W-7 HYDROCHLORIDE Chemical Properties

Melting point:

220-222 °C

storage temp. 

-20°C

solubility 

methanol: 25 mg/mL, clear, colorless

form 

Off-white crystalline solid

color 

White to Off-White

BRN 

6030174

InChI

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

InChIKey

OMMOSRLIFSCDBL-UHFFFAOYSA-N

SMILES

C1(C=CC=C2C(Cl)=CC=CC=12)S(=O)(=O)NCCCCCCN.Cl

CAS DataBase Reference

61714-27-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

QK0786000

F 

3-10

HS Code 

2935909099

MSDS

• Language:English Provider:SigmaAldrich

W-7 HYDROCHLORIDE Usage And Synthesis

Description

Calmodulin is a calcium-dependent protein that regulates the activity of a diverse array of enzymes, ion channels, and other proteins and thus has diverse roles in cell function. W-7 is a cell-permeable antagonist of calmodulin (K_i = 11 μM). Two molecules of W-7 bind to calcium-binding domains in each calmodulin molecule, blocking its interaction with target proteins. W-7 also associates, at lower affinities, with calcium-binding domains of other proteins, including troponin C and myosin light chain kinase (K_i = 70 and 300 μM, respectively).

Chemical Properties

White Crystalline Solid

Uses

W7 is a vascular relaxing agent which affects vascular smooth muscle actomyosin. W7, an inhibitor of actomyosin superprecipitation, produces relaxation of isolated rabbit arterial strips and antagonizes the contraction of the strips induced by various contractile agonists. W7 is also a calmodulin antagonist that binds to calmodulin and inhibits Ca2+/calmodulin-regulated enzyme activities.

Uses

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

General Description

A cell-permeable and reversible calmodulin antagonist that inhibits myosin light chain kinase (IC₅₀ = 51 μM) and Ca²⁺-calmodulin-dependent phosphodiesterase (IC₅₀ = 28 μM).

Biological Activity

Calmodulin antagonist. Inhibits Ca 2+ -calmodulin-dependent phosphodiesterase (IC 50 = 28 μ M) and myosin light chain kinase (IC 50 = 51 μ M).

Biochem/physiol Actions

Cell permeable: yes

storage

Store at RT

References

[1] G. BENAIM A V. Phosphorylation of calmodulin. Functional implications.[J]. European journal of biochemistry, 2002, 61 1: 3619-3631. DOI: 10.1046/j.1432-1033.2002.03038.x
[2] D CHIN  A R M. Calmodulin: a prototypical calcium sensor.[J]. Trends in Cell Biology, 2000, 10 8: 322-328. DOI: 10.1016/s0962-8924(00)01800-6
[3] OSAWA M, SWINDELLS M, TANIKAWA J, et al. SOLUTION NMR STRUCTURE OF CALMODULIN/W-7 COMPLEX: THE BASIS OF DIVERSITY IN MOLECULAR RECOGNITION, 30 STRUCTURES[C]. 1998: 0. DOI: 10.2210/pdb1mux/pdb
[4] H HIDAKA. N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide, a calmodulin antagonist, inhibits cell proliferation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1981, 78 7: 4354-4357. DOI: 10.1073/pnas.78.7.4354
[5] BISHOW B ADHIKARI  Kuan W. Interplay of troponin- and Myosin-based pathways of calcium activation in skeletal and cardiac muscle: the use of W7 as an inhibitor of thin filament activation.[J]. Biophysical journal, 2004, 86 1 Pt 1: 359-370. DOI: 10.1016/s0006-3495(04)74112-0
[6] RYAN M. B. HOFFMAN  Brian D S. Structure of the Inhibitor W7 Bound to the Regulatory Domain of Cardiac Troponin C[J]. Biochemistry Biochemistry, 2009, 48 24: 5541-5552. DOI: 10.1021/bi9001826

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