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 inJournal of the American Chemical Society Vol. 143; no. 4; pp. 2138 - 2155
Main Authors Boyko, Yaroslav D, Huck, Christopher J, Ning, Shang, Shved, Alexander S, Yang, Cheng, Chu, Tiffany, Tonogai, Emily J, Hergenrother, Paul J, Sarlah, David
Format Journal Article
LanguageEnglish
Published United States 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.
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
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/33464048$$D View this record in MEDLINE/PubMed
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Snippet The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis...
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Title Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques
URI http://dx.doi.org/10.1021/jacs.0c12569
https://www.ncbi.nlm.nih.gov/pubmed/33464048
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