Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• and especially in the case of TRIMEB [30]. The TRIMEB·2ME complex is thus another example of a synthetic system that displays host–guest adaptation on complexation, complementing our recently reported analogous observations for inclusion complexes between methylated CDs and the antioxidant trans

• -resveratrol [26]. Hydrogen bonding between the 17-OH group of 2ME and glycosidic (O4) oxygen atoms within the cavity of the host CDs generally occurs, while in unit D of the TRIMEB complex, where there are two 17-OH disorder components, the major component hydrogen bonds to a host methoxy O6 atom and the

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• Taramelli 12, 27100 Pavia, Italy 10.3762/bjoc.10.331 Abstract The phytoalexin trans-resveratrol, 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol, is a well-known, potent antioxidant having a variety of possible biomedical applications. However, its adverse physicochemical properties (low stability

• , poor aqueous solubility) limit such applications and its inclusion in cyclodextrins (CDs) has potential for addressing these shortcomings. Here, various methods of the attempted synthesis of inclusion complexes between trans-resveratrol and three methylated cyclodextrins (permethylated α-CD

• derivatised) to establish their effect on the aqueous solubility of trans-resveratrol and to estimate association constants for complex formation. Keywords: cyclodextrin; inclusion complexes; thermal analysis; trans-resveratrol; X-ray structures; Introduction The naturally occurring phytoalexin trans