SBA-15 type mesoporous silica has been modified to produce a covalent bond with β-cyclodextrin by two different synthetic approaches to obtain an hybrid system able to work as a drug delivery system for progesterone. In the first approach, SBA-15 silica was first let to react with 3-glycidyloxypropyltrimethoxysilane to produce an epoxide ring functional group on mesoporous silica. The latter was then reacted under basic conditions with mono-6-deoxy-6-mercapto-β-cyclodextrin (β-CDCH2SH), prepared in its turn in two steps from β-cyclodextrin (β-CD) through monotosylation to give β-CDCH2OTs followed by thiolation with thiourea. In the second approach, a silica suitably functionalized with a terminal thiol group (obtained by the reaction of SBA-15 silica with 3-mercaptopropyltrimethoxysilane) was reacted with β-CDCH2OTs. The obtained materials were characterized by X-Ray powder diffraction, nitrogen adsorption, 13C Cross Polarization Magic Angle Spin Nuclear Magnetic Resonance (13C CP/MAS NMR). Progesterone was loaded on the materials producing complete filling of mesopores and cyclodextrin cavities. Its release was studied at different pH values. Only one of the two progesterone-loaded delivery device is able to retain the drug in the system during the first period at acid pH (2 h) and release it after pH increase.

Progesterone inclusion into cyclodextrin-functionalized mesoporous silica

PASQUA, LUIGI;VELTRI, Lucia;GABRIELE, Bartolo;TESTA, Flaviano;
2013

Abstract

SBA-15 type mesoporous silica has been modified to produce a covalent bond with β-cyclodextrin by two different synthetic approaches to obtain an hybrid system able to work as a drug delivery system for progesterone. In the first approach, SBA-15 silica was first let to react with 3-glycidyloxypropyltrimethoxysilane to produce an epoxide ring functional group on mesoporous silica. The latter was then reacted under basic conditions with mono-6-deoxy-6-mercapto-β-cyclodextrin (β-CDCH2SH), prepared in its turn in two steps from β-cyclodextrin (β-CD) through monotosylation to give β-CDCH2OTs followed by thiolation with thiourea. In the second approach, a silica suitably functionalized with a terminal thiol group (obtained by the reaction of SBA-15 silica with 3-mercaptopropyltrimethoxysilane) was reacted with β-CDCH2OTs. The obtained materials were characterized by X-Ray powder diffraction, nitrogen adsorption, 13C Cross Polarization Magic Angle Spin Nuclear Magnetic Resonance (13C CP/MAS NMR). Progesterone was loaded on the materials producing complete filling of mesopores and cyclodextrin cavities. Its release was studied at different pH values. Only one of the two progesterone-loaded delivery device is able to retain the drug in the system during the first period at acid pH (2 h) and release it after pH increase.
SBA-15; Hybrid mesoporous silica; Progesterone-loaded cyclodextrins
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/134541
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