Email the author Hydrogel films based on sodium alginate modified with octane-1-amine: enhanced pore formation and potential applications in drug delivery systems
DOI: https://doi.org/10.15407/hftp15.01.043
Abstract
The use of wound dressings is gaining more and more popularity, especially in the field of tactical and military medicine. Developing wound dressings capable of facilitating wound treatment and reducing healing time is one of the challenges of modern science. So, sodium alginate (Alg) is a good candidate for the development of wound dressings due to its bio- and hemocompatibility and biodegradability. However, Alg has its shortcomings, which can be dispatched by modification.
The purpose of this work was to investigate the effect of Alg modification on the kinetics of ethonium release from crosslinked with Ca2+ ions samples. For this purpose, a method of Alg modifying with octane-1-amine was developed without the use of organic solvents and with the use of 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide hydrochloride (EDCl) as an initiator. The optimal parameters of alginate modification process were defined as 60 °С temperature and 24 hours duration. Physicochemical methods confirmed the success of the modification. Films based on the alginate modified with octane-1-amine (AlgM) were obtained using a calcium chloride solution as a crosslinker. The kinetics of swelling was studied and we found that the degree of swelling of the sample based on AlgM after 10 minutes is twice as large (α = 0.71) as for Alg (α = 0.37), which indicates a faster release of drugs.
It has been found that the kinetics of release of ethonium depends not only on the kinetics of swelling but also on the chemical nature of the drug. The ethonium was immobilised in alginate films as a model of bactericidal drug. The kinetics of ethonium release was studied at different pH values corresponding to the pH of healthy skin (5.5), open wounds (7.2) and inflamed wounds (8.2). It was found that the release of ethonium from the sample based on AlgM is more pH-sensitive and prolonged, compared to the sample based on Alg. This effect is explained by the appearance of an additional mechanism of retention of ethonium by AlgM due to hydrophobic-hydrophobic interactions in the films.
The prolonged release properties observed in the drug-loaded samples make them promising candidates for the development of targeted drug delivery systems and wound dressings, which are particularly relevant for the treatment of chronic and burn wounds. Future research will focus on optimizing the crosslinking method and exploring potential applications of modified alginate-based materials in biomedical sciences.
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References
1. Boateng J.S., Matthews K.H., Stevens H.N., Eccleston G.M. Wound healing dressings and drug delivery systems: a review. J. Pharm. Sci. 2008. 97(8): 2892. https://doi.org/10.1002/jps.21210
2. Moura L.I., Dias A.M., Carvalho E., de Sousa H.C. Recent advances on the development of wound dressings for diabetic foot ulcer treatment - A review. Acta Biomater. 2013. 9(7): 7093. https://doi.org/10.1016/j.actbio.2013.03.033
3. Kovalenko O.M. Suchasni ranovi pokryttia. Suchasni med. tekhnolohii. 2010. 4: 88. [in Ukrainian].
4. Laurén P., Somersalo P., Pitkänen I., Lou Y.R., Urtti A., Partanen J., Seppälä J., Madetoja M., Laaksonen T., Mäkitie A., Yliperttula M. Nanofibrillar cellulose-alginate hydrogel coated surgical sutures as cell-carrier systems. PLoS One. 2017. 12(8): e0183487. https://doi.org/10.1371/journal.pone.0183487
5. Paul W., Sharma C.P. Alginates: wound dressings. In: Encyclopedia of biomedical polymers and polymeric biomaterials. (Taylor & Francis, 2015). P. 134. https://doi.org/10.1081/E-EBPP-120051065
6. Abasalizadeh F., Moghaddam S.V., Alizadeh E., Akbari E., Kashani E., Fazljou S.M., Torbati M., Akbarzadeh A. Alginate-based hydrogels as drug delivery vehicles in cancer treatment and their applications in wound dressing and 3D bioprinting. J. Biol. Eng. 2020. 14(1): 8. https://doi.org/10.1186/s13036-020-0227-7
7. Parhi R. Cross-Linked hydrogel for pharmaceutical applications: a review. Adv. Pharm. Bull. 2017. 7(4): 515. https://doi.org/10.15171/apb.2017.064
8. Keil C., Hübner C., Richter C., Lier S., Barthel L., Meyer V., Subrahmanyam R., Gurikov P., Smirnova I., Haase H. Ca-Zn-Ag alginate aerogels for wound healing applications: swelling behavior in simulated human body fluids and effect on macrophages. Polymers. 2020. 12(11): 2741. https://doi.org/10.3390/polym12112741
9. Zimmermann K.A., LeBlanc J.M., Sheets K.T., Fox R.W., Gatenholm P. Biomimetic design of a bacterial cellulose/hydroxyapatite nanocomposite for bone healing applications. Mater. Sci. Eng. 2011. 31(1): 43. https://doi.org/10.1016/j.msec.2009.10.007
10. Vasile B.S., Birca A.C., Musat M.C., Holban A.M. Wound dressings coated with silver nanoparticles and essential oils for the management of wound infections. Materials. 2020. 13(7): 1682. https://doi.org/10.3390/ma13071682
11. Hu T., Lo A.C. Collagen-Alginate composite hydrogel: application in tissue engineering and biomedical sciences. Polymers. 2021. 13(11): 1852.
https://doi.org/10.3390/polym13111852
12. Zhang H., Cheng J., Ao Q. Preparation of alginate-based biomaterials and their applications in biomedicine. Mar. Drugs. 2021. 19(5): 264. https://doi.org/10.3390/md19050264
13. Yang J.S., Xie Y.J., He W. Research progress on chemical modification of alginate: a review. Carbohydr. Polym. 2011. 84(1): 33. https://doi.org/10.1016/j.carbpol.2010.11.048
14. Vallée F., Müller C., Durand A., Schimchowitsch S., Dellacherie E., Kelche C., Cassel J.C., Leonard M. Synthesis and rheological properties of hydrogels based on amphiphilic alginate-amide derivatives. Carbohydr. Res. 2009. 344(2): 223. https://doi.org/10.1016/j.carres.2008.10.029
15. Wang C., Wang Z., Zhang X. Amphiphilic Building Blocks for Self-Assembly: From Amphiphiles to Supra-amphiphiles. Acc. Chem. Res. 2012. 45(4): 608. https://doi.org/10.1021/ar200226d
16. Nigmatullin R., Johns M.A., Muñoz-García J.C., Gabrielli V., Schmitt J., Angulo J., Khimyak Y.Z., Scott J.L., Edler K.J., Eichhorn S.J. Hydrophobization of Cellulose Nanocrystals for Aqueous Colloidal Suspensions and Gels. Biomacromolecules. 2020. 21(5): 1812. https://doi.org/10.1021/acs.biomac.9b01721
17. Hill J., Shrestha L., Ishihara S., Ji Q., Ariga K. Self-Assembly: From Amphiphiles to Chromophores and Beyond. Molecules. 2014. 19(6): 8589. https://doi.org/10.3390/molecules19068589
18. Yao B., Ni C., Xiong C., Zhu C., Huang B. Hydrophobic modification of sodium alginate and its application in drug-controlled release. Bioprocess Biosyst. Eng. 2010. 33(4): 457. https://doi.org/10.1007/s00449-009-0349-2
19. Bolton L.L., Johnson C.L., Van Rijswijk L. Occlusive dressings: therapeutic agents and effects on drug delivery. Clinics in Dermatology. 1991. 9(4): 573. https://doi.org/10.1016/0738-081X(91)90087-2
20. Park M., Kim S., Kim I.S., Son D. Healing of a porcine burn wound dressed with human and bovine amniotic membranes. Wound Repair Regen. 2008. 16(4): 520. https://doi.org/10.1111/j.1524-475X.2008.00399.x
21. Saffle J.R. Closure of the excised burn wound: temporary skin substitutes. Clin. Plast. Surg. 2009. 36(4): 627. https://doi.org/10.1016/j.cps.2009.05.005
22. Rezvanian M., Amin M.C., Ng S.F. Development and physicochemical characterization of alginate composite film loaded with simvastatin as a potential wound dressing. Carbohydr. Polym. 2016. 137: 295. https://doi.org/10.1016/j.carbpol.2015.10.091
23. Yasasvini S., Anusa R., VedhaHari B., Prabhu P., RamyaDevi D. Topical hydrogel matrix loaded with Simvastatin microparticles for enhanced wound healing activity. Mater. Sci. Eng. 2017. 72: 160. https://doi.org/10.1016/j.msec.2016.11.038
24. Rojewska A., Karewicz A., Karnas K., Wolski K., Zając M., Kamiński K., Szczubiałka K., Zapotoczny S., Nowakowska M. Pioglitazone-Loaded nanostructured hybrid material for skin ulcer treatment. Materials. 2020. 13(9): 2050. https://doi.org/10.3390/ma13092050
25. Sakai S., Sato K., Tabata Y., Kishi K. Local release of pioglitazone (a peroxisome proliferator-activated receptor γ agonist) accelerates proliferation and remodeling phases of wound healing. Wound Repair Regen. 2015. 24(1): 57. https://doi.org/10.1111/wrr.12376
26. Kim J.O., Choi J.Y., Park J.K., Kim J.H., Jin S.G., Chang S.W., Li D.X., Hwang M.R., Woo J.S., Kim J.A., Lyoo W.S., Yong C.S., Choi H.G. Development of clindamycin-loaded wound dressing with polyvinyl alcohol and sodium alginate. Biol. Pharm. Bull. 2008. 31(12): 2277. https://doi.org/10.1248/bpb.31.2277
27. Nurjanah A., Amran M.B., Rusnadi. Mechanical properties of alginate based biopolymers as wound dressing material. In: IOP Conference Series: Materials Science and Engineering. V. 833. 2020. P. 012030. https://doi.org/10.1088/1757-899X/833/1/012030
28. Wang J., Hu H., Yang Z., Wei J., Li J. IPN hydrogel nanocomposites based on agarose and ZnO with antifouling and bactericidal properties. Mater. Sci. Eng. 2016. 61: 376. https://doi.org/10.1016/j.msec.2015.12.023
29. Lootens D., Capel F., Durand D., Nicolai T., Boulenguer P., Langendorff V. Influence of pH, Ca concentration, temperature and amidation on the gelation of low methoxyl pectin. Food Hydrocoll. 2003. 17(3): 237. https://doi.org/10.1016/S0268-005X(02)00056-5
30. Lee K.Y., Mooney D.J. Alginate: properties and biomedical applications. Prog. Polym. Sci. 2012. 37(1): 106. https://doi.org/10.1016/j.progpolymsci.2011.06.003
31. Suzuki Y., Nishimura Y., Tanihara M., Suzuki K., Nakamura T., Shimizu Y., Yamawaki Y., Kakimaru Y. Evaluation of a novel alginate gel dressing: cytotoxicity to fibroblastsin vitro and foreign-body reaction in pig skinin vivo. J. Biomed. Mater. Res. 1998. 39(2): 317. https://doi.org/10.1002/(SICI)1097-4636(199802)39:2<317::AID-JBM20>3.0.CO;2-8
32. Ivantsyk L.B., Drogovoz S.M., Gerbina N.A., Kalko K.A., Shtroblia V.V. Advantages of the composition and actyvity of a new combined ointment with ethony for treatment of the wound process. Likarska Sprava. 2019. (1-2): 126. https://doi.org/10.31640/JVD.1-2.2019(19)
33. Ainurofiq A., Choiri S. Model and release pattern of water soluble drug from natural-polymer based sustained release tablet dosage form. Int. J. Pharm. Pharm. Sci. 2014. 6(9): 179.
34. Niether D., Wiegand S. Thermodiffusion and hydrolysis of 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). Eur. Phys. J. E. 2019. 42(9): 117. https://doi.org/10.1140/epje/i2019-11880-1
35. Nastaj J., Przewłocka A., Rajkowska-Myśliwiec M. Biosorption of Ni(II), Pb(II) and Zn(II) on calcium alginate beads: equilibrium, kinetic and mechanism studies. Pol. J. Chem. Techol. 2016. 18(3): 81. https://doi.org/10.1515/pjct-2016-0052
36. Ji Y., Yang X., Ji Z., Zhu L., Ma N., Chen D., Jia X., Tang J., Cao Y. DFT-calculated IR spectrum amide I, II, and III band contributions of N-methylacetamide fine components. ACS Omega. 2020. 5(15): 8572. https://doi.org/10.1021/acsomega.9b04421
37. Karmakar P., Pujol C.A., Damonte E.B., Ghosh T., Ray B. Polysaccharides from Padina tetrastromatica: Structural features, chemical modification and antiviral activity. Carbohydr. Polym. 2010. 80: 513. https://doi.org/10.1016/j.carbpol.2009.12.014
38. Rowbotham J.S., Dyer P.W., Greenwell H.C., Selby D., Theodorou M.K. Copper(II)-mediated thermolysis of alginates: a model kinetic study on the influence of metal ions in the thermochemical processing of macroalgae. Interface Focus. 2013. 3(1): 20120046. https://doi.org/10.1098/rsfs.2012.0046
39. Kolesnyk I.S., Borodulin Yu.V., Antoniuk N.H., Burban A.F. PH-chutlyvi mikrokapsuly na osnovi natrii alhinatu, modyfikovanoho L-asparahinovoiu ta L-hlutaminovoiu kyslotamy. Nauk. zap. Khim. nauky i tekhnolohii. 2015. 170: 9. [in Ukrainian].
40. Sun J.Y., Zhao X., Illeperuma W.R., Chaudhuri O., Oh K.H., Mooney D.J., Vlassak J.J., Suo Z. Highly stretchable and tough hydrogels. Nature. 2012. 489(7414): 133. https://doi.org/10.1038/nature11409
DOI: https://doi.org/10.15407/hftp15.01.043
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