Binding of the five multistate species of the anthocyanin analog 7-β-D-glucopyranosyloxy-4′-hydroxyflavylium to the β-cyclodextrin derivative captisol

Mendoza, Johan; Basílio, Nuno; Dangles, Olivier; Mora, Nathalie; Bittar, Sheiraz Al; Piña, Fernando

doi:10.1016/j.dyepig.2017.04.061

Cited by 9 publications

(7 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The selectivity of CD toward more hydrophobic species has been widely explored to devise many different stimuli responsive systems using guest molecules that change their polarity or ionization state upon application of stimuli such as light, redox potential, temperature, or added chemicals. ,− In this context, synthetic flavylium compounds were found to be excellent candidates for photoresponsive host–guest cyclodextrin-based systems owing to their potential to interconvert between neutral and charged species using light inputs. − …”

Section: Stimuli-responsive Host–guest Systemsmentioning

confidence: 99%

“…The influence of β-CD complexation on the kinetics and thermodynamics of the network of reactions involving different synthetic flavylium derivatives was investigated in great detail using different techniques, including NMR, ITC, circular dichroism, UV–vis, and stopped-flow. − All these studies revealed that, among the flavylium multistate species, the neutral uncolored species (B, Cc, and Ct) bind with higher affinity ( K usually in the 10 3 M –1 range) to the hydrophobic cavity of β-CD while the respective flavylium cations do not bind or show much weaker affinities.…”

Section: Stimuli-responsive Host–guest Systemsmentioning

confidence: 99%

See 1 more Smart Citation

Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color

et al. 2021

Self Cite

View full text Add to dashboard Cite

Flavylium compounds are a well-known family of pigments because they are prevalent in the plant kingdom, contributing to colors over a wide range from shades of yellow-red to blue in fruits, flowers, leaves, and other plant parts. Flavylium compounds include a large variety of natural compound classes, namely, anthocyanins, 3deoxyanthocyanidins, auronidins, and their respective aglycones as well as anthocyaninderived pigments (e.g., pyranoanthocyanins, anthocyanin-flavan-3-ol dimers). During the past few decades, there has been increasing interest among chemists in synthesizing different flavylium compounds that mimic natural structures but with different substitution patterns that present a variety of spectroscopic characteristics in view of their applications in different industrial fields. This Review provides an overview of the chemistry of flavylium-based compounds, in particular, the synthetic and enzymatic approaches and mechanisms reported in the literature for obtaining different classes of pigments, their physical-chemical properties in relation to their pH-dependent equilibria network, and their chemical and enzymatic degradation. The development of flavylium-based systems is also described throughout this Review for emergent applications to explore some of the physical-chemical properties of the multistate of species generated by these compounds.

show abstract

Section: Stimuli-responsive Host–guest Systemsmentioning

confidence: 99%

Section: Stimuli-responsive Host–guest Systemsmentioning

confidence: 99%

Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…The intermediate B may also be confined in SBECD to a smaller extent. A previous study of a structurally similar anthocyanin, 7-β-D-glucopyranosyloxy-4′-hydroxyflavylium complexation with SBECD, demonstrated the largest affinity of the Cc form to the host macrocycle [ 41 ]. We found considerable alteration of the spectrum when the solution containing 20.84 mg/mL SBECD was kept for 3 h in the dark.…”

Section: Resultsmentioning

confidence: 99%

Halochromic Behavior and Anticancer Effect of New Synthetic Anthocyanidins Complexed with β-Cyclodextrin Derivatives

Păușescu

Kántor

Babos

et al. 2022

IJMS

View full text Add to dashboard Cite

Anthocyanidins, the aglycons of anthocyanins, are known, beyond their function in plants, also as compounds with a wide range of biological and pharmacological activities, including cytostatic effect against various cancer cells. The nature and position of the substituents in the flavylium cation is essential for such biological properties, as well as the equilibrium between the multistate of the different chemical species that are generated by the flavylium cation, including quinoidal base, hemiketal, and cis- and trans-chalcones. In this work, eight new flavylium derivatives were synthesized, characterized for confirmation of the structure by FT-IR and 2D-NMR, and investigated in vitro as possible cytostatic compounds against HCT116 and HepG2 cancer cells. The most active two compounds were explored for their halochromic properties that can influence the biological activity and subjected to molecular encapsulation in β-cyclodextrin derivatives in order to increase their solubility in water and bioavailability. The anticancer effect was influenced by the position (6-, 7-, or 8-) of the methoxy group in the β-ring of the methoxy-4’-hydroxy-3’-methoxyflavylium cation, while the study of the halochromic properties revealed the important role played by the chalcone species of the pH-dependent multistate in both the uncomplexed and inclusion complex forms of these anthocyanidins.

show abstract

“…[16] The stabilization of naturala nthocyaninsa nd flavylium analogs by developing host-guests ystemsi sp oorly reportedi nt he literature. [17][18][19] In the case of cyclodextrins, ad e-stabilization of the red flavyliumc ation generally occursb ecause the colorless hemiketals pecies is preferentially encapsulated by the receptor.T ot he best of our knowledge,d endrimers have never been used as hosts for color tuning of anthocyanins with pH. Ar ecent study demonstrated the use of silica-PAMAM [poly(amidoamine)] dendrimer nanoparticles to encapsulate anthocyanins and to further evaluated their antiproliferative activity against neuroblastoma( Neuro 2A).…”

Section: Introductionmentioning

confidence: 99%

“…Several hosts have been described for inclusion of guest molecules such as crown ethers, porphyrins, cyclodextrins, cucurbiturils, nanoparticles and nanotubes, liposomes, and dendrimers . The stabilization of natural anthocyanins and flavylium analogs by developing host–guest systems is poorly reported in the literature . In the case of cyclodextrins, a destabilization of the red flavylium cation generally occurs because the colorless hemiketal species is preferentially encapsulated by the receptor.…”

Section: Introductionmentioning

confidence: 99%

Impact of a Water‐Soluble Gallic Acid‐Based Dendrimer on the Color‐Stabilizing Mechanisms of Anthocyanins

Cruz

Basílio

Mendoza

et al. 2019

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

The interaction of two anthocyaninsw ith aw atersoluble polyanionic dendrimerw as studied through UV/Vis, stopped-flow,a nd NMR spectroscopy. Cyanidin-3-glucoside (cy3glc)r evealed as tronger interactiont han malvidin-3-glucoside (mv3glc) at pH 1a ccording to their apparent association constants. Ah igher color increased was also obtained for cy3glca tp H3.5 as ar esult of this strongeri nteraction.A high-frequency chemical shift of the cy3glc aromatic protons suggest the formation of ionic pairs. The interaction parame-ters (K % 700 m À1 , n % 295) indicated the binding of approximately two anthocyanin molecules by each sulfate group. The equilibriuma nd ratec onstantso fc y3glc in the presence of dendrimer showed an increased stability of the flavylium cationand ahigher protectiono fthis speciesf rom hydration (pK' a and pK h increased almost one pH unit).T he tuning and color stabilizationo fa nthocyanins by using this dendrimer allow novel applications as colorimetric sensors for food packaging.[a] L. Cruz, N. Mateus,V .d eFreitas Supporting Information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

show abstract

Binding of the five multistate species of the anthocyanin analog 7-β-D-glucopyranosyloxy-4′-hydroxyflavylium to the β-cyclodextrin derivative captisol

Abstract: Binding of the five multistate species of the anthocyanin analog 7-b-D-glucopyranosyloxy-4 0-hydroxyflavylium to the b-cyclodextrin derivative captisol

Cited by 9 publications

References 24 publications

Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color

Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color

Halochromic Behavior and Anticancer Effect of New Synthetic Anthocyanidins Complexed with β-Cyclodextrin Derivatives

Impact of a Water‐Soluble Gallic Acid‐Based Dendrimer on the Color‐Stabilizing Mechanisms of Anthocyanins

Contact Info

Product

Resources

About