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A3281 Sigma

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

Synonym: W-7

  • CAS Number 61714-27-0

  • Empirical Formula (Hill Notation) C16H21ClN2O2S · HCl

  • Molecular Weight 377.33

  •  Beilstein Registry Number 6030174

  •  MDL number MFCD00012559

  •  PubChem Substance ID 24278067

  • Popular Documents:  RAMAN FTIR (PDF)  

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Description

Biochem/physiol Actions

A calmodulin antagonist; inhibits Ca2+/calmodulin activated phosphodiesterase and myosin light chain kinase.

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<I>N</I>-<WBR>(4-<WBR>Aminobutyl)<WBR>-<WBR>2-<WBR>naphthalenesulfonamide hydrochloride

analytical standard, for drug analysis

Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Discover Bioactive Small Molecules for Cyclic Nucleotides

Transmission of an extracellular signal across the cell membrane is initiated by activation of many types of hormone and neurotransmitter receptors, such as G-protein coupled receptors (GPCRs), and c...
Keywords: Antivirals, Cancer, Cardiovascular, Cellular processes, Diabetes, Diseases, Hormones, Neurotransmitters

Peer-Reviewed Papers

References

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Identification of a calmodulin-binding domain in Sema4D that regulates its exodomain shedding in platelets. Mou P, Zeng Z, Li Q, et al. Blood 121(20), 4221-30, (2013)

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Ca(2+)-related signaling and protein phosphorylation abnormalities play central roles in a new experimental model of electrical storm. Tsuji Y, Hojo M, Voigt N, et al. Circulation 123(20), 2192-203, (2011)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Calcium/calmodulin and cAMP/protein kinase-A pathways regulate sperm motility in the stallion. Lasko J, Schlingmann K, Klocke A, et al. Anim. Reprod. Sci. 132(3-4), 169-77, (2012)

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Characterization and expression of calmodulin gene during larval settlement and metamorphosis of the polychaete Hydroides elegans. Chen ZF, Wang H, and Qian PY Comp. Biochem. Physiol. B Biochem. Mol. Biol. 162(4), 113-9, (2012)

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Evidence for calmodulin inter-domain compaction in solution induced by W-7 binding. Osawa, M., et al. FEBS Lett. 442, 173-177, (1999)

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Interactions of Bordetella pertussis adenylyl cyclase toxin CyaA with calmodulin mutants and calmodulin antagonists: comparison with membranous adenylyl cyclase I. Schuler D, Lübker C, Lushington GH, et al. Biochem. Pharmacol. 83(7), 839-48, (2012)

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Calcium-calmodulin and pH regulate protein tyrosine phosphorylation in stallion sperm. González-Fernández L, Macías-García B, Velez IC, et al. Reproduction 144(4), 411-22, (2012)

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Relevance of calmodulin/CaMKII activation for arrhythmogenesis in the AV block dog. Bourgonje VJ, Schoenmakers M, Beekman JD, et al. Heart Rhythm 9(11), 1875-83, (2012)

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Electromagnetic fields instantaneously modulate nitric oxide signaling in challenged biological systems. Pilla AA Biochem. Biophys. Res. Commun. 426(3), 330-3, (2012)

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The chloroplast calcium sensor CAS is required for photoacclimation in Chlamydomonas reinhardtii. Petroutsos D, Busch A, Janssen I, et al. Plant Cell 23(8), 2950-63, (2011)

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Multidirectional effects of calmodulin kinase II on transmitter release in mature and newly formed mouse motor synapses. Bogatcheva PO and Balezina OP Bull. Exp. Biol. Med. 154(3), 316-9, (2013)

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[Effect of inhibitors serine/threonine protein kinases and protein phosphatases on mitosis progression of synchronized tobacco by-2 cells]. Sheremet IaA, Emets AI, Azmi A, et al. Tsitol. Genet. 46(2), 3-11, (2012)

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[In vitro effect of N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide on differentiation from human adipose-derived mesenchymal stem cells to endothelial cells]. Zhai YJ, Chen J, Zhang HG, et al. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 33(3), 306-12, (2011)

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Potassium channel mutant KCNJ5 T158A expression in HAC-15 cells increases aldosterone synthesis. Oki K, Plonczynski MW, Luis Lam M, et al. Endocrinology 153(4), 1774-82, (2012)

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Calmodulin-sensitive adenylyl cyclases mediate AVP-dependent cAMP production and Cl- secretion by human autosomal dominant polycystic kidney cells. Pinto CS, Reif GA, Nivens E, et al. Am. J. Physiol. Renal Physiol. 303(10), F1412-24, (2012)

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A novel calmodulin-like protein from the liver fluke, Fasciola hepatica. Russell SL, McFerran NV, Moore CM, et al. Biochimie 94(11), 2398-406, (2012)

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Calmodulin expression distinguishes the smooth muscle cell population of human carotid plaque. Coen M, Marchetti G, Palagi PM, et al. Am. J. Pathol. 183(3), 996-1009, (2013)

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Modulation of Ca2+ channel-gated Ca2+ release by W-7 in cardiac myocytes. Suzuki, Y.J., et al. Cell Calcium 25, 191-198, (1999)

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Ca2+ signaling regulates ecmB expression, cell differentiation and slug regeneration in Dictyostelium. Poloz Y and O'Day DH Differentiation 84(2), 163-75, (2012)

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Roles of osmolality, calcium - Potassium antagonist and calcium in activation and flagellar beating pattern of sturgeon sperm. Alavi SM, Gela D, Rodina M, et al. Comp. Biochem. Physiol. A. Mol. Integr. Physiol. 160(2), 166-74, (2011)

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Deletion of the calmodulin-binding domain of Grb7 impairs cell attachment to the extracellular matrix and migration. García-Palmero I and Villalobo A Biochem. Biophys. Res. Commun. 436(2), 271-7, (2013)

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Calmodulin protects androgen receptor from calpain-mediated breakdown in prostate cancer cells. Sivanandam A, Murthy S, Chinnakannu K, et al. J. Cell Physiol. 226(7), 1889-96, (2011)

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The calmodulin antagonist W-7 inhibits the epithelial Na+/H+ exchanger via modulating membrane surface potential. Jaumouillé V, Krishnan D, and Alexander RT Channels (Austin.) 5(4), 308-13, (2011)

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GABA induces the differentiation of small into large cholangiocytes by activation of Ca(2+) /CaMK I-dependent adenylyl cyclase 8. Mancinelli R, Franchitto A, Glaser S, et al. Hepatology 58(1), 251-63, (2013)

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Biochemical characterization of a recombinant Swainsona canescens calcium-dependent protein kinase (ScCPK1). Srideshikan SM, Vanishree VL, and Jayabaskaran C Plant Physiol. Biochem. 54, 27-33, (2012)

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RyRCa2+ leak limits cardiac Ca2+ window current overcoming the tonic effect of calmodulinin mice. Fernández-Velasco M, Ruiz-Hurtado G, Rueda A, et al. PLoS ONE 6(6), e20863, (2011)

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Interrelationship between calmodulin (CaM) and H2O2 in abscisic acid-induced antioxidant defense in the seedlings of Panax ginseng. Parvin S, Lee OR, Sathiyaraj G, et al. Mol. Biol. Rep. 39(7), 7327-38, (2012)

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Dynamic secondary structural changes in Ca²⁺-saturated calmodulin upon interaction with the antagonist, W-7. Sasakura D, Nunomura W, and Takakuwa Y Biochem. Biophys. Res. Commun. 423(2), 360-5, (2012)

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Calmodulin and PI(3,4,5)P₃ cooperatively bind to the Itk pleckstrin homology domain to promote efficient calcium signaling and IL-17A production. Wang X, Boyken SE, Hu J, et al. Sci. Signal. 7(337), ra74, (2014)

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Platelet-derived growth factor-BB activates calcium/calmodulin-dependent and -independent mechanisms that mediate Akt phosphorylation in the neurofibromin-deficient human Schwann cell line ST88-14. Farrer RG, Farrer JR, and DeVries GH J. Biol. Chem. 288(16), 11066-73, (2013)

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A quantitative analysis to unveil specific binding proteins for bioactive compounds. Arai T, Uehata M, Akatsuka H, et al. Protein Eng. Des. Sel. 26(4), 249-54, (2013)

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Calcium-calmodulin signaling elicits mitochondrial dysfunction and the release of cytochrome c during cadmium-induced apoptosis in primary osteoblasts. Liu W, Zhao H, Wang Y, et al. Toxicol. Lett. 224(1), 1-6, (2014)

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