The rutin/beta-cyclodextrin interactions in fully aqueous solution: spectroscopic studies and biological assays.
In the present work the feasibility of beta-cyclodextrin complexation was explored, as a tool for improving the aqueous solubility and antioxidant efficacy of rutin. By means of 1H NMR, UV-vis and circular dichroism spectroscopy the single aromatic ring of rutin was found to be inserted into the beta-cyclodextrin cavity to form a 1:1 inclusion complex. The effect of beta-cyclodextrin on the spectral features of rutin was quantitatively investigated, in fully aqueous medium, by holding the concentration of the guest constant and varying the host concentration. The associated binding constants were estimated to be 142+/-20 and 153+/-20 M(-1), respectively, on the basis of the observed UV-vis absorption and circular dichroism intensities. The antioxidant activity of rutin was also investigated, as affected by molecular encapsulation within beta-cyclodextrin (batophenanthroline test; comet assay; lipid peroxidation); the inclusion complex revealed improved antioxidant efficacy that may be in part explained by an increased solubility in the biological moiety.
Calabrò
M L
ML
Dipartimento Farmaco-Chimico, Facoltà di Farmacia, Università di Messina, Viale Annunziata, 98168 Messina, ME, Italy.
Tommasini
S
S
Donato
P
P
Stancanelli
R
R
Raneri
D
D
Catania
S
S
Costa
C
C
Villari
V
V
Ficarra
P
P
Ficarra
R
R
D000818:Animals; D002942:Circular Dichroism; D020552:Comet Assay / Q000379:methods; D004347:Drug Interactions; D006801:Humans; D007962:Leukocytes / Q000378:metabolism; D015227:Lipid Peroxidation; D019999:Pharmaceutical Solutions / Q000032:analysis / Q000378:metabolism; D010618:Phenanthrolines / Q000378:metabolism; D051381:Rats; D012431:Rutin / Q000032:analysis* / Q000378:metabolism; D012995:Solubility; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D047392:beta-Cyclodextrins / Q000032:analysis* / Q000378:metabolism
D019999:Pharmaceutical Solutions; D010618:Phenanthrolines; D012996:Solutions; D047392:beta-Cyclodextrins; C017049:bathophenanthroline disulfonic acid; D012431:Rutin; C031215:betadex