Prediction of Critical Micelle Concentration Using a Quantitative Structure–Property Relationship Approach

Huibers, Paul D. T.; Lobanov, Victor S.; Katritzky, Alan R.; Shah, Dinesh O.; Karelson, Mati

doi:10.1006/jcis.1996.4680

Cited by 120 publications

(96 citation statements)

References 27 publications

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“…CMC values for alkyl sulfate detergents in water at 40°C were calculated as described previously (25).…”

Section: Methodsmentioning

confidence: 99%

“…25). The slope of this relationship is proportional to the free energy contribution of transferring methylene groups from solvent to micelles (25). When measured in the presence of Assembly Buffer (without tau), the relationship between log CMC and alkyl chain length remained linear but was depressed toward lower CMCs (Fig.…”

Section: Aa-induced Tau Fibrillizationmentioning

confidence: 96%

“…4; Ref. 25). The slope of this relationship is proportional to the free energy contribution of transferring methylene groups from solvent to micelles (25).…”

Section: Aa-induced Tau Fibrillizationmentioning

confidence: 99%

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Anionic Micelles and Vesicles Induce Tau Fibrillization in Vitro

Chirita

Necula

Kuret

2003

Journal of Biological Chemistry

217

255

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Alzheimer's disease is defined in part by the intraneuronal accumulation of filaments comprised of the microtubule-associated protein tau. In vitro, fibrillization of recombinant tau can be induced by treatment with various agents, including phosphotransferases, polyanionic compounds, and fatty acids. Here we characterize the structural features required for the fatty acid class of tau fibrillization inducer using recombinant fulllength tau protein, arachidonic acid, and a series of straight chain anionic, cationic, and nonionic detergents. Induction of measurable tau fibrillization required an alkyl chain length of at least 12 carbons and a negative charge consisting of carboxylate, sulfonate, or sulfate moieties. All detergents and fatty acids were micellar at active concentrations, due to a profound, taudependent depression of their critical micelle concentrations. Anionic surfaces larger than detergent micelles, such as those supplied by phosphatidylserine vesicles, also induced tau fibrillization with resultant filaments originating from their surface. These data suggest that anionic surfaces presented as micelles or vesicles can serve to nucleate tau fibrillization, that this mechanism underlies the activity of fatty acid inducers, and that anionic membranes may serve this function in vivo.

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“…CMC values for alkyl sulfate detergents in water at 40°C were calculated as described previously (25).…”

Section: Methodsmentioning

confidence: 99%

Section: Aa-induced Tau Fibrillizationmentioning

confidence: 96%

See 1 more Smart Citation

Anionic Micelles and Vesicles Induce Tau Fibrillization in Vitro

Chirita

Necula

Kuret

2003

Journal of Biological Chemistry

217

255

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“…The slope of this relationship is proportional to the free energy contribution of transferring methylene groups from solvent to micelles (49). When measured in the presence of assembly buffer (without ␣-synuclein), the relationship between log CMC and alkyl chain length remained linear but was depressed (relative to values measured in water) because of the presence of neutral electrolyte (100 mM NaCl) in the buffer (50).…”

Section: Efficient Induction Of ␣-Synucleinmentioning

confidence: 99%

“…CMC and alkyl chain length when analyzed in water (49). The slope of this relationship is proportional to the free energy contribution of transferring methylene groups from solvent to micelles (49).…”

Section: Efficient Induction Of ␣-Synucleinmentioning

confidence: 99%

Rapid Anionic Micelle-mediated α-Synuclein Fibrillization in Vitro

Necula¹,

Chirita²,

Kuret

2003

Journal of Biological Chemistry

198

206

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Parkinson's disease is characterized by the aggregation of ␣-synuclein into filamentous forms within affected neurons of the basal ganglia. Fibrillization of purified recombinant ␣-synuclein is inefficient in vitro but can be enhanced by the addition of various agents including glycosaminoglycans and polycations. Here we report that fatty acids and structurally related anionic detergents greatly accelerate fibrillization of recombinant ␣-synuclein at low micromolar concentrations with lag times as short as 11 min and apparent first order growth rate constants as fast as 10.4 h ؊1 . All detergents and fatty acids were micellar at active concentrations because of an ␣-synuclein-dependent depression of their critical micelle concentrations. Other anionic surfaces, such as those supplied by anionic phospholipid vesicles, also induced ␣-synuclein fibrillization, with resultant filaments originating from their surface. These data suggest that anionic surfaces presented as micelles or vesicles can serve to nucleate ␣-synuclein fibrillization, that this mechanism underlies the inducer activity of anionic surfactants, and that anionic membranes may serve this function in vivo.

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A Comprehensive QSAR Treatment of the Genotoxicity of Heteroaromatic and Aromatic Amines

Maran

Karelson

Katritzky³

1999

Quant. Struct.-Act. Relat.

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A quantitative structure-activity relationship with R 2 0X8344 R 0X9135 has been derived from a set of 95 heteroaromatic and aromatic amines to correlate and predict their mutagenic activity. It consists of six descriptors calculated from the molecular structures with quantumchemical methods. The descriptors in the model reveal the importance in mutagenic interactions of heteroaromatic amines of hydrogen bonding, of effects induced by the solvent, and of the size of compound. The model also suggests that the amino group is critical for the reactive site.

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Prediction of Critical Micelle Concentration Using a Quantitative Structure–Property Relationship Approach

Cited by 120 publications

References 27 publications

Anionic Micelles and Vesicles Induce Tau Fibrillization in Vitro

Anionic Micelles and Vesicles Induce Tau Fibrillization in Vitro

Rapid Anionic Micelle-mediated α-Synuclein Fibrillization in Vitro

A Comprehensive QSAR Treatment of the Genotoxicity of Heteroaromatic and Aromatic Amines

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