362330

GAG Antagonist, Surfen

The GAG Antagonist, Surfen controls the biological activity of GAG. This small molecule/inhibitor is primarily used for Activators/Inducers applications.

• Synonym(s): GAG Antagonist, Surfen, Gβγ Activator, 12155, NSC12155, bis-2-Methyl-4-amino-quinolyl-6-carbamide, diHCl, trihydrate, Glycosaminoglycans Antagonist
• Empirical Formula (Hill Notation): C₂₁H₂₀N₆O · 2HCl · 3H₂O
• Molecular Weight: 499.39
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic); protect from light
• color: white
• solubility: DMSO: 50 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C

Description

General description

A symmetrical quinolyl-urea compound that binds GAGs (glycosaminoglycans) via electrostatic interaction with the negatively charged sulfate and carboxyl moieties present in heparan sulfate (HS), heparin, and dermatan sulfate, resulting in effective blockage of GAGs interactions with their protein binding partners. Surfen is shown to effectively neutralize HS- and heparin-mediated thrombin inhibition of Factor Xa activity as well as heparin′s anti-clotting activity. Also reported to inhibit FGF2-induced Erk phosphorylation and tubulation in murine lung endothelial cultures (IC₅₀ ~5 µM), fibronectin HS-binding domain-dependent CHO cell adhesion (IC₅₀ = 3 µM), and HSV-1 infection of glucosaminyl 3-O-sulfotransferase-3A-expressing CHO cells (complete inhibition at 5 µM). Surfen analogs with improved potency may serve as promising candidates as less toxic alternatives to Protamine (Cat. No. 539122) in clinical applications.Reported to directly bind Gβγ subunit in a reversible manner, displace Gα-GDP from Gβγ, and acutely activate Gβγ signaling without Gα activation.

A symmetrical quinolyl-urea compound that binds GAGs (glycosaminoglycans) via electrostatic interaction with the negatively charged sulfate and carboxyl moieties present in heparan sulfate (HS), heparin, and dermatan sulfate, resulting in effective blockage of GAGs interactions with their protein binding partners. Surfen is shown to effectively neutralize HS- and heparin-mediated thrombin inhibition of Factor Xa activity as well as heparin′s anti-clotting activity. Also reported to inhibit FGF2-induced Erk phosphorylation and tubulation in murine lung endothelial cultures (IC₅₀ ~5 µM), fibronectin HS-binding domain-dependent CHO cell adhesion (IC₅₀ = 3 µM), and HSV-1 infection of glucosaminyl 3-O-sulfotransferase-3A-expressing CHO cells (complete inhibition at 5 µM). Surfen analogs with improved potency may serve as promising candidates as less toxic alternatives to Protamine (Cat. No. 539122) in clinical applications.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot into glass vials and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Surve, C.R., et al. 2016. Sci. Signal.9, ra22.
Schuksz, M., et al. 2008. Proc. Natl. Acad. Sci. USA105, 13074.
Hunter, D.T. Jr., and Hill, J.M. 1961. Nature191, 1378.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable