Boron phenyl alanine targeted chitosan–PNIPAAm core–shell thermo-responsive nanoparticles: boosting drug delivery to glioblastoma in BNCT

References

• Miyatake S-I, Kawabata S, Hiramatsu R, et al. Boron neutron capture therapy for malignant brain tumors. Neurol Med Chir. 2016;56(7):361–371.
   PubMed Web of Science ®Google Scholar
• Juratli TA, Schackert G, Krex D. Current status of local therapy in malignant gliomas—a clinical review of three selected approaches. Pharmacol Ther. 2013;139(3):341–358.
   PubMed Web of Science ®Google Scholar
• Thakur A, Gahane A, Bhadoriya SS, et al. Major hurdles for brain tumour therapy and the ways to overcome them: a review. J Pharm Res. 2011;4:1315.
   Google Scholar
• Mahmoud BS, AlAmri AH, McConville C. Polymeric nanoparticles for the treatment of malignant gliomas. Cancers. 2020;12(1):175.
   Web of Science ®Google Scholar
• Bredel M. Anticancer drug resistance in primary human brain tumors. Brain Res Brain Res Rev. 2001;35(2):161–204.
   PubMedGoogle Scholar
• Cerecetto H, Couto M. Medicinal chemistry of boron-bearing compounds for BNCT- Glioma treatment: current challenges and perspectives. In: Omerhodžić I, Arnautović K, editors. Glioma - Contemporary Diagnostic and Therapeutic Approaches [Internet]. London: IntechOpen; 2018 [cited 2022 Feb 01]. Available from: https://www.intechopen.com/chapters/61749 doi: https://doi.org/10.5772/intechopen.76369
   Google Scholar
• Ferrari C, Bakeine J, Ballarini F, et al. In vitro and in vivo studies of boron neutron capture therapy: boron uptake/washout and cell death. Radiat Res. 2011;175(4):452–462.
   PubMed Web of Science ®Google Scholar
• Barth RF, Zhang Z, Liu T. A realistic appraisal of boron neutron capture therapy as a cancer treatment modality. Cancer Commun. 2018;38(1):36.
   Web of Science ®Google Scholar
• Kawasaki R, Sasaki Y, Akiyoshi K. Intracellular delivery and passive tumor targeting of a self-assembled nanogel containing carborane clusters for boron neutron capture therapy. Biochem Biophys Res Commun. 2017;483(1):147–152.
   PubMed Web of Science ®Google Scholar
• Luderer MJ, de la Puente P, Azab AK. Advancements in tumor targeting strategies for boron neutron capture therapy. Pharm Res. 2015;32(9):2824–2836.
   PubMed Web of Science ®Google Scholar
• Farias RO, Garabalino MA, Ferraris S, et al. Toward a clinical application of ex situ boron neutron capture therapy for lung tumors at the RA-3 reactor in Argentina. Med Phys. 2015;42(7):4161–4173.
   PubMed Web of Science ®Google Scholar
• Feng B, Tomizawa K, Michiue H, et al. Delivery of sodium borocaptate to glioma cells using immunoliposome conjugated with anti-EGFR antibodies by ZZ-His. Biomaterials. 2009;30(9):1746–1755.
   PubMed Web of Science ®Google Scholar
• Sherlock Huang LC, Hsieh WY, Chen JY, et al. Drug delivery system design and development for boron neutron capture therapy on cancer treatment. Appl Radiat Isot. 2014;88:89–93.
   PubMed Web of Science ®Google Scholar
• Barth RF, Coderre JA, Vicente MG, et al. Boron neutron capture therapy of cancer: current status and future prospects. Clin Cancer Res. 2005;11(11):3987–4002.
   PubMed Web of Science ®Google Scholar
• Ichikawa H, Taniguchi E, Fujimoto T, et al. Biodistribution of BPA and BSH after single, repeated and simultaneous administrations for neutron-capture therapy of cancer. Appl Radiat Isot. 2009;67(7–8 Suppl.):S111–S114.
   PubMed Web of Science ®Google Scholar
• Calabrese G, Daou A, Barbu E, et al. Towards carborane-functionalised structures for the treatment of brain cancer. Drug Discov Today. 2018;23(1):63–75.
   PubMed Web of Science ®Google Scholar
• Nedunchezhian K, Aswath N, Thiruppathy M, et al. Boron neutron capture therapy – a literature review. J Clin Diagn Res. 2016;10(12):ZE01–ZE04.
   PubMedGoogle Scholar
• Barth RF, Mi P, Yang W. Boron delivery agents for neutron capture therapy of cancer. Cancer Commun. 2018;38(1):35.
   Web of Science ®Google Scholar
• Gao Z, Horiguchi Y, Nakai K, et al. Use of boron cluster-containing redox nanoparticles with ROS scavenging ability in boron neutron capture therapy to achieve high therapeutic efficiency and low adverse effects. Biomaterials. 2016;104:201–212.
   PubMed Web of Science ®Google Scholar
• Abolmaali SS, Tamaddon AM, Dinarvand R. A review of therapeutic challenges and achievements of methotrexate delivery systems for treatment of cancer and rheumatoid arthritis. Cancer Chemother Pharmacol. 2013;71(5):1115–1130.
   PubMed Web of Science ®Google Scholar
• Khan ZA, Tripathi R, Mishra B. Methotrexate: a detailed review on drug delivery and clinical aspects. Expert Opin Drug Deliv. 2012;9(2):151–169.
   PubMed Web of Science ®Google Scholar
• Hassan M, Farid D, Mahdi A, et al. Methotrexate-loaded PLGA nanoparticles: preparation, characterization and their cytotoxicity effect on human glioblastoma U87MG cells. Int J Med Nano Res. 2017;4(1).
   Google Scholar
• De Jong WH, Borm PJ. Drug delivery and nanoparticles: applications and hazards. Int J Nanomedicine. 2008;3(2):133–149.
   PubMed Web of Science ®Google Scholar
• Fahmy TM, Fong PM, Goyal A, et al. Targeted for drug delivery. Mater Today. 2005;8(8):18–26.
   Web of Science ®Google Scholar
• Iqbal J, Anwar F, Afridi S. Targeted drug delivery systems and their therapeutic applications in cancer and immune pathological conditions. Infect Disord Drug Targets. 2017;17(3):149–159.
   PubMedGoogle Scholar
• Patra JK, Das G, Fraceto LF, et al. Nano based drug delivery systems: recent developments and future prospects. J Nanobiotechnol. 2018;16(1):71.
   PubMed Web of Science ®Google Scholar
• Ye Z, Zhang T, He W, et al. Methotrexate-loaded extracellular vesicles functionalized with therapeutic and targeted peptides for the treatment of glioblastoma multiforme. ACS Appl Mater Interfaces. 2018;10(15):12341–12350.
   PubMed Web of Science ®Google Scholar
• Mura S, Nicolas J, Couvreur P. Stimuli-responsive nanocarriers for drug delivery. Nat Mater. 2013;12(11):991–1003.
   PubMed Web of Science ®Google Scholar
• Yang M, Hu J, Meng J, et al. A thermo and photoresponsive dual performing hydrogel for multiple controlled release mechanisms. Iran Polym J. 2020;29(10):891–900.
   Web of Science ®Google Scholar
• Hu S, Li H, Fang Q, et al. A core–shell double-layer structured polylactic acid/chitosan delivery system containing large molecular protein. Iran Polym J. 2020;29(11):997–1006.
   Web of Science ®Google Scholar
• Huang G, Mei X, Xiao F, et al. Applications of important polysaccharides in drug delivery. Curr Pharm Des. 2015;21(25):3692–3696.
   PubMed Web of Science ®Google Scholar
• Shelke NB, James R, Laurencin CT, et al. Polysaccharide biomaterials for drug delivery and regenerative engineering. Polym Adv Technol. 2014;25(5):448–460.
   Web of Science ®Google Scholar
• Esfahani RE, Zahedi P, Zarghami R. 5-Fluorouracil-loaded poly(vinyl alcohol)/chitosan blend nanofibers: morphology, drug release and cell culture studies. Iran Polym J. 2021;30(2):167–177.
   Web of Science ®Google Scholar
• Ruel-Gariépy E, Shive M, Bichara A, et al. A thermosensitive chitosan-based hydrogel for the local delivery of paclitaxel. Eur J Pharm Biopharm. 2004;57(1):53–63.
   PubMed Web of Science ®Google Scholar
• Rejinold NS, Sreerekha PR, Chennazhi KP, et al. Biocompatible, biodegradable and thermo-sensitive chitosan-g-poly (N-isopropylacrylamide) nanocarrier for curcumin drug delivery. Int J Biol Macromol. 2011;49(2):161–172.
   PubMed Web of Science ®Google Scholar
• Alvarez-Lorenzo C, Concheiro A, Dubovik AS, et al. Temperature-sensitive chitosan-poly(N-isopropylacrylamide) interpenetrated networks with enhanced loading capacity and controlled release properties. J Control Release. 2005;102(3):629–641.
   PubMed Web of Science ®Google Scholar
• Cho JH, Kim SH, Park KD, et al. Chondrogenic differentiation of human mesenchymal stem cells using a thermosensitive poly(N-isopropylacrylamide) and water-soluble chitosan copolymer. Biomaterials. 2004;25(26):5743–5751.
   PubMed Web of Science ®Google Scholar
• Wang J, Wu W, Jiang X. Nanoscaled boron-containing delivery systems and therapeutic agents for cancer treatment. Nanomedicine. 2015;10(7):1149–1163.
   PubMed Web of Science ®Google Scholar
• Freitag R, Fischer F. Microwave-induced chain transfer polymerization of a stimuli-responsive polymer and determination of its critical solution temperature. J Chem Educ. 2006;83(3):447.
   Web of Science ®Google Scholar
• Sun G, Feng C, Kong M, et al. Development of part-dissolvable chitosan fibers with surface N-succinylation for wound care dressing. Front Mater Sci. 2015;9(3):272–281.
   Web of Science ®Google Scholar
• Kustov LM, Finashina ED, Shuvalova EV, et al. Pd–Fe nanoparticles stabilized by chitosan derivatives for perchloroethene dechlorination. Environ Int. 2011;37(6):1044–1052.
   PubMed Web of Science ®Google Scholar
• Keller O, Keller WE, Look G, et al. Tert‐butoxycarbonylation of amino acids and their derivatives: N‐tert‐butoxycarbonyl‐l‐phenylalanine: l‐phenylalanine, N‐[(1,1‐dimethylethoxy) carbonyl]. Org Synth. 2003;63:160.
   Google Scholar
• Zhang J, Zhou X, Zhou Z, et al. Preparation and characterization of l-phenylalanine modified chitosan resin for aromatic amino acid adsorption. Macromol Res. 2014;22(5):515–522.
   Web of Science ®Google Scholar
• Constantin M, Cristea M, Ascenzi P, et al. Lower critical solution temperature versus volume phase transition temperature in thermoresponsive drug delivery systems. Express Polym Lett. 2011;5(10):839–848.
   Web of Science ®Google Scholar
• Yoneoka S, Park KC, Nakagawa Y, et al. Synthesis and evaluation of thermoresponsive boron-containing poly(N-isopropylacrylamide) diblock copolymers for self-assembling nanomicellar boron carriers. Polymers. 2018;11(1):42.
   Web of Science ®Google Scholar
• Abreu CM, Paula HC, Seabra V, et al. Synthesis and characterization of non-toxic and thermo-sensitive poly(N-isopropylacrylamide)-grafted cashew gum nanoparticles as a potential epirubicin delivery matrix. Carbohydr Polym. 2016;154:77–85.
   PubMed Web of Science ®Google Scholar
• Elshaarawy RFM, Mustafa FHA, Herbst A, et al. Surface functionalization of chitosan isolated from shrimp shells, using salicylaldehyde ionic liquids in exploration for novel economic and ecofriendly antibiofoulants. RSC Adv. 2016;6(25):20901–20915.
   Web of Science ®Google Scholar
• Bao H, Li L, Leong WC, et al. Thermo-responsive association of chitosan-graft-poly(N-isopropylacrylamide) in aqueous solutions. J Phys Chem B. 2010;114(32):10666–10673.
   PubMed Web of Science ®Google Scholar
• Yang X, Zhang Q, Wang Y, et al. Self-aggregated nanoparticles from methoxy poly(ethylene glycol)-modified chitosan: synthesis; characterization; aggregation and methotrexate release in vitro. Colloids Surf B Biointerfaces. 2008;61(2):125–131.
   PubMed Web of Science ®Google Scholar
• Rahimi M, Kilaru S, Sleiman GE, et al. Synthesis and characterization of thermo-sensitive nanoparticles for drug delivery applications. J Biomed Nanotechnol. 2008;4(4):482–490.
   PubMed Web of Science ®Google Scholar
• Patil AS, Gadad AP. Development and evaluation of high oxaliplatin loaded CS-g-PNIPAAm co-polymeric nanoparticles for thermo and pH responsive delivery. Indian J Pharm Educ Res. 2018;52(1):62–70.
   Web of Science ®Google Scholar
• Mazzotta E, De Benedittis S, Qualtieri A, et al. Actively targeted and redox responsive delivery of anticancer drug by chitosan nanoparticles. Pharmaceutics. 2019;12(1):26.
   Web of Science ®Google Scholar
• Chen J, Huang L, Lai H, et al. Methotrexate-loaded PEGylated chitosan nanoparticles: synthesis, characterization, and in vitro and in vivo antitumoral activity. Mol Pharm. 2014;11(7):2213–2223.
   PubMed Web of Science ®Google Scholar
• Tromsdorf UI, Bruns OT, Salmen SC, et al. A highly effective, nontoxic T1 MR contrast agent based on ultrasmall PEGylated iron oxide nanoparticles. Nano Lett. 2009;9(12):4434–4440.
   PubMed Web of Science ®Google Scholar
• Huang C-H, Wang C-F, Don T-M, et al. Preparation of pH- and thermo-sensitive chitosan–PNIPAAm core–shell nanoparticles and evaluation as drug carriers. Cellulose. 2013;20(4):1791–1805.
   Web of Science ®Google Scholar
• Sethi S, Kaith BS, Kaur M, et al. Cross-linked xanthan gum-starch hydrogels as promising materials for controlled drug delivery. Cellulose. 2020;1–25.
   Google Scholar
• Eleftheriou K, Kaminari A, Panagiotaki KN, et al. A combination drug delivery system employing thermosensitive liposomes for enhanced cell penetration and improved in vitro efficacy. Int J Pharm. 2020;574:118912.
   PubMedGoogle Scholar
• Shah SA, Majeed A, Shafique M, et al. Cell viability study of thermo-responsive core–shell superparamagnetic nanoparticles for multimodal cancer therapy. Appl Nanosci. 2014;4(2):227–232.
   Web of Science ®Google Scholar
• van Meerloo J, Kaspers GJ, Cloos J. Cell sensitivity assays: the MTT assay. Methods Mol Biol. 2011;731:237–245.
   PubMedGoogle Scholar
• Mogharbel BF, Francisco JC, Irioda AC, et al. Fluorescence properties of curcumin-loaded nanoparticles for cell tracking. Int J Nanomedicine. 2018;13:5823–5836.
   PubMed Web of Science ®Google Scholar
• Kasesaz Y, Khalafi H, Rahmani F, et al. Design and construction of a thermal neutron beam for BNCT at Tehran Research Reactor. Appl Radiat Isot. 2014;94:149–151.
   PubMed Web of Science ®Google Scholar
• Ferreira TH, Miranda MC, Rocha Z, et al. An assessment of the potential use of BNNTs for boron neutron capture therapy. Nanomaterials. 2017;7(4):82.
   Web of Science ®Google Scholar
• Bashir S, Teo YY, Ramesh S, et al. N-succinyl chitosan preparation, characterization, properties and biomedical applications: a state of the art review. Rev Chem Eng. 2015;31(6).
   Google Scholar
• Kumar MN, Muzzarelli RA, Muzzarelli C, et al. Chitosan chemistry and pharmaceutical perspectives. Chem Rev. 2004;104(12):6017–6084.
   PubMed Web of Science ®Google Scholar
• Park JH, Saravanakumar G, Kim K, et al. Targeted delivery of low molecular drugs using chitosan and its derivatives. Adv Drug Deliv Rev. 2010;62(1):28–41.
   PubMed Web of Science ®Google Scholar
• Kong X, Xu W, Zhang C, et al. Chitosan temperature-sensitive gel loaded with drug microspheres has excellent effectiveness, biocompatibility and safety as an ophthalmic drug delivery system. Exp Ther Med. 2018;15(2):1442–1448.
   PubMed Web of Science ®Google Scholar
• Chuang C-Y, Don T-M, Chiu W-Y. Synthesis and characterization of stimuli-responsive porous/hollow nanoparticles by self-assembly of chitosan-based graft copolymers and application in drug release. J Polym Sci A Polym Chem. 2010;48(11):2377–2387.
   Web of Science ®Google Scholar
• Krishnaiah D, Anisuzzaman SM, Shi SF, et al. Effect of 3-mercaptopropionic acid on polymerization of thermo-responsive poly(N-isopropylacrylamide). In: Pogaku R., Bono A., Chu C, editors. Developments in Sustainable Chemical and Bioprocess Technology. Boston, MA: Springer. https://doi.org/https://doi.org/10.1007/978-1-4614-6208-8_43 2013. p. 365–70.
   Google Scholar
• Lee SB, Ha DI, Cho SK, et al. Temperature/pH-sensitive comb-type graft hydrogels composed of chitosan and poly(N-isopropylacrylamide). J Appl Polym Sci. 2004;92(4):2612–2620.
   Web of Science ®Google Scholar
• Valeur E, Bradley M. Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev. 2009;38(2):606–631.
   PubMed Web of Science ®Google Scholar
• Reading M, Luget A, Wilson R. Modulated differential scanning calorimetry. Thermochim Acta. 1994;238:295–307.
   Web of Science ®Google Scholar
• Jaiswal MK, Banerjee R, Pradhan P, et al. Thermal behavior of magnetically modalized poly(N-isopropylacrylamide)-chitosan based nanohydrogel. Colloids Surf B Biointerfaces. 2010;81(1):185–194.
   PubMed Web of Science ®Google Scholar
• Baghaei S, Khorasani MT. Preparation and characterization of a thermal responsive of poly(N-isopropylacrylamide)/chitosan/gelatin hydrogels. Biomater Biomed Eng. 2014;1(2):105–116.
   Google Scholar
• Sosnik A, Imperiale JC, Vazquez-Gonzalez B, et al. Mucoadhesive thermo-responsive chitosan-g-poly(N-isopropylacrylamide) polymeric micelles via a one-pot gamma-radiation-assisted pathway. Colloids Surf B Biointerfaces. 2015;136:900–907.
   PubMed Web of Science ®Google Scholar
• Tauer K, Gau D, Schulze S, et al. Thermal property changes of poly(N-isopropylacrylamide) microgel particles and block copolymers. Colloid Polym Sci. 2009;287(3):299–312.
   Web of Science ®Google Scholar
• Yu Y, Chang X, Ning H, et al. Synthesis and characterization of thermoresponsive hydrogels cross-linked with chitosan. Open Chemistry. 2008;6(1):107–113.
   Google Scholar
• Zhu M, Nie G, Meng H, et al. Physicochemical properties determine nanomaterial cellular uptake, transport, and fate. Acc Chem Res. 2013;46(3):622–631.
   PubMed Web of Science ®Google Scholar
• Akinc A, Battaglia G. Exploiting endocytosis for nanomedicines. Cold Spring Harb Perspect Biol. 2013;5(11):a016980.
   PubMed Web of Science ®Google Scholar
• Ekinci M, Ilem-Ozdemir D, Gundogdu E, et al. Methotrexate loaded chitosan nanoparticles: preparation, radiolabeling and in vitro evaluation for breast cancer diagnosis. J Drug Deliv Sci Technol. 2015;30:107–113.
   Web of Science ®Google Scholar
• Bordat A, Boissenot T, Nicolas J, et al. Thermoresponsive polymer nanocarriers for biomedical applications. Adv Drug Deliv Rev. 2019;138:167–192.
   PubMed Web of Science ®Google Scholar
• Lazzari G, Couvreur P, Mura S. Multicellular tumor spheroids: a relevant 3D model for the in vitro preclinical investigation of polymer nanomedicines. Polym Chem. 2017;8(34):4947–4969.
   Web of Science ®Google Scholar
• Smilgys B, Guedes S, Morales M, et al. Boron thin films and CR-39 detectors in BNCT: a method to measure the 10B (n, α) 7Li reaction rate. Radiat Meas. 2013;50:181–186.
   Web of Science ®Google Scholar
• Pawar VM, Beck M, Shetgaonkar AD, et al. Synthesis and application of boron polymers for enhanced thermal neutron dosimetry. Nucl Instrum Methods Phys Res Sect B. 2020;462:169–176.
   Web of Science ®Google Scholar