Enhancing bio-availability of β-naphthoflavone by supramolecular complexation with 6,6′-thiobis(methylene)-β-cyclodextrin dimer

Choi, Joo Hee; Cho, Eunae; Lee, Benel; Jeong, Dae‐Yong; Choi, Youngjin; Yu, Jae‐Hyuk; Jung, Seunho

doi:10.1016/j.carbpol.2016.05.046

Cited by 12 publications

(10 citation statements)

References 30 publications

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“…CDs can enhance the aqueous solubility of lipophilic molecules and/or enhance their cellular uptake; therefore, the biological action of CD complexes with different compounds or the cellular uptake of encapsulated guest molecules are commonly tested in cell experiments [ 32 , 33 , 34 ]. Because the stability of these CD complexes are typically low, micromolar concentrations of guest molecules should be accompanied by millimolar CD concentrations for achieving encapsulation of the guest at considerable level.…”

Section: Resultsmentioning

confidence: 99%

Complex Formation of Resorufin and Resazurin with Β-Cyclodextrins: Can Cyclodextrins Interfere with a Resazurin Cell Viability Assay?

et al. 2018

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Resazurin (or Alamar Blue) is a poorly fluorescent dye. During the cellular reduction of resazurin, its highly fluorescent product resorufin is formed. Resazurin assay is a commonly applied method to investigate viability of bacterial and mammalian cells. In this study, the interaction of resazurin and resorufin with β-cyclodextrins was investigated employing spectroscopic and molecular modeling studies. Furthermore, the influence of β-cyclodextrins on resazurin-based cell viability assay was also tested. Both resazurin and resorufin form stable complexes with the examined β-cyclodextrins (2.0–3.1 × 103 and 1.3–1.8 × 103 L/mol were determined as binding constants, respectively). Cells were incubated for 30 and 120 min and treated with resazurin and/or β-cyclodextrins. Our results suggest that cyclodextrins are able to interfere with the resazurin-based cell viability assay that presumably results from the following mechanisms: (1) inhibition of the cellular uptake of resazurin and (2) enhancement of the fluorescence signal of the formed resorufin.

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Section: Resultsmentioning

confidence: 99%

Complex Formation of Resorufin and Resazurin with Β-Cyclodextrins: Can Cyclodextrins Interfere with a Resazurin Cell Viability Assay?

et al. 2018

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“…Enhancing fluorescence yields and lifetimes, causing large pK a shifts, inhibiting aggregation in aqueous solutions, increasing photostability, enhancing chemical stability, providing preferences for selective conformational structures, controlling pro‐drug to drug conversion and vice versa, enhancing bio‐availability of drugs, etc. are some of the noteworthy modulations favorably introduced by supramolecular host‐guest interactions . The supramolecularly assisted modulations in the photophysical and other chemical properties of the dyes/drugs and their possible applications in diverse areas like fluorescent sensing, functional materials, nano‐medicines, chemical sensors, catalysis, dye lasers, biochemical sciences, etc .…”

Section: Introductionmentioning

confidence: 99%

pH‐Responsive Interaction of Fluorogenic Antimalarial Drug Quinine with Macrocyclic Host Cucurbit[7]uril: Modulations in Photophysical and Acid‐Base Properties

et al. 2017

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Intriguing changes in photophysical and acid-base properties of fluorogenic antimalarial drug, quinine (QN), are presented on its interaction with macrocyclic cucurbit[7]uril (CB7)host. While dicationic QNH 2 2 + form shows large enhancement in both steady state and time-resolved fluorescence, monocationic QNH + and neutral QN forms show significant reductions. The pK a (1) and pK a (2) values of the drug undergo~1 and~1.7 units of upward shifts, respectively, on its binding to CB7 host, substantiating the differential binding strengths of various prototropic forms. Whereas the QNH 2 2 + and QNH + forms undergo 1:2 (dye to CB7) inclusion complex formation, the neutral QN is suggested to form 1:1 inclusion complex with CB7.Interestingly, the observed results in the present study are substantially different and in some cases quite contrasting to the results reported in a recently published paper (Phys. Chem. Chem. Phys., 2016, 18, 30520). In the present study we could unequivocally establish that there were many serious inconsistencies in the above paper, which we could now convincingly rectify, designing appropriate experimental and sample conditions. With the intriguing modulations observed in the photophysical and acid-base properties, the quinine-CB7 system is suggested to act as an improved fluorimetric standard than the free quinine system. Additionally, the modulations have implications in drug stabilization, drug delivery, sensors and other applications.

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“…Fortunately, these problems have been solved by the bridged cyclodextrin in some degree. 42 Two adjacent cyclodextrin cavities exist in them, which could act synergistically when bridged cyclodextrins interact with substrates. These bridged cyclodextrins can not only strengthen interactions between host and guest, but also improve the selectivity in molecular recognition process.…”

Section: -8mentioning

confidence: 99%

Molecular recognition with cyclodextrin polymer: a novel method for removing sulfides efficiently

Duan

Chen

et al. 2017

RSC Adv.

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A series of cyclodextrin polymers (CDPs) were synthesized and they were used for removing different sulfides by molecular recognition. Different CDPs showed a higher desulfurization efficiency for sulfides with an aromatic ring structure than those with an aliphatic chain structure. For different cyclodextrin polymers, b-CDP has a more suitable cavity size for removing DBT. Moreover, it has a good synergetic effect of adjacent cyclodextrin cavities and good electronic interactions with DBT.For these reasons, b-CDP showed the best desulfurization performance, in particular it has good performance for deep desulfurization by forming inclusion complexes and excellent selectivity for removing DBT. Meanwhile, the b-CDP showed good regeneration performance. Various characterization measurements were used to characterize the b-CDP before and after desulfurization of DBT, the results of which showed that it had advantages of wide application temperature range and good structure stability before and after desulfurization. Finally, a molecular recognition mechanism for removing sulfides efficiently was proposed.

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Enhancing bio-availability of β-naphthoflavone by supramolecular complexation with 6,6′-thiobis(methylene)-β-cyclodextrin dimer

Cited by 12 publications

References 30 publications

Complex Formation of Resorufin and Resazurin with Β-Cyclodextrins: Can Cyclodextrins Interfere with a Resazurin Cell Viability Assay?

Complex Formation of Resorufin and Resazurin with Β-Cyclodextrins: Can Cyclodextrins Interfere with a Resazurin Cell Viability Assay?

pH‐Responsive Interaction of Fluorogenic Antimalarial Drug Quinine with Macrocyclic Host Cucurbit[7]uril: Modulations in Photophysical and Acid‐Base Properties

Molecular recognition with cyclodextrin polymer: a novel method for removing sulfides efficiently

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