Investigation of Orientational Isomers of Cyclodextrin ...

Investigation of Orientational Isomers of Cyclodextrin ...

1 Differentiating geometrical isomers of retinoids and controlling their photo-isomerization by complexation with cyclodextrins

Analytica Chimica Acta 468 (2002) 161-170 2 Cyclodextrins Cyclic oligosaccharides

Composed of D(+)glucopyranose units Hollow, torus-shape cavity Cylinders with a hydrophilic exterior and a hydrophobic interior 3

Cyclodextrins :Different types -cyclodextrin : six sugar ring molecules -cyclodextrin : seven sugar ring molecules -cyclodextrin : eight sugar ring molecules

4 Structure of -CD 5

Structure of -CD Structure of -CD 6

Cyclodextrins They form inclusion complexes with a .variety of molecules Insertion of a hydrophobic guest in aqueous solutions of cyclodextrins leads to

complexation which no covalent bonds are .broken or formed 7 Applications of Cyclodextrins in Drug

delivery technology To improve the physical and chemical properties of drugs To reduce the side effects of drugs To enhance the bio-availibility of poorly

soluble drugs 8 Applications of Cyclodextrins in Food industry

To stabilize flavors and fragrances To mask undesired tastes in the food and cosmetic industries 9

Applications of Cyclodextrins Chemistry Separation techniques HPLC and Increasing the solubility and the stability of the analytes and therefore sensitivity of the detection of these analytes Increasing or decreasing the rate of a variety of

reactions 10 Retinoids :Very significant biological molecules due to

Their role in the vision process (retinal)As vitamins (retinol and its esters)Their influence in the cell growth (retinoic acid , ) 11 All trans retinal 12

H-NMR spectra of the pure -CD solution (C=1.0 x 10-2 M) 13

H-NMR spectra of the complex of all-trans-retinal/ -CD at .concentrations 4.0 x 10-3 and 1.0 x 10-2 M respectively 14 Chemical shifts in H-NMR

15 Stoichiometry determination 16

Association constants determination 17 Cis retinal-9

18 Effect of the inclusion process on the photo-isomerization of retinoids

19 Ethanolic solution 20

All-trans-retinal 21 All-trans-retinoic acid

22 Thank s 23

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