Total Synthesis of Bio-orthogonally Functionalized Securinega Alkaloids
Total Synthesis of 4α-Hydroxyallosecurinine and Securingine F, Securinega Alkaloids with a C4-Hydroxy Handle for Biofunctional Derivatizations: S. Park, D. Kim, W. Yang, S. Han
Synlett 2023, DOI: 10.1055/a-2047-9680
Securinega alkaloids, such as 4α-hydroxyallosecurinine and securingine F, display potent antitumor activity due to their cytotoxicity, as well as cell differentiation–induction activity, and the capacity to reverse multidrug resistance. For these reasons they could be used as payloads in target-directed constructs based for example on antibody formats. However, it would be necessary to introduce or identify suitable chemical handles on these alkaloids for further bioorthogonal functionalization with a linker, to be attached to the antibody or to another antigen-targeting molecule. Recently, the group of Professor Sankyu Han from the Korea Advanced Institute of Science and Technology (KAIST), Daejeon (Republic of Korea) reported a strategy that could allow the preparation of securinega alkaloid-based bio-orthogonal constructs.
Professor Han said: “We have successfully synthesized securinega alkaloids that contain a C4-hydroxyl group, which has potential for use as a biofunctional handle in various applications.”