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Total Synthesis of Strictosidine, a Precursor to Vinblastine

Institution: University of California, Los Angeles
Investigator(s): Sarah Anthony,
Award Cycle: 2019 (Cycle 29) Grant #: T29DT0359 Award: $133,677
Subject Area: Cancer
Award Type: Dissertation Awards

Initial Award Abstract
Lung cancer is the leading cause of cancer related deaths in California and the United States each year. The statistics for are astounding. Almost 160,000 Americans and 12,000 Californians die from lung cancer each year and, within five years of diagnosis, 82% of patients pass away. The link between smoking tobacco and lung cancer is well established and almost all lung cancer cases result from tobacco use. Unfortunately, most lung cancer diagnoses are not treatable by surgery, so chemotherapy has remained the preferred method of treatment. Therefore, it is critical to provide rapid and cost-effective access to lung cancer medications.

Vinblastine and vincristine are two frontline anti-cancer therapeutics used to treat multiple cancers, including lung cancer. The industrial production of both of these drugs still relies on isolation from their natural plant source via an expensive and source-dependent process. Thus, vinblastine and vincristine remain some of the most expensive small molecule, off-patent chemotherapeutics on the market. Vinblastine and vincristine could be affordable with an efficient method of production; however, a viable alternative has not been developed.

Toward the development of a new and efficient means to access vinblastine and vincristine, I propose to prepare secologanin and strictosidine. These compounds are Nature's precursors to vinblastine and vincristine. It is envisioned that these studies will lay the foundation for future studies directed toward the conversion of strictosidine to vinblastine and vincristine using enzymes. Thus, the proposed studies would represent a significant milestone toward a scalable and affordable means for the chemoenzymatic production of vinblastine and vincristine.