Biological Activities of Aqueous Extracts from Marine Sponges and Cytotoxic Effects of 3-Alkylpyridinium Polymers from Reniera sarai

Sepčić, Kristina; Batista, Urška; Vacelet, Jean; Maček, Peter; Turk, Tom

doi:10.1016/s0742-8413(97)85597-1

Cited by 23 publications

(28 citation statements)

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“…The mechanism of AChE inhibition is rather complex with a predominant irreversible inhibition component. A detailed mechanism of inhibition kinetics is described by Sepčić et al 21 Poly-APS are lytic for erythrocytes and some other types of cells, 10 as previously reported for the halitoxin complex. 2 The hemolytic activity of oligo-APS, which readily passed a 3000-Da cut-off ultrafiltration membrane, was very low, which is consistent with their weak AChE-inhibitory activity.…”

Section: Resultsmentioning

confidence: 86%

“…We found that aqueous extracts from the marine sponge Reniera ()Haliclona) sarai Pulitzer-Finali (Haliclonidae) possess strong anticholinesterase and hemolytic activity as well as moderate antimicrobial and cytotoxic activities. 10 In the present paper we report isolation and some structural characteristics of poly-APS (5). Isolated poly-APS are structurally related to the EGF-active factors, 1 but of a significantly higher polymerization degree and solubility in H 2 O.…”

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confidence: 91%

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Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera sarai in Aqueous Solutions

et al. 1997

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From the marine sponge Reniera sarai 3-alkylpyridinium oligomers and polymers have been isolated. 3-Alkylpyridinium polymers are potent anticholinesterase agents; in addition, they show hemolytic and cytotoxic activities. Oligomers with a molecular weight lower than 3000 Da do not possess any significant activity. We report structural characterization of 3-alkylpyridinium polymers and their behavior in aqueous solutions. We found that biologically active polymers are composed of head-to-tail 3-alkylpyridinium units. According to MALDI-TOF spectrometry two species of polymers exist, the smaller with a molecular weight of 5520 Da and the larger with a molecular weight of 18 900 Da. Both polymers are soluble only in water, while low molecular oligomers are readily soluble in organic solvents. Polymers form large water-dissolved supramolecular structures with an average hydrodynamic radius of 23 ( 2 nm and, therefore, cannot be separated with size-exclusion chromatography.Recently, several 3-alkylpyridinium compounds endowed with potent biological activities have been isolated from various marine sponges. These compounds have been described as constituted of 3-alkylpyridinium salt subunits (APS). The 3-alkyl chain is bound headto-tail to the nitrogen of the adjacent subunit as in (a) epidermal growth factor (EFG)-active factors, constituted of oligomers built on straight C 8 alkyl chains (1); 1 (b) halitoxin, built on C 8 -C 11 methyl branched alkyl chains (2); 2 (c) cyclostellettamines, composed of straight C 12 -C 15 alkyl chains (3); 3 and (d) amphitoxin, which is composed of oligomeric chains of 3-alkylpyridinium and 3-alkenylpyridinium units (4a, 4b). 4 Related to these compounds are niphatoxins, non-ring oligomers with uncharged pyridine end groups, 5 and haliclamines, trihydropyridine cyclic compounds. 6 These have been proposed as models of biogenic precursors for many complex alkaloids, such as the manzamines 7 and the petrosins, 8 all isolated from marine sponges.The isolated compounds exerted cytotoxicity towards tumor cell lines and hemolysis, 2 inhibition of the epidermal growth factor and toxicity to fish and mice, 1 inhibition of binding of methyl quinuclidinyl benzilate to muscarinic acetylcholine receptors, 3 and strong antifeeding activity. 4 3-Alkylpyridinium oligomers mimicking the EGF-active factors, with an oxygen atom in place of a methylene group in the alkyl chain, have been recently synthesized. 9 Some of these studies revealed that the higher the polymerization degree the higher were both biological activity 1,9 and hydrophilicity. 9Despite the well-defined structure of a single 3-alkylpyridinium unit, little is known about the size of 3-alkylpyridinium polymers (poly-APS) and their possible formation of supramolecular structures in aqueous solutions that might also have an impact on their biological activities. We found that aqueous extracts from the marine sponge Reniera ()Haliclona) sarai Pulitzer-Finali (Haliclonidae) possess strong anticholinesterase and hemolytic activity as well as ...

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Section: Resultsmentioning

confidence: 86%

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confidence: 91%

Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera sarai in Aqueous Solutions

et al. 1997

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“…Saponins are natural surfactants found in many plants and are able to disrupt cell membranes through cholesterol binding [18]. Polymeric alkylpyridinium salts are surfactant-like compounds isolated from the Adriatic marine sponge Reniera sarai [19], and have cytotoxic [20], haemolytic [21], and antitumour activities [22].…”

Section: Introductionmentioning

confidence: 99%

Hazardous potential of manufactured nanoparticles identified by in vivo assay

Valant

Drobne

Sepčić

et al. 2009

Journal of Hazardous Materials

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“…This includes anti-bacterial [6], anti-fouling [9,11], potent anti-acetylcholinesterase (anti-AChE) activity with a rather unusual pattern of inhibition [29] and both haemolytic [18] and cytotoxic [27] activities. In addition, it showed selective toxicity toward NSCLC cells whilst having no apparent toxicity towards normal lung fibroblast cells and tissue in vitro and in vivo [22].…”

Section: Introductionmentioning

confidence: 99%

Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins

et al. 2010

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Two new large poly-1,3-dodecylpyridinium salts, APS12 and APS12-2 of 12.5-and 14.7-kDa size, respectively, were synthesised and tested for their pore-forming and transfection capabilities in HEK 293 and undifferentiated mouse ES cells using patch-clamp recording, Ca 2+ imaging and flow cytometry. Polymerisation reactions were enhanced by microwaves, and the product sizes were controlled by altering the irradiation time. This method can also be applied to obtain polymers with variable linking chains as shown by the preparation of poly-(1,3-octylpyridinium) salt of 11.9-kDa size. Molecular weights of the final products were determined using ESIMS analysis, which also indicated the products to be amongst the largest macro-cycles ever recorded, up to a 900-membered ring. Anti-bacterial, haemolytic and anti-acetylcholinesterase activities were also reported for the two dodecyl pyridinium polymers. These biological activities are characteristic to the structurally related marine toxin, poly-APS.

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Biological Activities of Aqueous Extracts from Marine Sponges and Cytotoxic Effects of 3-Alkylpyridinium Polymers from Reniera sarai

Cited by 23 publications

References 31 publications

Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera sarai in Aqueous Solutions

Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera sarai in Aqueous Solutions

Hazardous potential of manufactured nanoparticles identified by in vivo assay

Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins

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