VR23 - 10mM in DMSO , CAS No.1624602-30-7

CAS: 1624602-30-7 Cat. No.: V421977 Summenformel: C₁₉H₁₆ClN₅O₆S Molekulargewicht: 477.88 EG-Nummer: 110-424-9 PubChem CID: 73442847

QUALITÄT & REINHEIT 10mM in DMSO

Synonyms

7-chloro-4-(4-(2,4-dinitrophenylsulfonyl)piperazin-1-yl)quinoline

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

Information

VR23 VR23 is a potent proteasome inhibitor with IC50 of 1 nM, 50-100 nM, and 3 μM for trypsin-like proteasomes, chymotrypsin-like proteasomes, and caspase-like proteasomes, respectively.

Targets

Trypsin-like proteasomes (in Hela cells); Chymotrypsin-like proteasomes (in Hela cells); Caspase-like proteasomes (in Hela cells) 1 nM; 100 nM; 3 μM

In vitro

In HeLa cells, VR23 induces ubiquitinated proteins accumulation. In RPMI 8226 and KAS 6 cells, VR23 inhibits cell growth with IC50 of 2.94 and 1.46 μM, respectively. VR23 is also equally effective on both bortezomib (BTZ)-sensitive and -resistant RPMI 8226 and ANBL6 cells cells. When used in combination of bortezomib in the cells above, VR23 shows synergistic effects on cell growth inhibition. In addition, VR23 selectively induces cancer cell apoptosis by causing the accumulation of ubiquitinated cyclin E.

In vivo

In ATH490 athymic mice engrafted with MDA-MB-231 metastatic breast cancer cells, VR23 (30mg/kg, i.p.) shows effective antitumor and antiangiogenic activities. VR23 also reduces adverse effects caused by paclitaxel in mice.

Cell Research(from reference)

Cell lines：RPMI 8226, KAS 6, 184B5, and MCF10A cells; bortezomib-resistant RPMI 8226 cells and bortezomib-resistant ANBL6 cells 

Concentrations：~20 μM 

Spezifikationen

Synonyme

7-chloro-4-(4-(2,4-dinitrophenylsulfonyl)piperazin-1-yl)quinoline

Spezifikationen & Reinheit

10mM in DMSO

Biochemische und physiologische Mechanismen

VR23 is a potent proteasome inhibitor with IC50 of 1 nM, 50-100 nM, and 3 μM for trypsin-like proteasomes, chymotrypsin-like proteasomes, and caspase-like proteasomes, respectively.

Storage

Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Produkteigenschaften

ALogP

3.215

Rotationsfähige Bindung

5

Namen und Kennungen

Pubchem Sid

528767649

Kanonisches Lächeln

C1CN(CCN1C2=C3C=CC(=CC3=NC=C2)Cl)S(=O)(=O)C4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]

IUPAC Name

7-chloro-4-[4-(2,4-dinitrophenyl)sulfonylpiperazin-1-yl]quinoline

InChIKey

PDQVZPPIHADUOO-UHFFFAOYSA-N

INCHI

1S/C19H16ClN5O6S/c20-13-1-3-15-16(11-13)21-6-5-17(15)22-7-9-23(10-8-22)32(30,31)19-4-2-14(24(26)27)12-18(19)25(28)29/h1-6,11-12H,7-10H2

Isomere SMILES

C1CN(CCN1C2=C3C=CC(=CC3=NC=C2)Cl)S(=O)(=O)C4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]

PubChem CID

73442847

Molekulargewicht

477.88

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Diazinanes
      • Subclass Piperazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Diazinanes
• Subclass: Piperazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridinylpiperazines
• Alternative Parents: N-arylpiperazines 4-aminoquinolines Chloroquinolines Benzenesulfonamides Benzenesulfonyl compounds Nitrobenzenes Nitroaromatic compounds Dialkylarylamines Aminopyridines and derivatives Organosulfonamides Aryl chlorides Heteroaromatic compounds Sulfonyls Organic oxoazanium compounds Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organic oxides Organochlorides Hydrocarbon derivatives Organic salts Organic zwitterions
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-arylpiperazine - Pyridinylpiperazine - Aminoquinoline - 4-aminoquinoline - Haloquinoline - Chloroquinoline - Quinoline - Benzenesulfonamide - Benzenesulfonyl group - Nitrobenzene - Nitroaromatic compound - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Aminopyridine - Organosulfonic acid amide - Aryl chloride - Aryl halide - Benzenoid - Pyridine - Monocyclic benzene moiety - Organosulfonic acid or derivatives - Heteroaromatic compound - Sulfonyl - Organic sulfonic acid or derivatives - Organic nitro compound - C-nitro compound - Tertiary amine - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Allyl-type 1,3-dipolar organic compound - Azacycle - Organic oxoazanium - Organic oxygen compound - Organochloride - Organohalogen compound - Organic salt - Organic nitrogen compound - Amine - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organosulfur compound - Organic zwitterion - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as pyridinylpiperazines. These are compounds containing a pyridinylpiperazine skeleton, which consists of a pyridine linked (not fused) to a piperazine by a bond by a single bond that is not part of a ring.
• 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

Chemische und physikalische Eigenschaften

• DMSO (mg/ml) Maximale Löslichkeit: 31
• DMSO (mM) Maximale Löslichkeit: 64.8698418
• Wasser (mg/ml) Maximale Löslichkeit: ＜1
• Molekulargewicht: 477.900 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 477.051 Da
• Monoisotopic Mass: 477.051 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 806.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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: 1