Magnetically responsive hydrophobic pockets for on–off drug release

Materials Today Chemistry - Tập 23 - Trang 100702 - 2022
J. Leganés1,2, A.M. Rodríguez2, M.A. Arranz1, C.A. Castillo-Sarmiento3,4, I. Ballesteros-Yáñez4,5, A.S. Migallón1, S. Merino1,2, E. Vázquez1,2
1Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, 13005 Ciudad Real, Spain
2Instituto Regional de Investigación Científica Aplicada (IRICA), 13005 Ciudad Real, Spain
3School of Physiotherapy and Nursing, Universidad de Castilla-La Mancha, 45071 Toledo, Spain
4Regional Center for Biomedical Research, Universidad de Castilla-La Mancha, 02071 Albacete, Spain
5Faculty of Medicine, Universidad de Castilla-La Mancha, 13071 Ciudad Real, Spain

Tài liệu tham khảo

Lipinski, 2000, Drug-like properties and the causes of poor solubility and poor permeability, J. Pharmacol. Toxicol. Methods, 44, 235, 10.1016/S1056-8719(00)00107-6 Merisko-Liversidge, 2008, Drug nanoparticles: formulating poorly water-soluble compounds, Toxicol. Pathol., 36, 43, 10.1177/0192623307310946 Peng, 2015, Supramolecular polymeric vesicles formed by p-sulfonatocalix[4]arene and chitosan with multistimuli responses, Soft Matter, 11, 290, 10.1039/C4SM02170C Cai, 2014, PH and redox-responsive mixed micelles for enhanced intracellular drug release, Colloids Surf. B Biointerfaces, 116, 424, 10.1016/j.colsurfb.2014.01.012 Bellomo, 2004, Stimuli-responsive polypeptide vesicles by conformation-specific assembly, Nat. Mater., 3, 244, 10.1038/nmat1093 Ashley, 2013, Hydrogel drug delivery system with predictable and tunable drug release and degradation rates, Proc. Natl. Acad. Sci. U.S.A., 110, 2318, 10.1073/pnas.1215498110 Li, 2016, Designing hydrogels for controlled drug delivery, Nat. Rev. Mater., 1, 16071, 10.1038/natrevmats.2016.71 Hoare, 2008, Hydrogels in drug delivery: progress and challenges, Polymer (Guildf), 49, 1993, 10.1016/j.polymer.2008.01.027 Beaune, 2010, In situ precipitation of magnetic fluid encapsulated in giant liposomes, J. Colloid Interface Sci., 343, 396, 10.1016/j.jcis.2009.11.016 Wiener, 2014, Overcoming confinement limited swelling in hydrogel thin films using supramolecular interactions, Soft Matter, 10, 6705, 10.1039/C4SM00815D Ozcelik, 2014, Highly porous and mechanically robust polyester poly(ethylene glycol) sponges as implantable scaffolds, Acta Biomater., 10, 2769, 10.1016/j.actbio.2014.02.019 Wang, 2018, A pH-responsive amphiphilic hydrogel based on pseudopeptides and poly(ethylene glycol) for oral delivery of hydrophobic drugs, ACS Biomater. Sci. Eng., 4, 4236, 10.1021/acsbiomaterials.8b01040 Wang, 2018, Self-assembled pH-responsive supramolecular hydrogel for hydrophobic drug delivery, RSC Adv., 8, 31581, 10.1039/C8RA06064A Feng, 2019, Dual pH- and thermal-responsive nanocomposite hydrogels for controllable delivery of hydrophobic drug baicalein, Polym. Int., 68, 494, 10.1002/pi.5738 Gao, 2020, A smart drug delivery system responsive to pH/enzyme stimuli based on hydrophobic modified sodium alginate, Eur. Polym. J., 133, 109779, 10.1016/j.eurpolymj.2020.109779 Puiggalí-Jou, 2020, Electroresponsive alginate-based hydrogels for controlled release of hydrophobic drugs, ACS Biomater. Sci. Eng., 6, 6228, 10.1021/acsbiomaterials.0c01400 Li, 2018, A tough composite hydrogel can controllably deliver hydrophobic drugs under ultrasound, Macromol. Mater. Eng., 303, 1, 10.1002/mame.201700483 Szymański, 2020, Retinoic acid and its derivatives in skin, Cells, 9, 1, 10.3390/cells9122660 Nagpal, 2019, All-trans retinoic acid as a versatile cytosolic signal modulator mediated by CRABP1, Int. J. Mol. Sci., 20, 1, 10.3390/ijms20153610 Jones, 2020, All-trans retinoic acid eluting poly(diol citrate) wafers for treatment of glioblastoma, J. Biomed. Mater. Res. B Appl. Biomater., 108, 619, 10.1002/jbm.b.34416 Mirani, 2019, A 3D bioprinted hydrogel mesh loaded with all-trans retinoic acid for treatment of glioblastoma, Eur. J. Pharmacol., 854, 201, 10.1016/j.ejphar.2019.04.007 Whitesides, 1991, Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures, Science (80-.), 254, 1312, 10.1126/science.1962191 Barberá, 2006, Propeller-like hydrogen-bonded banana-melamine complexes inducing helical supramolecular organizations, J. Am. Chem. Soc., 128, 4487, 10.1021/ja0585477 Maly, 2006, Self-assembly of columnar mesophases from diaminotriazines, J. Mater. Chem., 16, 4695, 10.1039/b610666h Asanuma, 1998, Precise recognition of nucleotides and their derivatives through hydrogen bonding in water by poly(vinyldiaminotriazine), Supramol. Sci., 5, 405, 10.1016/S0968-5677(98)00040-6 Tang, 2011, Robust MeO2MA/vinyl-4,6-diamino-1,3,5-triazine copolymer hydrogels-mediated reverse gene transfection and thermo-induced cell detachment, Biomaterials, 32, 1943, 10.1016/j.biomaterials.2010.11.019 Wang, 2012, High-strength hydrogel as a reusable adsorbent of copper ions, J. Hazard Mater., 213–214, 258, 10.1016/j.jhazmat.2012.01.092 Tang, 2010, High-strength hydrogels with integrated functions of H-bonding and thermoresponsive surface-mediated reverse transfection and cell detachment, Adv. Mater., 22, 2652, 10.1002/adma.200904016 Bairi, 2011, PH and anion sensitive silver(i) coordinated melamine hydrogel with dye absorbing properties: metastability at low melamine concentration, J. Mater. Chem., 21, 11747, 10.1039/c1jm11994j Baraka, 2019, A new cationic silver(I)/melamine coordination polymer, [Ag 2 (melamine)] n2n+ : synthesis, characterization and potential use for aqueous contaminant anion exchange, J. Solid State Chem., 274, 168, 10.1016/j.jssc.2019.03.038 Wiles, 2006, Copper (I) and (II) complexes of melamine, Polyhedron, 25, 776, 10.1016/j.poly.2005.08.022 Merino, 2015, Nanocomposite hydrogels: 3D polymer–nanoparticle synergies for on-demand drug delivery, ACS Nano, 9, 4686, 10.1021/acsnano.5b01433 Wang, 2018, Tough magnetic chitosan hydrogel nanocomposites for remotely stimulated drug release, Biomacromolecules, 19, 3351, 10.1021/acs.biomac.8b00636 Li, 2013, Magnetic hydrogels and their potential biomedical applications, Adv. Funct. Mater., 23, 660, 10.1002/adfm.201201708 Jung, 2006, Involvement of Bcl-2 family and caspases cascade in sodium fluoride-induced apoptosis of human gingival fibroblasts, Korean J. Physiol. Pharmacol., 10, 289 Chu, 2001, The convolution equation of Choquet and Deny on [IN]-groups, Integr. Equ. Operat. Theor., 40, 391, 10.1007/BF01198136 Soler, 2002, The SIESTA method for ab initio order-N materials simulation, J. Phys. Condens. Matter, 14, 2745, 10.1088/0953-8984/14/11/302 Leganés Bayón, 2020, On-demand hydrophobic drug release based on microwave-responsive graphene hydrogel scaffolds, Chem. Eur J., 26, 17069, 10.1002/chem.202001429 Rödling, 2018, Magnetic macroporous hydrogels as a novel approach for perfused stem cell culture in 3D scaffolds via contactless motion control, Adv. Healthc. Mater., 7, 1, 10.1002/adhm.201701403 Leganés, 2020, Stimuli-responsive graphene-based hydrogel driven by disruption of triazine hydrophobic interactions, Nanoscale, 12, 7072, 10.1039/C9NR10588C Galindo, 2019, Physically cross-linked hydrogel based on phenyl-1,3,5-triazine: soft scaffold with aggregation-induced emission, ACS Macro Lett., 8, 1391, 10.1021/acsmacrolett.9b00712 Sawa, 1987 Xu, 2015, Hydrogen-bonding toughened hydrogels and emerging CO 2 -responsive shape memory effect, Macromol. Rapid Commun., 36, 1585, 10.1002/marc.201500256 Pike, 2002, 1,3,5-Triazine templated self-assembly of a hexameric copper(I) chloride triphenyl phosphite core, Inorg. Chem., 41, 631, 10.1021/ic015605q Nagireddy, 2011, Preparation and characterization of magnetic nanoparticles embedded in hydrogels for protein purification and metal extraction, J. Polym. Res., 18, 2285, 10.1007/s10965-011-9642-2 Li, 2013, Magnetic hydrogels and their potential biomedical applications, Adv. Funct. Mater., 23, 660, 10.1002/adfm.201201708 Sun, 2012, Highly stretchable and tough hydrogels, Nature, 489, 133, 10.1038/nature11409 Oliva, 2017, Designing hydrogels for on-demand therapy, Acc. Chem. Res., 50, 669, 10.1021/acs.accounts.6b00536 Feksa, 2018, Hydrogels for biomedical applications, vol. 64, 403 Monazam, 2014, Kinetics of magnetite (Fe3O4) oxidation to hematite (Fe2O3) in air for chemical looping combustion, Ind. Eng. Chem. Res., 53, 13320, 10.1021/ie501536s Mircescu, 2012, FTIR, FT-Raman, SERS and DFT study on melamine, Vib. Spectrosc., 62, 165, 10.1016/j.vibspec.2012.04.008 Valiey, 2019, Melamine-modified chitosan materials: an efficient and recyclable bifunctional organocatalyst for green synthesis of densely functionalized bioactive dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives, Int. J. Biol. Macromol., 129, 407, 10.1016/j.ijbiomac.2019.01.027 Alirezvani, 2018, Melamine-Functionalized chitosan: a new bio-based reusable bifunctional organocatalyst for the synthesis of cyanocinnamonitrile intermediates and densely functionalized nicotinonitrile derivatives, ChemistrySelect, 3, 10450, 10.1002/slct.201802010 Vrandečić, 2010, Kinetic analysis of thermal degradation of poly(ethylene glycol) and poly(ethylene oxide)s of different molecular weight, Thermochim. Acta, 498, 71, 10.1016/j.tca.2009.10.005 Honda, 1991, Molecular recognition of barbiturates by diaminotriazine functionalized monolayers, Chem. Lett., 20, 681, 10.1246/cl.1991.681 Velázquez-Palenzuela, 2011, Carbon-Supported Fe-Nx catalysts synthesized by pyrolysis of the Fe(II)-2,3,5,6-tetra(2-pyridyl)pyrazine complex: structure, electrochemical properties, and oxygen reduction reaction activity, J. Phys. Chem. C, 115, 12929, 10.1021/jp2020897 Cui, 2014, Fe-N/C catalysts synthesized by heat-treatment of iron triazine carboxylic acid derivative complex for oxygen reduction reaction, RSC Adv., 4, 12168, 10.1039/c3ra44958k Kothandaraman, 2009, Non-precious oxygen reduction catalysts prepared by high-pressure pyrolysis for low-temperature fuel cells, Appl. Catal. B Environ., 92, 209, 10.1016/j.apcatb.2009.07.005 Worm, 1991, Domain size, closure domains, and the importance of magnetostriction in magnetite, Earth Planet Sci. Lett., 102, 71, 10.1016/0012-821X(91)90018-D Binns, 2002, Magnetic behaviour of thin films produced by depositing pre-formed Fe and Co nanoclusters Magnetic behaviour of thin films produced by depositing pre-formed Fe and Co nanoclusters, New J. Phys., 4, 85, 10.1088/1367-2630/4/1/385 Stearns, 1994, Determination of para and ferromagnetic components of magnetization and magnetoresistance of granular Co/Ag films (invited) Giant Magnetoresistance in Granular Materials Determination of para- and ferromagnetic components of magnetization and magnetor, J. Appl. Phys., 75, 6894, 10.1063/1.356773 Abdelrazek, 2018, Structural, optical, morphological and thermal properties of PEO/PVP blend containing different concentrations of biosynthesized Au nanoparticles, J. Mater. Res. Technol., 7, 419, 10.1016/j.jmrt.2017.06.009 Patterson, 1939, The scherrer formula for X-ray particle size determination, Phys. Rev., 56, 978, 10.1103/PhysRev.56.978 Wahajuddin, 2012, Superparamagnetic iron oxide nanoparticles: magnetic nanoplatforms as drug carriers, Int. J. Nanomed., 7, 3445, 10.2147/IJN.S30320 Singh, 2008, Composite – super paramagnetic behavior and variable range hopping 1D conduction mechanism – synthesis and characterization, Polym. Adv. Technol., 229, 10.1002/pat.1003