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S6951

Sigma-Aldrich

Surfen hydrate

≥98% (HPLC)

Synonyme(s) :

(bis-2-methyl-4-amino-quinolyl-6-carbamide hydrate, 1,3-Bis(4-amino-2-methyl-6-quinolyl)urea hydrate, Aminokinuride, Aminoquincarbamide, Aminoquinuride, N,N′-Bis(4-amino-2-methyl-6-quinolyl)urea, NSC 12155

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About This Item

Formule empirique (notation de Hill):
C21H20N6O · xH2O
Numéro CAS:
1241801-02-4
Poids moléculaire :
372.42 (anhydrous basis)
Numéro MDL:
MFCD17215963
Code UNSPSC :
12352200
ID de substance PubChem :
329824572
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

O.Cc1cc(N)c2cc(NC(=O)Nc3ccc4nc(C)cc(N)c4c3)ccc2n1

InChI

1S/C21H20N6O.H2O/c1-11-7-17(22)15-9-13(3-5-19(15)24-11)26-21(28)27-14-4-6-20-16(10-14)18(23)8-12(2)25-20;/h3-10H,1-2H3,(H2,22,24)(H2,23,25)(H2,26,27,28);1H2

Clé InChI

UXYZYUHSZVKWTR-UHFFFAOYSA-N

Application

Surfen hydrate may be used as an antagonist to heparin.
Surfen hydrate has been used in the inhibition of multiple voltage-gated calcium channels in human embryonic kidney cells.

Actions biochimiques/physiologiques

Surfen is a heparan sulfate antagonist, originally developed in the late thirties as an excipient for the production of depot insulin. Heparan sulfate (HS) is structurally related to heparin but contains fewer sulfate groups per disaccharide, and it exists almost exclusively attached to protein cores of proteoglycans, which cells either display on the plasma membrane or secrete into the extracellular matrix. Surfen binds to the chains of glycosaminoglycan (GAG)/HS and prevents binding of the enzymes and proteins thus act as HS antagonist. Surfen is more potent than protamine, a clinically used heparin antagonist.

Mentions de danger

H413

Conseils de prudence

P273 - P501

Classification des risques

Aquatic Chronic 4

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Elodie Monsellier et al.
PloS one, 15(8), e0237328-e0237328 (2020-08-14)
α-Synuclein (αSyn) fibrils spread from one neuronal cell to another. This prion-like phenomenon is believed to contribute to the progression of the pathology in Parkinson's disease and other synucleinopathies. The binding of αSyn fibrils originating from affected cells to the
urfen is a broad-spectrum calcium channel inhibitor with analgesic properties in mouse models of acute and chronic inflammatory pain
Rivas-Ramirez P, et al.
Pflugers Archiv : European Journal of Physiology, 469, 1325-1334 (2017)
Carl W White et al.
iScience, 24(1), 102011-102011 (2021-01-26)
Secreted chemokines are critical mediators of cellular communication that elicit intracellular signaling by binding membrane-bound receptors. Here we demonstrate the development and use of a sensitive real-time approach to quantify secretion and receptor binding of native chemokines in live cells
Sapthaswaran Veerapathiran et al.
eLife, 9 (2020-11-26)
Wnt3 proteins are lipidated and glycosylated signaling molecules that play an important role in zebrafish neural patterning and brain development. However, the transport mechanism of lipid-modified Wnts through the hydrophilic extracellular environment for long-range action remains unresolved. Here we determine
Anne Marie W Bartosch et al.
Scientific reports, 11(1), 11386-11386 (2021-06-02)
This study aimed to clarify the role of glypican-1 and PECAM-1 in shear-induced nitric oxide production in endothelial cells. Atomic force microscopy pulling was used to apply force to glypican-1 and PECAM-1 on the surface of human umbilical vein endothelial
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