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Publication Date

Fall 2017

Degree Type

Thesis - Campus Access Only

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

Marc d'Alarcao

Keywords

2-hexadecyl-myo-inositol, 2-palmitoyl-myo-inosito, cancer, Inositol glycans

Subject Areas

Organic chemistry; Biochemistry

Abstract

Glucose is an important source of energy for the body to function effectively. The maintenance of blood glucose concentration within the normal range of 4-6 mM is accomplished by two pancreatic hormones, insulin and glucagon. Inositol glycans (IGs) are a group of natural molecules that stimulate insulin-sensitive cells in the absence of insulin. The structural similarity of IGs and glycosylphosphatidylinositols (GPI) enables design and synthesis of IGs. Excitingly, IG-1, an analog of IG, has selectively killed cultured tumor cells by stimulating normal glucose metabolism in them (by reversing the Warburg effect). Due to the instability of IG-1, Dr. d’Alarcao’s lab has synthesized an analog of IG-1, a disaccharide which exhibited insulin-mimetic activity and reversed the Warburg effect in cancer cells. After careful study of various IG-1 analogs, it is assumed that a palmitoyl group at the C-2 position of myo-inositol has a crucial role in insulin-mimetic activity. This led to an idea to synthesize 2-palmitoyl-myo-inositol. However, the ester linkage in 2-palmitoyl-myo-inositol is sensitive under physiological conditions, so it was proposed to synthesize 2-hexadecyl-myo-inositol by incorporating an ether linkage in place of the hydrolysable ester moiety. In future, each compound will be tested for its insulin-mimetic activity and its effect on cancer cells after its successful synthesis. Any positive result of these compounds will allow the development of low molecular weight compounds with fewer synthetic steps compared to IG-1.

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