Interaction of quercetin, genistein and its derivatives with lipid bilayers – An ATR IR-spectroscopic study

Cieślik-Boczula, Katarzyna; Maniewska, Jadwiga; Grynkiewicz, Grzegorz; Szeja, W.; Koll, A.; Hendrich, Andrzej B.

doi:10.1016/j.vibspec.2012.05.010

Cited by 40 publications

(20 citation statements)

References 34 publications

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“…When using vibrational spectroscopy to investigate the interaction between luteolin and its environment in ordered systems (protein binding pocket, co-crystals, complexes with oligosaccharides…) some key features emerge: 1) Differently from other flavonoids, and from other natural molecules, no band can be directly interpreted as arising mainly from a C_O stretching. This makes the interpretation of the spectra in terms of luteolin-molecular environment more difficult, and straightforward piece of information about the polarity of the environment surrounding the C_O cannot be derived, as done for other flavonoids interacting with specific environment or matrices ( [18,20,42,19] and refs. therein);…”

Section: Relevance To Biophysical Studies On Luteolinmentioning

confidence: 99%

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Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Marrassini

Idrissi

Waele

et al. 2015

Journal of Molecular Liquids

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Section: Relevance To Biophysical Studies On Luteolinmentioning

confidence: 99%

“…binding sites of biomacromolecules ( [17][18][19] and refs. therein), organic nanoparticles [20], and nanocomposites [21], have been published.…”

Section: Introductionmentioning

confidence: 99%

Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Marrassini

Idrissi

Waele

et al. 2015

Journal of Molecular Liquids

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“…In turn, a decrease in the wavenumber of the maximum of this band indicates that the lipid phosphate polar head group is located in more polar environments and that head group hydration increased [62]. Similar changes are also observed when the membrane embeds compounds having OH groups in their structure, which may also form hydrogen bonds with the phosphoric group lipids, e.g., polyphenols, plant extracts, carotenoids, complexes of platinum [61,[63][64][65][66][67]. Therefore, the band located at 1235 cm −1 (for RBCMs) shifted toward lower frequencies in the presence of lactones probably indicates an interaction via hydrogen bonds between the PO 2 -group of the lipid and lactone 1 molecules.…”

Section: Fourier Transform Infrared Spectroscopymentioning

confidence: 77%

Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

et al. 2020

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The aim of this work was the examination of biological activity of three selected racemic cis-β-aryl-δ-iodo-γ-lactones. Tested iodolactones differed in the structure of the aromatic fragment of molecule, bearing isopropyl (1), methyl (2), or no substituent (3) on the para position of the benzene ring. A broad spectrum of biological activity as antimicrobial, antiviral, antitumor, cytotoxic, antioxidant, and hemolytic activity was examined. All iodolactones showed bactericidal activity against Proteus mirabilis, and lactones 1,2 were active against Bacillus cereus. The highest cytotoxic activity towards HeLa and MCF7 cancer cell lines and NHDF normal cell line was found for lactone 1. All assessed lactones significantly disrupted antioxidative/oxidative balance of the NHDF, and the most harmful effect was determined by lactone 1. Contrary to lactone 1, lactones 2 and 3 did not induce the hemolysis of erythrocytes after 48 h of incubation. The differences in activity of iodolactones 1–3 in biological tests may be explained by their different impact on physicochemical properties of membrane as the packing order in the hydrophilic area and fluidity of hydrocarbon chains. This was dependent on the presence and type of alkyl substituent. The highest effect on the membrane organization was observed for lactone 1 due to the presence of bulky isopropyl group on the benzene ring.

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“…Cieślik-Boczula et al 2012 ). Measurements were done in various temperatures between 25 and 50 °C to assess the influence of the investigated complex on the DPPC bilayer’s structure, both in gel and liquid crystal phase and to check how the compound’s presence impacts the main phase transition of liposomes (Pentak 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Interaction of Newly Platinum(II) with Tris(2-carboxyethyl)phosphine Complex with DNA and Model Lipid Membrane

2017

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Structural properties of plasmid DNA and model lipid membrane treated with newly synthesized platinum(II) complex cis-[PtCl2{P(CH2CH2COOH)3}2] (cis-DTCEP for short) were studied and compared with effects of anticancer drug cisplatin, cis-[Pt(NH3)2Cl2] (cis-DDP for short). Time Correlated Single Photon Counting Fluorescence Correlation Spectroscopy (TCSPC-FCS) was employed to study interactions between those platinum complexes and DNA. The TCSPC-FCS results suggest that bonding of cis-DTCEP derivative to DNA leads to plasmid strain realignment towards much more compact structure than in the case of cis-DDP. Application of both differential scanning calorimetry and infrared spectroscopy to platinum complexes/DPPC showed that cis-DTCEP slightly increases the phospholipid’s main phase transition temperature resulting in decreased fluidity of the model membrane. The newly investigated compound—similarly to cis-DDP—interacts mainly with the DPPC head group however not only by the means of electrostatic forces: this compound probably enters into hydrophilic region of the lipid bilayer and forms hydrogen bonds with COO groups of glycerol and PO2 − group of DPPC.

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Interaction of quercetin, genistein and its derivatives with lipid bilayers – An ATR IR-spectroscopic study

Cited by 40 publications

References 34 publications

Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

Interaction of Newly Platinum(II) with Tris(2-carboxyethyl)phosphine Complex with DNA and Model Lipid Membrane

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