Chemistry (all); Chemical Engineering (all); General Chemical Engineering; General Chemistry
Abstract :
[en] The mesoporous SBA-15 material was surface-functionalized with amino and carboxylic acid groups and used as a platform to investigate the interaction of these chemical groups with tetracycline, kanamycin, and ampicillin antibiotics. The interactions between the antibiotic and the functionalized surfaces were characterized using two-dimensional 1H-13C HETCOR CP MAS and FTIR spectroscopy and indicated that -COO- NH3 + bondings had been formed between chemical groups on the silica surface and drug molecules. The surface modification resulted in higher kanamycin and ampicillin loadings and a slow-release rate, and all synthesized systems showed antibacterial activity against susceptible Escherichia coli bacteria. Almost total death of bacteria was obtained using a few ppm of tetracycline- and kanamycin-loaded systems, whereas the ampicillin-loaded one showed lower bactericidal activity than free ampicillin.
Disciplines :
Chemistry
Author, co-author :
Bouchmella, Karim ; Brazilian Synchrotron Light Laboratory (LNLS), Brazilian Center for Research in Energy and Materials (CNPEM), P.O. Box 6192, Campinas CEP 13083-970, SP, Brazil ; Chemistry Institute (IQ), Universidade Estadual de Campinas (UNICAMP), P.O. Box 6154, Campinas CEP 13083-970, SP, Brazil ; ICGM, University Montpellier, CNRS, ENSCM, 34095 Montpellier, France
Lion, Quentin ; Université de Liège - ULiège > GIGA > GIGA Stem Cells - Medical Chemistry ; Brazilian Synchrotron Light Laboratory (LNLS), Brazilian Center for Research in Energy and Materials (CNPEM), P.O. Box 6192, Campinas CEP 13083-970, SP, Brazil
Gervais, Christel ; LCMCP - Laboratoire de Chimie de la Matière Condensée de Paris, Sorbonne Université, 4 place Jussieu, 75252 Paris Cedex 05, France
Cardoso, Mateus Borba ; Brazilian Synchrotron Light Laboratory (LNLS), Brazilian Center for Research in Energy and Materials (CNPEM), P.O. Box 6192, Campinas CEP 13083-970, SP, Brazil ; Chemistry Institute (IQ), Universidade Estadual de Campinas (UNICAMP), P.O. Box 6154, Campinas CEP 13083-970, SP, Brazil
Language :
English
Title :
Impact of Mesoporous Silica Functionalization Fine-Tuning on Antibiotic Uptake/Delivery and Bactericidal Activity.
CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico [BR] FAPESP - Fundação de Amparo à Pesquisa do Estado de São Paulo [BR] CAPES - Coordenação de Aperfeicoamento de Pessoal de Nível Superior [BR] Brazilian Synchrotron Light Laboratory [BR] LNNano - Laboratório Nacional de Nanotecnologia [BR]
Funding text :
M.B.C. thanks the support of FAPESP (Grant Nos. 2014/22322-2, 2015/25406-5, and 2021/12071-6) and the productivity research fellowship granted by CNPq (Grant No. 309107/2014-8). K.B. and Q.L. acknowledge the support of Capes (CSF-PAJT - 88887.091023/2014-00). NMR spectroscopic calculations were performed using HPC resources from GENCI-IDRIS (Grant 097535). The French Région Ile de France-SESAME program is acknowledged for financial support (700 MHz spectrometer). The authors would like to thank LNLS and LNNano for all financial support along this work. D1B and D2A SAXS beamlines (LNLS-Brazil) are acknowledged for the usage of the SAXS beamlines. We thank Jessica Fernanda Affonso de Oliveira, Agustin S. Picco, and Murilo Izidoro Santos for fruitful insights in the fluorescence spectroscopy, bactericidal experiments, and drug derivatization for spectroscopic quantification. Pr Ahmad Mehdi is acknowledged for fruitful discussions. We thank Dr. Marcio Chaim Bajgelman (LNBio - Campinas, Brazil) for providing E. coli bacteria (DH5α) for biological assays.
Vallet-Regi, M.; Rámila, A.; del Real, R. P.; Pérez-Pariente, J. A New Property of MCM-41: Drug Delivery System. Chem. Mater. 2001, 13, 308- 311, 10.1021/cm0011559
Vallet-Regí, M.; Balas, F.; Arcos, D. Mesoporous materials for drug delivery. Angew. Chem., Int. Ed. 2007, 46, 7548- 7558, 10.1002/anie.200604488
Wang, Y.; Zhao, Q.; Hu, Y.; Sun, L.; Bai, L.; Jiang, T.; Wang, S. Ordered nanoporous silica as carriers for improved delivery of water insoluble drugs: a comparative study between three dimensional and two dimensional macroporous silica. Int. J. Nanomed. 2012, 8, 4015- 4031
Jain, K. K., Drug Delivery Systems - An Overview. In Drug Delivery Systems, Jain, K. K., Ed. Humana Press: Totowa, NJ, 2008; pp. 1- 50, 10.1007/978-1-59745-210-6_1.
Yoo, J.-W.; Irvine, D. J.; Discher, D. E.; Mitragotri, S. Bio-inspired, bioengineered and biomimetic drug delivery carriers. Nat. Rev. Drug Discov. 2011, 10, 521- 535, 10.1038/nrd3499
Li, Z.; Barnes, J. C.; Bosoy, A.; Stoddart, J. F.; Zink, J. I. Mesoporous silica nanoparticles in biomedical applications. Chem. Soc. Rev. 2012, 41, 2590- 2605, 10.1039/c1cs15246g
Manzano, M.; Vallet-Regí, M. New developments in ordered mesoporous materials for drug delivery. J. Mater. Chem. 2010, 20, 5593- 5604, 10.1039/b922651f
Bernardos, A.; Piacenza, E.; Sancenón, F.; Hamidi, M.; Maleki, A.; Turner, R. J.; Martínez-Máñez, R. Mesoporous Silica-Based Materials with Bactericidal Properties. Small 2019, 15, 1900669- 1900702, 10.1002/smll.201900669
Chircov, C.; Spoială, A.; Păun, C.; Crăciun, L.; Ficai, D.; Ficai, A.; Andronescu, E.; Turculeţ, Ş. C. Mesoporous Silica Platforms with Potential Applications in Release and Adsorption of Active Agents. Molecules 2020, 25, 3814- 3848, 10.3390/molecules25173814
Gaslain, F. O. M.; Delacôte, C.; Walcarius, A.; Lebeau, B. One-step preparation of thiol-modified mesoporous silica spheres with various functionalization levels and different pore structures. J. Sol-Gel Sci. Technol. 2009, 49, 112- 124, 10.1007/s10971-008-1845-6
Zapilko, C.; Widenmeyer, M.; Nagl, I.; Estler, F.; Anwander, R.; Raudaschl-Sieber, G.; Groeger, O.; Engelhardt, G. Advanced Surface Functionalization of Periodic Mesoporous Silica: Kinetic Control by Trisilazane Reagents. J. Am. Chem. Soc. 2006, 128, 16266- 16276, 10.1021/ja065444v
Bouchmella, K.; Campanaro, F. D.; Mondo, G. B.; Santos, M. I.; Franco, C. H.; Moraes, C. B.; Biolley, C.; Mehdi, A.; Cardoso, M. B. Tetracycline@silver ions-functionalized mesoporous silica for high bactericidal activity at ultra-low concentration. Nanomedicine 2018, 13, 1731- 1751, 10.2217/nnm-2018-0027
Ritter, H.; Brühwiler, D. Accessibility of Amino Groups in Postsynthetically Modified Mesoporous Silica. J. Phys. Chem. C 2009, 113, 10667- 10674, 10.1021/jp901983j
Crisci, A. J.; Tucker, M. H.; Lee, M.-Y.; Jang, S. G.; Dumesic, J. A.; Scott, S. L. Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration. ACS Catal. 2011, 1, 719- 728, 10.1021/cs2001237
Azaïs, T.; Tourné-Péteilh, C.; Aussenac, F.; Baccile, N.; Coelho, C.; Devoisselle, J.-M.; Babonneau, F. Solid-State NMR Study of Ibuprofen Confined in MCM-41 Material. Chem. Mat. 2006, 18, 6382- 6390, 10.1021/cm061551c
Azaïs, T.; Hartmeyer, G.; Quignard, S.; Laurent, G.; Tourné-Péteilh, C.; Devoisselle, J.-M.; Babonneau, F. Solid-state NMR characterization of drug-model molecules encapsulated in MCM-41 silica. Pure Appl. Chem. 2009, 81, 1345- 1355, 10.1351/PAC-CON-08-11-10
Fiorilli, S.; Onida, B.; Bonelli, B.; Garrone, E. In Situ Infrared Study of SBA-15 Functionalized with Carboxylic Groups Incorporated by a Co-condensation Route. J. Phys. Chem. B 2005, 109, 16725- 16729, 10.1021/jp045362y
Tang, Q.; Xu, Y.; Wu, D.; Sun, Y. A study of carboxylic-modified mesoporous silica in controlled delivery for drug famotidine. J. Solid State Chem. 2006, 179, 1513- 1520, 10.1016/j.jssc.2006.02.004
Sevimli, F.; Yilmaz, A. Surface functionalization of SBA-15 particles for amoxicillin delivery. Microporous Mesoporous Mater. 2012, 158, 281- 291, 10.1016/j.micromeso.2012.02.037
Hashemikia, S.; Hemmatinejad, N.; Ahmadi, E.; Montazer, M. Optimization of tetracycline hydrochloride adsorption on amino modified SBA-15 using response surface methodology. J. Colloid Interface Sci. 2015, 443, 105- 114, 10.1016/j.jcis.2014.11.020
Bibent, N.; Mehdi, A.; Silly, G.; Henn, F.; Devautour-Vinot, S. Proton Conductivity versus Acidic Strength of One-Pot Synthesized Acid-Functionalized SBA-15 Mesoporous Silica. Eur. J. Inorg. Chem. 2011, 2011, 3214- 3225, 10.1002/ejic.201100186
Chen, Y.; Zhang, Y. Fluorescent quantification of amino groups on silica nanoparticle surfaces. Anal. Bioanal. Chem. 2011, 399, 2503- 2509, 10.1007/s00216-010-4622-7
Giannozzi, P.; Baroni, S.; Bonini, N.; Calandra, M.; Car, R.; Cavazzoni, C.; Ceresoli, D.; Chiarotti, G. L.; Cococcioni, M.; Dabo, I.; Dal Corso, A.; de Gironcoli, S.; Fabris, S.; Fratesi, G.; Gebauer, R.; Gerstmann, U.; Gougoussis, C.; Kokalj, A.; Lazzeri, M.; Martin-Samos, L.; Marzari, N.; Mauri, F.; Mazzarello, R.; Paolini, S.; Pasquarello, A.; Paulatto, L.; Sbraccia, C.; Scandolo, S.; Sclauzero, G.; Seitsonen, A. P.; Smogunov, A.; Umari, P.; Wentzcovitch, R. M. QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials. J. Phys.: Condens. Matter 2009, 21, 395502- 395521
Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, 3865- 3868, 10.1103/PhysRevLett.77.3865
Troullier, N.; Martins, J. L. Efficient pseudopotentials for plane-wave calculations. Phys. Rev. B 1991, 43, 1993- 2006, 10.1103/PhysRevB.43.1993
Kleinman, L.; Bylander, D. M. Efficacious Form for Model Pseudopotentials. Phys. Rev. Lett. 1982, 48, 1425- 1428, 10.1103/PhysRevLett.48.1425
Pickard, C. J.; Mauri, F. All-electron magnetic response with pseudopotentials: NMR chemical shifts. Phys. Rev. B 2001, 63, 245101- 245126, 10.1103/PhysRevB.63.245101
Zhao, D.; Huo, Q.; Feng, J.; Chmelka, B. F.; Stucky, G. D. Nonionic Triblock and Star Diblock Copolymer and Oligomeric Surfactant Syntheses of Highly Ordered, Hydrothermally Stable, Mesoporous Silica Structures. J. Am. Chem. Soc. 1998, 120, 6024- 6036, 10.1021/ja974025i
Boullanger, A.; Gracy, G.; Bibent, N.; Devautour-Vinot, S.; Clément, S.; Mehdi, A. From an Octakis(3-cyanopropyl)silsesquioxane Building Block to a Highly COOH-Functionalized Hybrid Organic-Inorganic Material. Eur. J. Inorg. Chem. 2012, 2012, 143- 150, 10.1002/ejic.201101037
Barczak, M. Functionalization of mesoporous silica surface with carboxylic groups by Meldrum’s acid and its application for sorption of proteins. J. Porous Mater. 2019, 26, 291- 300, 10.1007/s10934-018-0655-7
Cheik Ibrahim, A.; Meyer, M.; Devautour-Vinot, S.; Habas, J.-P.; Clément, S.; Naoufal, D.; Mehdi, A. A facile synthesis of proton-conducting organic-inorganic membranes. J. Membr. Sci. 2014, 470, 189- 196, 10.1016/j.memsci.2014.07.012
Gunathilake, C.; Dassanayake, R. S.; Abidi, N.; Jaroniec, M. Amidoxime-functionalized microcrystalline cellulose-mesoporous silica composites for carbon dioxide sorption at elevated temperatures. J. Mater. Chem. A 2016, 4, 4808- 4819, 10.1039/C6TA00261G
Alauzun, J.; Mehdi, A.; Reyé, C.; Corriu, R. J. P. Direct synthesis of bifunctional mesoporous organosilicas containing chelating groups in the framework and reactive functional groups in the channel pores. J. Mater. Chem. 2007, 17, 349- 356, 10.1039/B613804G
Liu, M.; Hou, L.-a.; Yu, S.; Xi, B.; Zhao, Y.; Xia, X. MCM-41 impregnated with A zeolite precursor: Synthesis, characterization and tetracycline antibiotics removal from aqueous solution. Chem. Eng. J. 2013, 223, 678- 687, 10.1016/j.cej.2013.02.088
Soni, S. S.; Brotons, G.; Bellour, M.; Narayanan, T.; Gibaud, A. Quantitative SAXS Analysis of the P123/Water/Ethanol Ternary Phase Diagram. J. Phys. Chem. B 2006, 110, 15157- 15165, 10.1021/jp062159p
Asleson, G. L.; Frank, C. W. Carbon-13 nuclear magnetic resonance spectral analysis of tetracycline hydrochloride and related antibiotics. J. Am. Chem. Soc. 1975, 97, 6246- 6248, 10.1021/ja00854a051
Eneva, G. I.; Spassov, S. L.; Haimova, M. Complete 1H and 13C NMR assignments for kanamycin A, kanamycin B and penta-N-acetyl-kanamycin B. Spectrochim. Acta, Part A 1991, 47, 875- 880, 10.1016/0584-8539(91)80274-M
Antzutkin, O. N.; Lee, Y. K.; Levitt, M. H. 13C and15N - Chemical Shift Anisotropy of Ampicillin and Penicillin-V Studied by 2D-PASS and CP/MAS NMR. J. Magn. Reson. 1998, 135, 144- 155, 10.1006/jmre.1998.1576
Kang, J.; Liu, H.; Zheng, Y.-M.; Qu, J.; Chen, J. P. Application of nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, UV-Visible spectroscopy and kinetic modeling for elucidation of adsorption chemistry in uptake of tetracycline by zeolite beta. J. Colloid Interface Sci. 2011, 354, 261- 267, 10.1016/j.jcis.2010.10.065
Wang, H.; Gao, X.; Wang, Y.; Wang, J.; Niu, X.; Deng, X. Effect of amine functionalization of SBA-15 on controlled baicalin drug release. Ceram. Int. 2012, 38, 6931- 6935, 10.1016/j.ceramint.2012.05.062
Kokunešoski, M.; Gulicovski, J.; Matović, B.; Logar, M.; Milonjić, S. K.; Babić, B. Synthesis and surface characterization of ordered mesoporous silica SBA-15. Mater. Chem. Phys. 2010, 124, 1248- 1252, 10.1016/j.matchemphys.2010.08.066
Szegedi, A.; Popova, M.; Goshev, I.; Mihaly, J. Effect of amine functionalization of spherical MCM-41 and SBA-15 on controlled drug release. J. Solid State Chem. 2011, 184, 1201- 1207, 10.1016/j.jssc.2011.03.005
Ilma, N.; Rizka, F. Quantitative vibrational methods development and its performance comparison to colorimetry on the assay of kanamycin sulfate. Int. J. Appl. Pharm. 2019, 11, 426- 435
Sabitha, M.; Rajiv, S. Preparation and characterization of ampicillin-incorporated electrospun polyurethane scaffolds for wound healing and infection control. Polym. Eng. Sci. 2015, 55, 541- 548, 10.1002/pen.23917
Moritz, M.; Łaniecki, M. SBA-15 mesoporous material modified with APTES as the carrier for 2-(3-benzoylphenyl)propionic acid. Appl. Surf. Sci. 2012, 258, 7523- 7529, 10.1016/j.apsusc.2012.04.076
Koneru, B.; Shi, Y.; Wang, Y.-C.; Chavala, S.; Miller, M.; Holbert, B.; Conson, M.; Ni, A.; Di Pasqua, A. Tetracycline-Containing MCM-41 Mesoporous Silica Nanoparticles for the Treatment of Escherichia coli. Molecules 2015, 20, 19690- 19698, 10.3390/molecules201119650
