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61714-27-0

61714-27-0 structure
61714-27-0 structure
  • Name: W-7 hydrochloride
  • Chemical Name: N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide,hydrochloride
  • CAS Number: 61714-27-0
  • Molecular Formula: C16H22Cl2N2O2S
  • Molecular Weight: 377.329
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-12-03 15:08:43
  • Modify Date: 2024-01-27 18:43:08
  • W-7 hydrochloride is a selective calmodulin antagonist. W-7 hydrochloride inhibits the Ca2+-calmodulin-dependent phosphodiesterase and myosin light chain kinase with IC50 values of 28 μM and 51 µM, respectively[1][2]. W-7 hydrochloride induces apoptosis and has antitumor activity[3].
Name N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide,hydrochloride
Synonyms W-7
n-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide hydrochloride
1-Naphthalenesulfonamide, N-(6-aminohexyl)-5-chloro-, hydrochloride (1:1)
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide,HCl
W-7 HYDROCHLORIDE
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride (1:1)
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide monohydrochloride
MFCD00012559
L66J BSWM6Z GG &&HCl
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride
N-(6-aminohexyl)-1-naphthalene sulfonamide hydrochloride
N-(6-Aminohexyl)-5-chloro-1-naphthalenesulfonamide, hydrochloride (1:1)
N-(6-Aminohexyl)-5-chloronaphthalene-1-sulfonamide hydrochloride (1:1)
Description W-7 hydrochloride is a selective calmodulin antagonist. W-7 hydrochloride inhibits the Ca2+-calmodulin-dependent phosphodiesterase and myosin light chain kinase with IC50 values of 28 μM and 51 µM, respectively[1][2]. W-7 hydrochloride induces apoptosis and has antitumor activity[3].
Related Catalog
Target

IC50: 28 μM (Phosphodiesterase) and 51 µM (Myosin light chain kinase)[1]

In Vitro W-7 is distributed mainly in the cytoplasm, and inhibits proliferation of Chinese hamster ovary K1 (CHO-K1) cells. W-7 selectively blocks the phase of the cell cycle (G1/S boundary phase) in a manner. 25 μM W-7 arrests the growth of the cells at the G1/S boundary phase of the cell cycle[1]. W-7 (100 μM) exhibits a similar extent of antagonism between the contractile responses to carbachol and KCl. The increase in myosin light chain (P-LC) phosphate content in response to 1-min stimulation with 10 μM carbachol is inhibited by W-7. W-7 antagonizes the smooth muscle contraction through the inhibition of the initial increase in the P-LC phosphorylation[2]. Treatment with W-7 results in the dose-dependent inhibition of cell proliferation in various human multiple myeloma cell lines. W-7 induces G1 phase cell cycle arrest by downregulating cyclins and upregulating p21cip1. W-7 induces apoptosis via caspase activation; this occurred partly through the elevation of intracellular calcium levels and mitochondrial membrane potential depolarization and through inhibition of the STAT3 phosphorylation and subsequent downregulation of Mcl-1 protein[3]. W-7 competitively inhibits Ca2+/calmodulin-dependent phosphodiesterase with a Ki value of 300 μM[4].
In Vivo W-7 (3 mg/kg; intraperitoneal injection; on 5 consecutive days per week; female BALB/c nu mice) treatment significantly reduces tumor growth in a murine MM model[3]. Animal Model: Female BALB/c nu mice (6-week-old) injected with RPMI 8226 cells[3] Dosage: 3 mg/kg Administration: Intraperitoneal injection; on 5 consecutive days per week Result: Significantly reduced tumor growth in a murine MM model.
References

[1]. H Hidaka, et al. N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide, a Calmodulin Antagonist, Inhibits Cell Proliferation. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4354-7.

[2]. M Asano. Divergent Pharmacological Effects of Three Calmodulin Antagonists, N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide (W-7), Chlorpromazine and Calmidazolium, on Isometric Tension Development and Myosin Light Chain Phosphorylation in Intact Bovine Tracheal Smooth Muscle. J Pharmacol Exp Ther. 1989 Nov;251(2):764-73.

[3]. H Itoh, et al. Direct Interaction of Calmodulin Antagonists With Ca2+/calmodulin-dependent Cyclic Nucleotide Phosphodiesterase. J Biochem. 1984 Dec;96(6):1721-6.

[4]. Shigeyuki Yokokura, et al. Calmodulin Antagonists Induce Cell Cycle Arrest and Apoptosis in Vitro and Inhibit Tumor Growth in Vivo in Human Multiple Myeloma. BMC Cancer. 2014 Nov 26;14:882.
Boiling Point 518.8ºC at 760 mmHg
Melting Point 220-222 °C
Molecular Formula C16H22Cl2N2O2S
Molecular Weight 377.329
Flash Point 267.6ºC
Exact Mass 376.077911
PSA 80.57000
LogP 6.26460
Storage condition −20°C
Water Solubility methanol: 25 mg/mL, clear, colorless
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS QK0786000

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