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

CAS: 1043444-18-3 Cat. No.: C413918 Fórmula: C₁₄H₁₉ClN₄O₂.C₂HF₃O₂ Peso molecular: 424.80

CALIDAD & PUREZA ≥97%

Synonyms

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

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

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 

Especificaciones

Sinónimos

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

Especificaciones y pureza

≥97%

Mecanismos bioquímicos y fisiológicos

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.

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

ACTIVATOR

Pureza

≥97%

Propiedades del producto

ALogP

1.333

hba_count

3

Recuento HBD

3

Enlace rotable

10

Nombres e identificadores

Pubchem Sid

508810394

Pubchem Sid Url

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

Sonrisas canónicas

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

Isómeros 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

CAS alternativo

1373232-26-8；913723-61-2

Peso molecular

424.80

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: 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) Solubilidad máxima: 84
• DMSO (mM) Solubilidad máxima: 197.740113
• Agua (mg/ml) Solubilidad máxima: 70
• Agua (mM) Solubilidad máxima: 164.7834275
• Peso molecular: 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