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A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for tuneable ibuprofen release

Sander Clerick (UGent) , Wannes Libbrecht (UGent) , Otto van den Berg (UGent) , Els De Canck (UGent) , Jeriffa De Clercq (UGent) and Pascal Van Der Voort (UGent)
(2014) ADVANCED POROUS MATERIALS. 2(3). p.157-164
Author
Organization
Abstract
Incorporation of organic functionalities within porous materials is a very elegant manner to control the administration of therapeutic drugs. Delayed drug-release profile originates from weak and reversible interactions (e.g., electrostatic, hydrophobic–hydrophobic and H-bonding interaction) between the modified carrier and the drug molecule. Two new silsesquioxane PMO precursors were synthesized in a quick and facile Schotten-Baumann reaction of (3-aminopropyltriethoxy)silane and (N-methyl-3-aminopropyltrimethoxy)-silane with malonylchloride, respectively. Based on these bis(3-(triethoxysilyl)propyl)malonamide (MA) and N,N-dimethyl-N,N-bis(3-(triethoxysilyl)propyl)malonamide (mMA) precursors, an extensive range of 2D hexagonal PMOs with high functional loading was obtained by the co-condensation with tetraethyl orthosilicate (TEOS) in a typical PMO synthesis (acidic medium, P123, KCl). The materials showed good ordering up to 20 mol% of functional loading, a large surface area (up to 550 m2/g) and wide pores (∼7 nm). The malonamide-type PMOs are capable to adsorb large amounts of ibuprofen (130 mg/g) as a hydrophobic model drug. Release experiments are performed in a phosphate buffer solution at pH 7.4 and show a controlled desorption of Ibuprofen over 24 hours; a largely expanded times pan compared to mesoporous silicas. Moreover, we are able to tune the release profile by varying the content of organic bridges in the PMO pores.
Keywords
CONTROLLED DRUG RELEASE, PERIODIC MESOPOROUS ORGANOSILICA, MALONAMIDE, IBUPROFEN

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Citation

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MLA
Clerick, Sander, et al. “A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for Tuneable Ibuprofen Release.” ADVANCED POROUS MATERIALS, vol. 2, no. 3, American Scientific Publishers, 2014, pp. 157–64.
APA
Clerick, S., Libbrecht, W., van den Berg, O., De Canck, E., De Clercq, J., & Van Der Voort, P. (2014). A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for tuneable ibuprofen release. ADVANCED POROUS MATERIALS, 2(3), 157–164.
Chicago author-date
Clerick, Sander, Wannes Libbrecht, Otto van den Berg, Els De Canck, Jeriffa De Clercq, and Pascal Van Der Voort. 2014. “A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for Tuneable Ibuprofen Release.” ADVANCED POROUS MATERIALS 2 (3): 157–64.
Chicago author-date (all authors)
Clerick, Sander, Wannes Libbrecht, Otto van den Berg, Els De Canck, Jeriffa De Clercq, and Pascal Van Der Voort. 2014. “A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for Tuneable Ibuprofen Release.” ADVANCED POROUS MATERIALS 2 (3): 157–164.
Vancouver
1.
Clerick S, Libbrecht W, van den Berg O, De Canck E, De Clercq J, Van Der Voort P. A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for tuneable ibuprofen release. ADVANCED POROUS MATERIALS. 2014;2(3):157–64.
IEEE
[1]
S. Clerick, W. Libbrecht, O. van den Berg, E. De Canck, J. De Clercq, and P. Van Der Voort, “A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for tuneable ibuprofen release,” ADVANCED POROUS MATERIALS, vol. 2, no. 3, pp. 157–164, 2014.
@article{6898594,
  abstract     = {Incorporation of organic functionalities within porous materials is a very elegant manner to control the administration of therapeutic drugs. Delayed drug-release profile originates from weak and reversible interactions (e.g., electrostatic, hydrophobic–hydrophobic and H-bonding interaction) between the modified carrier and the drug molecule. Two new silsesquioxane PMO precursors were synthesized in a quick and facile Schotten-Baumann reaction of (3-aminopropyltriethoxy)silane and (N-methyl-3-aminopropyltrimethoxy)-silane with malonylchloride, respectively. Based on these bis(3-(triethoxysilyl)propyl)malonamide (MA) and N,N-dimethyl-N,N-bis(3-(triethoxysilyl)propyl)malonamide (mMA) precursors, an extensive range of 2D hexagonal PMOs with high functional loading was obtained by the co-condensation with tetraethyl orthosilicate (TEOS) in a typical PMO synthesis (acidic medium, P123, KCl). The materials showed good ordering up to 20 mol% of functional loading, a large surface area (up to 550 m2/g) and wide pores (∼7 nm). The malonamide-type PMOs are capable to adsorb large amounts of ibuprofen (130 mg/g) as a hydrophobic model drug. Release experiments are performed in a phosphate buffer solution at pH 7.4 and show a controlled desorption of Ibuprofen over 24 hours; a largely expanded times pan compared to mesoporous silicas. Moreover, we are able to tune the release profile by varying the content of organic bridges in the PMO pores.},
  author       = {Clerick, Sander and Libbrecht, Wannes and van den Berg, Otto and De Canck, Els and De Clercq, Jeriffa and Van Der Voort, Pascal},
  journal      = {ADVANCED POROUS MATERIALS},
  keywords     = {CONTROLLED DRUG RELEASE,PERIODIC MESOPOROUS ORGANOSILICA,MALONAMIDE,IBUPROFEN},
  language     = {eng},
  number       = {3},
  pages        = {157--164},
  publisher    = {American Scientific Publishers},
  title        = {A Novel Malonamide Periodic Mesoporous Organosilica (PMO) for tuneable ibuprofen release},
  url          = {http://dx.doi.org/10.1166/apm.2014.1067},
  volume       = {2},
  year         = {2014},
}

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