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A3281

Sigma-Aldrich

N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride

Synonym(s):

W-7

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About This Item

Empirical Formula (Hill Notation):
C16H21ClN2O2S · HCl
CAS Number:
61714-27-0
Molecular Weight:
377.33
Beilstein/REAXYS Number:
6030174
MDL number:
MFCD00012559
UNSPSC Code:
12352200
PubChem Substance ID:
24278067
NACRES:
NA.77

form

powder

Quality Level

200

mode of action

cell membrane | interferes
enzyme | inhibits

storage temp.

−20°C

SMILES string

Cl[H].NCCCCCCNS(=O)(=O)c1cccc2c(Cl)cccc12

InChI

1S/C16H21ClN2O2S.ClH/c17-15-9-5-8-14-13(15)7-6-10-16(14)22(20,21)19-12-4-2-1-3-11-18;/h5-10,19H,1-4,11-12,18H2;1H

InChI key

OMMOSRLIFSCDBL-UHFFFAOYSA-N

Gene Information

human ... CAMK2A(815) , CAMK2B(816)

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Application

N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride has been used to study its effect of on coated pit staining.

Biochem/physiol Actions

N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide (W-7) is a calmodulin antagonist. It can prevent calcium-dependent protein kinase, that is sensitive to phospholipid.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Osawa et al.
FEBS letters, 442(2-3), 173-177 (1999-02-03)
Small-angle X-ray scattering and nuclear magnetic resonance were used to investigate the structural change of calcium-bound calmodulin (Ca2+/CaM) in solution upon binding to its antagonist, N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide (W-7). The radius of gyration was 17.4+/-0.3 A for Ca2+/CaM-W-7 with a molar ratio
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide (W-7), a calmodulin antagonist, also inhibits phospholipid sensitive calcium-dependent protein kinase
Schatzman RC, et al.
Biochimica et biophysica acta. General subjects, 755(1), 144-147 (1983)
L H Wang et al.
The Journal of cell biology, 123(5), 1107-1117 (1993-12-01)
The clathrin-coated pit lattice is held onto the plasma membrane by an integral membrane protein that binds the clathrin AP-2 subunit with high affinity. In vitro studies have suggested that this protein controls the assembly of the pit because membrane
Valentin Jaumouillé et al.
Channels (Austin, Tex.), 5(4), 308-313 (2011-06-10)
NHE3 is regulated via alterations in membrane surface charge. This is achieved through altered binding of cationic regions in the cytosolic-terminus of the exchanger with the inner leaflet of the plasma membrane. Calmodulin antagonists, including W-7, regulate surface potential and
Matteo Coen et al.
The American journal of pathology, 183(3), 996-1009 (2013-07-11)
Several observations suggest the expansion of a distinct medial smooth muscle cell (SMC) subset in atherosclerosis and restenosis. We characterized the phenotypic features of SMC subsets in cultures derived from human carotid endarterectomy specimens. Specimens comprised an undiseased portion (thin
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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