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Open Access Publications from the University of California

Synthesis of Caged Garcinia Xanthones and Rational Design of Fluorescent Sensors for Amyloid Detection /

  • Author(s): Elbel, Kristyna M.
  • et al.

The family of caged Garcinia xanthones (CGX) possess a unique chemical structure along with promising antitumor and anti-inflammatory pharmacological profiles. We report the synthesis and biological evaluation of A-ring oxygenated structures related to the natural product, which reveal pharmacophoric insights into the SAR profile of CGXs. This synthesis is achieved utilizing a Pd(0)- catalyzed reverse prenylation and a unique tandem Claisen/ Diels-Alder reaction. Fluorescent molecular rotors possess a unique structure which give them an intrinsic ability to detect various properties of their environment through both an increase of quantum yield and a hypsochromic shift. Our lab has synthesized a family of fluorescent molecular rotors, which have the ability to selectively bind to beta-amyloid protein, seen in Alzheimer's disease (AD). These compounds were tested for their stability, binding ability, and fluorescence profile in order to further develop a rational design of novel fluorescent molecular rotors

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