Carbonate-β-Cyclodextrin-Based Nanosponge as a Nanoencapsulation System for Piperine: Physicochemical Characterization

Garrido, B.; González, Sofía; Hermosilla, Jeyson; Millao, Sonia; Quilaqueo, Marcela; Guineo, J.; Acevedo, Francisca; Pesenti, Héctor; Rolleri, Aldo; Shene, Carolina; Rubilar, Mónica

doi:10.1007/s42729-019-00062-7

Cited by 27 publications

(21 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The second and main weight loss step was observed at 350 °C, which corresponds to degradation of NSs [ 38 , 41 ]. The thermograms show that the inclusion of MPH and CYT in the cavities of the NSs might increase the thermal stability of the drugs [ 21 , 29 , 41 , 42 , 43 , 44 ]. The decomposition temperatures for MPH, CYT and the ICs are summarized in Table 3 .…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrin Nanosponges Inclusion Compounds Associated with Gold Nanoparticles for Potential Application in the Photothermal Release of Melphalan and Cytoxan

Salazar

Yutronic

Kogan

et al. 2021

IJMS

View full text Add to dashboard Cite

This article describes the synthesis and characterization of β-cyclodextrin-based nano-sponges (NS) inclusion compounds (IC) with the anti-tumor drugs melphalan (MPH) and cytoxan (CYT), and the addition of gold nanoparticles (AuNPs) onto both systems, for the potential release of the drugs by means of laser irradiation. The NS-MPH and NS-CYT inclusion compounds were characterized using scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), energy dispersive spectroscopy (EDS), thermogravimetric analysis (TGA), UV–Vis, and proton nuclear magnetic resonance (1H-NMR). Thus, the inclusion of MPH and CYT inside the cavities of NSs was confirmed. The association of AuNPs with the ICs was confirmed by SEM, EDS, TEM, and UV–Vis. Drug release studies using NSs synthesized with different molar ratios of β-cyclodextrin and diphenylcarbonate (1:4 and 1:8) demonstrated that the ability of NSs to entrap and release the drug molecules depends on the crosslinking between the cyclodextrin monomers. Finally, irradiation assays using a continuous laser of 532 nm showed that photothermal drug release of both MPH and CYT from the cavities of NSs via plasmonic heating of AuNPs is possible.

show abstract

Section: Resultsmentioning

confidence: 99%

Cyclodextrin Nanosponges Inclusion Compounds Associated with Gold Nanoparticles for Potential Application in the Photothermal Release of Melphalan and Cytoxan

Salazar

Yutronic

Kogan

et al. 2021

IJMS

View full text Add to dashboard Cite

show abstract

“…In order to obtain information about the AITC complexation with β-CD, the IC and PM were analyzed by FTIR spectroscopy ( Figure 4 ). The pure β-CD spectrum showed bands at 3,274, 2,925, 1,644, 1,152, 1,077, and 1,020 cm −1 related to hydroxyl groups (–OH stretching), methylene groups (C–H stretching), H–O–H bending of hydroxyl groups, glycoside skeleton (–C–O– stretching), and the secondary and primary O–H bending of hydroxyl groups, respectively ( 41 , 42 ). On the other hand, the AITC spectrum showed bands at 2,080, 1,416, and 920 cm −1 that were assigned to isothiocyanate group stretching (–NCS), –CH-CH– shear, and R–C-CH 2 bending of the allyl group, respectively ( 43 , 44 ).…”

Section: Resultsmentioning

confidence: 99%

Development of Inclusion Complexes With Relative Humidity Responsive Capacity as Novel Antifungal Agents for Active Food Packaging

et al. 2022

View full text Add to dashboard Cite

Background: Allyl isothiocyanate is an excellent antimicrobial compound that has been applied in the development of active food packaging materials in the last years. However, the high volatility of this compound could prevent a lasting effect over time. In order to avoid this problem, cyclodextrin inclusion complexes have been proposed as an alternative, being beta-cyclodextrin (β-CD) as the main candidate. In addition, β-CD could act as a relative humidity-responsive nanoparticle. In this regard, the aim of this study was to develop inclusion complexes based on β-CD and AITC as relative humidity-responsive agents, which can be used in the design of active food packaging materials.Methods: Two different β-CD:AITC inclusion complexes (2:1 and 1:1 molar ratios) were obtained by the co-precipitation method. Entrapment efficiency was determined by gas chromatography, while inclusion complexes were characterized through thermal, structural, and physicochemical techniques. Antifungal capacity of inclusion complexes was determined in a headspace system. Furthermore, the AITC release from inclusion complexes to headspace at different percentages of relative humidity was evaluated by gas chromatography, and this behavior was related with molecular dynamic studies.Key Findings and Conclusions: The entrapment efficiency of inclusion complexes was over to 60%. Two coexisting structures were proposed for inclusion complexes through spectroscopic analyses and molecular dynamic simulation. The water sorption capacity of inclusion complexes depended on relative humidity, and they exhibited a strong fungicide activity against Botrytis cinerea. Furthermore, the AITC release to headspace occurred in three stages, which were related with changes in β-CD conformational structure by water sorption and the presence of the different coexisting structures. In addition, a strong influence of relative humidity on AITC release was evidenced. These findings demonstrate that β-CD:AITC inclusion complexes could be used as potential antifungal agents for the design of food packaging materials, whose activity would be able to respond to relative humidity changes.

show abstract

“…Water allows the removal of CD in excess and ethanol/acetone allows the elimination of the unreacted crosslinker and still other impurities such as phenol or imidazole, formed when DPC or CDI linkers are used, respectively. Typically, the phenoxide ion formed from phenol is soluble in water, so the rinse with a base (NaOH) will ensure the total removal of this impurity, which can be observed using a ferric salt ( Garrido et al, 2019 ; Kumar et al, 2021 ), UV-vis spectroscopy or HPLC ( Sadjadi et al, 2018c ).…”

Section: Cyclodextrin-based Nanosponges: Synthesis and Propertiesmentioning

confidence: 99%

“…Typically, an excess of crosslinking agent is used in CD:crosslinker molar ratios in the range of 1:2 to 1:16 ( Jain et al, 2020 ). In general, after the reaction, the recovery of NSs may involve precipitation using water, acetone ( Khajeh Dangolani et al, 2019 ) or ethyl acetate ( Cecone et al, 2018 , 2019 ; Matencio et al, 2020b ) among other possible solvents ( Ferro et al, 2014 ; Appell et al, 2018 ; Garrido et al, 2019 ; Lo Meo et al, 2020 ; Pawar and Shende, 2021 ).…”

Section: Cyclodextrin-based Nanosponges: Synthesis and Propertiesmentioning

confidence: 99%

Cyclodextrin-Based Nanosponges: Overview and Opportunities

et al. 2022

View full text Add to dashboard Cite

Nanosponges are solid cross-linked polymeric nano-sized porous structures. This broad concept involves, among others, metal organic frameworks and hydrogels. The focus of this manuscript is on cyclodextrin-based nanosponges. Cyclodextrins are cyclic oligomers of glucose derived from starch. The combined external hydrophilicity with the internal hydrophobic surface constitute a unique “microenvironment”, that confers cyclodextrins the peculiar ability to form inclusion host‒guest complexes with many hydrophobic substances. These complexes may impart beneficial modifications of the properties of guest molecules such as solubility enhancement and stabilization of labile guests. These properties complemented with the possibility of using different crosslinkers and high polymeric surface, make these sponges highly suitable for a large range of applications. Despite that, in the last 2 decades, cyclodextrin-based nanosponges have been developed for pharmaceutical and biomedical applications, taking advantage of the nontoxicity of cyclodextrins towards humans. This paper provides a critical and timely compilation of the contributions involving cyclodextrins nanosponges for those areas, but also paves the way for other important applications, including water and soil remediation and catalysis.

show abstract

Carbonate-β-Cyclodextrin-Based Nanosponge as a Nanoencapsulation System for Piperine: Physicochemical Characterization

Cited by 27 publications

References 38 publications

Cyclodextrin Nanosponges Inclusion Compounds Associated with Gold Nanoparticles for Potential Application in the Photothermal Release of Melphalan and Cytoxan

Cyclodextrin Nanosponges Inclusion Compounds Associated with Gold Nanoparticles for Potential Application in the Photothermal Release of Melphalan and Cytoxan

Development of Inclusion Complexes With Relative Humidity Responsive Capacity as Novel Antifungal Agents for Active Food Packaging

Cyclodextrin-Based Nanosponges: Overview and Opportunities

Contact Info

Product

Resources

About