1. Studies toward the total synthesis of Itralamide B and biological evaluation of its structural analogs.
- Author
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Wang X, Lv C, Feng J, Tang L, Wang Z, Liu Y, Meng Y, Ye T, and Xu Z
- Subjects
- Antineoplastic Agents chemical synthesis, Antineoplastic Agents chemistry, Caribbean Region, Cell Line, Tumor, Cell Proliferation drug effects, Cyanobacteria chemistry, Cyanobacteria growth & development, Cyanobacteria isolation & purification, Depsipeptides chemical synthesis, Depsipeptides chemistry, Drug Design, HEK293 Cells, Hepatocytes metabolism, Humans, Liver Neoplasms metabolism, Lyngbya Toxins chemical synthesis, Lyngbya Toxins chemistry, Molecular Structure, Oligopeptides chemical synthesis, Oligopeptides chemistry, Oligopeptides toxicity, Osmolar Concentration, Peptide Fragments chemical synthesis, Peptide Fragments chemistry, Peptide Fragments toxicity, Protein Conformation, Stereoisomerism, Structure-Activity Relationship, Antineoplastic Agents pharmacology, Depsipeptides pharmacology, Drug Discovery, Hepatocytes drug effects, Liver Neoplasms drug therapy, Lyngbya Toxins pharmacology
- Abstract
Itralamides A and B were isolated from the lipophilic extract of Lyngbya majuscula collected from the eastern Caribbean. Itralamide B (1) showed cytotoxic activity towards human embryonic kidney cells (HEK293, IC50 = 6 μM). Preliminary studies disapproved the proposed stereochemistry of itralamide. In this paper, we will provide a full account of the total synthesis of four stereoisomers of itralamide B and the results derived from biological tests of these structural congeners.
- Published
- 2015
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