CAS Number61714-27-0
SynonymsW-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)
Molecular FormulaC16H22Cl2N2O2S
Molecular Weight340.87 (free base basis)
Purity≥98 (TLC)%
Boiling Point518.8ºC at 760 mmHg
Melting Point220-222 °C
Appearancecrystalline solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 61714-27-0 |
| Catalog No. | 2A-9070076 |
| Chinese Name | N-(6-氨基己基)-5-氯-1-萘磺酰胺盐酸盐 |
| 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) |
| Molecular Formula | C16H22Cl2N2O2S |
| Molecular Weight | 340.87 (free base basis) |
| Purity | ≥98 (TLC) |
| Boiling Point | 518.8ºC at 760 mmHg |
| Melting Point | 220-222 °C |
| Appearance | crystalline solid |
| Water Solubility | methanol: 25 mg/mL, clear, colorless |
| Storage Condition | Store in an airtight container in a cool, dry plac |
| Application | W-7 hydrochloride is a selective calmodulin antagonist. W-7 hydrochloride inhibits Ca2+-calmodulin-dependent phosphodiesterase and myosin light chain kinase with IC50 values of 28 μM and 51 μM, resp |
| PubChem ID | 519820 |
| MDL Number | MFCD00012559 |
| SMILES | [S](=O)(=O)(NCCCCCCN)c1c2c(c(ccc2)Cl)ccc1.[Cl-].[H+] |
| 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/70076_1_61714_27_0.pdf |
| Bioactivity | 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 Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Signaling Pathways >> Neuronal Signaling >> CaMK Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Signaling Pathways >> Cytoskeleton >> Myosin 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. Chemical & Physical Properties 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 InChIKey OMMOSRLIFSCDBL-UHFFFAOYSA-N SMILES Cl.NCCCCCCNS(=O)(=O)c1cccc2c(Cl)cccc12 Storage condition −20°C Water Solubility methanol: 25 mg/mL, clear, colorless |
| Use of | 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]. Properties Articles36 Name N-(6-aminohexyl)-5-chloronaphthalene-1-sulfonamide,hydrochloride Synonym More Synonyms W-7 hydrochloride Biological Activity 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 Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Signaling Pathways >> Neuronal Signaling >> CaMK Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Signaling Pathways >> Cytoskeleton >> Myosin IC50: 28 μM (Phosphodiesterase) and 51 µM (Myosin light chain kinase)[1] 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. Chemical & Physical Properties Exact Mass 376.077911 PSA 80.57000 LogP 6.26460 InChIKey OMMOSRLIFSCDBL-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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