3-Alkylpyridinium Compounds as Potential Non-Toxic Antifouling Agents

Sepčić, Kristina; Turk, Tom

doi:10.1007/3-540-30016-3_4

“…3-Alkylpyridinium and 3-alkylpyridine compounds and their biological activities have been described in detail in several reviews [1–4]. The majority of these compounds are monomeric and display mainly cytotoxic and/or antibacterial activities at concentrations of a few micrograms per mL [3,4]. A smaller number of oligomeric and polymeric 3-alkylpyridinium salts have also been isolated and partially characterized.…”

Section: Biological Activity and Toxicity Of 3-alkylpyridinium Commentioning

confidence: 99%

“…A smaller number of oligomeric and polymeric 3-alkylpyridinium salts have also been isolated and partially characterized. Linear and cyclic 3-alkylpyridinium dimers and trimers are reported to be cytotoxic, antimitotic and inhibitory to muscarinic acetylcholine receptors and to some enzymes like histone deacetylase [reviewed in 3,4]. Polymeric compounds on the other hand, like halitoxins [10–12], amphitoxins [13], natural and synthetic epidermal growth factor (EGF)-active factors [14,15] and poly-APS [5] (Figure 1), show many more diverse and potent biological activities.…”

Section: Biological Activity and Toxicity Of 3-alkylpyridinium Commentioning

confidence: 99%

Mechanisms of Toxicity of 3-Alkylpyridinium Polymers from Marine Sponge Reniera sarai

Turk

¹

,

Frangež

²

,

Sepčić

³

2007

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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 enzymeinhibitor 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.

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“…They occur mainly in sponges belonging to the order Haplosclerida, and can therefore also 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]. The majority of these compounds are monomeric and display mainly cytotoxic and/or antibacterial activities at concentrations of a few micrograms per mL [3,4].…”

Section: Biological Activity and Toxicity Of 3-alkylpyridinium Compoumentioning

confidence: 99%

“…A smaller number of oligomeric and polymeric 3-alkylpyridinium salts have also been isolated and partially characterized. Linear and cyclic 3-alkylpyridinium dimers and trimers are reported to be cytotoxic, antimitotic and inhibitory to muscarinic acetylcholine receptors and to some enzymes like histone deacetylase [reviewed in 3,4]. Polymeric compounds on the other hand, like halitoxins [10][11][12], amphitoxins [13], natural and synthetic epidermal growth factor (EGF)-active factors [14,15] and poly-APS [5] (Figure 1), show many more diverse and potent biological activities.…”

Section: Biological Activity and Toxicity Of 3-alkylpyridinium Compoumentioning

confidence: 99%

“…Monomeric, 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]. In general, the variety and potency of the biological effects of these compounds increase with their degree of polymerisation, resulting in complex and unprecedented mechanisms of action and/or toxicity.…”

Section: Introductionmentioning

confidence: 99%

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Mechanisms of Toxicity of 3-Alkylpyridinium Polymers from Marine Sponge Reniera sarai

Turk

¹

2007

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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 enzymeinhibitor 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.

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