidine is an irreversible pan-peptidylarginine deiminase (PAD) inhibitor with IC50 values of 5.9 ± 0.3 μM, 0.8 ± 0.3 μM, 6.2 ± 1.0 μM for PAD4, PAD1 and PAD3, respectively. Cl-amidine induces apoptosis.

保管条件

Store at -20°C

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

アクションタイプ

ACTIVATOR

純度

≥97%

製品の性質

ALogP

1.333

hba_count

3

HBD数

3

回転可能な結合

10

名前と識別子

パブケム・シド

508810394

パブケム・シド・ウル

https://pubchem.ncbi.nlm.nih.gov/substance/508810394

カノニカル・スマイル

C1=CC=C(C=C1)C(=O)NC(CCCN=C(CCl)N)C(=O)N.C(=O)(C(F)(F)F)O

IUPAC Name

N-[(2S)-1-amino-5-[(1-amino-2-chloroethylidene)amino]-1-oxopentan-2-yl]benzamide;2,2,2-trifluoroacetic acid

InChIKey

WUSNMVYWOLUWDD-MERQFXBCSA-N

INCHI

1S/C14H19ClN4O2.C2HF3O2/c15-9-12(16)18-8-4-7-11(13(17)20)19-14(21)10-5-2-1-3-6-10;3-2(4,5)1(6)7/h1-3,5-6,11H,4,7-9H2,(H2,16,18)(H2,17,20)(H,19,21);(H,6,7)/t11-;/m0./s1

異性体SMILES

C1=CC=C(C=C1)C(=O)N[C@@H](CCCN=C(CCl)N)C(=O)N.C(=O)(C(F)(F)F)O

代替CAS番号

1373232-26-8；913723-61-2

分子量

424.80

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • 分類 Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Benzamides
          • Level6 Hippuric acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 分類: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Benzamides
• Direct Parent: Hippuric acids and derivatives
• Alternative Parents: N-acyl-alpha amino acids and derivatives Benzoyl derivatives Fatty amides Alpha-halocarboxylic acids Secondary carboxylic acid amides Primary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Carboxamidines Monocarboxylic acids and derivatives Carboximidamides Carboxylic acids Hydrocarbon derivatives Organic oxides Carbonyl compounds Organochlorides Organofluorides Alkyl fluorides Alkyl chlorides
• Molecular Framework: Not available
• Substituents: Hippuric acid or derivatives - N-acyl-alpha amino acid or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Benzoyl - Fatty acyl - Fatty amide - Alpha-halocarboxylic acid - Alpha-halocarboxylic acid or derivatives - Carboxamide group - Secondary carboxylic acid amide - Primary carboxylic acid amide - Amidine - Organic 1,3-dipolar compound - Carboxylic acid amidine - Propargyl-type 1,3-dipolar organic compound - Carboxylic acid derivative - Carboxylic acid - Carboximidamide - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Carbonyl group - Alkyl fluoride - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Alkyl chloride - Organonitrogen compound - Organohalogen compound - Organochloride - Organofluoride - Aromatic homomonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as hippuric acids and derivatives. These are compounds containing a hippuric acid or a derivative, with a structure characterized the presence of a benzoyl group linked to the N-terminal of a glycine.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

関連ターゲット（人間）

PADI1 Tchem Protein-arginine deiminase type-1 (1 Activities)

Discover Target: PADI1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HL-60 (67320 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PADI4 Tchem Protein-arginine deiminase type-4 (309 Activities)

Discover Target: PADI4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PADI1 Tchem Protein-arginine deiminase type-1 (130 Activities)

Discover Target: PADI1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PADI2 Tchem Protein-arginine deiminase type-2 (138 Activities)

Discover Target: PADI2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PADI3 Tchem Protein-arginine deiminase type-3 (118 Activities)

Discover Target: PADI3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

作用メカニズム

化学的性質と物理的性質

• 溶解度: Solubility (25°C) In vitro DMSO: 84 mg/mL warmed with 50ºC Water: bath (197.74 mM); Ethanol: 84 mg/mL warmed with 50ºC Water: bath (197.74 mM); Water: 70 mg/mL warmed with 50ºC Water: bath (164.78 mM)
• DMSO（mg / mL） 最大溶解度: 84
• DMSO（mM） 最大溶解度: 197.740113
• 水（mg / mL） 最大溶解度: 70
• 水（mM） 最大溶解度: 164.7834275
• 分子量: 424.800 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 424.113 Da
• Monoisotopic Mass: 424.113 Da
• Topological Polar Surface Area: 148.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 465.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3