W-7

Structural formula
General
Surname	W-7
other names	N - (6-Aminohexyl) -5-chloro-1-naphthalenesulfonamide ( IUPAC ); W7;
Molecular formula	C 16 H 21 ClN 2 O 2 S
External identifiers / databases
PubChem	5681
DrugBank	DB04513
Wikidata	Q2536561
properties
Molar mass	340.87 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N - (6-Aminohexyl) -5-chloro-1-naphthalenesulfonamide , W-7 or W7 for short, is an organic- chemical compound that is derived from naphthalene . W7 is a calmodulin - antagonist which does not occur in nature, but for research into the biochemistry of cells has significance. It was synthesized for the first time in 1978. The substance is often used as a hydrochloride .

W7 binds calcium within the cells of eukaryotes (all animals and plants except bacteria and archaea ), transports it out of the cells and thus prevents the formation of the calcium-calmodulin (CaM) complex, which is necessary in the metabolism to activate many enzymes . W7 and substances with a similar effect are therefore called calmodulin antagonists , which at higher concentrations can even prevent cell division .

Structure of the ineffective W5

The almost identical W5 (or W-5 ), which only lacks the chlorine atom on the naphthalene structure, has no inhibitory effect on calmodulin.

A large number of calmodulin antagonists are used for biochemical studies of calcium-CaM-dependent signaling pathways in animals and plants, including W7, trifluoperazine ( TFP ), calmidazolium chloride and fluophenazine- N- 2-chloroethane dihydrochloride ( SKF-7171 ). For example, it has been shown that many of these substances inhibit the slowly activated ion channels in plant vacuoles . In the biochemical cell research concentrations are in the range of 250 to 600 μ M (dissolved in 0.1% DMSO - water mixture) used. The related substance N- (6-aminohexyl) -1-naphthalenesulfonamide ( W5 , W-5 ) is mostly used as a negative control for W7-dependent CaM inhibition experiments.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Gisela Skopp, Gerhard Schwenker: Synthesis of the calmodulin antagonist N- (6-aminohexyl) -5-chloro-1-naphthalenesulfonamide (W-7). In: Archives of Pharmacy . (1984) 317, 649-650; doi : 10.1002 / ardp.19843170715 (online version available as PDF)
↑ Frederick L. Crane, D. James Morre: Oxidoreduction at the Plasma Membrane: Relation to Growth and Transport , (1990), CRC Press, ISBN 0-8493-6938-X .
↑ H Hidaka, Y Sasaki, T Tanaka, T Endo, S Ohno, Y Fujii, and T Nagata: N- (6-aminohexyl) -5-chloro-1-naphthalenesulfonamide, a calmodulin antagonist, inhibits cell proliferation. In: Proc. Natl. Acad. Sci. USA (1981), Vol. 78, pp. 4354-4357; PMID 6945588 ; PMC 319788 (free full text, PDF).
↑ B. Schulz-Lessdorf, P. Dietrich I. Marten, G. Lohse, H. Busch, R. Hedrich: Coordination of plasma membrane and vacuolar membrane ion channels during stomatal movement. In: Symp. Soc. Exp. Biol. (1994) Vol. 48, pp. 99-112; PMID 7541165 .
↑ T. Romeis, P. Piedras, JD Jones: Resistance gene-dependent activation of a calcium-dependent protein kinase in the plant defense response. In: Plant. Cell. (2000) Vol. 12, pp. 803-816; PMID 10810151 .
↑ Boaz Kaplan, Olga Davydov, Heather Knight, Yael Galon, Marc R. Knight, Robert Fluhr and Hillel Fromm: Rapid Transcriptome Changes Induced by Cytosolic Ca ²⁺ Transients Reveal ABRE-Related Sequences as Ca ²⁺ -Responsive cis Elements in Arabidopsis. In: Plant. Cell. (2006), Vol. 18, pp. 2733-2748; PMID 16980540 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] Gisela Skopp, Gerhard Schwenker: Synthesis of the calmodulin antagonist N- (6-aminohexyl) -5-chloro-1-naphthalenesulfonamide (W-7). In: Archives of Pharmacy . (1984) 317, 649-650; doi : 10.1002 / ardp.19843170715 (online version available as PDF)

[3] Frederick L. Crane, D. James Morre: Oxidoreduction at the Plasma Membrane: Relation to Growth and Transport , (1990), CRC Press, ISBN 0-8493-6938-X .

[4] H Hidaka, Y Sasaki, T Tanaka, T Endo, S Ohno, Y Fujii, and T Nagata: N- (6-aminohexyl) -5-chloro-1-naphthalenesulfonamide, a calmodulin antagonist, inhibits cell proliferation. In: Proc. Natl. Acad. Sci. USA (1981), Vol. 78, pp. 4354-4357; PMID 6945588 ; PMC 319788 (free full text, PDF).

[5] B. Schulz-Lessdorf, P. Dietrich I. Marten, G. Lohse, H. Busch, R. Hedrich: Coordination of plasma membrane and vacuolar membrane ion channels during stomatal movement. In: Symp. Soc. Exp. Biol. (1994) Vol. 48, pp. 99-112; PMID 7541165 .

[6] T. Romeis, P. Piedras, JD Jones: Resistance gene-dependent activation of a calcium-dependent protein kinase in the plant defense response. In: Plant. Cell. (2000) Vol. 12, pp. 803-816; PMID 10810151 .

[7] Boaz Kaplan, Olga Davydov, Heather Knight, Yael Galon, Marc R. Knight, Robert Fluhr and Hillel Fromm: Rapid Transcriptome Changes Induced by Cytosolic Ca ²⁺ Transients Reveal ABRE-Related Sequences as Ca ²⁺ -Responsive cis Elements in Arabidopsis. In: Plant. Cell. (2006), Vol. 18, pp. 2733-2748; PMID 16980540 .