Synthesis of Carbohydrate Analogues of the THF-Acetogenin 4-Deoxyannomontacin and Their Cytotoxicity Against Human Prostate Cancer Cell Lines
| Autor: | Patricia Gonzalez Periche, Amanda Ramdular, Naga V.S.D.K. Bhupathiraju, Teja Kalidindi, Delissa S. Johnson, Nagavarakishore Pillarsetty, David R. Mootoo |
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| Rok vydání: | 2022 |
| Předmět: |
Male
History Acetogenins Polymers and Plastics Organic Chemistry Carbohydrates Prostatic Neoplasms Antineoplastic Agents Thiophenes General Medicine Alkenes Biochemistry Industrial and Manufacturing Engineering Analytical Chemistry 4-Butyrolactone Cell Line Tumor Humans Business and International Management Trichothecenes Mannose |
| Zdroj: | SSRN Electronic Journal. |
| ISSN: | 1556-5068 |
| Popis: | The THF containing acetogenin 4-deoxyannonmontacin (4-DAN) has attracted interest for its potent cytotoxicity against a broad range of human tumor cell lines, and relatively simple structure. Herein is described the synthesis and cytotoxicity of C-10 epimers of 4-DAN and analogues thereof comprising carbohydrate and thiophene substitutes for the THF and butenolide moieties respectively. The key synthetic ploy was the union of THF and butenolide segments or their substitutes, via an alkene cross metathesis. The different analogues showed cytotoxicity in the low micromolar to nanomolar range against the human prostate cancer cell lines LNCaP and PC3. A relatively simple mannose-linked thiophene analog was found to be similar in activity to 4-DAN. |
| Databáze: | OpenAIRE |
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