pH-controlled release of auxin plant hormones from cucurbit[7]uril macrocycle

Nuzzo, Assunta; Scherman, Oren A.; Mazzei, Pierluigi; Piccolo, Alessandro

doi:10.1186/2196-5641-1-2

Cited by 12 publications

(12 citation statements)

References 42 publications

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“…Several host-guest systems were reported with applications in food [10][11][12]. However, few specific examples were reported on the implications of the reversible response of CB host-guest systems to chemical stimuli on food technology, which include the use of CB6 to encapsulate 1-methylcyclopropene (1-MCP), an ethylene antagonist, generating a response to sodium bicarbonate and benzoic acid chemical competitors [13], and host-guest complexes of auxin plant hormones to CB7 with a response to pH [14].…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

et al. 2020

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Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-CA by cucurbit[7]uril (CB7) and show that photoisomerization reactions can be more efficiently controlled in aqueous solutions by utilizing this supramolecular approach. Measurements of UV–visible absorption and proton NMR spectra at different pH values confirm that E-CA and its methyl ester, methyl-E-cinnamate (MC), form stronger 1:1 host–guest complexes with CB7 compared to cucurbit[8]uril (CB8) or three cyclodextrins (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host–guest complex formation.

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Section: Introductionmentioning

confidence: 99%

Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

et al. 2020

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“…1b) was discovered in 200010 and still has wide research prospects. Currently, most reported studies on CB[7] have focused on the inclusion mechanism with drugs at a molecular level111213. Further developments of CB[7]-containing drug dosage forms, such as tablets for oral delivery, have been seldom described.…”

mentioning

confidence: 99%

Co-grinding Effect on Crystalline Zaltoprofen with β-cyclodextrin/Cucurbit[7]uril in Tablet Formulation

Lin

et al. 2017

Sci Rep

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This work aimed to investigate the co-grinding effects of β-cyclodextrin (β-CD) and cucurbit[7]uril (CB[7]) on crystalline zaltoprofen (ZPF) in tablet formulation. Crystalline ZPF was prepared through anti-solvent recrystallization and fully analyzed through single-crystal X-ray diffraction. Co-ground dispersions and mono-ground ZPF were prepared using a ball grinding process. Results revealed that mono-ground ZPF slightly affected the solid state, solubility, and dissolution of crystalline ZPF. Co-ground dispersions exhibited completely amorphous states and elicited a significant reinforcing effect on drug solubility. UV-vis spectroscopy, XRPD, FT-IR, DSC, ssNMR, and molecular docking demonstrated the interactions in the amorphous product. Hardness tests on blank tablets with different β-CD and CB[7] contents suggested the addition of β-CD or CB[7] could enhance the compressibility of the powder mixture. Disintegration tests showed that CB[7] could efficiently shorten the disintegrating time. Dissolution tests indicated that β-CD and CB[7] could accelerate the drug dissolution rate via different mechanisms. Specifically, CB[7] could accelerate the dissolution rate by improving disintegration and β-CD showed a distinct advantage in solubility enhancement. Based on the comparative study on β-CD and CB[7] for tablet formulation combined with co-grinding, we found that CB[7] could be considered a promising drug delivery, which acted as a disintegrant.

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“…However, the important advantage of CDs is their ability to increase the solubility of poorly soluble drugs 5 . Our group 10 – 12 among others 13 – 16 have utilized CBs-induced p K a shifts to simulate natural receptors in their modulation of acid-base equilibrium 17 that is displayed by some potential bioactive molecules 10 , 13 , pharmaceutical drugs 11 , 12 , 14 , 15 and hormones 16 . Generally, supramolecular approach utilizing CBs and CDs has also been employed to control several biological phenomena such as enzymatic activities 18 , or chemical sensing in fish 19 , just to name a few.…”

Section: Introductionmentioning

confidence: 99%

“…There have been several host-guest systems reported in aqueous solution for developing biologically relevant molecules with stimuli-responsive abilities. For examples, cucurbit[6]uril (CB6)-encapsulated 1-methylcyclopropene (1-MCP), an ethylene antagonist, that responses to sodium bicarbonate and benzoic acid as chemical competitors 22 , host-guest complexes of auxin plant hormones with cucurbit[7]uril (CB7) that response to pH, in which only at low pH inclusion complexes were formed 16 , CB7-encapsulated cadaverine (CAD) that responses to photoinduced pH jump resulting from photoreaction of 2-nitrobenzaldehyde 23 , and phototriggered release of memantine from CB7 cavity utilizing reversibly switchable photochromic system 24 . Aside from studies in water media, the validations of reversible response of supramolecular host-guest nanostructured materials to external stimuli in vitro 25 – 28 or even in vivo 29 have also been confirmed over the past two years.…”

Section: Introductionmentioning

confidence: 99%

Host-guest complexes of imazalil with cucurbit[8]uril and β-cyclodextrin and their effect on plant pathogenic fungi

Al-Dubaili

El‐Tarabily

Saleh

2018

Sci Rep

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We report the control of imazalil (IMZ) antifungal activity utilizing its non-covalent assembly with β-cyclodextrins (β-CD) and cucurbit[8]uril (CB8) macrocycles, as well as its stimuli-responsive disassembly with cadaverine. The NMR results are consistent with inclusion of a single IMZ molecule inside the cavities of either CB8 from its aromatic site or β-CD from its aliphatic end. Efficient complex formation with both host molecules and controlled released upon the addition of cadaverine is supported by NMR measurements. The stimuli-responsiveness of the same host-guest assemblies with cadaverine was validated against seven economically important plant pathogenic fungi which cause agriculturally important plant diseases across the globe. While loading the drug into macrocycles cavities suppressed its activity, subsequent adding of cadaverine efficiently restored it up. The results in the present paper enable researchers working in the area of mycology and plant pathology to inhibit or reduce the fungal growth on demand in order to control these economically important plant pathogenic fungi.

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pH-controlled release of auxin plant hormones from cucurbit[7]uril macrocycle

Abstract: Background: The influence of pH on the formation of host-guest complexes between the cucurbit [7]uril (CB [7]) macrocyclic host and three auxin plant hormones, namely indole-3-acetic acid (IAA), 2-naphthalene acetic acid (2-NAA), and 2,4-dichlorophenoxyacetic acid (2,4-D), was studied by

Cited by 12 publications

References 42 publications

Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

Co-grinding Effect on Crystalline Zaltoprofen with β-cyclodextrin/Cucurbit[7]uril in Tablet Formulation

Host-guest complexes of imazalil with cucurbit[8]uril and β-cyclodextrin and their effect on plant pathogenic fungi

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