Hydrophobic π-π stacking interactions and hydrogen bonds drive self-aggregation of luteolin in water

Deogratias, Geradius; Shadrack, Daniel M.; Munissi, Joan J. E.; Kinunda, Grace; Jacob, Fortunatus R; Mtei, Regina P; Masalu, Rose; Mwakyula, Issakwisa Habakkuk; Kiruri, Lucy W.; Nyandoro, Stephen S.

doi:10.1016/j.jmgm.2022.108243

Cited by 8 publications

(5 citation statements)

References 49 publications

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“…Collectively, the π–π stacking interactions of S-2 in the current cocrystal contribute to a certain superiority in hydrophobicity compared with S-1 in free FLCY, due to the reinforcing effect on the stability of the crystal structure. 69 This stacking pattern of S-2 being conducive to the thermodynamic stability of the cocrystal further supports the conclusion of topology analysis from the perspective of the stacking mode.…”

Section: Resultssupporting

confidence: 77%

Self-assembly of antifungal agent 5-fluorocytosine and nutrient trans-p-coumaric acid furnishes a cocrystal with the potential to reduce toxicity and side effects for the drug: a case study combining theory with experiment

et al. 2023

New J. Chem.

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Section: Resultssupporting

confidence: 77%

Self-assembly of antifungal agent 5-fluorocytosine and nutrient trans-p-coumaric acid furnishes a cocrystal with the potential to reduce toxicity and side effects for the drug: a case study combining theory with experiment

et al. 2023

New J. Chem.

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“…All this proved that there was a weak interaction of π‐π stacking between [BMIM]HSO 4 and the PPBAS gel. The type of π‐π stacking was face‐to‐face or edge‐to‐face, which was a noncovalent bond interaction that often exists between aromatic rings 29.…”

Section: Resultsmentioning

confidence: 99%

“…All this proved that there was a weak interaction of π-π stacking between [BMIM]HSO 4 and the PPBAS gel. The type of π-π stacking was face-to-face or edge-to-face, which was a noncovalent bond interaction that often exists between aromatic rings [29]. The new spectra indicated that the three-dimensional network structure in the PPBAS gel was formed by the reversible dynamic covalent bonds of -CO-NH- [30,31] and B-O-C [32,33] cross-linked with 3,5-Da, PVA, and PEI.…”

Section: Rheological Analysis Of the Ilgmentioning

confidence: 89%

Synthesis of Phase‐Selective Ionic Liquid Gels and Application to the Synthesis of Ethyl Acetate

Liu,

Xie,

2023

Chem Eng & Technol

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Novel and environment‐friendly ionic liquid gels (ILG) were synthesized based on polymers, phenylboronic acid, and [BMIM]HSO4, in order to solve the problems in esterification, such as poor selectivity, difficult separation of product and catalyst, and catalyst recycling. The stability and structures of the ILG were characterized by rheology, thermogravimetric analysis, Fourier transform infrared and 1H nuclear magnetic resonance spectroscopy, and energy calculation. The solubility data proved that the ILG had phase selectivity, which could enable a homogeneous reaction. The synthesis of ethyl acetate was chosen to evaluate the catalytic activity, with the product yields being higher than 80 %. The catalyst could be recycled directly, without any post‐treatment. Thus, the ILG could enhance the industrial application of esterification.

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“…A structure-activity relationship study of tylophorine demonstrated that the rigid phenanthrene structure is a prerequisite for high anti-cancer activity [13,26,27]. We reasoned, however, that this moiety can lead to strong intermolecular π-π stacking interactions, which results in poor aqueous solubility [28]. To address this issue, we strategically designed gem-dimethyl-tylophorine analogues, which are molecules with two methyl groups at the benzylic position of tylophorine.…”

Section: Highlightsmentioning

confidence: 99%

Photoredox-catalyzed reaction as a powerful tool for rapid natural product Gem-dimethylation modification: discovery of potent anti-cancer agents with improved druggability

Zhang,

Song,

Sun

et al. 2023

Acta Materia Medica

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Tylophorine has diverse biological activities; however, the stability, solubility, and central nervous system toxicity have severely limited use of tylophorine. The gem-dimethyl group is an organic chemistry functional group that consists of two methyl groups bonded to the same carbon atom. This feature has gained significant attention in medicinal chemistry due to its unique properties and potential applications in drug design. We applied a new photoredox methodology to tylophorine modification, resulting in a series of gem-dimethyl tylophorine analogues. Among the analogues, compound 4b demonstrated promising activity against a wide range of tumor cell lines and exhibited significantly improved drug-like properties, including enhanced solubility and stability. Compound 4b showed an exceptional inhibitory effect (7.8 nM) against a C481S mutation-induced ibrutinib-resistant non-Hodgkin’s lymphoma cell line, as well as primary tumor cell lines obtained from patients. Importantly, compound 4b exhibited significantly reduced anti-proliferative activity against the normal cell line tested, indicating the potential for an enhanced therapeutic window for compound 4b. Based on these early-stage data, we believe that our study provides a solid foundation for the development of new therapeutic agents for potential drug-resistant cancer treatment in the near future.

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Hydrophobic π-π stacking interactions and hydrogen bonds drive self-aggregation of luteolin in water

Cited by 8 publications

References 49 publications

Self-assembly of antifungal agent 5-fluorocytosine and nutrient trans-p-coumaric acid furnishes a cocrystal with the potential to reduce toxicity and side effects for the drug: a case study combining theory with experiment

Self-assembly of antifungal agent 5-fluorocytosine and nutrient trans-p-coumaric acid furnishes a cocrystal with the potential to reduce toxicity and side effects for the drug: a case study combining theory with experiment

Synthesis of Phase‐Selective Ionic Liquid Gels and Application to the Synthesis of Ethyl Acetate

Photoredox-catalyzed reaction as a powerful tool for rapid natural product Gem-dimethylation modification: discovery of potent anti-cancer agents with improved druggability

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