Posters
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Discipline Track
Biomedical Science
Abstract Type
Research/Clinical
Abstract
Purpose: Isoquinolinequinones are a group of organic compounds which are composed of an isoquinoline fused to a quinone ring. This class of molecules is known to exhibit a wide variety of biological activities, including cytotoxic and antitumor properties. Among the many families of isoquinolinequinones are the Caulibugulones and Mansouramycins, which exhibit anticancer properties and are thus desirable subjects for cancer-related research. They are obtained by isolation from marine bryozoan Caulibugula intermis and marine Streptomyces sp respectively, however these compounds are difficult to extract. Thus, organic synthesis is being explored as a method of obtaining them; this project focuses on the synthesis of Mansouramycin A. This research aims to test a heterocyclization pathway for the total synthesis of Mansouramycin A.
Methods: In order to test this multistep synthesis pathway, the process is divided into two parts. In part one, we will synthesize an aminoacetal from an amino acid in a series of 4 reactions. After each reaction is done, the reaction mixture is extracted with a specified solvent (mainly DCM or ethyl acetate); washing with water, NaHCO3, and/or brine; drying with Na2SO4, and concentration under reduced pressure. The presence and purity of the product of each reaction is measured using NMR spectroscopy. If further purification of a product is needed, various solvents are assessed with thin-layer chromatography, and a subsequent column chromatography is performed. In part two, we will combine the aminoacetal synthesized in part one with a 2-5 dimethoxybenzaldehyde followed by cyclization and aromatization of the fused ring. This process will be done similarly to part one, and each reaction will be subsequently verified with NMR and purified with a column chromatography. This process of reactions and purification will be done to produce the isoquinolinequinone Mansouramycin A.
Results: The process of synthesizing the final product Mansouramycin A is still being done. Thus far, multiple attempts have been made in which the product is of insignificant yield to determine the success of the reaction pathway. As of writing this abstract, we have completed the first reaction of part one, verified using NMR, and purified the product with a column chromatography. Within subsequent weeks, we will complete part one and begin part two. We will have completed the total synthesis of Mansouramycin A.
Conclusion: Developing a total synthesis pathway for the isoquinolinequinone Mansouramycin A would serve as a gateway for more research to be done regarding development of anticancer drugs. This project hopes to make Mansouramycin A and analogs more accessible for future research on the effects of Mansouramycins on cancer cells, potentially making its way into clinical trials and aiding patients in battles against various forms of cancers.
Presentation Type
Poster
Recommended Citation
Dantu, Aditya; Madrigal, Gabriella L.; Gondi, Neel; Osazee, David; Amro, Ahmad; Alsabbagh, Whard; and Mito, Shizue, "Total Synthesis of the Marine Cytotoxic Mansouramycin and Derivatives" (2025). Research Colloquium. 45.
https://scholarworks.utrgv.edu/colloquium/2025/posters/45
Included in
Chemical Actions and Uses Commons, Heterocyclic Compounds Commons, Organic Chemicals Commons, Other Chemicals and Drugs Commons, Pharmaceutical Preparations Commons, Polycyclic Compounds Commons
Total Synthesis of the Marine Cytotoxic Mansouramycin and Derivatives
Purpose: Isoquinolinequinones are a group of organic compounds which are composed of an isoquinoline fused to a quinone ring. This class of molecules is known to exhibit a wide variety of biological activities, including cytotoxic and antitumor properties. Among the many families of isoquinolinequinones are the Caulibugulones and Mansouramycins, which exhibit anticancer properties and are thus desirable subjects for cancer-related research. They are obtained by isolation from marine bryozoan Caulibugula intermis and marine Streptomyces sp respectively, however these compounds are difficult to extract. Thus, organic synthesis is being explored as a method of obtaining them; this project focuses on the synthesis of Mansouramycin A. This research aims to test a heterocyclization pathway for the total synthesis of Mansouramycin A.
Methods: In order to test this multistep synthesis pathway, the process is divided into two parts. In part one, we will synthesize an aminoacetal from an amino acid in a series of 4 reactions. After each reaction is done, the reaction mixture is extracted with a specified solvent (mainly DCM or ethyl acetate); washing with water, NaHCO3, and/or brine; drying with Na2SO4, and concentration under reduced pressure. The presence and purity of the product of each reaction is measured using NMR spectroscopy. If further purification of a product is needed, various solvents are assessed with thin-layer chromatography, and a subsequent column chromatography is performed. In part two, we will combine the aminoacetal synthesized in part one with a 2-5 dimethoxybenzaldehyde followed by cyclization and aromatization of the fused ring. This process will be done similarly to part one, and each reaction will be subsequently verified with NMR and purified with a column chromatography. This process of reactions and purification will be done to produce the isoquinolinequinone Mansouramycin A.
Results: The process of synthesizing the final product Mansouramycin A is still being done. Thus far, multiple attempts have been made in which the product is of insignificant yield to determine the success of the reaction pathway. As of writing this abstract, we have completed the first reaction of part one, verified using NMR, and purified the product with a column chromatography. Within subsequent weeks, we will complete part one and begin part two. We will have completed the total synthesis of Mansouramycin A.
Conclusion: Developing a total synthesis pathway for the isoquinolinequinone Mansouramycin A would serve as a gateway for more research to be done regarding development of anticancer drugs. This project hopes to make Mansouramycin A and analogs more accessible for future research on the effects of Mansouramycins on cancer cells, potentially making its way into clinical trials and aiding patients in battles against various forms of cancers.
