Abstract
Polymeric 3-alkylpyridinium salts (poly-APS) present in the marine sponge Reniera sarai show a broad spectrum of biological activities. They are lytic to erythrocytes and various other mammalian cells, enabling the transfection of the latter with alien DNA. Furthermore, they show inhibitory effects to marine bacteria and can inhibit fouling of micro- and macroorganisms to submerged surfaces. Finally, poly-APS act as potent cholinesterase inhibitors. The kinetics of acetylcholinesterase inhibition by poly-APS in vitro is complex and comprises several successive phases ending in irreversible inhibition of the enzyme. The latter is accounted for by aggregation and precipitation of the enzyme-inhibitor complexes. Poly-APS are lethal to rats in concentrations above 2.7 mg/kg. Monitoring of the basic vital functions and histopathological analysis showed that the effects directly ascribable to acetylcholinesterase inhibition are only observed after application of lower concentrations of poly-APS. At higher concentrations, such effects were masked by other, more pronounced and faster developing lethal effects of the toxin, such as haemolysis and platelet aggregation.
Highlights
Oligomeric and polymeric 3-alkylpyridiniums and 3-alkylpyridines comprise a group of biologically active compounds found in several sponges of the order Haplosclerida [1,2,3,4]
The aim of this review is to summarize current knowledge on the biological activity and toxicity of poly-APS, with particular emphasis on mechanisms of poly-APS toxicity in vivo, and to correlate their structural characteristics and behaviour in aqueous solution with their observed biological effects
Around 30 and 50 structurally different 3-alkylpyridinium and 3-alkylpyridine compounds have been isolated, respectively, from marine sponges. They occur mainly in sponges belonging to the order Haplosclerida, and can be used as chemical markers for the determination of haplosclerid sponges. 3-Alkylpyridinium and 3-alkylpyridine compounds and their biological activities have been described in detail in several reviews [1,2,3,4]
Summary
Oligomeric and polymeric 3-alkylpyridiniums and 3-alkylpyridines comprise a group of biologically active compounds found in several sponges of the order Haplosclerida [1,2,3,4]. At concentrations of more than 0.23 mg/mL they form large supramolecular aggregates with an average hydrodynamic radius of 23±2 nm [5]. This behaviour resembles that of other structurally related cationic detergents like cetylpyridinium chloride (CPC) and cetyltrimethylammonium bromide (CTAB) [6]. The concentrations of poly-APS that produce biological effects are far below their aggregation point, strongly suggesting that the observed activities are properties of the monomolecular form of the compounds. The aim of this review is to summarize current knowledge on the biological activity and toxicity of poly-APS, with particular emphasis on mechanisms of poly-APS toxicity in vivo, and to correlate their structural characteristics and behaviour in aqueous solution with their observed biological effects
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