Curcuma logna is used as spice in South Asian cooking, as a cosmetic and in the ancient Ayurvedic system of medicine. Turmeric or Haldi is the dried powdered rhizome derived from the plant. Curcuminoids constitute around 5% of most turmeric preparations and can be readily isolated from the plant. There has recently been tremendous interest in curcumin, [(1E, 6E)-1, 7-bis (4-hydroxy-3-methoxyphenyl) hepta-1,6-dience 3,5-dione] the primary active ingredient in turmeric, because it has been shown to have antioxidant, anticancer, anti-inflammatory, anti-Alzheimer's disease activity and antiobiotic activity.Hence, we plan to develop convenient routes to water soluble curcumin conjugates and polyvalent curcumin polymers via the synthesis of novel mono-functional curcumin derivatives in which one of the phenolic groups of curcumin has been chemically modified with reactive groups (alkyne, carboxylic acid and sugar moiety. The synthesis of mono-functional curcumin derivatives affords two advantages: (a) The presence of at least one free phenolic group is necessary for the biological activity of many antioxidants like curcumin (b) Bioconjugation and polymer modifications using mono-functional derivatives produce soluble conjugates in high yields whereas bi-functional derivatives would result in insoluble cross-linked products. There has been a recent report describing the multi-step synthesis of a mono-functional alkyl fluoride derivative of curcumin starting from a vanillin derivative, in contrast to the previous report, the approach we plan involves direct one/two step covalent modification of curcumin to produce reactive mono-funcational derivatives. We plan to develop a general methodology for preparing reactive mono-functional curcumin derivatives; the unique carboxylic acid/azide/alkyne groups serve as covalent functional handles for modifying both synthetic polymers and proteins.

Synthesis of Water-soluble Curcumin Derivatives

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.