pp 1–16 | Cite as

Fabrication and bioevaluation of a medicated electrospun mat based on azido-cellulose acetate via click chemistry

  • Ahmed A. NadaEmail author
  • Faten Hassan Hassan Abdellatif
  • Ahmed A. F. Soliman
  • Jialong Shen
  • Samuel M. Hudson
  • Nabil Y. Abou-Zeid
Original Research


Cellulose acetate (CA) electrospun fibers have been used in different medical applications such as drug delivery systems to release various drugs. CA, usually available with a typical degree of substitution (DS) of 2.4–2.5, shows little control over the release rate of the incorporated substances, due to the lack of active functional groups. In this work, click chemistry was used to activate CA and produce crosslinked electrospun mats to provide sustained release for topical administration. CA was activated by introducing azide functional groups on the residual hydroxyl groups of the polymer chains with a DSAzido of 0.24 by a coupling reaction. Azido-CA was then electrospun to produce nanofibers, in which capsaicin and sodium diclofenac, as pain-relieving drugs were encapsulated. Propargylated maltose was synthesized as a crosslinker to the Azido-CA via triazole chemistry. Spectral analysis was used to confirm the chemical structure of the new derivatives and the click-matrices. SEM morphological analysis of the Azido-CA electrospun fibers showed a range of diameters from 140 to 270 nm, with clear, smooth surfaces. Samples of the matrices were assessed for cytotoxicity and showed an acceptable cell viability. In a rat model, sodium diclofenac and capsaicin-loaded electrospun mats of Azido-CA showed superior closure rates over the untreated rats and those treated with a commercial cream. Rats treated with electrospun mat of CA, Azido-CA loaded with drugs showed normal intact histological structure of the epidermis and dermis.


Electrospun fiber Click-scaffold Azidation Controlled release Wound healing Topical applications 



Authors are grateful for the funding provided by the U.S.-Egypt Science and Technology Joint Fund, administered by the National Academy of Science. (US: CFDA # 98.00-AID, Subaward 2000007149). Authors are grateful to National Research Centre (Scopus affiliation ID: 60014618) for the provided facilities and analytical support and for the financial support from the Science and Technology Development Fund (STDF) through the US-Egypt Project, Cycle 17 and I.D. 114, entitled” A Medical Textile for Comprehensive Wound Care: A Laminated Multifunctional Electrospun Fabric that is Hemostatic, Anti-inflammatory and Anti-microbial”. All rats were handled in accordance with the NIH Guidelines for the Care and Use of Laboratory Animals and with the recommendations of the Institutional Ethical Committee (Reg. No. 17-055).

Compliance with ethical standards

Conflict of interest

Authors have declared no conflicts of interest.

Supplementary material

10570_2019_2739_MOESM1_ESM.docx (416 kb)
Supplementary material 1 (DOCX 416 kb)


  1. Abdel A, Attia M, Shafik M et al (2019) Processing and fundamental characterization of carbon fibers and cellulose nanocrystals derived from bagasse. Carbon Lett 29:145–154. Google Scholar
  2. Abdellatif FHH, Babin J, Arnal-Herault C, Jonquieres A (2015) Grafting of cellulose and cellulose derivatives by CuAAC click chemistry. In: Thakur VK (ed) Cellulose-based graft copolymers: structure and chemistry. CRC Press, Boca RatonGoogle Scholar
  3. Abdellatif FHH, Babin J, Arnal-Herault C et al (2016) Grafting of cellulose acetate with ionic liquids for biofuel purification by a membrane process: influence of the cation. Carbohydr Polym 147:313–322. CrossRefGoogle Scholar
  4. Abdellatif FHH, Babin J, Arnal-Herault C et al (2017) Bio-based membranes for ethyl tert-butyl ether (ETBE) bio-fuel purification by pervaporation. J Membr Sci 524:449–459. CrossRefGoogle Scholar
  5. Abdellatif FHH, Babin J, Arnal-Herault C et al (2018) Grafting cellulose acetate with ionic liquids for biofuel purification membranes: influence of the anion. Carbohydr Polym 196:176–186. CrossRefGoogle Scholar
  6. Abdelmoez S, Abd El Azeem RA, Nada AA, Khattab TA (2016) Electrospun PDA-CA nanofibers toward hydrophobic coatings. Zeitschrift fur Anorg und Allg Chemie 642:219–221. CrossRefGoogle Scholar
  7. Abo-Shosha MH, Fahmy HM, Hassan FH et al (2009) Tetracycline hydrate and gentamicine sulfate containing carboxymethylated cotton fabric suitable for moist wound healing dressings: properties and evaluation. J Ind Text 38:341–360. CrossRefGoogle Scholar
  8. Acton QA (2013) Sodium hydroxide. In: Acton QA (ed) Sodium compounds—advances in research and application. Scholarly Editions, Atlanta, p 247Google Scholar
  9. Ahmed HM, Abdellatif MM, Ibrahim S, Abdellatif FHH (2019) Mini-emulsified copolymer/silica nanocomposite as effective binder and self-cleaning for textiles coating. Prog Org Coat. Google Scholar
  10. Aravamudhan A, Ramos DM, Nada AA, Kumbar SG (2014) Natural polymers: polysaccharides and their derivatives for biomedical applications. In: Kumbar S, Laurencin C, Deng M (eds) Natural and synthetic biomedical polymers. Elsevier, Amsterdam, pp 67–89CrossRefGoogle Scholar
  11. BeMiller JN (ed) (2012) Industrial gums: polysaccharides and their derivatives, 3rd revised edn. Academic Press, New YorkGoogle Scholar
  12. Cheng Y, Nada AA, Valmikinathan CM et al (2014) In situ gelling polysaccharide-based hydrogel for cell and drug delivery in tissue engineering. J Appl Polym Sci 131:38834 (1–11). Google Scholar
  13. Ding CL, Ju BZ, Zhang SF (2014) Preparation and properties of novel starch derivatives containing the sulfonic acid of the group and carboxymethyl. Asian J Chem 26:3166–3170. CrossRefGoogle Scholar
  14. Eid BM, Hassabo AG, Nada AA et al (2018) Nano-structured metal oxides: synthesis, characterization and application for multifunctional cotton fabric. Adv Nat Sci Nanosci Nanotechnol 9:035014. CrossRefGoogle Scholar
  15. EL Azeem RA, Nada AA (2015) Chitosan liposomal microspheres for ricinoleic acid encapsulation. J Appl Pharm Sci 5:55–62. CrossRefGoogle Scholar
  16. Fischer S, Thümmler K, Volkert B et al (2008) Properties and applications of cellulose acetate. Macromol Symp 262:89–96. CrossRefGoogle Scholar
  17. Han SO, Youk JH, Min KD et al (2008) Electrospinning of cellulose acetate nanofibers using a mixed solvent of acetic acid/water: effects of solvent composition on the fiber diameter. Mater Lett 62:759–762. CrossRefGoogle Scholar
  18. Hassabo AG, Mohamed AL, Nada AA, Abou Zeid NY (2015a) Controlled release of drugs from cellulosic wound bandage using silica microsphere as drug encapsulator module. J Appl Pharm Sci 5:67–73. CrossRefGoogle Scholar
  19. Hassabo AG, Nada AA, Ibrahim HM, Abou-Zeid NY (2015b) Impregnation of silver nanoparticles into polysaccharide substrates and their properties. Carbohydr Polym. Google Scholar
  20. Hurst SJ (ed) (2011) Biomedical nanotechnology: methods and protocols. Humana Press, New YorkGoogle Scholar
  21. Ibrahim NA, Eid BM, Abdellatif FHH (2018a) Advanced materials and technologies for antimicrobial finishing of cellulosic textiles. In: Yusuf M (ed) Handbook of renewable materials for coloration and finishing. Wiley, HobokenGoogle Scholar
  22. Ibrahim NA, Nada AA, Eid BM (2018b) Polysaccharide-based polymer gels and their potential applications. In: Thakur VK, Thakur MK (eds) Polymer gels—synthesis and characterization. Springer, Singapore, pp 97–126Google Scholar
  23. Konwarh R, Karak N, Misra M (2013) Electrospun cellulose acetate nanofibers: the present status and gamut of biotechnological applications. Biotechnol Adv 31:421–437. CrossRefGoogle Scholar
  24. Liu H, Hsieh Y-L (2002) Ultrafine fibrous cellulose membranes from electrospinning of cellulose acetate. J Polym Sci Part B Polym Phys 40:2119–2129. CrossRefGoogle Scholar
  25. Nada AA, Hauser P, Hudson SM (2011) The grafting of per-(2,3,6-O-allyl)-β cyclodextrin onto derivatized cotton cellulose via thermal and atmospheric plasma techniques. Plasma Chem Plasma Process 31:605–621. CrossRefGoogle Scholar
  26. Nada AA, James R, Shelke NB et al (2014) A smart methodology to fabricate electrospun chitosan nanofiber matrices for regenerative engineering applications. Polym Adv Technol 25:507–515. CrossRefGoogle Scholar
  27. Nada AAA, Hassabo AGAG, Fayad W et al (2015) Biomaterials based on essential fatty acids and carbohydrates for chronic wounds. J Appl Pharm Sci 5:13–21. Google Scholar
  28. Nada A, Hassabo A, Mohamed A, Zaghloul S (2016a) Encapsulation of nicotinamide into cellulose based electrospun fibers. J Appl Pharm Sci 6:013–021. CrossRefGoogle Scholar
  29. Nada AA, Abd El-Azeem RA, Elghandour AH, Abou-Zeid NY (2016b) Encapsulation of ricinoleic acid into electrospun ethyl cellulose fibers. J Nat Fibers 13:670–681. Google Scholar
  30. Nada AA, Hassabo AG, Mohamed AL et al (2016c) Liposomal microencapsulation of rodent-repelling agents onto jute burlaps: assessment of cytotoxicity and rat behavioral test. J Appl Pharm Sci 6:142–150. CrossRefGoogle Scholar
  31. Nada AA, Montaser AS, Abdel Azeem RA, Mounier MM (2016d) Eco-friendly gelatin-based electrospun fibers to control the release of chloramphenicol. Fibers Polym 17:1985–1994. CrossRefGoogle Scholar
  32. Nada AA, Abdelazeem RA, Elghandour AH, Abou-Zeid NY (2018a) Protection of conjugated linoleic acid into hydrophobic/hydrophilic electrospun fibers. J Drug Deliv Sci Technol 44:482–490. CrossRefGoogle Scholar
  33. Nada AA, Abdellatif FHH, Ali EA et al (2018b) Cellulose-based click-scaffolds: synthesis, characterization and biofabrications. Carbohydr Polym 199:610–618. CrossRefGoogle Scholar
  34. Nada AA, Arul MR, Ramos DM et al (2018c) Bioactive polymeric formulations for wound healing. Polym Adv Technol 29:1815–1825. CrossRefGoogle Scholar
  35. Nada AA, Soliman AAF, Aly AA, Abou-Okeil A (2018d) Stimuli-free and biocompatible hydrogel via hydrazone chemistry: synthesis, characterization and bioassessment. Starch Stärke. Google Scholar
  36. Nada AA, Ali EA, Soliman AAF (2019a) Biocompatible chitosan-based hydrogel with tunable mechanical and physical properties formed at body temperature. Int J Biol Macromol 131:624–632. CrossRefGoogle Scholar
  37. Nada AA, El Aref AT, Sharaf SS (2019b) The synthesis and characterization of zinc-containing electrospun chitosan/gelatin derivatives with antibacterial properties. Int J Biol Macromol 133:538–544. CrossRefGoogle Scholar
  38. Neises B, Steglich W (2003) Esterification of carboxylic acids with dicyclohexylcarbodiimide/4-dimethylaminopyridine: tert-butyl ethyl fumarate. In: Danheiser RL (ed) Organic syntheses. Wiley, Hoboken, p 183CrossRefGoogle Scholar
  39. Nepogodiev SA, Dedola S, Marmuse L et al (2007) Synthesis of triazole-linked pseudo-starch fragments. Carbohydr Res 342:529–540. CrossRefGoogle Scholar
  40. Salcido R, Popescu A, Ahn C (2007) Animal models in pressure ulcer research. J Spinal Cord Med 30:107–116CrossRefGoogle Scholar
  41. Schulze B, Schubert US (2014) Beyond click chemistry—supramolecular interactions of 1,2,3-triazoles. Chem Soc Rev 43:2522. CrossRefGoogle Scholar
  42. Skoog DA, Holler FJ, Crouch SR (2017) Chapter 16: principles of instrumental analysis, 7th edn. Cengage LearningGoogle Scholar
  43. Suvarna SK, Layton C, Bancroft JD (2013) Bancroft’s theory and practice of histological techniques. Elsevier, Churchill LivingstoneGoogle Scholar
  44. Suwantong O, Ruktanonchai U, Supaphol P (2008) Electrospun cellulose acetate fiber mats containing asiaticoside or Centella asiatica crude extract and the release characteristics of asiaticoside. Polymer (Guildf) 49:4239–4247. CrossRefGoogle Scholar
  45. Taepaiboon P, Rungsardthong U, Supaphol P (2007) Vitamin-loaded electrospun cellulose acetate nanofiber mats as transdermal and dermal therapeutic agents of vitamin A acid and vitamin E. Eur J Pharm Biopharm 67:387–397. CrossRefGoogle Scholar
  46. Tungprapa S, Jangchud I, Supaphol P (2007a) Release characteristics of four model drugs from drug-loaded electrospun cellulose acetate fiber mats. Polymer (Guildf) 48:5030–5041. CrossRefGoogle Scholar
  47. Tungprapa S, Puangparn T, Weerasombut M et al (2007b) Electrospun cellulose acetate fibers: effect of solvent system on morphology and fiber diameter. Cellulose 14:563–575. CrossRefGoogle Scholar
  48. Verreck G, Chun I, Peeters J et al (2003) Preparation and characterization of nanofibers containing amorphous drug dispersions generated by electrostatic spinning. Pharm Res 20:810–817. CrossRefGoogle Scholar
  49. Zain G, Nada AA, Attaby FA, Waly A (2018a) Starch derivatives bearing aromatic sulfonated functional groups. Starch/Staerke 70:1700229. CrossRefGoogle Scholar
  50. Zain G, Nada AA, El-Sheikh MA et al (2018b) Superabsorbent hydrogel based on sulfonated-starch for improving water and saline absorbency. Int J Biol Macromol 115:61–68. CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Ahmed A. Nada
    • 1
    Email author
  • Faten Hassan Hassan Abdellatif
    • 1
  • Ahmed A. F. Soliman
    • 2
  • Jialong Shen
    • 3
  • Samuel M. Hudson
    • 3
  • Nabil Y. Abou-Zeid
    • 1
  1. 1.Textile Research Division, Pre-treatment and Finishing of Cellulosic Fabric DepartmentNational Research Centre (Scopus Affiliation ID 60014618)Dokki, GizaEgypt
  2. 2.Pharmaceutical and Drug Industries Division, Department of PharmacognosyNational Research CentreDokki, GizaEgypt
  3. 3.Department of Textile Engineering Chemistry and ScienceNorth Carolina State UniversityRaleighUSA

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