A metallomicelle enzyme model for phospholipase C catalysis and inhibition

Kriste, Angela G.; Vizitiu, Dragos; Thatcher, Gregory R. J.

doi:10.1039/cc9960000913

Cited by 10 publications

(3 citation statements)

References 9 publications

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“…Metallosurfactants are a special class of surfactants: they are amphiphilic (d- or f-block) metal complexes that show surface or interface activity . These complexes find various applications, for example, in sensing, catalysis, or enzyme mimics . In such classical metallosurfactants, a metal cation is integrated in the headgroup of a surfactant ligand or well-shielded by the presence of chelating ligands .…”

Section: Introductionmentioning

confidence: 99%

Interfacial Activity of Metal β-Diketonato Complexes: In Situ Generation of Amphiphiles by Water Coordination

et al. 2011

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Symmetric transition metal complexes of 2,4-pentanedione (acetyl acetone) are interfacially active: Spinning drop tensiometry reveals lowering of the interfacial tension at the water-organic interface, most pronounced for [Cr(acac)(3)], [Fe(acac)(3)], [Zr(acac)(4)], and [Hf(acac)(4)]. The interfacial activity is explained by the in situ generation of amphiphilic species. Based on tensiometry and (1)H and diffusion-ordered NMR spectroscopy (DOSY NMR), hydrogen bonding of the organically dissolved complexes with water, in some cases in combination with inner-sphere hydrolytic coordination, is identified as the primary origin of this amphiphilicity. The complexes are a rare example of symmetric molecules that turn amphiphilic only upon interfacial interaction with water.

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Section: Introductionmentioning

confidence: 99%

Interfacial Activity of Metal β-Diketonato Complexes: In Situ Generation of Amphiphiles by Water Coordination

et al. 2011

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“…Metallosurfactants are amphiphilic ( d - or f -block) metal complexes that show surface or interface activity or can form micellar structures . Such complexes are not only of fundamental interest, but also give rise to many applications: , The metal introduces functionality and increased reactivity into the surfactant, such that they may be used, e.g., for the formation of catalytic metallomicelles or as enzyme mimics . Conversely, they provide a means to direct metal ions toward polar/apolar solvent interfaces, enabling, for instance, catalysis at the interface, templating the formation of metal-bearing mesostructures, or the buildup of optoelectronic thin films …”

Section: Introductionmentioning

confidence: 99%

Alkylsulfides of Ag(I) and Au(I) as Metallosurfactants

et al. 2010

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Several representative, interfacially active silver(I) nitrate alkylsulfide complexes were synthesized and characterized in detail. The complexes form extended structures in the solid state and in solution. Interestingly, a two-phase approach, in which aqueous silver nitrate is combined with organically dissolved sulfides, leads to the in situ formation of the complexes at the water-organic interface and a strong reduction of the surface tension. Despite their low solubility in water or organic solvent, these complexes are capable of stabilizing eicosane emulsions and dispersions in water. Thus, these silver nitrate alkyl sulfides represent a new class of metallosurfactants in which the metal ion is crucial for the interfacial activity. Gold(I) chloride alkyl sulfides show the same effect to a lesser extent.

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“…To achieve ester hydrolysis near physiological pH, metal-complexing amphiphiles demonstrate impressive results. , These are also interesting biomimetic models of hydrolytic metalloenzymes . Coordination of the nucleophilic side chains or water molecules to the metal ion enhances their acidity, facilitating deprotanation near physiological pH and thereby accelerating reaction with electrophilic substrates, e.g., ester or phosphates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Cu(II)-Chelating Ligand Amphiphiles and Their Esterolytic Properties in Cationic Micelles

2003

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Four new tetradentate 2,6-disubstituted pyridine and tridentate 2-substituted pyridine ligands were synthesized. Two of these compounds possessed a metal ion binding subunit in the form of a 2,6-disubstituted-4-N,N'-dimethylamine pyridine moiety. Cu(2+)-complexes of these ligands incorporated in cetyltrimethylammonium bromide (CTABr) micelles speeded the cleavage of p-nitrophenyldiphenyl phosphate and p-nitrophenyl hexanoate at pH 7.6. On the basis of a kinetic version of Job plot analysis, a 1:1 ligand/Cu(2+) stoichiometry was found to be the most active species. In CTABr micelles, the pK(a) values for the Cu(2+)-coordinated hydroxyl or pendant -CH(2)OH in these ligands were between 7.8 and 7.9. The metallomicellar systems displayed catalytic (turnover) behavior in the presence of excess substrates.

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A metallomicelle enzyme model for phospholipase C catalysis and inhibition

Abstract: A CU" metallomicelle mimics phospholipase C enzymes in catalysis and inhibition of transesterification reactions of phosphate diesters.

Cited by 10 publications

References 9 publications

Interfacial Activity of Metal β-Diketonato Complexes: In Situ Generation of Amphiphiles by Water Coordination

Interfacial Activity of Metal β-Diketonato Complexes: In Situ Generation of Amphiphiles by Water Coordination

Alkylsulfides of Ag(I) and Au(I) as Metallosurfactants

Synthesis of New Cu(II)-Chelating Ligand Amphiphiles and Their Esterolytic Properties in Cationic Micelles

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