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United States Department of Agriculture

Agricultural Research Service

Title: Medicinal Chemistry: Oxidation of Disaccharides to Synthesize Transition Metal Complexants

Authors
item Brimberry, Racheal
item Price, Neil
item Cote, Gregory

Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: September 15, 2005
Publication Date: September 15, 2005
Citation: Brimberry, R.M., Price, N.P., Cote, G.L. 2005. Medicinal chemistry: oxidation of disaccharides to synthesize transition metal complexants [abstract]. American Chemical Society. p. 1.

Technical Abstract: The carbohydrate trehalose was a preliminary test model to be used as a replacement conjugate in an alternate transition-metal complex. Using an oxidant, we hypothesized that if the primary alcohols formed aldehyde functional groups upon oxidation then the transition metal could complex with the trehalose derivative. The ultimate goal of the experiment was to find an alternative transition-metal complex to overcome drug-resistant tumors, replacing cisplatin and carboplatin pharmaceutical treatments. Two solvents were compared: DMF, a common organic solvent, and an ionic solvent, [bmim] BF4, as a green alternative, and were used to dissolve trehalose. Dess-Martin Periodinane, DMP, a less toxic alternative oxidant to PCC, was used to oxidize the carbohydrate hydroxyl groups. Trehalose dissolved readily in DMF. The ionic solvent [bmim] BF4 partially dissolved the trehalose. When the oxidant DMP was applied to the solutions, both the primary and secondary alcohols were oxidized and aldehydes and ketones were formed. (Note: Ketones are not able to complex with transition metals such as platinum.) This research was explored to create a new generation of cancer treatments utilizing carbohydrates. The rational is if carbohydrates were utilized they would be less toxic to patients. The main concern was overcoming drug-resistant tumors so further studies may be needed to explore the viability of carbohydrate-based pharmaceuticals.

Last Modified: 8/30/2014
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