GW280264X - Moligand™, ≥97% , CAS No.866924-39-2

CAS: 866924-39-2 Cat. No.: G646226 Molecular Weight: 575.72 PubChem CID: 91885425

GRADE & PURITY Moligand™, ≥97%

Synonyms

Benzyl ((S)-5-((2R,3S)-3-(N-hydroxyformamido)-2-isobutylhexanamido)-6-oxo-6-(thiazol-2-ylamino)hexyl)carbamate | Carbamic acid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

GW280264X is the mixed ADAM10/TACE (ADAM17) metalloproteinases inhibitor. GW280264X potently blocks TACE (ADAM17) and ADAM10 with IC 50 s of 8.0 nM and 11.5 nM, respectively ADAM10 and 17 modulate the immunogenicity of glioblastoma-initiating cells .

In Vitro

The proliferation of GS-7 cells was significantly reduced upon treatment with GW280264X or ADAM10/17 co-knockdown. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: Glioblastoma-initiating cells (GIC) GS-7 cells Concentration: 0.1, 1, and 3 µM Incubation Time: 48 hours Result: Proliferation of GIC is inhibited through inhibition of ADAM10 and ADAM17.

In Vivo

Pharmacological inhibition of ADAM10 and ADAM17 improves functional recovery after spinal cord injury (SCI). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: C57BL/6 miceDosage: 100  µg/kg Administration: I.p. injected; every day for one week starting 4 h post-surgery Result: Showed significantly improved functional recovery compared to the control group.

Form:Solid

IC50& Target:ADAM17 8 nM (IC 50 ) ADAM10 11.5 nM (IC 50 )

Specifications

Synonyms

Benzyl ((S)-5-((2R, 3S)-3-(N-hydroxyformamido)-2-isobutylhexanamido)-6-oxo-6-(thiazol-2-ylamino)hexyl)carbamate | Carbamic acid

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

GW280264X is the mixed ADAM10/TACE (ADAM17) metalloproteinases inhibitor. GW280264X potently blocks TACE (ADAM17) and ADAM10 with IC 50 s of 8.0 nM and 11.5 nM, respectively. ADAM10 and 17 modulate the immunogenicity of glioblastoma-initiating cells

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥97%

Names and Identifiers

• Canonical Smiles: CCCC(C(CC(C)C)C(=O)NC(CCCCNC(=O)OCC1=CC=CC=C1)C(=O)NC2=NC=CS2)N(C=O)O
• IUPAC Name: benzyl N-[(5S)-5-[[(2R,3S)-3-[formyl(hydroxy)amino]-2-(2-methylpropyl)hexanoyl]amino]-6-oxo-6-(1,3-thiazol-2-ylamino)hexyl]carbamate
• InChIKey: SKJLITFHSZNZMQ-SGNDLWITSA-N
• INCHI: 1S/C28H41N5O6S/c1-4-10-24(33(38)19-34)22(17-20(2)3)25(35)31-23(26(36)32-27-29-15-16-40-27)13-8-9-14-30-28(37)39-18-21-11-6-5-7-12-21/h5-7,11-12,15-16,19-20,22-24,38H,4,8-10,13-14,17-18H2,1-3H3,(H,30,37)(H,31,35)(H,29,32,36)/t22-,23+,24+/m1/s1
• Isomeric SMILES: CCC[C@@H]([C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)NC2=NC=CS2)N(C=O)O
• PubChem CID: 91885425
• Molecular Weight: 575.72

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: N-acyl-alpha amino acids and derivatives Alpha amino acid amides Beta amino acids and derivatives Benzyloxycarbonyls N-arylamides N-acyl amines Thiazoles Heteroaromatic compounds Carbamate esters Secondary carboxylic acid amides Organic carbonic acids and derivatives Hydroxamic acids Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hybrid peptide - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Beta amino acid or derivatives - Benzyloxycarbonyl - Alpha-amino acid or derivatives - N-substituted-alpha-amino acid - N-arylamide - Fatty acyl - Benzenoid - N-acyl-amine - Fatty amide - Monocyclic benzene moiety - Heteroaromatic compound - Carbamic acid ester - Thiazole - Azole - Secondary carboxylic acid amide - Carbonic acid derivative - Hydroxamic acid - Carboxamide group - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
• 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

Chemical and Physical Properties

• Solubility: DMSO : 125 mg/mL (217.12 mM; ultrasonic and warming and heat to 60°C)
• Molecular Weight: 575.700 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 575.278 Da
• Monoisotopic Mass: 575.278 Da
• Topological Polar Surface Area: 178.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 782.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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