Advertisement

Chemical and biological behaviours of hydrogels based on oxidized carboxymethylcellulose coupled to chitosan

  • Lamia MansouriEmail author
  • Saida Benghanem
  • Meriem Elkolli
  • Bounekhel Mahmoud
Original Paper
  • 2 Downloads

Abstract

Carboxymethylcellulose (CMC) was subjected to partial oxidation reaction by 2,2,6,6-tetramethylpiperidine-1-oxyl in the presence of sodium hypochlorite (NaOCl) and sodium bromide (NaBr). Hydroxylamine and acid–base assay methods were used to quantify the aldehyde and carboxyl groups, respectively. Chitosan (CS) was then coupled to CMC or oxidized CMC (OCMC). The carboxyl groups carried by CMC and the free amines by CS were estimated by potentiometry and conductimetry. Characterization and identification of the obtained materials were made by Fourier transform infrared spectroscopy, Ultraviolet–visible spectroscopy and X-ray fluorescence. The blood compatibility test shows that the haemolysis percentages of films are less than 5%, which indicates their good blood compatibility and their non-haemotoxicity. The anti-inflammatory activity reveals that the materials possess an ability to inhibit the denaturation of proteins. The mucoadhesion tests exhibit a marked increase in adhesion times of CMC/CS and OCMC/CS hydrogels on the intestinal mucosa. Besides, swelling behaviour and biodegradability were established.

Keywords

Carboxymethylcellulose Oxidation Chitosan Blood compatibility Anti-inflammatory activity Mucoadhesion Biodegradability 

Notes

References

  1. 1.
    Lin Q, Gao M, Chang J, Ma H (2016) Adsorption properties of crosslinking carboxy-methylcellulose grafting dimethyldiallylammonium chloride for cationic and anionic dyes. Carbohydr Polym 151:283–294.  https://doi.org/10.1016/j.carbpol.2016.05.064 CrossRefGoogle Scholar
  2. 2.
    Algarra M, Vázquez MI, Alonso B, Casado CM, Casado J, Benavente J (2014) Characterization of an engineered cellulose based membrane by thiol dendrimer for heavy metals removal. Chem Eng J 253:472–477.  https://doi.org/10.1016/j.cej.2014.05.082 CrossRefGoogle Scholar
  3. 3.
    Jiang X, Yang Z, Peng Y, Hana B, Lia Z, Lia X, Liu W (2016) Preparation, characterization and feasibility study of dialdehyde carboxymethyl cellulose as a novel crosslinking reagent. Carbohydr Polym 137:632–641.  https://doi.org/10.1016/j.carbpol.2016.05.064 CrossRefGoogle Scholar
  4. 4.
    Pasqui D, De Cagna M, Barbucci R (2012) Polysaccharide-based hydrogels: the key role of water in affecting mechanical properties. Polymers 4:1517–1534.  https://doi.org/10.3390/polym4031517 CrossRefGoogle Scholar
  5. 5.
    Bello M, Ochoa N, Balsamo V, Carrasquero FL, Collc S, Monsalved A, González G (2010) Modified cassava starches as corrosion inhibitors of carbon steel: an electrochemical and morphological approach. Carbohydr Polym 82:561–568.  https://doi.org/10.1016/j.carbpol.2010.05.019 CrossRefGoogle Scholar
  6. 6.
    Wang MJ, Xie YL, Zheng QD, Yao SJ (2009) A novel, potential microflora-activated carrier for a colon-specific drug delivery system and its characteristics. Ind Eng Chem Res 48:5276–5284.  https://doi.org/10.1021/ie801295y CrossRefGoogle Scholar
  7. 7.
    Freyman TM, Yannas IV, Gibson LJ (2001) Cellular materials as porous scaffolds for tissue engineering. Prog Mater Sci 46:273–282.  https://doi.org/10.1016/S0079-6425(00)00018-9 CrossRefGoogle Scholar
  8. 8.
    Synytsya A, Copíková J (2015) Preparation of amidated derivatives of carboxymethylcellulose. Int J Biol Macromol 72:11–18.  https://doi.org/10.1016/j.ijbiomac.2014.07.049 CrossRefGoogle Scholar
  9. 9.
    Hebeish A, Higazy A, Sharaf S (2010) Synthesis of carboxymethyl cellulose (CMC) and starch-based hybrids and their applications in flocculation and sizing. Carbohydr Polym 79:60–69.  https://doi.org/10.1016/j.carbpol.2009.07.022 CrossRefGoogle Scholar
  10. 10.
    Laschet M, Plog JP, Clasen C, Kulicke WM (2004) Examination of the flow behaviour of HEC and hmHEC solutions using structure-property relationships and rheo-optical methods. Colloid Polym Sci 282:373–380.  https://doi.org/10.1007/s00396-003-0949-3 CrossRefGoogle Scholar
  11. 11.
    Benchabane A, Bekkour K (2008) Rheological properties of carboxymethyl cellulose (CMC) solutions. Colloid Polym Sci 286:1173–1180.  https://doi.org/10.1007/s00396-008-1882-2 CrossRefGoogle Scholar
  12. 12.
    Shen JN, Yu CC, Zeng GN, van der Bruggen B (2013) Preparation of a facilitated transport membrane composed of carboxymethyl chitosan and polyethylenimine for CO2/N2 separation. Int J Mol Sci 14:3621–3638.  https://doi.org/10.3390/ijms14023621 CrossRefGoogle Scholar
  13. 13.
    Ravi Kumar MN (2000) A review of chitin and chitosan applications. React Funct Polym 46:1–27.  https://doi.org/10.1016/S1381-5148(00)00038-9 CrossRefGoogle Scholar
  14. 14.
    Benghanem S, Chetouani A, Elkolli M, Bounekhel M, Benachour D (2017) Grafting of oxidized carboxymethyl cellulose with hydrogen peroxide in presence of Cu(II) to chitosan and biological elucidation. Biocybern Biomed Eng 37:94–102.  https://doi.org/10.1016/j.bbe.2016.09.003 CrossRefGoogle Scholar
  15. 15.
    Hao J, Lu J, Xu N, Linhardt RJ, Zhang Z (2016) Specific oxidation pattern of soluble starch with TEMPO–NaBr–NaClO system. Carbohydr Polym 146:238–244.  https://doi.org/10.1016/j.carbpol.2016.03.040 CrossRefGoogle Scholar
  16. 16.
    Kato Y, Kaminaga J, Matsuo R, Isogai A (2004) TEMPO-mediated oxidation of chitin, regenerated chitin and N-acetylated chitosan. Carbohydr Polym 58:421–426.  https://doi.org/10.1016/j.carbpol.2004.08.011 CrossRefGoogle Scholar
  17. 17.
    Isogai A, Saito T, Shibata I, Masahiro Y, Yumiko k, Kengo M, Naoto H (2005) TEMPO-mediated oxidation of celluloses. In: Appita Annual Conference. pp 237–241Google Scholar
  18. 18.
    Dang Z, Zhang J, Ragauskas AJ (2007) Characterizing TEMPO-mediated oxidation of ECF bleached softwood kraft pulps. Carbohydr Polym 70:310–317.  https://doi.org/10.1016/j.carbpol.2007.04.014 CrossRefGoogle Scholar
  19. 19.
    Park KM, Kim YN, Choi SJ, Park JH, Chang PS (2015) Chemoselective oxidation of C6 primary hydroxyl groups of polysaccharides in rice bran for the application as a novel water-soluble dietary fiber. Int J Food Prop 18:1664–1676.  https://doi.org/10.1080/10942912.2014.926370 CrossRefGoogle Scholar
  20. 20.
    Carlsson DO, Lindh J, Nyholm L, Stromme M, Mihranyan A (2014) Cooxidant-free TEMPO-mediated oxidation of highly crystalline nanocellulose in water. RSC Adv 4:52289–52298.  https://doi.org/10.1039/C4RA11182F CrossRefGoogle Scholar
  21. 21.
    Li H, Wu B, Mu C, Lin W (2011) Concomitant degradation in periodate oxidation of carboxymethylcellulose. Carbohydr Polym 84:881–886.  https://doi.org/10.1016/j.carbpol.2010.12.026 CrossRefGoogle Scholar
  22. 22.
    Kumar V, Yang T (1999) Analysis of carboxyl content in oxidized celluloses by solid-state 13C CP/MAS NMR spectroscopy. Int J Pharm 184:219–226.  https://doi.org/10.1016/S0378-5173(99)00098-8 CrossRefGoogle Scholar
  23. 23.
    Zamani A, Henriksson D, Taherzadeh MJ (2010) A new foaming technique for production of superabsorbents from carboxymethyl chitosan. Carbohydr Polym 80:1091–1101.  https://doi.org/10.1016/j.carbpol.2010.01.029 CrossRefGoogle Scholar
  24. 24.
    Raymond L, Morin FG, Marchessault RH (1993) Degree of deacetylation of chitosan using conductometric titration and solid-state NMR. Carbohydr Res 246:331–336.  https://doi.org/10.1016/0008-6215(93)84044-7 CrossRefGoogle Scholar
  25. 25.
    Fan L, Sun Y, Xie W, Zheng H, Liu S (2012) Oxidized pectin cross-linked carboxymethyl chitosan: a new class of hydrogels. J Biomater Sci Polym 23:2119–2132.  https://doi.org/10.1163/092050611X611675 CrossRefGoogle Scholar
  26. 26.
    Alhakmani F, Kumar S, Khan SA (2013) Estimation of total phenolic content, in vitro antioxidant and anti-inflammatory activity of flowers of Moringa oleifera. Asian Pac J Trop Biomed 3:623–627.  https://doi.org/10.1016/S2221-1691(13)60126-4 CrossRefGoogle Scholar
  27. 27.
    Cerchiara T, Abruzzo A, Parolin C, Vitalia B, Biguccia F, Galluccib MC, Nicolettac FP, Luppi B (2016) Microparticles based on chitosan/carboxymethylcellulose polyelectrolyte complexes for colon delivery of vancomycin. Carbohydr Polym 143:124–130.  https://doi.org/10.1016/j.carbpol.2016.02.020 CrossRefGoogle Scholar
  28. 28.
    Agarwal T, Narayana SNGH, Pal K, Pramanik K, Giri S, Banerjee I (2015) Calcium alginate-carboxymethyl cellulose beads for colon-targeted drug delivery. Int J Biol Macromol 75:409–417.  https://doi.org/10.1016/j.ijbiomac.2014.12.052 CrossRefGoogle Scholar
  29. 29.
    Barbeck M, Serra T, Booms P, Stojanovic S, Najman S, Engel E, Sader R, Kirkpatrick CJ, Navarro M, Ghanaati S (2017) Analysis of the in vitro degradation and the in vivo tissue response to bi-layered 3D-printed scaffolds combining PLA and biphasic PLA/bioglass components—Guidance of the inflammatory response as basis for osteochondral regeneration. Bioact Mater.  https://doi.org/10.1016/j.bioactmat.2017.06.001 Google Scholar
  30. 30.
    Silverstein RM, Webster FX, Kiemle D (2005) Spectrometric identification of organic compounds, 7th edn. Wiley, New YorkGoogle Scholar
  31. 31.
    Muzzarelli RAA, Tanfani F, Emanuelli M, Mariotti S (1982) N-(carboxy-methylidene)chitosans and N-(carboxymethyl)chitosans: novel chelating polyampholytes obtained from chitosan glyoxylate. Carbohydr Res 107:199–214.  https://doi.org/10.1016/S0008-6215(00)80539-X CrossRefGoogle Scholar
  32. 32.
    Liuyun J, Yubao L, Chengdong X (2009) Preparation and biological properties of a novel composite scaffold of nano-hydroxyapatite/chitosan/carboxymethyl cellulose for bone tissue engineering. J Biomed Sci 10:1–10.  https://doi.org/10.1186/1423-0127-16-65 Google Scholar
  33. 33.
    Ren JL, Sun RC, Peng F (2008) Carboxymethylation of hemicelluloses isolated from sugarcane bagasse. Polym Degrad Stab 93:786–793.  https://doi.org/10.1016/j.polymdegradstab.2008.01.011 CrossRefGoogle Scholar
  34. 34.
    Bragd PL, Bekkum HV, Besemer AC (2004) TEMPO-mediated oxidation of polysaccharides: survey of methods and applications. Top Catal 27:49–66.  https://doi.org/10.1023/B:TOCA.0000013540.69309.46 CrossRefGoogle Scholar
  35. 35.
    Gómez-Burgaz M, García-Ochoa B, Torrado-Santiago S (2008) Chitosan-carboxymethylcellulose interpolymer complexes for gastric-specific delivery of clarithromycin. Int J Pharm 359:135–143.  https://doi.org/10.1016/j.ijpharm.2008.03.042 CrossRefGoogle Scholar
  36. 36.
    Cao W, Cheng M, Ao Q, Gong Y, Zhao N, Zhang X (2005) Physical, mechanical and degradation properties, and Schwann cell affinity of cross-linked chitosan films. J Biomater Sci Polym 16:791–807.  https://doi.org/10.1163/1568562053992496 CrossRefGoogle Scholar
  37. 37.
    Lu G, Kong L, Sheng B, Wang G, Gong Y, Zhang X (2007) Degradation of covalently cross-linked carboxymethyl chitosan and its potential application for peripheral nerve regeneration. Eur Polym J 43:3807–3818.  https://doi.org/10.1016/j.eurpolymj.2007.06.016 CrossRefGoogle Scholar
  38. 38.
    Andreopoulos AG (1989) Hydrophilic polymer networks for agricultural uses. Eur Polym J 25:977–979.  https://doi.org/10.1190/segam2013-0137.1 CrossRefGoogle Scholar
  39. 39.
    Chetouani A, Elkolli M, Bounekhel M, Benachour D (2017) Chitosan/oxidized pectin/PVA blend film: mechanical and biological properties. Polym Bull 74:4297–4310.  https://doi.org/10.1007/s00289-017-1953-y CrossRefGoogle Scholar
  40. 40.
    Lee D, Powers K, Baney R (2004) Physicochemical properties and blood compatibility of acylated chitosan nanoparticles. Carbohydr Polym 58:371–377.  https://doi.org/10.1016/j.carbpol.2004.06.033 CrossRefGoogle Scholar
  41. 41.
    Yi H, Wu LQ, Bentley WE, Ghodssi R, Rubloff GW, Culver JN, Payne GF (2005) Biofabrication with chitosan. Biomacromol 6:2881–2894.  https://doi.org/10.1021/bm050410l CrossRefGoogle Scholar
  42. 42.
    He N, Wang R, He Y, Dang X (2012) Fabrication, structure and surface charges of albumin-chitosan hybrids. Sci China Chem 55:1788–1795.  https://doi.org/10.1007/s11426-012-4604-z CrossRefGoogle Scholar
  43. 43.
    Kim MS, Hyun JY, Mi KY, Kim NS, Shim BS, Kim HM (2004) Inhibitory effect of water-soluble chitosan on TNF-α and IL-8 secretion from HMC-1 cells. Immunopharmacol Immunotoxicol 26:401–409.  https://doi.org/10.1081/IPH-200026887 CrossRefGoogle Scholar
  44. 44.
    Kulchaiyawat C (2015) Modification of egg albumen to improve thermal stability. Dissertation, Iowa State University CapstonesGoogle Scholar
  45. 45.
    Takeuchi H, Yamamoto H, Kawashima Y (2001) Mucoadhesive nanoparticulate systems for peptide drug delivery. Adv Drug Deliv Rev 47:39–54.  https://doi.org/10.1016/S0169-409X(00)00120-4 CrossRefGoogle Scholar
  46. 46.
    Caramella CM, Rossi S, Bonferoni MC (1999) A rheological approach to explain the mucoadhesive behavior of polymer gels. In: Mathiowitz E, Chickering DE III, Lehr CM (eds) Bioadhesive drug delivery systems fundamentals, novel approaches, and development. Marcel Dekker, New York, pp 25–65CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Laboratory of Multiphasic and Polymeric Materials (LPMAMPM), Faculty of TechnologyFerhat ABBAS Setif 1 UniversitySetifAlgeria

Personalised recommendations