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Merck
CN

S6951

Surfen hydrate

≥98% (HPLC), Heparan sulfate antagonist, powder

Synonym(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

Empirical Formula (Hill Notation):
C21H20N6O · xH2O
CAS Number:
1241801-02-4
Molecular Weight:
372.42 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329824572
NACRES:
NA.77
MDL number:
MFCD17215963

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Product Name

Surfen hydrate, ≥98% (HPLC)

SMILES string

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

InChI key

UXYZYUHSZVKWTR-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

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.

Biochem/physiol Actions

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.
Surfen is a heparan sulfate antagonist.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000124185
0000127288
0000088640
0000088639
0000061156

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Elodie Monsellier et al.
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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)
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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
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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.
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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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