Browsing by Subject "Cyclodextrins"

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Open Access
Antibacterial activity of cyclodextrin-Azo dye inclusion complex encapsulated electrospun polycaprolactone nanofibers
(Wiley-VCH Verlag GmbH & Co. KGaA, 2021-10-12) Demirci, Serkan; Çelebioğlu, Aslı; Demirci, S. K.; İdil, Ö.
Polycaprolactone (PCL) nanofibers incorporating azo dye/γ-cyclodextrin inclusion complex (Azo/γ-CD-IC) were successfully produced. The characteristics of the Azo/γ-CD-IC and PCL/Azo/γ-CD-IC nanofibers were investigated by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA). Based on the SEM analysis the prepared nanofiber has a smooth surface with a size diameter below 500 nm. Meanwhile, the thermal stability of Azo was further improved after being embedded into Azo/γ-CD-IC and the PCL/Azo/γ-CD-IC nanofibers. Proton nuclear magnetic resonance (1H-NMR) was used to calculate the molar ratio of Azo/γ-CD. The antibacterial activity of the PCL/Azo/γ-CD-IC and PCL/Azo nanofibers was investigated using colony counting method and bacterial strains of Escherichia coli and Staphylococcus aureus were used. The results indicated that PCL/Azo/γ-CD-IC nanofibers have enhanced antibacterial activity against Escherichia coli and Staphylococcus aureus compared to PCL/Azo owing to inclusion complexation. Therefore, these PCL/Azo/γ-CD-IC nanofibers might have potential applications in the biomedical field.
Open Access
Antibacterial electrospun nanofibers from triclosan/cyclodextrin inclusion complexes
(Elsevier, 2014) Celebioglu A.; Umu, O. C. O.; Tekinay, T.; Uyar, Tamer
The electrospinning of nanofibers (NF) from cyclodextrin inclusion complexes (CD-IC) with an antibacterial agent (triclosan) was achieved without using any carrier polymeric matrix. Polymer-free triclosan/CD-IC NF were electrospun from highly concentrated (160% CD, w/w) aqueous triclosan/CD-IC suspension by using two types of chemically modified CD; hydroxypropyl-beta-cyclodextrin (HPβCD) and hydroxypropyl-gamma-cyclodextrin (HPγCD). The morphological characterization of the electrospun triclosan/CD-IC NF by SEM elucidated that the triclosan/HPβCD-IC NF and triclosan/HPγCD-IC NF were bead-free having average fiber diameter of 520±250nm and 1100±660nm, respectively. The presence of triclosan and the formation of triclosan/CD-IC within the fiber structure were confirmed by 1H-NMR, FTIR, XRD, DSC, and TGA studies. The initial 1:1molar ratio of the triclosan:CD was kept for triclosan/HPβCD-IC NF after the electrospinning and whereas 0.7:1molar ratio was observed for triclosan/HPγCD-IC NF and some uncomplexed triclosan was detected suggesting that the complexation efficiency of triclosan with HPγCD was lower than that of HPβCD. The antibacterial properties of triclosan/CD-IC NF were tested against Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria. It was observed that triclosan/HPβCD-IC NF and triclosan/HPγCD-IC NF showed better antibacterial activity against both bacteria compared to uncomplexed pure triclosan.
Open Access
Antibacterial electrospun poly(lactic acid) (PLA) nanofibrous webs incorporating triclosan/cyclodextrin inclusion complexes
(2013) Kayaci F.; Umu O.C.O.; Tekinay, T.; Uyar, T.
Solid triclosan/cyclodextrin inclusion complexes (TR/CD-IC) were obtained and then incorporated in poly(lactic acid) (PLA) nanofibers via electrospinning. α-CD, β-CD, and γ-CD were tested for the formation of TR/CD-IC by a coprecipitation method; however, the findings indicated that α-CD could not form an inclusion complex with TR, whereas β-CD and γ-CD successfully formed TR/CD-IC crystals, and the molar ratio of TR to CD was found to be 1:1. The structural and thermal characteristics of TR/CD-IC were investigated by 1H NMR, FTIR, XRD, DSC, and TGA studies. Then, the encapsulation of TR/β-CD-IC and TR/γ-CD-IC in PLA nanofibers was achieved. Electrospun PLA and PLA/TR nanofibers obtained for comparison were uniform, whereas the aggregates of TR/CD-IC crystals were present and distributed within the PLA fiber matrix as confirmed by SEM and XRD analyses. The antibacterial activity of these nanofibrous webs was investigated. The results indicated that PLA nanofibers incorporating TR/CD-IC showed better antibacterial activity against Staphylococcus aureus and Escherichia coli bacteria compared to PLA nanofibers containing only TR without CD-IC. Electrospun nanofibrous webs incorporating TR/CD-IC may be applicable in active food packaging due to their very high surface area and nanoporous structure as well as efficient antibacterial property. © 2013 American Chemical Society.
Open Access
Antibacterial electrospun zein nanofibrous web encapsulating thymol/cyclodextrin-inclusion complex for food packaging
(Elsevier, 2017-10) Aytac Z.; Ipek, S.; Durgun, Engin; Tekinay, T.; Uyar, Tamer
Thymol (THY)/γ-Cyclodextrin(γ-CD) inclusion complex (IC) encapsulated electrospun zein nanofibrous webs (zein-THY/γ-CD-IC-NF) were fabricated as a food packaging material. The formation of THY/γ-CD-IC (1:1 and 2:1) was proved by experimental (X-ray diffraction (XRD), thermal gravimetric analysis (TGA), 1H NMR) and computational techniques. THY/γ-CD-IC (2:1) exhibited higher preservation rate and stability than THY/γ-CD-IC (1:1). It is worth mentioning that zein-THY/γ-CD-IC-NF (2:1) preserved much more THY as observed in TGA and stability of THY/γ-CD-IC (2:1) was higher, as shown by a modelling study. Therefore, much more THY was released from zein-THY/γ-CD-IC-NF (2:1) than zein-THY-NF and zein-THY/γ-CD-IC-NF (1:1). Similarly, antibacterial activity of zein-THY/γ-CD-IC-NF (2:1) was higher than zein-THY-NF and zein-THY/γ-CD-IC-NF (1:1). It was demonstrated that zein-THY/γ-CD-IC-NF (2:1) was most effective in inhibiting the growth of bacteria on meat samples. These webs show potential application as an antibacterial food packaging material.
Open Access
Antioxidant vitamin E/cyclodextrin inclusion complex electrospun nanofibers: enhanced water solubility, prolonged shelf life, and photostability of vitamin E
(American Chemical Society, 2017) Çelebioğlu, Aslı; Uyar, Tamer
Here, we demonstrated the electrospinning of polymer-free nanofibrous webs from inclusion complex (IC) between hydroxypropyl-β-cyclodextrin (HPβCD) and Vitamin E (Vitamin E/HPβCD-IC NF). The inclusion complexation between HPβCD and Vitamin E was prepared by using two different molar ratios (Vitamin E/HPβCD; 1:2 and 1:1), which correspond to theoretical value of ∼13% (w/w) and 26% (w/w) loading of Vitamin E in the nanofiber (NF) matrix. After electrospinning and storage, a very high loading of Vitamin E (up to ∼11% w/w, with respect to fiber matrix) was preserved in Vitamin E/HPβCD-IC NF. Because of the cyclodextrin inclusion complexation, only a minimal weight loss (only ∼2% w/w) was observed. While pure Vitamin E is insoluble in water, Vitamin E/HPβCD-IC NF web has displayed fast-dissolving behavior. Because of the greatly enhanced water-solubility of Vitamin E, Vitamin E/HPβCD-IC NF web has shown effective antioxidant activity. Additionally, Vitamin E/HPβCD-IC NF web has provided enhanced photostability for the sensitive Vitamin E by the inclusion complexation in which Vitamin E/HPβCD-IC NF still kept its antioxidant activity even after exposure to UV-light. Moreover, a 3 year-old Vitamin E/HPβCD-IC NF sample has shown very similar antioxidant efficiency when compared with freshly prepared Vitamin E/HPβCD-IC NF indicating that long-term stability was achieved for Vitamin E in the CD-IC fiber matrix. In brief, our results suggested that polymer-free electrospun Vitamin E/HPβCD-IC nanofibrous webs could have potential applications in food, pharmaceuticals, and healthcare thanks to its efficient antioxidant activity along with enhanced water-solubility, prolonged shelf life, and high photostability of Vitamin E.
Open Access
Bioactive peptide functionalized aligned cyclodextrin nanofibers for neurite outgrowth
(Royal Society of Chemistry, 2017) Hamsici, S.; Cinar, G.; Celebioglu A.; Uyar, Tamer; Tekinay, A. B.; Güler, Mustafa O.
Guidance of neurite extension and establishment of neural connectivity hold great importance for neural tissue regeneration and neural conduit implants. Although bioactive-epitope functionalized synthetic or natural polymeric materials have been proposed for the induction of neural regeneration, chemical modifications of these materials for neural differentiation still remain a challenge due to the harsh conditions of chemical reactions, along with non-homogeneous surface modifications. In this study, a facile noncovalent functionalization method is proposed by exploiting host-guest interactions between an adamantane-conjugated laminin derived bioactive IKVAV epitope and electrospun cyclodextrin nanofibers (CDNFs) to fabricate implantable scaffolds for peripheral nerve regeneration. While electrospun CDNFs introduce a three-dimensional biocompatible microenvironment to promote cellular viability and adhesion, the bioactive epitopes presented on the surface of electrospun CDNFs guide the cellular differentiation of PC-12 cells. In addition to materials synthesis and smart functionalization, physical alignment of the electrospun nanofibers guides the cells for enhanced differentiation. Cells cultured on aligned and IKVAV functionalized electrospun CDNFs had significantly higher expression of neuron-specific βIII-tubulin and synaptophysin. The neurite extension is also higher on the bioactive aligned scaffolds compared to random and non-functionalized electrospun CDNFs. Both chemical and physical cues were utilized for an effective neuronal differentiation process. © The Royal Society of Chemistry.
Open Access
Cyclodextrin functionalized poly(methyl methacrylate) (PMMA) electrospun nanofibers for organic vapors waste treatment
(Elsevier BV, 2010) Uyar, Tamer; Havelund, R.; Nur, Y.; Balan, A.; Hacaloglu, J.; Toppare, L.; Besenbacher, F.; Kingshott, P.
Poly(methyl methacrylate) (PMMA) nanofibers containing the inclusion complex forming betacyclodextrin (_-CD) were successfully produced by means of electrospinning in order to develop functional nanofibrous webs for organic vapor waste treatment. Electrospinning of uniform PMMA nanofibers containing different loadings of _-CD (10%, 25% and 50% (w/w)) was achieved. The surface sensitive spectroscopic techniques; X-ray photoelectron spectroscopy (XPS) and time-of-flight secondary ion mass spectrometry (ToF-SIMS) showed that some of the _-CD molecules are present on the surface of the PMMA nanofibers, which is essential for the trapping of organic vapors by inclusion complexation. Direct pyrolysis mass spectrometry (DP-MS) studies showed that PMMA nanowebs containing _-CD can entrap organic vapors such as aniline, styrene and toluene from the surroundings due to inclusion complexation with _-CD that is present on the fiber surface. Our study showed that electrospun nanowebs functionalized with cyclodextrinsmayhave the potential to be used as molecular filters and/or nanofilters for the treatment of organic vapor waste and air filtration purposes.
Open Access
Cyclodextrin-functionalized mesostructured silica nanoparticles for removal of polycyclic aromatic hydrocarbons
(Academic Press Inc., 2017) Topuz, F.; Uyar, T.
Polycyclic aromatic hydrocarbons (PAHs) are the byproducts of the incomplete combustion of carbon-based fuels, and have high affinity towards DNA strands, ultimately exerting their carcinogenic effects. They are ubiquitous environmental contaminants, and can accumulate on tissues due to their lipophilic nature. In this article, we describe a novel concept for PAH removal from aqueous solutions using cyclodextrin-functionalized mesostructured silica nanoparticles (CDMSNs) and pristine mesostructured silica nanoparticles (MSNs). The adsorption applications of MSNs are greatly restricted due to the absence of surface functional groups on such particles. In this regard, cyclodextrins can serve as ideal functional molecules with their toroidal, cone-type structure, capable of inclusion-complex formation with many hydrophobic molecules, including genotoxic PAHs. The CDMSNs were synthesized by the surfactant-templated, NaOH-catalyzed condensation reactions of tetraethyl orthosilicate (TEOS) in the presence of two different types of cyclodextrin (i.e. hydroxypropyl-β-cyclodextrin (HP-β-CD) and native β-cyclodextrin (β-CD)). The physical incorporation of CD moieties was supported by XPS, FT-IR, NMR, TGA and solid-state 13C NMR. The CDMSNs were treated with aqueous solutions of five different PAHs (e.g. pyrene, anthracene, phenanthrene, fluorene and fluoranthene). The functionalization of MSNs with cyclodextrin moieties significantly boosted the sorption capacity (q) of the MSNs up to ∼2-fold, and the q ranged between 0.3 and 1.65 mg per gram CDMSNs, of which the performance was comparable to that of the activated carbon.
Open Access
Drug delivery system based on cyclodextrin-naproxen inclusion complex incorporated in electrospun polycaprolactone nanofibers
(Elsevier, 2014) Canbolat, M. F.; Celebioglu A.; Uyar, Tamer
In this study, we select naproxen (NAP) as a reference drug and electrospun poly (e-caprolactone) (PCL) nanofibers as a fibrous matrix for our drug-delivery system. NAP was complexed with beta-cyclodextrin (βCD) to form inclusion complex (NAP-βCD-IC) and then NAP-βCD-IC was incorporated into PCL nanofibers via electrospinning. The incorporation of NAP without CD-IC into electrospun PCL was also carried out for a comparative study. Our aim is to analyze the release profiles of NAP from PCL/NAP and PCL/NAP-βCD-IC nanofibers and we investigate the effect of CD-IC on the release behavior of NAP from the nanofibrous PCL matrix. The characterization of NAP-βCD-IC and the presence of CD-IC in PCL/NAP-βCD-IC nanofibers were studied by FTIR, XRD, TGA, NMR and SEM. The SEM imaging of the electrospun PCL/NAP and PCL/NAP-βCD-IC nanofibers reveal that the average fiber diameter of these nanofibers is around 300. nm, in addition, the aggregates of CD-IC in PCL/NAP-βCD-IC nanofibers is observed. The release study of NAP in buffer solution elucidate that the PCL/NAP-βCD-IC nanofibers have higher release amount of NAP than the PCL/NAP nanofibers due to the solubility enhancement of NAP by CD-IC.
Open Access
Electrospinning of cyclodextrin/linalool-inclusion complex nanofibers: fast-dissolving nanofibrous web with prolonged release and antibacterial activity
(Elsevier, 2017-09) Aytac Z.; Yildiz, Z. I.; Kayaci-Senirmak, F.; Tekinay, T.; Uyar, Tamer
The volatility and limited water solubility of linalool is a critical issue to be solved. Here, we demonstrated the electrospinning of polymer-free nanofibrous webs of cyclodextrin/linalool-inclusion complex (CD/linalool-IC-NFs). Three types of modified cyclodextrin (HPβCD, MβCD, and HPγCD) were used to electrospin CD/linalool-IC-NFs. Free-standing CD/linalool-IC-NFs facilitate maximum loading of linalool up to 12% (w/w). A significant amount of linalool (45–89%) was preserved in CD/linalool-IC-NFs, due to enhancement in the thermal stability of linalool by cyclodextrin inclusion complexation. Remarkably, CD/linalool-IC-NFs have shown fast-dissolving characteristics in which these nanofibrous webs dissolved in water within two seconds. Furthermore, linalool release from CD/linalool-IC-NFs inhibited growth of model Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria to a great extent. Briefly, characteristics of liquid linalool have been preserved in a solid nanofiber form and designed CD/linalool-IC-NFs confer high loading capacity, enhanced shelf life and strong antibacterial activity of linalool.
Open Access
Electrospinning of functional poly(methyl methacrylate) nanofibers containing cyclodextrin-menthol inclusion complexes
(Institute of Physics Publishing, 2009) Uyar, Tamer; Nur, Y.; Hacaloglu, J.; Besenbacher, F.
Electrospinning of nanofibers with cyclodextrin inclusion complexes (CD-ICs) is particularly attractive since distinct properties can be obtained by combining the nanofibers with specific functions of the CD-ICs. Here we report on the electrospinning of poly(methyl methacrylate) (PMMA) nanofibers containing cyclodextrin-menthol inclusion complexes (CD-menthol-ICs). These CD-menthol-IC functionalized nanofibers were developed with the purpose of producing functional nanofibers that contain fragrances/flavors with high temperature stability, and menthol was used as a model fragrance/flavor material. The PMMA nanofibers were electrospun with CD-menthol-ICs using three type of CD: α-CD, β-CD, and γ-CD. Direct pyrolysis mass spectrometry (DP-MS) studies showed that the thermal evaporation of menthol occurred over a very high and a broad temperature range (100-355 °C) for PMMA/CDmenthol-IC nanowebs, demonstrating the complexation of menthol with the CD cavity and its high temperature stability. Furthermore, as the size of CD cavity increased in the order α-CD<β-CD<γ-CD, the thermal evolution of menthol shifted to higher temperatures, suggesting that the strength of interaction between menthol and the CD cavity is in the order γ-CD>β-CD>α-CD. © 2009 IOP Publishing Ltd.
Open Access
Electrospinning of polymer-free cyclodextrin/geraniol-inclusion complex nanofibers: enhanced shelf-life of geraniol with antibacterial and antioxidant properties
(Royal Society of Chemistry, 2016) Aytac Z.; Yildiz, Z. I.; Kayaci-Senirmak, F.; Keskin, S. N. O.; Tekinay, T.; Uyar, Tamer
Free-standing nanofibrous webs of cyclodextrin/geraniol-inclusion complex (CD/geraniol-IC-NF) showing antibacterial, antioxidant activity and slow release of geraniol were developed as flavour/fragrance releasing materials via electrospinning. The electrospinning of CD/geraniol-IC-NFs with uniform and bead-free morphology was achieved without using a polymer matrix. Three types of CDs modified with hydroxypropyl and methyl groups (HPβCD, MβCD, and HPγCD) were used to obtain CD/geraniol-IC-NFs. The polymer-free CD/geraniol-IC-NFs allow us to attain much higher geraniol loading (∼11%, w/w) when compared to electrospun polymeric nanofibers containing CD/geraniol-IC (∼5%, w/w). Geraniol has a volatile nature, yet, a significant amount of geraniol (∼60-90%) was preserved in CD/geraniol-IC-NFs due to the complexation, whereas evaporation of geraniol was unavoidable for polymeric nanofibers incorporating geraniol without cyclodextrin. Short-term (3 h) temperature dependent release (37 °C, 50 °C, and 75 °C) and long-term open air (50 days, at RT) release tests revealed that MβCD/geraniol-IC-NF released less geraniol compared to HPβCD/geraniol-IC-NF and HPγCD/geraniol-IC-NF, indicating that much stronger inclusion complexation was formed between MβCD and geraniol. The release of geraniol from CD/geraniol-IC-NFs prevented the colonization of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria to a great extent, as observed in the antibacterial activity results. It was observed that CD/geraniol-IC-NFs had higher antioxidant activity compared to pure geraniol due to the solubility increase. In brief, the results reported here may open a new door to enhance the performance of essential oils and flavour/fragrances, to preserve volatile compounds from evaporation and to better understand the potential of CD/IC-NFs as carrier systems for guest compounds in the food, cosmetic and household cleaning industries.
Open Access
Electrospun nylon 6,6 nanofibers functionalized with cyclodextrins for removal of toluene vapor
(John Wiley and Sons Inc., 2015) Kayaci, F.; Sen, H. S.; Durgun, Engin; Uyar, Tamer
Functional nylon 6,6 nanofibers incorporating cyclodextrins (CD) were developed via electrospinning. Enhanced thermal stability of the nylon 6,6/CD nanofibers was observed due to interaction between CD and nylon 6,6. X-ray photoelectron spectroscopy and attenuated total reflectance Fourier transform infrared spectroscopy studies indicated the existence of some CD molecules on the surface of the nanofibers. Electrospun nylon 6,6 nanofibers without having CD were ineffective for entrapment of toluene vapor from the environment, whereas nylon 6,6/CD nanofibrous membranes can effectively entrap toluene vapor from the surrounding by taking advantage of the high surface-volume ratio of nanofibers with the added advantage of inclusion complexation capability of CD presenting on the nanofiber surface. The modeling studies for formation of inclusion complex between CD and toluene were also performed by using ab initio techniques. Our results suggest that nylon 6,6/CD nanofibrous membranes may have potential to be used as air filters for the removal of organic vapor waste from surroundings.
Open Access
Encapsulation of active agents in electrospun nanofibers/nanowebs
(The Fiber Society, 2013) Kayaci, Fatma; Aytac, Zeynep; Celebioglu, Asli; Uyar, Tamer
In this study, we produce functional nanofibers/nanowebs containing active agents such as essential oils, antibacterials, antioxidants, flavors/fragrances via electrospinning technique. The encapsulation of these active agents into electrospun nanofibers/nanowebs was quite possible, however, their stability and/or shelf-life was limited due to their volatile nature. Nevertheless, by forming cyclodextrin inclusion complexes (CD-IC) with these active agents and incorporating CD-IC into electrospun nanofibers/nanowebs, we achieved high temperature stability, slow release and prolonged shelf-life for these active agents. These functional electrospun nanofibers/nanowebs containing active agents can be quite applicable in active food packaging, textiles, biotechnology, etc.
Open Access
Encapsulation of gallic acid/cyclodextrin inclusion complex in electrospun polylactic acid nanofibers: release behavior and antioxidant activity of gallic acid
(Elsevier, 2016-06) Aytac Z.; Kusku S. I.; Durgun, Engin; Uyar, Tamer
Cyclodextrin-inclusion complexes (CD-ICs) possess great prominence in food and pharmaceutical industries due to their enhanced ability for stabilization of active compounds during processing, storage and usage. Here, CD-IC of gallic acid (GA) with hydroxypropyl-beta-cyclodextrin (GA/HPβCD-IC) was prepared and then incorporated into polylactic acid (PLA) nanofibers (PLA/GA/HPβCD-IC-NF) using electrospinning technique to observe the effect of CD-ICs in the release behavior of GA into three different mediums (water, 10% ethanol and 95% ethanol). The GA incorporated PLA nanofibers (PLA/GA-NFs) were served as control. Phase solubility studies showed an enhanced solubility of GA with increasing amount of HPβCD. The detailed characterization techniques (XRD, TGA and 1H-NMR) confirmed the formation of inclusion complex between GA and HPβCD. Computational modeling studies indicated that the GA made an efficient complex with HPβCD at 1:1 either in vacuum or aqueous system. SEM images revealed the bead-free and uniform morphology of PLA/GA/HPβCD-IC-NF. The release studies of GA from PLA/GA/HPβCD-IC-NF and PLA/GA-NF were carried out in water, 10% ethanol and 95% ethanol, and the findings revealed that PLA/GA/HPβCD-IC-NF has released much more amount of GA in water and 10% ethanol system when compared to PLA/GA-NF. In addition, GA was released slowly from PLA/GA/HPβCD-IC-NF into 95% ethanol when compared to PLA/GA-NF. It was also observed that electrospinning process had no negative effect on the antioxidant activity of GA when GA was incorporated in PLA nanofibers.
Open Access
Encapsulation of vanillin/cyclodextrin inclusion complex in electrospun polyvinyl alcohol (PVA) nanowebs: prolonged shelf-life and high temperature stability of vanillin
(2012-08) Kayaci, F.; Uyar, Tamer
We produced functional nanowebs, containing vanillin, having prolonged shelf-life and high temperature stability facilitated by cyclodextrin (CD) inclusion complexation. Polyvinyl alcohol (PVA) nanowebs incorporating vanillin/cyclodextrin inclusion complex (vanillin/CD-IC) were produced via electrospinning technique. The vanillin/CD-IC was prepared with three types of CDs; α-CD, β-CD and γ-CD to find out the most favourable CD type for the stabilization of vanillin. PVA/vanillin/CD-IC nanofibres, having fibre diameters around ∼200 nm, were successfully electrospun from aqueous mixture of PVA and vanillin/CD-IC. Our results indicated that vanillin with enhanced durability and high temperature stability was achieved for PVA/vanillin/CD-IC nanowebs due to complexation of vanillin with CD, whereas the PVA nanofibres without CD-IC could not effectively preserve the vanillin. Additionally, we observed that PVA/vanillin/γ-CD-IC nanoweb was more effective for the stabilization and slow release of vanillin suggesting that the strength of interaction between vanillin and the γ-CD cavity is stronger when compared to α-CD and β-CD. © 2012 Elsevier Ltd. All rights reserved.
Open Access
Fast-dissolving, prolonged release, and antibacterial cyclodextrin/limonene-inclusion complex nanofibrous webs via polymer-free electrospinning
(American Chemical Society, 2016) Aytac Z.; Yildiz, Z. I.; Kayaci-Senirmak, F.; S. Keskin, N. O.; Kusku, S. I.; Durgun, Engin; Tekinay, T.; Uyar, Tamer
We have proposed a new strategy for preparing free-standing nanofibrous webs from an inclusion complex (IC) of a well-known flavor/fragrance compound (limonene) with three modified cyclodextrins (HPβCD, MβCD, and HPγCD) via electrospinning (CD/limonene-IC-NFs) without using a polymeric matrix. The experimental and computational modeling studies proved that the stoichiometry of the complexes was 1:1 for CD/limonene systems. MβCD/limonene-IC-NF released much more limonene at 37, 50, and 75 °C than HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF because of the greater amount of preserved limonene. Moreover, MβCD/limonene-IC-NF has released only 25% (w/w) of its limonene, whereas HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF released 51 and 88% (w/w) of their limonene in 100 days, respectively. CD/limonene-IC-NFs exhibited high antibacterial activity against E. coli and S. aureus. The water solubility of limonene increased significantly and CD/limonene-IC-NFs were dissolved in water in a few seconds. In brief, CD/limonene-IC-NFs with fast-dissolving character enhanced the thermal stability and prolonged the shelf life along with antibacterial properties could be quite applicable in food and oral care applications.
Open Access
Functional electrospun polymeric nanofibers incorporating geraniol-cyclodextrin inclusion complexes: high thermal stability and enhanced durability of geraniol
(Elsevier Ltd, 2014) Kayaci, F.; Sen, H. S.; Durgun, Engin; Uyar, Tamer
In this study, solid geraniol/cyclodextrin inclusion complexes (geraniol/CD-IC) were successfully prepared by using three types of native CD (α-CD, β-CD and γ-CD). The modeling studies for inclusion complexation between CD and geraniol were performed by using ab initio techniques. Both experimentally and theoretically, the complexation efficiency between geraniol and γ-CD was higher; therefore, geraniol/γ-CD-IC was chosen and then incorporated into polyvinyl alcohol (PVA) nanofibers (NF) via electrospinning. The scanning electron microscopy imaging elucidated that the aggregates of geraniol/γ-CD-IC crystals were distributed in the PVA NF, whereas bead-free and uniform PVA and PVA/geraniol NF without CD-IC were obtained. Higher thermal stability of geraniol was observed in the electrospun PVA/geraniol/γ-CD-IC NF. However, geraniol molecules having volatile nature could not be preserved without CD-IC during electrospinning or during storage; therefore, the complete evaporation of geraniol in PVA/geraniol NF was unavoidable even after one day of its production. On the contrary, the loss of geraniol was minimal (~. 10%) for PVA/geraniol/γ-CD-IC NF even after storage of these NF for two years owing to inclusion complexation. Our study demonstrated that electrospun NF incorporating CD-IC may be quite applicable in food industry, e.g.: active food packaging or functional foods, due to very high surface area and nanoporous structure of NF; high thermal stability and enhanced durability of active agents and functional food ingredients.
Open Access
Menthol/cyclodextrin inclusion complex nanofibers: Enhanced water-solubility and high-temperature stability of menthol
(Elsevier, 2018) Yildiz, Z. I.; Celebioglu A.; Kilic, M. E.; Durgun, Engin; Uyar, Tamer
Cyclodextrins are capable of forming non-covalent host-guest inclusion complexation with variety of molecules in order to enhance water-solubility and thermal stability of such hydrophobic and volatile molecules. Menthol, an efficient antibacterial and flavour/fragrance agent, is used in various applications like food, pharmacy, cosmetics, however, its low water-solubility and high volatility somewhat limit its application. In this study, menthol/cyclodextrin-inclusion complex (menthol/CD-IC) was formed in highly concentrated aqueous solution by using hydroxypropyl-β-cyclodextrin (HPβCD) and hydroxypropyl-γ-cyclodextrin (HPγCD). The phase solubility studies and computational modeling studies revealed that menthol and these two CDs (HPβCD and HPγCD) formed stable inclusion complexes with the optimal molar ratio of 1:1 (menthol:CD) and inclusion complex formation enhanced the water-solubility of menthol. The electrospinning of nanofibers (NFs) from highly concentrated aqueous solutions (160%, w/v) of menthol/CD-IC was successfully performed without using additional fiber forming polymer and bead-free and uniform menthol/CD-IC NFs in the form of self-standing and flexible nanofibrous webs were produced. The initial molar ratio (1:1, menthol:CD) of the menthol/CD-IC in the solutions was mostly preserved in the menthol/CD-IC NFs (above 0.70:1.00, menthol:CD). The water-solubility of menthol was enhanced and menthol/CD-IC NFs have shown fast-dissolving character. The slow-release of menthol was achieved for menthol/CD-IC NFs, and the evaporation of menthol was shifted to much higher temperature (up to 275 °C) for menthol/CD-IC NFs which proved the high-temperature stability for menthol due to inclusion complexation.
Open Access
Molecular encapsulation of cinnamaldehyde within cyclodextrin inclusion complex electrospun nanofibers: fast-dissolution, enhanced water solubility, high temperature stability, and antibacterial activity of cinnamaldehyde
(American Chemical Society, 2019) Yıldız, Zehra İrem; Kılıç, Mehmet Emin; Durgun, Engin; Uyar, Tamer
The electrospinning of nanofibers (NFs) of cinnamaldehyde inclusion complexes (ICs) with two different hydroxypropylated cyclodextrins (CDs), hydroxypropyl-β-cyclodextrin (HP-β-CD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CD), was successfully performed in order to produce cinnamaldehyde/CD-IC NFs without using an additional polymer matrix. The inclusion complexation between cinnamaldehyde and hydroxypropylated CDs was studied by computational molecular modeling, and the results suggested that HP-β-CD and HP-γ-CD can be inclusion complexed with cinnamaldehyde at 1:1 and 2:1 (cinnamaldehyde/CD) molar ratios. Additionally, molecular modeling and phase solubility studies showed that water solubility of cinnamaldehyde dramatically increases with cyclodextrin inclusion complex (CD-IC) formation. The HP-β-CD has shown slightly stronger binding with cinnamaldehyde when compared to HP-γ-CD for cinnamaldehyde/CD-IC. Although cinnamaldehyde is a highly volatile compound, it was effectively preserved with high loading by the cinnamaldehyde/CD-IC NFs. It was also observed that cinnamaldehyde has shown much higher temperature stability in cinnamaldehyde/CD-IC NFs compared to uncomplexed cinnamaldehyde because of the inclusion complexation state of cinnamaldehyde within the hydroxypropylated CD cavity. Moreover, cinnamaldehyde still has kept its antibacterial activity in cinnamaldehyde/CD-IC NF samples when tested against Escherichia coli. In addition, cinnamaldehyde/CD-IC NF mats were fast-dissolving in water, even though pure cinnamaldehyde has a water-insoluble nature. In brief, self-standing nanofibrous mats of electrospun cinnamaldehyde/CD-IC NFs are potentially applicable in food, oral-care, healthcare, and pharmaceutics because of their fast-dissolving character, enhanced water solubility, stability at elevated temperature, and promising antibacterial activity.