Jayanudin, Rochmadi, Moh. Fahrurrozi, Sang Kompiang Wirawan
Jayanudin1*, Rochmadi2, Moh. Fahrurrozi2, Sang Kompiang Wirawan2
1Chemical Engineering Department, Faculty of Engineering, Universitas Sultan Ageng Tirtayasa, Jl. Jenderal Sudirman km.3, Cilegon, 42435, Indonesia.
2Chemical Engineering Department, Faculty of Engineering, Universitas Gadjah Mada, Jl. Grafika No. 2 Yogyakarta, 55281, Indonesia.
Volume - 14,
Issue - 6,
Year - 2021
The aim of this study was to determine the characterization of ionic and covalent interactions to form a crosslinking network with chitosan as a wall material of microcapsules. Red ginger oleoresin microcapsule was prepared by emulsion crosslinking method. Red ginger oleoresin was mixed and stirred with chitosan solution to form an emulsion, then added to corn oil and stirred again to form a second emulsion. Crosslinking agents of glutaraldehyde saturated toluene (GST) or sodium tripolyphosphate (TPP) solution was slowly added to the emulsion. When using a crosslinking agent of TPP solution was added glacial acetic acid to adjust pH. Red ginger oleoresin microcapsules were filtered and washed with petroleum ether followed by n-hexane and then dried in an oven. Microcapsules from chitosan that are cross-linked with GST produce higher yield and size of microcapsules compared to TPP. Whereas, the highest encapsulation efficiency produced from chitosan cross-linked with TPP was 91.63±0.02%. Meanwhile, the highest cumulative release was obtained from TPP cross-linked chitosan microcapsules of 63.71% and the lowest was 50.01% from chitosan microcapsules that cross-linked with GST. The conclusion of this study was the differences between ionic and covalent crosslinking agents produce different microcapsule characteristics. Microcapsules from chitosan cross-linked with GST generated more compact with a smoother surface than with TPP.
Cite this article:
Jayanudin, Rochmadi, Moh. Fahrurrozi, Sang Kompiang Wirawan. Characterization of cross-linked chitosan by ionic and covalent crosslinking agents as wall material of red ginger oleoresin microcapsules. Research Journal of Pharmacy and Technology. 2021; 14(6):3380-8. doi: 10.52711/0974-360X.2021.00588
Jayanudin, Rochmadi, Moh. Fahrurrozi, Sang Kompiang Wirawan. Characterization of cross-linked chitosan by ionic and covalent crosslinking agents as wall material of red ginger oleoresin microcapsules. Research Journal of Pharmacy and Technology. 2021; 14(6):3380-8. doi: 10.52711/0974-360X.2021.00588 Available on: https://rjptonline.org/AbstractView.aspx?PID=2021-14-6-78
1. Jacob J, Haponiuk JT, Thomas S, Gopi S. Biopolymer based nanomaterials in drug delivery systems: A Review. Materials Today Chemistry. 2018; 9: 43–55.
2. Zhou G, Zhang J, Tai J, Han Q, Wang L, Wang K, Wang S, Fan Y. Comparison of chitosan microsphere versus O-carboxymethyl chitosan microsphere for drug delivery systems. Journal of Bioactive and Compatible Polymers. 2017; 32(5): 469–486.
3. Sinha VR, Singla AK, Wadhawan S, Kaushik R, Kumria R, Bansal K, Dhawan S. Chitosan microspheres as a potential carrier for drugs. International Journal of Pharmaceutics. 2004; 274(1-2): 1–33.
4. Mitra A and Dey B. Chitosan Microspheres in Novel Drug Delivery Systems. Indian Journal of Pharmaceutical Sciences. 2011; 4(73): 355–366.
5. Madene A, Jacquot M, Scher J, Desobry S. Flavour encapsulation and controlled release - A review. International Journal of Food Science and Technology. 2006; 41(1): 1–21.
6. Manjanna KM, Shivakumar B, Kumar TMP. Microencapsulation: An Acclaimed Novel Drug-Delivery System for NSAIDs in Arthritis. Critical Reviews™ in Therapeutic Drug Carrier Systems. 2010; 27(6): 509–537.
7. Gonçalves VL, Laranjeira MCM, Fávere VT, Pedrosa RC. Effect of Crosslinking Agents on Chitosan Microspheres in Controlled Release of Diclofenac Sodium. Polímeros: Ciência e Tecnologia. 2005; 15(1): 6–12.
8. Campos E, Coimbra P, Gil M. An improved method for preparing glutaraldehyde cross-linked chitosan–poly(vinyl alcohol) microparticles. Polymer Bulletin. 2013; 70(2): 549–561.
9. Ofokansi KC, Kenechukwu FC, Isah AB, Okigbo EL. Formulation and evaluation of glutaraldehyde-crosslinked chitosan microparticles for the delivery of ibuprofen. Tropical Journal of Pharmaceutical Research. 2013; 12(1): 19–25.
10. Jameela SR and Jayakrishnan A. Glutaraldehyde cross-linked chitosan microspheres as a long acting biodegradable drug delivery vehicle: studies on the vitro release of mitoxantrone and in viva degradation of microspheres in rat muscle. Biomaterials. 1995; 16(10): 769–775.
11. Thanoo BC, Sunny MC, Jayakrishnan A. Cross-linked Chitosan Microspheres: Preparation and Evaluation as a Matrix for the Controlled Release of Pharmaceuticals. Journal of Pharmacy and Pharmacology. 1992; 44(4): 283–286.
12. Al-Helw A, Al-Angary A, Mahrous G, Al-Dardari M. Preparation and evaluation of sustained release cross-linked chitosan microspheres containing phenobarbitone. Journal of microencapsulation. 1997; 15(3): 373–382.
13. Denkbas EB, Seyyal M, Piskin E. 5-Fluorouracil loaded chitosan microspheres for chemoembolization. Journal of Microencapsulation. 1999; 16(6): 741–749.
14. Jayanudin, Fahrurrozi M, Wirawan SK, Rochmadi. Preparation of Chitosan Microcapsules Containing Red Ginger Oleoresin Using Emulsion Crosslinking Method. Journal of Applied Biomaterials & Functional Materials. 2019; 17(1): 1–9.
15. Martins AF, De Oliveira DM, Pereira AGB, Rubira AF, Muniz EC. Chitosan/TPP Microparticles Obtained by Microemulsion Method Applied in Controlled Release of Heparin. International Journal of Biological Macromolecules. 2012; 51(5): 1127–1133.
16. Vaidya S, Bhosale R, Singhal RS. Microencapsulation of Cinnamon Oleoresin by Spray Drying Using Different Wall Materials, Drying Technology. 2006; 24(8): 983–992.
17. Campos E, Coimbra P, Gil MH. An improved method for preparing glutaraldehyde cross-linked chitosan-poly(vinyl alcohol) microparticles. Polymer Bulletin. 2013; 70(2): 549–561.
18. Jarudilokkul S, Tongthammachat A, Boonamnuayvittaya V. Preparation of chitosan nanoparticles for encapsulation and release of protein. Korean Journal of Chemical Engineering. 2011; 28(5): 1247–1251.
19. Tan LH, Chan LW, Heng PWS. Effect of oil loading on microspheres produced by spray drying. Journal of Microencapsulation. 2005; 22(3): 253–259.
20. Tonon RV, Grosso CRF, Hubinger MD. Influence of emulsion composition and inlet air temperature on the microencapsulation of flaxseed oil by spray drying. Food Research International. 2011; 44(1): 282–289.
21. Jayanudin, Fahrurrozi M, Wirawan SK, Rochmadi. Antioxidant activity and controlled release analysis of red ginger oleoresin (Zingiber officinale var rubrum) encapsulated in chitosan cross-linked by glutaraldehyde saturated toluene. Sustainable Chemistry and Pharmacy. 2019; 12: 100132.
22. Siepmann J and Siepmann F. Modeling of diffusion controlled drug delivery. Journal of Controlled Release. 2012; 161(2): 351–362.
23. Jóźwiak T, Filipkowska U, Szymczyk P, Rodziewicz J, Mielcarek A. Effect of ionic and covalent crosslinking agents on properties of chitosan beads and sorption effectiveness of Reactive Black 5 dye. Reactive and Functional Polymers. 2017; 114: 58–74.
24. Jayakrishnan A and Jameela SR. Glutaraldehyde as a fixative in bioprotheses and drug delivery matrices, Biomaterials. 1996; 17(5): 471–484.
25. Bhumkar DR and Pokharkar VB. Studies on effect of pH on cross-linking of chitosan with sodium tripolyphosphate: a technical note., AAPS PharmSciTech. 2006; 7(2): 1-6.
26. Mi FL, Shyu SS, Kuan CY, Lee ST, Lu KT, Jang SF. Chitosan-polyelectrolyte complexation for the preparation of gel beads and controlled release of anticancer drug. I. Effect of phosphorus polyelectrolyte complex and enzymatic hydrolysis of polymer. Journal of Applied Polymer Science. 1999; 74(7): 1868–1879.
27. Jayanudin, Fahrurrozi M, Wirawan SK, Rochmadi, Characterization and release kinetics of red ginger oleoresin encapsulation based on the effect of glutaraldehyde concentration as crosslinking agent. Research Journal of Chemistry and Environment. 2019; 23(3): 1–12.
28. Panchal A, Patel K, Patel M, Oza P, Jobanputra U, Meghnathi U. Preparation and Evaluation Glutaraldehyde Cross Linked Chitosan Microspheres Containing Rivastigmine Tartrate. International Journal for Pharmaceutical Research Scholars. 2012; 1(2): 206–213.
29. Patel PN, Patel LJ, Patel JK, Vidyadham SPS. Development and testing of novel temoxifen citrate loaded chitosan nanoparticles using ionic gelation method, Pelagia Research Library. 2011; 2(4): 17–25.
30. Patil SS, Gupta VRM, Gupta KS, Doddayya H. Formulation and characterization of tpp cross-linked chitosan microspheres loaded with lornoxicam. Journal of Biomedical and Pharmaceutical Research. 2014; 3(3): 51–58.
31. Babak VG. Effect of interfacial tension and droplet size on coagulation, adhesion and rheology of concentrated emulsions, Colloids Surfaces A Physicochem. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 1994; 85(2-3): 279–294.
32. Aronson MP. The Role of Free Surfactant in Destabilizing Oil-in-Water Emulsions. Langmuir. 1989; 5(2): 494–501.
33. Sharipova A, Aidarova S, Mutaliyeva B, Babayev A, Issakhov M, Issayeva A, Madybekova G, Grigoriev D, Miller R. The Use of Polymer and Surfactants for the Microencapsulation and Emulsion Stabilization. Colloids and Interfaces. 2017; 1(1): 1-15.
34. Wu J, Wang Y, Yang H, Liu X, Lu Z. Preparation and biological activity studies of resveratrol loaded ionically cross-linked chitosan-TPP nanoparticles. Carbohydrate Polymers. 2017; 175: 170–177.
35. Hosseini SF, Zandi M, Rezaei M, Farahmandghavi F. Two-step method for encapsulation of oregano essential oil in chitosan nanoparticles: Preparation, characterization and in vitro release study. Carbohydrate Polymers. 2013; 95(1): 50–56.
36. Peniche C, Zaldivar D, Bulay A. Study of the thermal degradation of poly (furfuryi methacrylate) by thermogravimetry. Polymer Degradation and Stability. 1993; 40: 287–295.
37. Ritger PL and Peppas NA. A simple equation for description of solute release II. Fickian and anomalous release from swellable devices. Journal of Controlled Release. 1987; 5(1): 37-42