Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques
The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes stelletin A, stelletin...
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Published in | Journal of the American Chemical Society Vol. 143; no. 4; pp. 2138 - 2155 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
03.02.2021
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Abstract | The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes stelletin A, stelletin E, and rhabdastrellic acid A, as well as the development of a general strategy to access other natural products within this unique family. High-throughput experimentation and computational chemistry methods were used in this endeavor. A preliminary structure–activity relationship study of stelletin A revealed the trans-syn-trans core motif of the isomalabaricanes to be critical for their cytotoxic activity. |
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AbstractList | The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes stelletin A, stelletin E, and rhabdastrellic acid A, as well as the development of a general strategy to access other natural products within this unique family. High-throughput experimentation and computational chemistry methods were used in this endeavor. A preliminary structure–activity relationship study of stelletin A revealed the trans-syn-trans core motif of the isomalabaricanes to be critical for their cytotoxic activity. The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes stelletin A, stelletin E, and rhabdastrellic acid A, as well as the development of a general strategy to access other natural products within this unique family. High-throughput experimentation and computational chemistry methods were used in this endeavor. A preliminary structure-activity relationship study of stelletin A revealed the core motif of the isomalabaricanes to be critical for their cytotoxic activity. |
Author | Yang, Cheng Shved, Alexander S Ning, Shang Boyko, Yaroslav D Hergenrother, Paul J Huck, Christopher J Chu, Tiffany Sarlah, David Tonogai, Emily J |
AuthorAffiliation | Cancer Center at Illinois Carl R. Woese Institute for Genomic Biology Roger Adams Laboratory, Department of Chemistry |
AuthorAffiliation_xml | – name: Roger Adams Laboratory, Department of Chemistry – name: Cancer Center at Illinois – name: Carl R. Woese Institute for Genomic Biology |
Author_xml | – sequence: 1 givenname: Yaroslav D orcidid: 0000-0002-8208-6877 surname: Boyko fullname: Boyko, Yaroslav D organization: Cancer Center at Illinois – sequence: 2 givenname: Christopher J orcidid: 0000-0002-1786-2470 surname: Huck fullname: Huck, Christopher J organization: Cancer Center at Illinois – sequence: 3 givenname: Shang surname: Ning fullname: Ning, Shang organization: Roger Adams Laboratory, Department of Chemistry – sequence: 4 givenname: Alexander S orcidid: 0000-0001-5979-179X surname: Shved fullname: Shved, Alexander S organization: Cancer Center at Illinois – sequence: 5 givenname: Cheng surname: Yang fullname: Yang, Cheng organization: Roger Adams Laboratory, Department of Chemistry – sequence: 6 givenname: Tiffany surname: Chu fullname: Chu, Tiffany organization: Roger Adams Laboratory, Department of Chemistry – sequence: 7 givenname: Emily J surname: Tonogai fullname: Tonogai, Emily J organization: Carl R. Woese Institute for Genomic Biology – sequence: 8 givenname: Paul J surname: Hergenrother fullname: Hergenrother, Paul J organization: Carl R. Woese Institute for Genomic Biology – sequence: 9 givenname: David orcidid: 0000-0002-8736-8953 surname: Sarlah fullname: Sarlah, David email: Sarlah@illinois.edu organization: Cancer Center at Illinois |
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