Studies of the Interaction of 5-(alkylthio)-3H-1,2-dithiole-3-thiones with b-cyclodextrin

MARTIN E. ZOLOFF MICHOFF; ALEJANDRO M. GRANADOS; RITA H. DE ROSSI

ARKIVOC - ONLINE JOURNAL OF ORGANIC CHEMISTRY

ARKAT USA INC

Lugar: Florida; Año: 2005 vol. 2005 p. 47 - 61

1551-7004

Dithiolthiones are a family of compounds which have a great current interest for their properties especially as anti carcinogens. The problem for the use of this type of compounds is that they are quite water insoluble and this represents a problem for their bioavalability. We have studied the interaction of 5-RS-3H-1,2-dithiole-3-thiones (R= ethyl, butyl, hexyl and octyl) with cyclodextrins and we report here that the ethyl and butyl derivatives form inclusion complexes with β-cyclodextrin with 1:1 stoichiometry. The complexes are characterized by Uv-vis, circular dichroism spectroscopy and by DSC analysis of the solid complexes. The solubility of the butyl derivative in water increases about two times in a solution of β-cyclodextrin 0.01M. The hexyl and octyl derivatives are aggregated in water even at 4-5x10-6 M and in the presence of 0.001 M β-CD they are associated with destruction of the aggregates. The spectroscopic behavior indicates that these derivatives form complexes of higher stoichiometry probably 1:2.