Binding and permeabilization of lipid bilayers by natural and synthetic 3-alkylpyridinium polymers

Grandič, Marjana; Zovko, Ana; Frangež, Robert; Turk, Tom; Sepčić, Kristina

doi:10.1016/j.bmc.2012.01.027

Cited by 14 publications

(12 citation statements)

References 34 publications

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“…Their length depended on the time of irradiation [28,29]. Interestingly, the critical micelle concentration of selected sAPS (APS7, APS8 and APS12-2) was found to be above 1 mg/mL [31], e.g., considerably higher than that determined for natural poly-APS [5]. …”

Section: Synthetic Analogues Of Polymeric Alkylpyridinium Saltsmentioning

confidence: 99%

“…The hemolytic activity for both is directly proportional to the length of the alkyl chain and the degree of polymerization [34,35]. The hemolytic activity of analogues with low molecular weights is very low or negligible [28,29,31]. The nature of the counter ion does not influence the hemolytic activity [29].…”

Section: Biological Activities Of Sapsmentioning

confidence: 99%

“…Since the latter can be produced at plasma potassium concentrations above 10 mM [43,44,45], the cardiotoxic effects of APS12-2 may be related to its hemolytic activity and hyperkalemia (10.44 ± 0.44 mM) [8,31]. Respiratory arrest could be produced by the stimulation of juxtapulmonary capillary receptors in lung parenchyma [46,47].…”

Section: Toxicity Of Aps12-2 and Aps3mentioning

confidence: 99%

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Pathophysiological Effects of Synthetic Derivatives of Polymeric Alkylpyridinium Salts from the Marine Sponge, Reniera sarai

Grandič

Frangež

2014

Marine Drugs

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Polymeric 3-alkylpyridinium salts (poly-APS) are among the most studied natural bioactive compounds extracted from the marine sponge, Reniera sarai. They exhibit a wide range of biological activities, and the most prominent among them are the anti-acetylcholinesterase and membrane-damaging activity. Due to their membrane activity, sAPS can induce the lysis of various cells and cell lines and inhibit the growth of bacteria and fungi. Because of their bioactivity, poly-APS are possible candidates for use in the fields of medicine, pharmacy and industry. Due to the small amounts of naturally occurring poly-APS, methods for the synthesis of analogues have been developed. They differ in chemical properties, such as the degree of polymerization, the length of the alkyl chains (from three to 12 carbon atoms) and in the counter ions present in their structures. Such structurally defined analogues with different chemical properties and degrees of polymerization possess different levels of biological activity. We review the current knowledge of the biological activity and toxicity of synthetic poly-APS analogues, with particular emphasis on the mechanisms of their physiological and pharmacological effects and, in particular, the mechanisms of toxicity of two analogues, APS12-2 and APS3, in vivo and in vitro.

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Section: Synthetic Analogues Of Polymeric Alkylpyridinium Saltsmentioning

confidence: 99%

Section: Biological Activities Of Sapsmentioning

confidence: 99%

Section: Toxicity Of Aps12-2 and Aps3mentioning

confidence: 99%

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Pathophysiological Effects of Synthetic Derivatives of Polymeric Alkylpyridinium Salts from the Marine Sponge, Reniera sarai

Grandič

Frangež

2014

Marine Drugs

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“…Given the role of AChE in the settlement of invertebrate biofouling organisms, the inhibition of AChE enzymatic activity has been used as a sensitive indicator of antifouling efficacy for diverse compounds, including territrem derivatives from the marine-derived fungus Aspergillus terreus SCSGAF0162 [ 29 ], pulmonarins A and B from the sub-Arctic ascidian Synoicum pulmonaria [ 30 , 31 ], and 3-alkylpyridinium oligomers and polymers (3-APS) as cholinergic antagonists [ 32 ]. Inhibition of AChE activity interrupts cholinergic signaling, thereby blocking neurotransmission and reducing the success of settlement of fouling organisms.…”

Section: Antifouling Compounds With Proposed Specific Targetsmentioning

confidence: 99%

“…Antifouling compounds, such as polygodial from the canelo tree Drimys winteri [ 65 , 66 ], synthetic 3-alkylpyridinium oligomers and polymers (3-APS) [ 32 ] and linoleic acid from the semi-evergreen plant Dryopteris crassirhizoma [ 67 ], show surfactant properties known to disrupt or solubilize the cell membrane of fouling organisms. In addition, cationic antifouling chemicals can interact with negatively-charged bacterial cells to cause lysis of cell membranes and leakage of cellular contents [ 57 , 58 , 60 , 68 , 69 , 70 ].…”

Section: Antifouling Compounds With Proposed General Targetsmentioning

confidence: 99%

Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012

Chen

Qian

2017

Marine Drugs

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Better understanding of the mechanisms of antifouling compounds is recognized to be of high value in establishing sensitive biomarkers, allowing the targeted optimization of antifouling compounds and guaranteeing environmental safety. Despite vigorous efforts to find new antifouling compounds, information about the mechanisms of antifouling is still scarce. This review summarizes the progress into understanding the molecular mechanisms underlying antifouling activity since 2012. Non-toxic mechanisms aimed at specific targets, including inhibitors of transmembrane transport, quorum sensing inhibitors, neurotransmission blockers, adhesive production/release inhibitors and enzyme/protein inhibitors, are put forward for natural antifouling products or shelf-stable chemicals. Several molecular targets show good potential for use as biomarkers in future mechanistic screening, such as acetylcholine esterase for neurotransmission, phenoloxidase/tyrosinase for the formation of adhesive plaques, N-acyl homoserine lactone for quorum sensing and intracellular Ca2+ levels as second messenger. The studies on overall responses to challenges by antifoulants can be categorized as general targets, including protein expression/metabolic activity regulators, oxidative stress inducers, neurotransmission blockers, surface modifiers, biofilm inhibitors, adhesive production/release inhibitors and toxic killing. Given the current situation and the knowledge gaps regarding the development of alternative antifoulants, a basic workflow is proposed that covers the indispensable steps, including preliminary mechanism- or bioassay-guided screening, evaluation of environmental risks, field antifouling performance, clarification of antifouling mechanisms and the establishment of sensitive biomarkers, which are combined to construct a positive feedback loop.

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Alkyl 2-furoates obtained by green chemistry procedures as suitable new antifoulants for marine protective coatings

et al. 2018

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Binding and permeabilization of lipid bilayers by natural and synthetic 3-alkylpyridinium polymers

Cited by 14 publications

References 34 publications

Pathophysiological Effects of Synthetic Derivatives of Polymeric Alkylpyridinium Salts from the Marine Sponge, Reniera sarai

Pathophysiological Effects of Synthetic Derivatives of Polymeric Alkylpyridinium Salts from the Marine Sponge, Reniera sarai

Review on Molecular Mechanisms of Antifouling Compounds: An Update since 2012

Alkyl 2-furoates obtained by green chemistry procedures as suitable new antifoulants for marine protective coatings

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