journal article·2018-04Open access

Encapsulation of camphor in cyclodextrin inclusion complex nanofibers via polymer-free electrospinning: enhanced water solubility, high temperature stability, and slow release of camphor

Asli Celebioglu, Zeynep Aytac, Mehmet Emin Kilic, Engin Durgun, Tamer Uyar

Journal of Materials Science· Volume 53· Issue 7

Abstract

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.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Electrospun Nanofibers in Biomedical Applications · Electrohydrodynamics and Fluid Dynamics · Advanced Sensor and Energy Harvesting Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (46)

Show source-provided references
1. Bakkali F, Averbeck S, Averbeck D, Idaomar M (2008) Biological effects of essential oils-a review. Food Chem Toxicol 46(2):446–47510.1016/j.fct.2007.09.106 ↗
2. 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):220–24310.1016/j.ijpharm.2014.12.069 ↗
3. Uyar T, Kny E (eds) (2017) Electrospun materials for tissue engineering and biomedical applications: research, design and commercialization. Woodhead Publishing, Cambridge
4. 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 65:9161–917910.1021/acs.jafc.7b02956 ↗
5. Wendorff JH, Agarwal S, Greiner A (2012) Electrospinning: materials, processing, and applications. Wiley, Weinheim10.1002/9783527647705 ↗
6. Bilensoy E (ed) (2011) Cyclodextrins in pharmaceutics, cosmetics, and biomedicine: current and future industrial applications. Wiley, Hoboken, New Jersey
7. Del Valle EM (2004) Cyclodextrins and their uses: a review. Process Biochem 39(9):1033–104610.1016/S0032-9592(03)00258-9 ↗
8. Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–175410.1021/cr970022c ↗
9. 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 120:125–13110.1016/j.colsurfb.2014.04.006 ↗
10. 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 233:117–12410.1016/j.foodchem.2017.04.095 ↗
11. 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):145–15010.1016/j.reactfunctpolym.2008.12.012 ↗
12. 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):641–64910.1016/j.foodchem.2012.01.040 ↗
13. Celebioglu A, Uyar T (2011) Electrospinning of polymer-free nanofibers from cyclodextrin inclusion complexes. Langmuir 27(10):6219–622610.1021/la1050223 ↗
14. Celebioglu A, Umu OC, Tekinay T, Uyar T (2014) Antibacterial electrospun nanofibers from triclosan/cyclodextrin inclusion complexes. Colloids Surf B 116:612–61910.1016/j.colsurfb.2013.10.029 ↗
15. 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):46089–4609910.1039/C6RA07088D ↗
16. 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):3141–315310.1039/C6FO00569A ↗
17. 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):7325–733410.1021/acs.jafc.6b02632 ↗
18. 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 231:192–20110.1016/j.foodchem.2017.03.113 ↗
19. 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):5404–541210.1021/acs.jafc.7b01562 ↗
20. 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.1356410.1111/ijfs.13564 ↗
21. Celebioglu A, Uyar T (2010) Cyclodextrin nanofibers by electrospinning. Chem Commun 46(37):6903–690510.1039/c0cc01484b ↗
22. Celebioglu A, Uyar T (2012) Electrospinning of nanofibers from non-polymeric systems: polymer-free nanofibers from cyclodextrin derivatives. Nanoscale 4(2):621–63110.1039/C1NR11364J ↗
23. 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):136–14010.1016/j.colsurfb.2006.04.008 ↗
24. Higuchi TK, Connors A (1965) Phase-solubility techniques. Adv Anal Chem Instrum 4:117–212
25. Yalkowsky SH, He Y, Jain P (2016) Handbook of aqueous solubility data. CRC Press, Boca Raton10.1201/EBK1439802458 ↗
26. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140(4A):A1133–A113810.1103/PhysRev.140.A1133 ↗
27. Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136(3B):B864–B87110.1103/PhysRev.136.B864 ↗
28. 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):11169–1118610.1103/PhysRevB.54.11169 ↗
29. 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):15–5010.1016/0927-0256(96)00008-0 ↗
30. Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77(18):3865–386810.1103/PhysRevLett.77.3865 ↗
31. Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem 27(15):1787–179910.1002/jcc.20495 ↗
32. Blöchl PE (1994) Projector augmented-wave method. Phys Rev B 50(24):17953–1797910.1103/PhysRevB.50.17953 ↗
33. Kresse G, Joubert D (1999) From ultrasoft pseudopotentials to the projector augmented-wave method. Phys Rev B 59(3):1758–177510.1103/PhysRevB.59.1758 ↗
34. 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):084106–08410810.1063/1.4865107 ↗
35. 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):535–54010.1016/j.jpba.2008.02.006 ↗
36. 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):333–33910.1016/S0731-7085(03)00529-6 ↗
37. 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):416–42010.1248/cpb.44.416 ↗
38. Ciobanu A, Landy D, Fourmentin S (2013) Complexation efficiency of cyclodextrins for volatile flavor compounds. Food Res Int 53(1):110–11410.1016/j.foodres.2013.03.048 ↗
39. 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):1034–104010.1016/j.carres.2010.03.020 ↗
40. Celebioglu A, Uyar T (2013) Electrospun gamma-cyclodextrin (γ-CD) nanofibers for the entrapment of volatile organic compounds. RSC Adv 3(45):22891–2289510.1039/c3ra44870c ↗
41. Celebioglu A, Uyar T (2013) Electrospinning of nanofibers from non-polymeric systems: electrospun nanofibers from native cyclodextrins. J Colloid Interface Sci 404:1–710.1016/j.jcis.2013.04.034 ↗
42. 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):3372–338410.1016/j.polymer.2005.03.011 ↗
43. Uyar T, Besenbacher F (2008) Electrospinning of uniform polystyrene fibers: the effect of solvent conductivity. Polymer 49(24):5336–534310.1016/j.polymer.2008.09.025 ↗
44. 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 128:331–33810.1016/j.colsurfb.2015.02.019 ↗
45. 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 509:80–8510.1016/j.colsurfa.2016.08.090 ↗
46. 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):97–10610.1002/pts.964 ↗