Skip to main content
Erschienen in: Journal of Sol-Gel Science and Technology 2/2012

01.11.2012 | Original Paper

Silica imprinted materials containing pharmaceuticals as a template: textural aspects

verfasst von: Everton C. Morais, Gabriel G. Correa, Rodrigo Brambilla, Paolo R. Livotto, João Henrique Z. dos Santos, Mateus Borba Cardoso

Erschienen in: Journal of Sol-Gel Science and Technology | Ausgabe 2/2012

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Silica-based materials were prepared by the acid catalyzed sol–gel method using different pharmaceuticals as a template. The template molecules investigated were fluoxetine, gentamicin, lidocaine, morphine, nifedipine, paracetamol and tetracycline. The resulting hybrid silicas underwent ultrasound extraction in the presence of several solvents and were characterized by elemental analysis, porosimetry by adsorption/desorption of nitrogen (BET method), small-angle X-ray scattering and X-ray diffraction. Drug extraction was carried out by the combination of solvent and ultra-sound. The textural characteristics of the hybrid xerogels and resulting imprinted materials were shown to be highly dependent on the molecular weight and molecular volume of the drug template. Increasing the molecular weight of the template results in a decrease in the encapsulation content of the resulting material. In the case of paracetamol and fluoxetine, the dimensions of the surface area are not sufficient to guarantee the adsorption of the smaller molecule. Instead, the shape generated through encapsulation and extraction during the production of the imprinted silica dictates the adsorption behavior.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Turner NW, Wright BE, Hlady V, Britt DW (2007) Formation of protein molecular imprints within Langmuir monolayers: a quartz crystal microbalance study. J Colloid Interface Sci 308:71–80CrossRef Turner NW, Wright BE, Hlady V, Britt DW (2007) Formation of protein molecular imprints within Langmuir monolayers: a quartz crystal microbalance study. J Colloid Interface Sci 308:71–80CrossRef
2.
Zurück zum Zitat Feng L, Liu Y, Zhou X, Hu J (2005) The fabrication and characterization of a formaldehyde odor sensor using molecularly imprinted polymers. J Colloid Interface Sci 284(1):378–382CrossRef Feng L, Liu Y, Zhou X, Hu J (2005) The fabrication and characterization of a formaldehyde odor sensor using molecularly imprinted polymers. J Colloid Interface Sci 284(1):378–382CrossRef
3.
Zurück zum Zitat Dai CM, Dai SU, Zhang YL, Zhang YJ, Zhou XF (2011) Selective removal of diclofenac from contaminated water using molecularly imprinted polymer microspheres. Environ Pollut 159(6):1660–1666CrossRef Dai CM, Dai SU, Zhang YL, Zhang YJ, Zhou XF (2011) Selective removal of diclofenac from contaminated water using molecularly imprinted polymer microspheres. Environ Pollut 159(6):1660–1666CrossRef
4.
Zurück zum Zitat Rebelo TSCR, Almeida SAA, Rafaela J, Guerreiro L, Conceição M, Montenegro BSM, Goreti M, Sales F (2011) Trimethoprim-selective electrodes with molecularly imprinted polymers acting as ionophores and potentiometric transduction on graphite solid-contact. Microchem J 98(1):21–28CrossRef Rebelo TSCR, Almeida SAA, Rafaela J, Guerreiro L, Conceição M, Montenegro BSM, Goreti M, Sales F (2011) Trimethoprim-selective electrodes with molecularly imprinted polymers acting as ionophores and potentiometric transduction on graphite solid-contact. Microchem J 98(1):21–28CrossRef
5.
Zurück zum Zitat Liu T, Liu Y, Wang Q, Li Q, Wang J, Yan Y (2011) Improving catalytic performance of Burkholderia cepacia lipase immobilized on macroporous resin NKA. J Mol Catal B Enzymatic 71(1–2):45–50CrossRef Liu T, Liu Y, Wang Q, Li Q, Wang J, Yan Y (2011) Improving catalytic performance of Burkholderia cepacia lipase immobilized on macroporous resin NKA. J Mol Catal B Enzymatic 71(1–2):45–50CrossRef
6.
Zurück zum Zitat Venkatesh S, Saha J, Pass S, Byrne ME (2008) Transport and structural analysis of molecular imprinted hydrogels for controlled drug delivery. Eu J Pharmaceutical Biopharmaceutical 69(3):852–860CrossRef Venkatesh S, Saha J, Pass S, Byrne ME (2008) Transport and structural analysis of molecular imprinted hydrogels for controlled drug delivery. Eu J Pharmaceutical Biopharmaceutical 69(3):852–860CrossRef
7.
Zurück zum Zitat Lee SW, Kunitake T (2006) Self-organized nanoescale materials, 1st edn. Springer, New York Lee SW, Kunitake T (2006) Self-organized nanoescale materials, 1st edn. Springer, New York
8.
Zurück zum Zitat Lieberzeit PA, Afzal A, Glanzing G, Dickert FL (2007) Molecularly imprinted sol–gel nanoparticles for mass-sensitive engine oil degradation sensing. Anal Bioanal Chem 389(2):441–446CrossRef Lieberzeit PA, Afzal A, Glanzing G, Dickert FL (2007) Molecularly imprinted sol–gel nanoparticles for mass-sensitive engine oil degradation sensing. Anal Bioanal Chem 389(2):441–446CrossRef
9.
Zurück zum Zitat Titirici MM, Sellergren B (2004) Peptide recognition via hierarchical imprinting. Anal Bioanal Chem 378(8):1913–1921CrossRef Titirici MM, Sellergren B (2004) Peptide recognition via hierarchical imprinting. Anal Bioanal Chem 378(8):1913–1921CrossRef
10.
Zurück zum Zitat Jin Y, Korean KHR (2005) Geological Review. J Chem Eng 51(3):264–267 Jin Y, Korean KHR (2005) Geological Review. J Chem Eng 51(3):264–267
11.
Zurück zum Zitat Beltran A, Caro E, Marcé RM, Cormack PAG, Sherrington DC, Borrull F (2007) Synthesis and application of a carbamazepine-imprinted polymer for solid-phase extraction from urine and wastewater. Anal Chimica Acta 597(1):6–11CrossRef Beltran A, Caro E, Marcé RM, Cormack PAG, Sherrington DC, Borrull F (2007) Synthesis and application of a carbamazepine-imprinted polymer for solid-phase extraction from urine and wastewater. Anal Chimica Acta 597(1):6–11CrossRef
12.
Zurück zum Zitat Mohajeri SA, Ebrahimi SA (2008) Preparation and characterization of a lamotrigine imprinted polymer and its application for drug assay in human serum. J Sep Sci 31(20):3595–3602CrossRef Mohajeri SA, Ebrahimi SA (2008) Preparation and characterization of a lamotrigine imprinted polymer and its application for drug assay in human serum. J Sep Sci 31(20):3595–3602CrossRef
13.
Zurück zum Zitat Amut E, Fu Q, Fang Q, Liu R, Xiao A, Zeng A, Chang C (2010) In situ polymerization preparation of chiral molecular imprinting polymers monolithic column for amlodipine and its recognition properties study. J Polym Res 17(3):401–409CrossRef Amut E, Fu Q, Fang Q, Liu R, Xiao A, Zeng A, Chang C (2010) In situ polymerization preparation of chiral molecular imprinting polymers monolithic column for amlodipine and its recognition properties study. J Polym Res 17(3):401–409CrossRef
14.
Zurück zum Zitat Kan X, Geng Z, Zhao Y, Wang Z, Zhu J (2009) Processing and structure of carbon nanofiber paper. Nanotechnology 20(1):1–7 Kan X, Geng Z, Zhao Y, Wang Z, Zhu J (2009) Processing and structure of carbon nanofiber paper. Nanotechnology 20(1):1–7
15.
Zurück zum Zitat Fernández-González A, Laíño RB, Diaz-García ME, Guardia L, Viale A (2004) Assessment of molecularly imprinted sol–gel materials for selective room temperature phosphorescence recognition of nafcillin. J Chromatrogr B 804(1):247–254CrossRef Fernández-González A, Laíño RB, Diaz-García ME, Guardia L, Viale A (2004) Assessment of molecularly imprinted sol–gel materials for selective room temperature phosphorescence recognition of nafcillin. J Chromatrogr B 804(1):247–254CrossRef
16.
Zurück zum Zitat Gonzáles GP, Hernando PF, Alegria JSD (2008) Determination of digoxin in serum samples using a flow-through fluorosensor based on a molecularly imprinted polymer. Biosens Bioelectron 23(11):1754–1758CrossRef Gonzáles GP, Hernando PF, Alegria JSD (2008) Determination of digoxin in serum samples using a flow-through fluorosensor based on a molecularly imprinted polymer. Biosens Bioelectron 23(11):1754–1758CrossRef
17.
Zurück zum Zitat Schubert U, Hüsing N (2005) Synthesis of inorganic materials, 2nd edn. Wiley, Weinheim Schubert U, Hüsing N (2005) Synthesis of inorganic materials, 2nd edn. Wiley, Weinheim
18.
Zurück zum Zitat Costa Silva RG, Augusto F (2006) Sol–gel molecular imprinted ormosil for solid-phase extraction of methylxanthines. J Chromatogr A 1114(1):216–223 Costa Silva RG, Augusto F (2006) Sol–gel molecular imprinted ormosil for solid-phase extraction of methylxanthines. J Chromatogr A 1114(1):216–223
19.
Zurück zum Zitat Ilavsky J, Jemian PR (2009) Irena: tool suite for modeling and analysis of small-angle scattering. J Appl Crystallogr 42(1):347–353CrossRef Ilavsky J, Jemian PR (2009) Irena: tool suite for modeling and analysis of small-angle scattering. J Appl Crystallogr 42(1):347–353CrossRef
20.
Zurück zum Zitat Kline SR (2006) Reduction and analysis of SANS and USANS data using IGOR Pro. J Appl Cryst 39(1):895–900CrossRef Kline SR (2006) Reduction and analysis of SANS and USANS data using IGOR Pro. J Appl Cryst 39(1):895–900CrossRef
21.
Zurück zum Zitat Beaucage G (1995) Approximations leading to a unified exponential/power-law approach to small-angle scattering. J Appl Crystallogr 28(1):717–728CrossRef Beaucage G (1995) Approximations leading to a unified exponential/power-law approach to small-angle scattering. J Appl Crystallogr 28(1):717–728CrossRef
22.
Zurück zum Zitat Beaucage G (1996) Small-angle scattering from polymeric mass fractals of arbitrary mass-fractal dimension. J Appl Crystallogr 29(1):134–146CrossRef Beaucage G (1996) Small-angle scattering from polymeric mass fractals of arbitrary mass-fractal dimension. J Appl Crystallogr 29(1):134–146CrossRef
23.
Zurück zum Zitat Becke AD (1993) Density-functional thermochemistry III. The role of exact exchange. J Chem Phys 98(1):5648–5652CrossRef Becke AD (1993) Density-functional thermochemistry III. The role of exact exchange. J Chem Phys 98(1):5648–5652CrossRef
24.
Zurück zum Zitat Lee C, Yang W, Parr RG (1988). Correlation-energy formula into a functional of the electron density. Phys Rev B 37(1):785–789 Lee C, Yang W, Parr RG (1988). Correlation-energy formula into a functional of the electron density. Phys Rev B 37(1):785–789
25.
Zurück zum Zitat Gogonea V, Osawa E (1995) An improved algorithm for the analytical computation of solvent-excluded volume. The treatment of singularities in solvent-accessible surface area and volume functions. J Comput Chem 16(7):817–842CrossRef Gogonea V, Osawa E (1995) An improved algorithm for the analytical computation of solvent-excluded volume. The treatment of singularities in solvent-accessible surface area and volume functions. J Comput Chem 16(7):817–842CrossRef
26.
Zurück zum Zitat Pascual-Ahuir JL, Silla E (1990) Docking by least-squares fitting of molecular surface patterns. J Comput Chem 9(1):1047–1052CrossRef Pascual-Ahuir JL, Silla E (1990) Docking by least-squares fitting of molecular surface patterns. J Comput Chem 9(1):1047–1052CrossRef
27.
Zurück zum Zitat Silla E, Tunon I, Pascual-Ahuir JL (1991) GEPOL: an improved description of molecular surfaces. II computing the molecular area and volume. J Comput Chem 12(1):1077–1088CrossRef Silla E, Tunon I, Pascual-Ahuir JL (1991) GEPOL: an improved description of molecular surfaces. II computing the molecular area and volume. J Comput Chem 12(1):1077–1088CrossRef
28.
Zurück zum Zitat Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery Jr JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui, Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A. 5. Gaussian, Inc., Pittsburgh Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery Jr JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui, Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A. 5. Gaussian, Inc., Pittsburgh
29.
Zurück zum Zitat Brinker CJ, Scherer GW (1990) Sol–gel science: the physics and chemistry of sol–gel processing. Academic Press, New York Brinker CJ, Scherer GW (1990) Sol–gel science: the physics and chemistry of sol–gel processing. Academic Press, New York
30.
Zurück zum Zitat Löffler D, Ternes TA (2003) Analytical method for the determination of the aminoglycoside gentamicin in hospital wastewater via liquid chromatography-electrospray-tandem mass spectrometry. J Chromatogr A 1000(1–2):583–588 Löffler D, Ternes TA (2003) Analytical method for the determination of the aminoglycoside gentamicin in hospital wastewater via liquid chromatography-electrospray-tandem mass spectrometry. J Chromatogr A 1000(1–2):583–588
31.
Zurück zum Zitat Moffat AC, Osselton MD, Widdop B (2004) Analysis of Drugs and Poisons, 3rd edn. Pharmaceutical Press, London Moffat AC, Osselton MD, Widdop B (2004) Analysis of Drugs and Poisons, 3rd edn. Pharmaceutical Press, London
32.
Zurück zum Zitat Al-Amoud AI, Clark BJ, Chrystyn H (2002) Determination of gentamicin in urine samples after inhalation by reversed-phase high-performance liquid chromatography using pre-column derivatisation with o-phthalaldehyde. J Chromatogr B 769(1):89–95CrossRef Al-Amoud AI, Clark BJ, Chrystyn H (2002) Determination of gentamicin in urine samples after inhalation by reversed-phase high-performance liquid chromatography using pre-column derivatisation with o-phthalaldehyde. J Chromatogr B 769(1):89–95CrossRef
33.
Zurück zum Zitat Kang L, Jun HW, McCall JW (1999) HPLC assay of Lidocaine in plasma with solid phase extraction and UV detection. J Pharm Biomed Anal 19(5):737–745CrossRef Kang L, Jun HW, McCall JW (1999) HPLC assay of Lidocaine in plasma with solid phase extraction and UV detection. J Pharm Biomed Anal 19(5):737–745CrossRef
34.
Zurück zum Zitat Niopas I, Daftsios AC (2003) Determination of nifedipine in human plasma by solid-phase extraction and high performance liquid chromatography: validation and adaptation to pharmacokinetic studies. J Pharm Biomed Anal 32(1):1213–1218CrossRef Niopas I, Daftsios AC (2003) Determination of nifedipine in human plasma by solid-phase extraction and high performance liquid chromatography: validation and adaptation to pharmacokinetic studies. J Pharm Biomed Anal 32(1):1213–1218CrossRef
35.
Zurück zum Zitat Yang S, Cha J, Carlson K (2005) Simultaneous extraction and analysis of 11 tetracycline and sulfonamide antibiotics in influent and effluent domestic wastewater by solid-phase extraction and liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr A 1097(1):40–53CrossRef Yang S, Cha J, Carlson K (2005) Simultaneous extraction and analysis of 11 tetracycline and sulfonamide antibiotics in influent and effluent domestic wastewater by solid-phase extraction and liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr A 1097(1):40–53CrossRef
36.
Zurück zum Zitat Díaz-García ME, Laíño RB (2005) Molecular imprinting in sol–gel materials: recent developments and applications. Microchim Acta 149(1–2):19–36 Díaz-García ME, Laíño RB (2005) Molecular imprinting in sol–gel materials: recent developments and applications. Microchim Acta 149(1–2):19–36
37.
Zurück zum Zitat Rouquerol J, Avnir D, Fairbridge CW, Everett DH, Haynes JH, Pernicone N, Ramsy JDF, Sing KSW, Unger KK (1994) Recommendations for the characterization of porous solids. Pure Appl Chem 66(8):1739–1758CrossRef Rouquerol J, Avnir D, Fairbridge CW, Everett DH, Haynes JH, Pernicone N, Ramsy JDF, Sing KSW, Unger KK (1994) Recommendations for the characterization of porous solids. Pure Appl Chem 66(8):1739–1758CrossRef
38.
Zurück zum Zitat Leirose GDS (2011) New nanoparticles data have been reported by G. D. S. Leirose and co-authors. J Pharm Sci 100(7):2826–2834CrossRef Leirose GDS (2011) New nanoparticles data have been reported by G. D. S. Leirose and co-authors. J Pharm Sci 100(7):2826–2834CrossRef
39.
Zurück zum Zitat Cardoso MB (2010) Protein localization in silica nanospheres derived via biomimetic mineralization. Adv Funct Mater 20(1):3031–3038CrossRef Cardoso MB (2010) Protein localization in silica nanospheres derived via biomimetic mineralization. Adv Funct Mater 20(1):3031–3038CrossRef
40.
Zurück zum Zitat Green DL, Lin JS, Lam Y, Hu MZ, Schaefer DW, Harris MT (2003) Size, volume fraction, and nucleation of Stober silica nanoparticles. J Colloid Interfaces Sci 266(2):346–358CrossRef Green DL, Lin JS, Lam Y, Hu MZ, Schaefer DW, Harris MT (2003) Size, volume fraction, and nucleation of Stober silica nanoparticles. J Colloid Interfaces Sci 266(2):346–358CrossRef
41.
Zurück zum Zitat Voronina NV, Meshkov IB, Myakushev VD, Laptinskaya TV, Papkov VS, Buzin MI, Il’Ina MN, Ozerin AN, Muzafarov AM (2010) Hybrid organo-inorganic globular nanospecies macromolecule to particle: transition from macromolecule to particle. J Polym Sci-b Part A Polym Chem 48(19):4310–4322CrossRef Voronina NV, Meshkov IB, Myakushev VD, Laptinskaya TV, Papkov VS, Buzin MI, Il’Ina MN, Ozerin AN, Muzafarov AM (2010) Hybrid organo-inorganic globular nanospecies macromolecule to particle: transition from macromolecule to particle. J Polym Sci-b Part A Polym Chem 48(19):4310–4322CrossRef
42.
Zurück zum Zitat Dirè S, Facchin G, Ceccato R, Guarino L, Sassi A, Gleria M (2002) Hydroxylated cyclophosphazene/silica hybrid materials: synthesis and characterization. J Inorg Organomet Polym 12(3–4):59–78CrossRef Dirè S, Facchin G, Ceccato R, Guarino L, Sassi A, Gleria M (2002) Hydroxylated cyclophosphazene/silica hybrid materials: synthesis and characterization. J Inorg Organomet Polym 12(3–4):59–78CrossRef
43.
Zurück zum Zitat Hair JF, Black WC, Babin BJ, Anderson RE (2009) Multivariate Analysis, 7th edn. Prentice Hall, Upper Saddle River Hair JF, Black WC, Babin BJ, Anderson RE (2009) Multivariate Analysis, 7th edn. Prentice Hall, Upper Saddle River
Metadaten
Titel
Silica imprinted materials containing pharmaceuticals as a template: textural aspects
verfasst von
Everton C. Morais
Gabriel G. Correa
Rodrigo Brambilla
Paolo R. Livotto
João Henrique Z. dos Santos
Mateus Borba Cardoso
Publikationsdatum
01.11.2012
Verlag
Springer US
Erschienen in
Journal of Sol-Gel Science and Technology / Ausgabe 2/2012
Print ISSN: 0928-0707
Elektronische ISSN: 1573-4846
DOI
https://doi.org/10.1007/s10971-012-2861-0

Weitere Artikel der Ausgabe 2/2012

Journal of Sol-Gel Science and Technology 2/2012 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.