Cyclic nucleotide phosphodiesterases: Pharmacology, biochemistry and function

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Publisher Summary This chapter describes the biopharmacological basis of naphthalenesulfonamides as calmodulin (CaM) antagonists and presents guidelines for the application of these agents to various biological systems. A comparison is made in the chapter between naphthalenesulfonamides and phenothiazines as CaM antagonists. N-(6-Aminohexyl)-[3H]-5-chloro-l-naphthalenesulfonamide (W-7) binds to purified CaM from the bovin aorta or brain in the presence of 0.1 mM CaCl2 as determined by equilibrium binding techniques; however, there is no binding in the absence of calcium ion. W-7 binds to CaM at two distinctly different types of sites: a high-affinity binding site and a low-affinity binding site. The chapter discusses a study in which the actions of naphthalenesulfonamides as CaM antagonists were shown to depend both on the chlorination of the naphthalene ring and on the length of the alkyl chain. The derivative with bromine was the most potent CaM antagonist and derivatives with chlorine or fluorine were intermediate in potency. The affinity of naphthalenesulfonamide, determined by the displacement of [3H]W-7 from purified CaM using an equilibrium-binding technique and the inhibition of Ca2+-dependent cyclic nucleotide phosphodiesterase, correlated well with their potency in the relaxation of vascular strips and in the inhibition of platelet aggregation. The compound with cyanogen was the least potent. In addition, the affinity of naphthalenesulfonamide correlated well with their hydrophobicity, determined as octanol-water partition coefficients.

Naphthalenesulfonamides as calmodulin antagonists.

Effects of N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide and other calmodulin antagonists (calmodulin interacting agents) on calcium-induced contraction of rabbit aortic strips.

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Effects of N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide and other calmodulin antagonists (calmodulin interacting agents) on calcium-induced contraction of rabbit aortic strips.