SC-9 - CAS 102649-78-5
Category: Inhibitor
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Molecular Formula:
C22H24ClNO2S
Molecular Weight:
401.95
COA:
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Targets:
PKC
Description:
SC-9 is a potent activator of protein kinase C in the presence of Ca2+.
Brife Description:
PKC activator
Purity:
≥99% by HPLC
Appearance:
Off-White to Pale Yellow Solid
Synonyms:
5-Chloro-N-(6-phenylhexyl)-1-naphthalenesulfonamide
MSDS:
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Melting Point:
85-86°C
InChIKey:
YUXMTDYHFPRPLG-UHFFFAOYSA-N
InChI:
InChI=1S/C22H24ClNO2S/c23-21-15-8-14-20-19(21)13-9-16-22(20)27(25,26)24-17-7-2-1-4-10-18-11-5-3-6-12-18/h3,5-6,8-9,11-16,24H,1-2,4,7,10,17H2
Canonical SMILES:
C1=CC=C(C=C1)CCCCCCNS(=O)(=O)C2=CC=CC3=C2C=CC=C3Cl
1.N-(6-phenylhexyl)-5-chloro-1-naphthalenesulfonamide, a novel activator of protein kinase C.
Ito M, Tanaka T, Inagaki M, Nakanishi K, Hidaka H. Biochemistry. 1986 Jul 29;25(15):4179-84.
Naphthalenesulfonamide derivatives were used to study the mechanism of regulation of Ca2+-dependent smooth muscle myosin light chain phosphorylation catalyzed by Ca2+-activated, phospholipid-dependent protein kinase (protein kinase C) and myosin light chain kinase. Derivatives such as N-(6-phenylhexyl)-5-chloro-1-naphthalenesulfonamide (SC-9), with a hydrophobic residue at the end of a hydrocarbon chain, stimulated Ca2+-activated, phospholipid-dependent myosin light chain phosphorylation in a Ca2+-dependent fashion. There was no significant effect of these compounds on Ca2+-calmodulin (CaM) dependent myosin light chain phosphorylation. On the other hand, derivatives with the guanidino or amino residue at the same position had an inhibitory effect on both Ca2+-phospholipid- and Ca2+-CaM-dependent myosin light chain phosphorylation. These observations suggest that activation of Ca2+-activated, phospholipid-dependent myosin light chain phosphorylation by naphthalenesulfonamide derivatives depends on the chemical structure at the end of hydrocarbon chain of each compound.
2.N-(6-phenylhexyl)-5-chloro-1-naphthalenesulfonamide is one of a new class of activators for Ca2+-activated, phospholipid-dependent protein kinase.
Nishino H, Kitagawa K, Iwashima A, Ito M, Tanaka T, Hidaka H. Biochim Biophys Acta. 1986 Nov 28;889(2):236-9.
N-(6-Phenylhexyl)-5-chloro-1-naphthalenesulfonamide (SC-9) activated Ca2+-activated, phospholipid-dependent protein kinase (protein kinase C). SC-9 acted as a substitute for phosphatidylserine, which is one of the endogenous factors in activating protein kinase C. SC-9 was also effective in regulating the physiological functions at the whole-cell level. For example, SC-9 stimulated hexose transport activity in mouse fibroblasts, a protein kinase C-regulated cellular function. Thus, SC-9 may be useful to study the molecular basis of the regulation of protein kinase C activity, and the biological significance of this enzyme.
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Chemical Structure

CAS 102649-78-5 SC-9

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