Hydrophilic carotenoids: surface properties and aggregation behavior of a highly unsaturated carotenoid lysophospholipid

Foss, Bjarne A.; Sliwka, Hans‐Richard; Partali, Vassilia; Naess, Stine Nalum; Elgsaeter, Arnljot; Melø, Thor-Bernt; Naqvi, K. Razi

doi:10.1016/j.chemphyslip.2004.12.008

Cited by 26 publications

(22 citation statements)

References 60 publications

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“…[41][42][43] Recently, a wide range of novel water-soluble and waterdispersible [44] carotenoid derivatives were synthesized. [45] The physical properties (i.e., surface tension, critical micelle concentration (cmc), aggregate size) of some of these compounds have been measured: 1) monopolar zwitterionic carotenoid lysophosphatidylcholine "Carp" 2; [38,39] 2) monopolar cationic oxime hydrochloride "Carox" 3; 3) dianionic bolaamphiphile Cardax "Card" 4; [40,46] 4) tetracationic bolaamphiphilic astaxanthin/lysine conjugate "Asly" 9.…”

Section: Introductionmentioning

confidence: 99%

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Sliwka

Melø

Foss

et al. 2007

Chemistry A European J

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The antioxidant activities-expressed as the electron-donating properties-of five hydrophilic carotenoids (carotenoid surfactants) and three related hydrophobic carotenoids were investigated by flash photolysis. The electron-transfer rates of the carotenoids to the triplet state of the sensitizer 2-nitronaphthalene and the energy transfer rates of triplet 2-nitronaphthalene to the carotenoids were determined. The results demonstrate that the electron-donating effects of the hydrophilic and hydrophobic carotenoids were comparable when evaluated in acetonitrile. In the presence of water, however, electron transfer (i.e., antioxidant efficiency) was enhanced by a factor of four for the hydrophilic carotenoids. The increased hydrophilicity of carotenoids, therefore, could expand their antioxidant properties, thus facilitating their use as aqueous-phase radical scavengers. At the same time, it was shown that supramolecular assembly ("aggregation") of the amphiphilic carotenoids prevented electron transfer, thus deactivating the antioxidant function. Modulation of the biophysical properties of carotenoids through synthetic modification is capable of increasing the biological and medical utility of this natural class of predominantly hydrophobic antioxidant compound.

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Section: Introductionmentioning

confidence: 99%

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Sliwka

Melø

Foss

et al. 2007

Chemistry A European J

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“…In principle, the observed optical activity of the aggregates could arise from a handed orientation of all monomers in a possibly existing unilamellar vesicle. [13,14] However, it is also possible that a few monomers first associate to give small primary units, which then constitute the supramolecular structure. To determine the origin of EOA in the aggregates, we tried to simulate the absorption and CD spectra.…”

Section: Resultsmentioning

confidence: 99%

“…[13,14] The strong absorption band of the monomeric solution observed at 445 nm in methanol (p-p* transitions of the polyene chain, Figure 1b), splits in water into two exciton bands, a prominent signal at 380 nm in the H-aggregate and a slightly visible shoulder at 510 nm in the J-aggregate region. [36,37] The association of Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, dynamic light scattering measurements did not detect oligomeric particles corresponding in size to the association of eight monomers. [13,14] Therefore, we define the oligomer unit as the lowest spatial extent of monomer association that displays all the spectroscopic and chiroptical properties of the aggregate. Such basic units in aggregates could possibly be compared with elementary (Bravais) units in crystals.…”

Section: Resultsmentioning

confidence: 99%

“…The chiroptical properties of (R)-5 result from the self-assembly of optically inactive monomers to give supramolecular structures. [13,14] By calculating the absorption and CD spectra of a manifold of oligomeric structures, we found that a helical oligomer composed of eight monomers may serve as a basic unit that explains satisfactorily the spectroscopic properties of (R)-5 aggregates.…”

Section: Introductionmentioning

confidence: 98%

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Optically Active Oligomer Units in Aggregates of a Highly Unsaturated, Optically Inactive Carotenoid Phospholipid

Foss

Sliwka

Partali

et al. 2005

Chemistry A European J

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Enantiomers of glycerophospholipids show low or no optical activity. Accordingly, optical activity was not observed with the R enantiomer of a highly unsaturated carotenoyl lysophospholipid in solution. In spite of this, strong Cotton effects are detected in water. The amphiphilic carotenoid-phospholipid monomers associate to form aggregates, whose optical activity is attributed to oligomeric entities. These small helical assemblies cannot exist independently. Yet, the calculated octamer represents the simplest repeating primary unit that sufficiently expresses the absorption properties and supramolecular optical activity.

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Syntheses with Carotenoids

Sliwka

Partali

2016

Carotenoids

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Hydrophilic carotenoids: surface properties and aggregation behavior of a highly unsaturated carotenoid lysophospholipid

Cited by 26 publications

References 60 publications

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Optically Active Oligomer Units in Aggregates of a Highly Unsaturated, Optically Inactive Carotenoid Phospholipid

Syntheses with Carotenoids

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