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Structural Studies and Cytotoxicity of Trimethyl(ferrocenylmethyl)ammonium Iodide Encapsulated in β‐Cyclodextrin
Author(s) -
Bruno Sofia M.,
Fernandes José A.,
Marques Joana,
Neto Sara C.,
RibeiroClaro Paulo J.,
Pillinger Martyn,
Paz Filipe A. Almeida,
Marques Maria Paula M.,
Braga Susana S.,
Gonçalves Isabel S.
Publication year - 2011
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201100657
Subject(s) - chemistry , iodide , crystallography , supramolecular chemistry , cyclodextrin , raman spectroscopy , thermogravimetric analysis , adduct , ammonium iodide , powder diffraction , crystal structure , stereochemistry , nuclear chemistry , inorganic chemistry , organic chemistry , physics , optics
Inclusion complexes that comprise β‐cyclodextrin (β‐CD) and trimethyl(ferrocenylmethyl)ammonium iodide ( 1 ) have been prepared by codissolution of the host and guest in ethanol/water, accompanied by either conventional heating at 40 °C for 26 h (to give 2 ) or microwave‐assisted heating for 30 min (to give 3 ). Solids were isolated and characterized by elemental and thermogravimetric analyses, powder X‐ray diffraction (XRD), and IR, Raman, and 13 C{ 1 H} CP/MAS NMR spectroscopy. Powder XRD indicated the presence of microcrystalline inclusion compounds with supramolecular structures that comprise β‐CD head‐to‐head dimers arranged into infinite channels. A small crop of single crystals of the inclusion compound 2 were obtained and analyzed by XRD. Despite diffraction being very poor above a resolution of around 1 Å, the data could be indexed to the space group P 1 (in agreement with powder XRD) and a reasonable structural model could be achieved when the asymmetric unit was composed of two directly located β‐CD hosts, 1.4 iron atoms, and a small fraction of iodide anions. By using these data as a starting point, DFT calculations were carried out and led to a model of the crystal structure that comprised 2:1 (host/guest) and 2:2 adducts. The cytotoxic and antiproliferative activities of 1 and 2 were tested against the breast adenocarcinoma MDA‐MB‐231 and osteosarcoma MG‐63 cell lines. Results indicate that both 1 and 2 are cytotoxic against the MDA‐MB‐231 line but exhibit negligible activity on the MG‐63 line.