This study includes the design of a chitosan membrane decorated with unsaturated fatty acid–based carrier system for cancer treatment and antibacterial application. For this, polystyrene-graft-polyoleic acid-graft-polyethylene glycol was prepared by free radical polymerization and characterized. Nanoparticles and caffeic acid–loaded nanoparticles were prepared by solvent evaporation technique and optimized. The short-term stability of nanoparticles was investigated at 4°C. Drug encapsulation and loading efficiency were evaluated. The chitosan membrane and caffeic acid–loaded nanoparticles embedded into chitosan membrane were fabricated. The caffeic acid loaded nanoparticles embedded into chitosan membrane showed controlled release. The mechanical properties of all samples were investigated. The caffeic acid–loaded nanoparticles embedded into chitosan membranes indicated excellent antibacterial properties against the Escherichia coli and Staphylococcus aureus. The anticancer activity of all the samples was evaluated against SaOS-2 human primary osteogenic sarcoma and MC3T3-E1 pre-osteoblast cell lines by 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide assay, the flow cytometry and double staining methods. As a result, the designed carrier system showed great potential to cancer-associated infections treatment in bone cancer cases.
SchneiderDSAyresJS.Two ways to survive infection: what resistance and tolerance can teach us about treating infectious diseases. Nat Rev Immunol2008; 8: 889–895.
2.
OliveiraDEMüller-CoanBGPaganoJS.Viral carcinogenesis beyondmalignant transformation: EBV in the progression of human cancers. Trends Microbiol2016; 24(8): 649–664.
3.
MagerD.Bacteria and cancer: cause, coincidence or cure? A review. J Transl med2006; 4(1): 14.
4.
BlaserMJWebbGF.Host demise as a beneficial function of indigenous mi-crobiota in human hosts. mBio2014; 5(6): e02262-14.
5.
NesherLRolstonKV.The current spectrum of infection in cancer patients with chemotherapy related neutro-penia. Infection2014; 42: 5–13.
6.
AguadoaJMCruzbJJVirizuelacJA, et al. Management of infection and febrile neutropenia in patients with solid cancer. Enfermedades Infecciosas Y Microbiologia Clinica2017; 35(7): 451–460.
7.
LawYNAbdul WahabMChoePL, et al. Polymeric membranes incorporated with metal/metal oxide nanoparticles: a comprehensive review. Desalination2013; 308: 15–33.
8.
DenkbasEBOttenbriteRM.Perspectives on: chitosan delivery systems based on their geometries. J. Bioact Compat Polym2006; 21: 351–368.
9.
DiasKBSilvaDPFerreiraLA, et al. Chitin and chitosan: characteristics, uses and production current perspectives. J Biotechnol Biodiversity2013; 4: 184–191.
10.
ShenviSSRashidSAIsmailAF, et al. Preparation and characterization of PPEES/chitosan composite nanofiltration membrane. Desalination2013; 315: 135–141.
11.
ShenviSIsmailAFIsloorAM.Preparation and characterization study of PPEES/chitosan composite membrane crosslinked with tripolyphosphate. Desalination2014; 344: 90–96.
12.
LavallRAssisOCampana-filhoSP.Βeta-chitin from the pens of loligo sp: extraction and characterization. Bioresour Technol2007; 98(13): 2465–2472.
13.
ArbiaWArbiaLAdourL, et al. Chitin extraction from crustacean shells using biological methods: a review. Food Technol Biotechnol2013; 51(1): 12–25.
14.
HosseinnejadMJafariSM.Evaluation of different factors affecting antimicrobial properties of chitosan. Int J Biol Macromol2016; 85: 467–475.
15.
ElsabeeMZAbdouES.Chitosan based edible films and coatings: a review. Mater Sci Eng C2013; 33(4): 1819–1841.
16.
LiJHWuYGZhaoLQ.Antibacterial activity and mechanism of chitosan with ultra high molecular weight. Carbohydr Polym2016; 148: 200–205.
17.
VårumKMHolmeHKIzumeM, et al. Determination of enzymatic hydrolysis specificity of partially N-acetylated chitosans. Biochim Biophys Acta1996; 1291: 5–15.
18.
PaolettiMGNorbertoLCozzariniE, et al. Role of chitinases in human stomach for chitin digestion: AMCase in the gastric digestion of chitin and chit in gastric pathologies. In: Binomium chitin-chitinas: recent issues, New York: Nova Science Publishers, Inc., 2009, pp. 339–358.
19.
BrazLRodriguesSFonteP, et al. Mechanisms of chemical and enzymatic chitosan biodegradability and its application on drug delivery. In: FeltonGP (ed.) Biodegradable polymers: processing, degradation and applications, Nova Science Publisher, New York2011; pp: 325–364.
20.
KeanTThanouM.Biodegradation, biodistribution and toxicity of chitosan. Adv Drug Deliv Rev2010; 62: 3–11.
21.
MoranHBTTurleyJLAnderssonM, et al. Immunomodulatory properties of chitosan polymers. Biomaterials2018; 184: 1–9.
22.
XiaWLiuPZhangJ, et al. Biological activities of chitosan and chitooligosaccharides. Food Hydrocoll2010; 25: 170–179.
23.
KimSWRajapakseN.Enzymatic production and biological activities of chitosan oligosaccharides (COS): a review. Carbohydr Polym2005; 62: 357–368.
24.
WuPImaiM. Novel biopolymer composite membrane involved with selective mass transfer and excellent water permeability. In: NingRY(ed.) Advancing desalination, Rijeka, Croatia: InTech, 2012, 57–81.
25.
LeeYMShinEM.Pervaporation separation of water-ethanol through modified chitosan membranes. IV phosphorylated chitosan membranes. J Membr Sci1991; 1191(64): 145–152.
26.
ThakurVKVoicuSI.Recent advances in cellulose chitosan based membranes for water purification: a concise review. Carbohydr Polym. 2016; 146: 148–165.
27.
HuangDNiuLLiJ, et al. Reinforced chitosan membranes by microspheres for guided bone regeneration. J Mech Behav Biomed Mater2018; 81: 195–201.
28.
LiL-HDengJ-CDengH-R, et al. Synthesis and characterization of chitosan/ZnO nanoparticle composite membranes. Carbohydr Res2010; 345: 994–998.
29.
WangZYuanLTrenorNM, et al. Sustainable thermoplastic elastomers derived from plant oil and their ‘click-coupling’ via TAD chemistry. Green Chem2015; 17: 3806.
30.
HazerBAkyolE.Efficiency of gold nano particles on the autoxidized soybean oil polymer: fractionation and structural analysis. J Am Oil Chem Soci2016; 93(2): 201–213.
31.
InceOAkyolESuluE, et al. Synthesis and characterization of novel rod-coil (tadpole) poly(linoleic acid) based graft copolymers. J Polym Res2016; 23: 5.
TouaibiaMJean-FrancoisJDoironJ.Caffeic acid, a versatile pharmacophore: an overview. Mini Rev Med Chem2011; 11(8): 695–713.
34.
OrsolicNKnezevic’AHSverL, et al. Immunomodulatory and antimetastatic action of propolis and related polyphenolic compounds. J Ethnopharmacol2004; 94: 307–315.
35.
ChungTMoonSChangY, et al. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth by dual mechanism. Faseb J2004; 18(14): 1670–1681.
36.
AytekinAOMorimuraSKidaK.Synthesis of chitosan–caffeic acid derivatives and evaluation of their antioxidant activities. J Biosci Bioeng2011; 111: 212–216.
37.
HazerBAyyildizEErenH, et al. Autoxidized oleic acid bifunctional macro peroxide initiators for free radical and condensation polymerization. Synthesis and characterization of multiblock copolymers. J Polymer Env2019; 27: 2562–2576.
38.
HazerBAyyildizEBahadırF.Synthesis of PNIPAM–PEG double hydrophilic polymers using oleic acid macro peroxide initiator. J Am Oil Chem Soc2017; 94(9): 1141–1151.
39.
KilicayEKarahalilogluZHazerB, et al. Concanavaline A conjugated bacterial polyester-based PHBHHx nanoparticles loaded with curcumin for breast cancer therapy. J Microencapsul2016; 33: 274–285.
40.
GajendiranMGopiVElangovanV, et al. Isoniazid loaded core shell nanoparticles derived from PLGA–PEG–PLGA tri-block copolymers: in vitro and in vivo drug release. Colloid Surfaces B2013; 104: 107–115.
41.
TamburaciSTihminliogluF.Diatomite reinforced chitosan compositemembrane as potential scaffold for guided bone regeneration. Materi Sci Eng C2017; 8: 222–231.
42.
InêsCPereira AnaSDAnaSN, et al. Chitosan and polyethylene glycol based membranes with antibacterial properties for tissue regeneration. Mater Sci Eng C2019; 96: 606–615.
43.
MotaJYuNCaridadeSG, et al. Chitosan/bioactive glass nanoparticle composite membranes for periodontal regeneration. Acta Biomaterialla2012; 8: 4173–4180.
44.
LecetaIGuerreroPCabaK.Functional properties of chitosan-based films. Carbohyd Polym2013; 93: 339–346.
45.
WangLDongYMenH, et al. Preparation and characterization of active films based on chitosan incorporated tea polyphenols. Food Hydrocoll2013; 32: 35–41.
46.
GiovinoCAyensuITettehJ, et al. Development and characterisation of chitosan films impregnated with insülin loaded PEG-b-PLA nanoparticles (NPs): a potential approach for buccal delivery of macromolecules. Int J Pharmaceut2012; 428: 143–151.
47.
ZhuYCaoHQiaoS, et al. Hierarchical micro/nanostructured titanium with balanced actions to bacterial and mammalian cells for dental implants. Int J Nanomed2015; 10: 6659–6674.
48.
XuaTXinMLiM, et al. Synthesis, characteristic and antibacterial activity of N, N,N-trimethyl chitosan and its carboxymethyl derivatives. Carbohyd Polym2010; 81: 931–936.
49.
UllahSZainolIIdrusRH.Incorporation of zinc oxide nanoparticles into chitosan-collagen 3D porous scaffolds: effect on morphology, mechanical properties andcytocompatibility of 3D porous scaffolds. Int J Biol Macromol2017; 104: 1020–1029.
50.
RitsemaJASHerschbergEMABorgosSE, et al. Relationship between polarities of antibiotic and polymer matrix on nanoparticle formulations based on aliphatic polyesters. Int J Pharmaceut2018; 548: 730–739.
51.
AlliSAlliAHazerB.Hyperbranched homo and thermoresponsive graft copolymers by using ATRP-macromonomer initiators. Appl Polym Sci2012; 124: 536–548.
52.
ZhaoYZouBShiZY, et al. The effect of 3-hydroxybutyrate on the in vitro differentiation of murine osteoblast MC3T3-E1 and in vivo bone formation in ovariectomized rats. Biomaterials2007; 28(20): 3063–3073.
53.
JeongIKimBSLeeH, et al. Prolonged analgesic effect of PLGA-encapsulated bee venom on formalin induced pain in rats. Int J Pharmaceut2009; 380(1-2): 62–66.
54.
ShahMNaseerMIChoiMH, et al. Amphi-philic PHAmPEG copolymeric nanocontainers for drug delivery: preparation, characterization and in vitro evaluation. Int J Pharmaceut2010; 400(1-2): 165–175.
55.
AnitaASreeranganathanMChennazhiKP, et al. In vitro combinatorial anticancer effects of 5-fluorouracil and curcumin loaded N, O-carboxymethyl chitosan nanoparticles toward colon cancer and in vivo pharmacokinetic studies. Eur J Pharmaceut Biopharmaceut2014; 88(1): 238–251.
56.
MunnawarIIqbalSSAnwarMN, et al. Synergistic effect of chitosan zinc oxide hybrid nanoparticles on antibiofouling and water disinfection of mixed matrix polyethersulfone nanocomposite membranes. Carbohyd Polym2017; 175: 661–670.
57.
GiovinoCAyensuITettehJ, et al. An integrated buccal delivery system combining chitosan films impregnated with peptide loaded PEG-b-PLA nanoparticles. Colloid Surfaces B2013; 112: 9–15.
58.
CaiNLiCHanC, et al. Tailoring mechanical and antibacterial properties of chitosan/gelatinnanofiber membranes with Fe3O4 nanoparticles for potential wounddressing application. Appl Surface Sci2016; 369: 492–500.
59.
ChenLSchadlerLSOzisikR.An experimental and theoretical investigation of the compressive properties of multi-walled carbon nanotube/poly(-methyl methacrylate) nanocomposite foams. Polymer2011; 52(13): 2899–2909.
60.
LvYDuYQiuW-Z, et al. Nanocomposite membranes via the Codeposition of polydopamine/polyethyleneimine with silica nanoparticles for enhanced mechanical strength and high water permeability. ACS Appl Mater Interfaces2017; 9(3): 2966–2972.
61.
AdolhassanSVossoughiMMahmoodiMN, et al. Efficient dye removal from aqueous solution by high-performance electrospun nanofibrous membranes through incorporation of SiO2 nanoparticles. J Cleaner Prod2018; 183: 1197–1206.
62.
LeeJKimKSNaK.Caffeic acid-coated multifunctional magnetic nanoparticles for the treatment and bimodal imaging of tumours. J Photochem Photobiol B2016; 160: 210–216.
63.
Woo OhGChun KoSYoung JeJ, et al. Fabrication, characterization and determination of biological activitiesof poly(Ɛ-caprolactone)/chitosan-caffeic acid composite fibrous matfor wound dressing application. Int J Biol Macromol2016; 93: 1549–1558.
64.
BrautiganDLGielataMHeoJ, et al. Selective toxicity of caffeic acid in hepatocellular carcinoma cells. Biochem Biophys Res Commun2018; 505: 612–617.
