Quaternized chitosan/κ-carrageenan/caffeic acid–coated poly(3-hydroxybutyrate) fibrous materials: Preparation, antibacterial and antioxidant activity

International Journal of Pharmaceutics

Volumn 513, Issue 1-2, 2016, Pages 528-537

  Ignatova, Milena ^a   Manolova, Nevena ^a   Rashkov, Iliya ^a   Markova, Nadya ^b  

^a INSTITUTE OF POLYMERS   (Bulgaria)

^b INSTITUTE OF MICROBIOLOGY   (Bulgaria)

Author keywords

Antibacterial fibers; Antioxidant activity; Caffeic acid; Electrospinning; Quaternized chitosan; Carrageenan

Indexed keywords

CAFFEIC ACID; CARRAGEENAN; CHITOSAN; POLY(3 HYDROXYBUTYRIC ACID); POLYELECTROLYTE; 1,1-DIPHENYL-2-PICRYLHYDRAZYL; ANTIINFECTIVE AGENT; ANTIOXIDANT; BIPHENYL DERIVATIVE; CAFFEIC ACID DERIVATIVE; HYDROXYBUTYRIC ACID; PICRIC ACID; POLY-BETA-HYDROXYBUTYRATE; POLYESTER;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; BACTERIUM ADHERENCE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG RELEASE; ELECTROSPINNING; ESCHERICHIA COLI; MATERIAL COATING; NONHUMAN; PARTICLE SIZE; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; X RAY DIFFRACTION; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; DRUG FORMULATION; GROWTH, DEVELOPMENT AND AGING; PHYSIOLOGY;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; BACTERIAL ADHESION; BIPHENYL COMPOUNDS; CAFFEIC ACIDS; CARRAGEENAN; CHITOSAN; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; DRUG LIBERATION; ESCHERICHIA COLI; HYDROXYBUTYRATES; PICRATES; POLYELECTROLYTES; POLYESTERS; STAPHYLOCOCCUS AUREUS;

EID: 84988702975     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2016.09.062     Document Type: Article

References (42)

1. Alipour, S.M., Nouri, M., Mokhtari, J., Bahrami, S.H., Electrospinning of poly(vinyl alcohol)-water-soluble quaternized chitosan derivative blend. Carbohydr. Res. 344 (2009), 2496–2501.
2. Barham, P.J., Keller, A., Otun, E.L., Holmes, P.A., Crystallization and morphology of a bacterial thermoplastic: poly-3-hydroxybutyrate. J. Mater. Sci. 19 (1984), 2781–2794.
3. Bhattarai, S.R., Bhattarai, N., Viswanathamurthi, P., Yi, H.K., Hwang, P.H., Kim, H.Y., Hydrophilic nanofibrous structure of polylactide; fabrication and cell affinity. J. Biomed. Mater. Res. A 78 (2006), 247–257.
4. Chang, W.-Ch., Hsieh, C.-H., Hsiao, M.-W., Lin, W.-C., Hung, Y.-C., Yе, J.-C., Caffeic acid induces apoptosis in human cervical cancer cells through the mitochondrial pathway. Taiwan J. Obstet. Gynecol 49 (2010), 419–424.
5. Chuysinuan, P., Pavasant, P., Supaphol, P., Preparation and characterization of caffeic acid-grafted electrospun poly(L-lactic acid) fiber mats for biomedical applications. ACS Appl. Mater. Interfaces 4 (2012), 3031–3040.
6. Cui, W., Li, X., Zhou, S., Weng, J., Degradation patterns and surface wettability of electrospun fibrous mats. Polym. Degrad. Stab. 93 (2008), 731–738.
7. Cunha, L., Grenha, A., Sulfated seaweed polysaccharides as multifunctional materials in drug delivery applications. Mar. Drugs, 14, 2016, 42.
8. Gülçin, İ., Antioxidant activity of caffeic acid (3, 4-dihydroxycinnamic acid). Toxicology 217 (2006), 213–220.
9. Guo, Z., Liu, H., Chen, X., Ji, X., Li, P., Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan. Bioorg. Med. Chem. Lett. 16 (2007), 6348–6350.
10. Guzman, J.D., Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity. Molecules 19 (2014), 19292–19349.
11. Han, J., Chen, T.-X., Branford-White, C.J., Zhu, L.-M., Electrospun shikonin-loaded PCL/PTMC composite fiber mats with potential biomedical applications. Int. J. Pharm. 382 (2009), 215–221.
12. Hirano, S., Chitin and chitosan as novel biotechnological materials. Polym. Int. 48 (1999), 732–734.
13. Ignatova, M., Manolova, N., Rashkov, I., Novel antibacterial fibers of quaternized chitosan and poly(vinyl pyrrolidone) prepared by electrospinning. Eur. Polym. J. 43 (2007), 1112–1122.
14. Ignatova, M., Manolova, N., Toshkova, R., Rashkov, I., Gardeva, E., Yossifova, L., Alexandrov, M., Quaternized chitosan-coated nanofibrous materials containing gossypol Preparation by electrospinning, characterization and antiproliferative activity towards HeLa cells. Int. J. Pharm. 436 (2012), 10–24.
15. Ignatova, M., Manolova, N., Rashkov, I., Electrospun antibacterial chitosan-based fibers. Macromol. Biosci. 13 (2013), 860–872.
16. Ignatova, M., Rashkov, I., Manolova, N., Drug-loaded electrospun materials in wound-dressing applications and in local cancer treatment. Expert Opin. Drug. Deliv. 10 (2013), 469–483.
17. Ignatova, M.G., Manolova, N.E., Rashkov, I.B., Markova, N.D., Toshkova, R.A., Georgieva, A.K., Nikolova, E.B., Poly(3-hydroxybutyrate)/caffeic acid electrospun fibrous materials coated with polyelectrolyte complex and their antibacterial activity and in vitro antitumor effect against HeLa cells. Mater. Sci. Eng. C 65 (2016), 379–392.
18. Jia, Z., Shen, D., Xu, W., Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohydr. Res. 333 (2001), 1–6.
19. Jiang, L., Lu, Y., Liu, X., Tu, H., Zhang, J., Shi, X., Deng, H., Du, Y., Layer-by-layer immobilization of quaternized carboxymethyl chitosan/organic rectorite and alginate onto nanofibrous mats and their antibacterial application. Carbohydr. Polym. 121 (2015), 428–435.
20. Juntaprama, K., Praphairaksit, N., Siraleartmukul, K., Muangsin, N., Electrosprayed polyelectrolyte complexes between mucoadhesive N,N,N-trimethylchitosan-homocysteine thiolactone and alginate/carrageenan for camptothecin delivery. Carbohydr. Polym. 90 (2012), 1469–1479.
21. Kalinov, K., Ignatova, M., Manolova, N., Rashkov, I., Markova, N., Momekova, D., N,N,N-trimethylchitosan iodide complexes with a weak or a strong polyacid and nanoparticles thereof. Colloid. Polym. Sci. 292 (2014), 2899–2912.
22. Kalinov, K., Ignatova, M., Maximova, V., Rashkov, I., Manolova, N., Modification of electrospun poly(ε-caprolactone) mats by formation of a polyelectrolyte complex between poly(acrylic acid) and quaternized chitosan for tuning of their antibacterial properties. Eur. Polym. J. 50 (2014), 18–29.
23. Kalinov, K.N., Ignatova, M.G., Manolova, N.E., Markova, N.D., Karashanova, D.B., Rashkov, I.B., Novel antibacterial electrospun materials based on polyelectrolyte complexes of a quaternized chitosan derivative. RSC Adv. 5 (2015), 54517–54526.
24. Kim, C.H., Choi, J.W., Chun, H.J., Choi, K.S., Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity. Polym. Bull. 38 (1997), 387–393.
25. Kim, Y.-J., Park, M.R., Kim, M.S., Kwon, O.H., Polyphenol-loaded polycaprolactone nanofibers for effective growth inhibition of human cancer cells. Mater. Chem. Phys. 133 (2012), 674–680.
26. Lenz, R.W., Marchessault, R.H., Bacterial polyesters: biosynthesis, biodegradable plastics and biotechnology. Biomacromolecules 6 (2005), 1–8.
27. Li, L., Hsieh, Y.-L., Chitosan bicomponent nanofibers and nanoporous fibers. Carbohydr. Res. 341 (2006), 374–381.
28. Llorens, E., del Valle, L.J., Díaz, A., Casas, M.T., Puiggalí, J., Polylactide nanofibers loaded with vitamin B6 and polyphenols as bioactive platform for tissue engineering. Macromol. Res. 21 (2013), 775–787.
29. Llorens, E., del Valle, L.J., Puiggalí, J., Inhibition of radical-induced oxidative DNA damage by antioxidants loaded in electrospun polylactide nanofibers. Macromol. Res. 22 (2014), 388–396.
30. Necas, J., Bartosikova, L., Carrageenan. a review. Vet. Med. 58 (2013), 187–205.
31. Parkar, S.G., Stevenson, D.E., Skinner, M.A., The potential influence of fruit polyphenols on colonic microflora and human gut health. Int. J. Food Microbiol. 124 (2008), 295–298.
32. Prajapati, V.D., Maheriya, P.M., Jani, G.K., Solanki, H.K., Carrageenan: a natural seaweed polysaccharide and its applications. Carbohydr. Polym. 105 (2014), 97–112.
33. Rasband, W.S., ImageJ, U.S. National Institute of Health, Bethesda, Maryland, USA, 1997–2006, http://rsb.info.nih.gov/ij/.
34. Suganya, S., Senthil, R.T., Lakshmi, B.S., Giridev, V.R., Herbal drug incorporated antibacterial nanofibrous mat fabricated by electrospinning: an excellent matrix for wound dressings. J. Appl. Polym. Sci. 121 (2011), 2893–2899.
35. Toncheva, A., Spasova, M., Paneva, D., Manolova, N., Rashkov, I., Polylactide (PLA)-based electrospun fibrous materials containing ionic drugs as wound dressing materials: a review. Int. J. Polym. Mater. Polym. Biomater. 63 (2014), 657–671.
36. Verheul, R.J., Slütter, B., Bal, S.M., Bouwstra, J.A., Jiskoot, W., Hennink, W.E., Covalently stabilized trimethyl chitosan-hyaluronic acid nanoparticles for nasal and intradermal vaccination. J. Control. Release 156 (2011), 46–52.
37. Wan, A., Xu, Q., Sun, Y., Li, H., Antioxidant activity of high molecular weight chitosan and N, O-quaternized chitosans. J. Agric. Food. Chem. 61 (2013), 6921–6928.
38. Wang, C., Hsu, C.-H., Hwang, I.-H., Scaling laws and internal structure for characterizing electrospun poly[(R)-3-hydroxybutyrate] fibers. Polymer 49 (2008), 4188–4195.
39. Xu, X., Chen, X., Wang, Z., Jing, X., Ultrafine PEG-PLA fibers loaded with both pacltaxel and doxorubicin hydrochloride and their in vitro cytotoxicity. Eur. J. Pharm. Biopharm. 72 (2009), 18–25.
40. Yakub, G., Toncheva, A., Manolova, N., Rashkov, I., Kussovski, V., Danchev, D., Curcumin-loaded poly(L-lactide-co-D,L-lactide) electrospun fibers: preparation and antioxidant, anticoagulant, and antibacterial properties. J. Bioactive Compatible Polymers 29 (2014), 607–627.
41. Yancheva, E., Paneva, D., Manolova, N., Mincheva, R., Danchev, D., Dubois Ph Rashkov, I., Tuning of the surface biological behavior of poly(L-lactide)-based electrospun materials by polyelectrolyte complex formation. Biomacromolecules 11 (2010), 521–532.
42. de Souza, M.C.R., Marques, C.T., Dore, C.M.G., da Silva, F.R.F., Rocha, H.A.O., Leite, E.L., Antioxidant activities of sulfated polysaccharides from brown and red seaweeds. J. Appl. Phycol. 19 (2007), 153–160.