Cyclodextrins
Cyclodextrin Chemistry Research Projects
- Aims:
- Synthesis (and utilization) of regioselectively substituted cyclodextrin derivatives.
- Head:
- Dr. Jindrich Jindrich
- JJ/1
- Synthesis of cyclodextrin dimer based carriers of porphyrine photodynamic sensitizers for cancer therapy
- JJ/2
- Synthesis of allyl type alkylation reagents and their use for complexation driven regioselective alkylation of cyclodextrins
- JJ/3
- Synthesis of regioselectively substituted aminoderivatives of cyclodextrin and their use as modifiers of senzoric response of optical senzors of chemical compounds based on porous silicon
JJ/1
Synthesis of cyclodextrin dimer carriers of photodynamic sensitizers for cancer therapy
- Cyclodextrins are routinely used in pharmacy as drug carriers due to their ability to include lipophilic compounds to their cavity and thus change their water solubility or stability.
- Porphyrine type photodynamic sensitizers (compounds that start to show cytostatic activity after irradiation with light) are also able to form complexes with cyclodextrins.
- Due to the shape of the porphyrine molecule especially strong complexation can be expected with cyclodextrin dimers.
- The aim of the project is to synthetize such dimer derivatives of cyclodextrins, based on reaction of 2I-O-carboxymethyl-, eventually 3I-O-carboxymethyl-cyclodextrin derivatives with oligoethylenediamines.
Structure of cyclodextrins (CDs)
Synthesis of cyclodextrin dimers
JJ/2
Synthesis of allyl type alkylation reagents and their use for complexation driven regioselective alkylation of cyclodextrins
- Regioselectively substituted cyclodextrin derivatives, due to their ability to selectively complex lipophilic compounds in water solution, can be used as e.g. pseudophases in capillary electrophoresis or chromatograpy, enzyme like catalysts, or chemosezors.
- Regioselective substitutions of cyclodextrins are still problematic and give small yields (mixtures of isomers are usually formed).
- It was found that selectivity of substitution can be increased if the alkylation reagent forms stable complex with cyclodextrin before the reaction takes place.
- The aim of the project is to synthetize several derivatives of cinnamyl bromide substituted on benzene ring with alkyl group(s) and determination of regioselectivity of the reaction of these reagents with cyclodextrins.
Complexation of alkylation reagent with cyclodextrin
JJ/3
Synthesis of regioselectively substituted aminoderivatives of cyclodextrin and their use as modifiers of senzoric response of optical senzors of chemical compounds based on porous silicon.
- Due to their complexation abilities cyclodextrins (CDs) can be used as modifiers of senzoric response with recognition capabilities. Thus CDs bound on the surface of porous silicon can be expected to raise a selectivity of the senzor.
- Optical senzors based on porous silicon (PS) belong to the modern type of senzors of chemical compouds that show high sensitivity to analytes in gas phase. Their senzoric response can be relatively easily modified by suitable derivatization of the surface with compouds with recognition abilities.
- The aim of the project is to synthetize several types of regioselectively substituted aminoderivatives of cyclodextrins and to connect them to the surface of PS modified by addition of undecene acid to Si-H bond.
Modification of PS surface with CDs
See presentation about porous silicon and its use for detection of alcohols.
