Electrospinning of polymer-free nanofibers (NF) was successfully performed from inclusion complexes (ICs) of modified cyclodextrins [hydroxypropyl-β-cyclodextrin (HPβCD) and hydroxypropyl-γ-cyclodextrin (HPγCD)] and camphor (HPβCD/camphor-IC-NF and HPγCD/camphor-IC-NF). Although camphor is a volatile and hydrophobic essential oil component, the improvement in the aqueous solubility and thermal stability of camphor by inclusion complexation with cyclodextrins was confirmed by phase solubility diagram and thermal analysis, respectively. Moreover, fast-dissolving characteristics of electrospun CD/camphor-IC-NF webs were also observed. Computational modeling study shows preferential orientation of camphor is variable depending on the CD types. In addition, the interaction of camphor molecule is slightly stronger with HPγCD when compared to HPβCD owing to the better allocation of guest (camphor) in host (CD) cavity originating from the better size match. Even though camphor has high volatility, significant amount of camphor was preserved in HPβCD/camphor-IC-NF and HPγCD/camphor-IC-NF after electrospinning. The molar ratio of HPβCD:camphor and HPγCD:camphor was determined as ~ 1.00:0.65 and ~ 1.00:0.90 in HPβCD/camphor-IC-NF and HPγCD/camphor-IC-NF, respectively. In short, encapsulation of camphor in cyclodextrin inclusion complex nanofibers via polymer-free electrospinning was attained, and enhanced water solubility, high temperature stability, and slow release of camphor were achieved for CD/camphor-IC-NF.
This is a preview of subscription content, log in to check access.
Buy single article
Instant unlimited access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
Bakkali F, Averbeck S, Averbeck D, Idaomar M (2008) Biological effects of essential oils-a review. Food Chem Toxicol 46(2):446–475
El Asbahani A, Miladi K, Badri W, Sala M, Addi EA, Casabianca H, El Mousadik A, Hartmann D, Jilale DA, Renaud FNR, Elaissari A (2015) Essential oils: from extraction to encapsulation. Int J Pharm 483(1):220–243
Uyar T, Kny E (eds) (2017) Electrospun materials for tissue engineering and biomedical applications: research, design and commercialization. Woodhead Publishing, Cambridge
Wen P, Wen Y, Zong M-H, Linhardt RJ, Wu H (2017) Encapsulation of bioactive compound in electrospun fibers and its potential application. J Agric Food Chem 65:9161–9179
Wendorff JH, Agarwal S, Greiner A (2012) Electrospinning: materials, processing, and applications. Wiley, Weinheim
Bilensoy E (ed) (2011) Cyclodextrins in pharmaceutics, cosmetics, and biomedicine: current and future industrial applications. Wiley, Hoboken, New Jersey
Del Valle EM (2004) Cyclodextrins and their uses: a review. Process Biochem 39(9):1033–1046
Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1754
Aytac Z, Dogan SY, Tekinay T, Uyar T (2014) Release and antibacterial activity of allyl isothiocyanate/β-cyclodextrin complex encapsulated in electrospun nanofibers. Colloids Surf B 120:125–131
Aytac Z, Ipek S, Durgun E, Tekinay T, Uyar T (2017) Antibacterial electrospun zein nanofibrous web encapsulating thymol/cyclodextrin-inclusion complex for food packaging. Food Chem 233:117–124
Uyar T, Hacaloglu J, Besenbacher F (2009) Electrospun polystyrene fibers containing high temperature stable volatile fragrance/flavor facilitated by cyclodextrin inclusion complexes. React Funct Polym 69(3):145–150
Kayaci F, Uyar T (2012) Encapsulation of vanillin/cyclodextrin inclusion complex in electrospun polyvinyl alcohol (PVA) nanowebs: prolonged shelf-life and high temperature stability of vanillin. Food Chem 133(3):641–649
Celebioglu A, Uyar T (2011) Electrospinning of polymer-free nanofibers from cyclodextrin inclusion complexes. Langmuir 27(10):6219–6226
Celebioglu A, Umu OC, Tekinay T, Uyar T (2014) Antibacterial electrospun nanofibers from triclosan/cyclodextrin inclusion complexes. Colloids Surf B 116:612–619
Aytac Z, Yildiz ZI, Kayaci-Senirmak F, San Keskin NO, Tekinay T, Uyar T (2016) Electrospinning of polymer-free cyclodextrin/geraniol-inclusion complex nanofibers: enhanced shelf-life of geraniol with antibacterial and antioxidant properties. RSC Adv 6(52):46089–46099
Celebioglu A, Kayaci-Senirmak F, Ipek S, Durgun E, Uyar T (2016) Polymer-free nanofibers from vanillin/cyclodextrin inclusion complexes: high thermal stability, enhanced solubility and antioxidant property. Food Funct 7(7):3141–3153
Aytac Z, Yildiz ZI, Kayaci-Senirmak F, San Keskin NO, Kusku SI, Durgun E, Tekinay T, Uyar T (2016) Fast-dissolving, prolonged release, and antibacterial cyclodextrin/limonene-inclusion complex nanofibrous webs via polymer-free electrospinning. J Agric Food Chem 64(39):7325–7334
Aytac Z, Yildiz ZI, Kayaci-Senirmak F, Tekinay T, Uyar T (2017) Electrospinning of cyclodextrin/linalool-inclusion complex nanofibers: fast-dissolving nanofibrous web with prolonged release and antibacterial activity. Food Chem 231:192–201
Celebioglu A, Uyar T (2017) Antioxidant vitamin E/cyclodextrin inclusion complex electrospun nanofibers: enhanced water-solubility, prolonged shelf-life and photostability of vitamin E. J Agric Food Chem 65(26):5404–5412
Celebioglu A, Yildiz ZI, Uyar T (2017) Electrospun nanofibers from cyclodextrin inclusion complexes with cineole and p-cymene: enhanced water solubility and thermal stability. Int J Food Sci Technol. https://doi.org/10.1111/ijfs.13564
Celebioglu A, Uyar T (2010) Cyclodextrin nanofibers by electrospinning. Chem Commun 46(37):6903–6905
Celebioglu A, Uyar T (2012) Electrospinning of nanofibers from non-polymeric systems: polymer-free nanofibers from cyclodextrin derivatives. Nanoscale 4(2):621–631
Chang CP, Leung TK, Lin SM, Hsu CC (2006) Release properties on gelatin-gum arabic microcapsules containing camphor oil with added polystyrene. Colloids Surf B 50(2):136–140
Higuchi TK, Connors A (1965) Phase-solubility techniques. Adv Anal Chem Instrum 4:117–212
Yalkowsky SH, He Y, Jain P (2016) Handbook of aqueous solubility data. CRC Press, Boca Raton
Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140(4A):A1133–A1138
Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136(3B):B864–B871
Kresse G, Furthmüller J (1996) Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set. Phys Rev B 54(16):11169–11186
Kresse G, Furthmüller J (1996) Efficiency of ab initio total energy calculations for metals and semiconductors using a plane-wave basis set. Comput Mater Sci 6(1):15–50
Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77(18):3865–3868
Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem 27(15):1787–1799
Blöchl PE (1994) Projector augmented-wave method. Phys Rev B 50(24):17953–17979
Kresse G, Joubert D (1999) From ultrasoft pseudopotentials to the projector augmented-wave method. Phys Rev B 59(3):1758–1775
Mathew K, Sundararaman R, Letchworth-Weaver K, Arias TA, Hennig RG (2014) Implicit solvation model for density-functional study of nanocrystal surfaces and reaction pathways. J Chem Phys 140(8):084106–084108
Aleem O, Kuchekar B, Pore Y, Late S (2008) Effect of β-cyclodextrin and hydroxypropyl β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir. J Pharm Biomed Anal 47(3):535–540
Pralhad T, Rajendrakumar K (2004) Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J Pharm Biomed Anal 34(2):333–339
Tanaka M, Matsuda H, Sumiyoshi H, Arima H, Hirayama F, Uekama K, Tsuchiya S (1996) 2-Hydroxypropylated cyclodextrins as a sustained-release carrier for fragrance materials. Chem Pharm Bull 44(2):416–420
Ciobanu A, Landy D, Fourmentin S (2013) Complexation efficiency of cyclodextrins for volatile flavor compounds. Food Res Int 53(1):110–114
Kokkinou A, Tsorteki F, Karpusas M, Papakyriakou A, Bethanis K, Mentzafos D (2010) Study of the inclusion of the (R)-and (S)-camphor enantiomers in α-cyclodextrin by X-ray crystallography and molecular dynamics. Carbohyd Res 345(8):1034–1040
Celebioglu A, Uyar T (2013) Electrospun gamma-cyclodextrin (γ-CD) nanofibers for the entrapment of volatile organic compounds. RSC Adv 3(45):22891–22895
Celebioglu A, Uyar T (2013) Electrospinning of nanofibers from non-polymeric systems: electrospun nanofibers from native cyclodextrins. J Colloid Interface Sci 404:1–7
Shenoy SL, Bates WD, Frisch HL, Wnek GE (2005) Role of chain entanglements on fiber formation during electrospinning of polymer solutions: good solvent, non-specific polymer-polymer interaction limit. Polymer 46(10):3372–3384
Uyar T, Besenbacher F (2008) Electrospinning of uniform polystyrene fibers: the effect of solvent conductivity. Polymer 49(24):5336–5343
Aytac Z, Sen HS, Durgun E, Uyar T (2015) Sulfisoxazole/cyclodextrin inclusion complex incorporated in electrospun hydroxypropyl cellulose nanofibers as drug delivery system. Colloids Surf B 128:331–338
Wang C, Wang H, Liu Y (2016) Purification of Pb(II) ions from aqueous solution by camphor leaf modified with succinic anhydride. Colloids Surf A 509:80–85
Hu CY, Chen M, Wang ZW (2012) Release of thymol, cinnamaldehyde and vanillin from soy protein isolate films into olive oil. Packag Technol Sci 25(2):97–106
Dr. A. Celebioglu thanks TUBITAK-BIDEB for the Ph.D. scholarship. Dr. Z. Aytac thanks TUBITAK-BIDEB and TUBITAK (Project # 213M185) for the Ph.D. scholarship.
Dr. Uyar acknowledges the Scientific and Technological Research Council of Turkey (TUBITAK)—Turkey (Project # 213M185) for funding this research. Dr. Uyar and Dr. Durgun also acknowledge the partial support from the Turkish Academy of Sciences—Outstanding Young Scientists Award Program (TUBA-GEBIP)—Turkey. The computational resources are provided by TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure), and the National Center for High Performance Computing of Turkey (UHeM) under Grant No. 5003622015.
Electronic supplementary material
Below is the link to the electronic supplementary material.
About this article
Cite this article
Celebioglu, A., Aytac, Z., Kilic, M.E. et al. Encapsulation of camphor in cyclodextrin inclusion complex nanofibers via polymer-free electrospinning: enhanced water solubility, high temperature stability, and slow release of camphor. J Mater Sci 53, 5436–5449 (2018) doi:10.1007/s10853-017-1918-4