Synthesis of C-glycoside analog for Improved autoimmune response and clinical cancer treatment.

Standing

Undergraduate

Type of Proposal

Oral Research Presentation

Faculty Sponsor

John Trant

Proposal

KRN 7000 is a bioactive glycolipid extract from the Japanese marine sponge Agelas mauritianus, has been the talk of the science community for over 20 years. It can direct the body’s immune response to attack specific cancer cells with the aid of natural killer T cells thus reducing tumor growth and size as well as tackling autoimmune diseases. The behavior observed paved way for manufacture of more of the same glycolipid but with different alternations like changing the anomeric group in order to increase the activity. One of these analogs increases the bioactivity nearly one hundred times in comparison to other analogs. These improvements show potential for clinical trials. The C-glycoside analogue increased molecular stability by removing the acetal functionality in the polar head of the glycolipid after which a methylene group replaces the anomeric oxygen. Through modification of the length of the linker, we are hoping to see promising results through further studies on the C-KRN. In order to understand the applications of this glycolipid, we are extending the linker by a single carbon in order to make three C-KRN analogues. After manufacturing the molecule with an extended linker, the next step on the agenda is understanding the variety functions of the KRN 7000 and studying the bioactivity.

Availability

12-2

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Synthesis of C-glycoside analog for Improved autoimmune response and clinical cancer treatment.

KRN 7000 is a bioactive glycolipid extract from the Japanese marine sponge Agelas mauritianus, has been the talk of the science community for over 20 years. It can direct the body’s immune response to attack specific cancer cells with the aid of natural killer T cells thus reducing tumor growth and size as well as tackling autoimmune diseases. The behavior observed paved way for manufacture of more of the same glycolipid but with different alternations like changing the anomeric group in order to increase the activity. One of these analogs increases the bioactivity nearly one hundred times in comparison to other analogs. These improvements show potential for clinical trials. The C-glycoside analogue increased molecular stability by removing the acetal functionality in the polar head of the glycolipid after which a methylene group replaces the anomeric oxygen. Through modification of the length of the linker, we are hoping to see promising results through further studies on the C-KRN. In order to understand the applications of this glycolipid, we are extending the linker by a single carbon in order to make three C-KRN analogues. After manufacturing the molecule with an extended linker, the next step on the agenda is understanding the variety functions of the KRN 7000 and studying the bioactivity.