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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Caribbean Region
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Cyanobacteria / chemistry
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Cyanobacteria / growth & development
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Cyanobacteria / isolation & purification
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Depsipeptides / chemical synthesis
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Depsipeptides / chemistry
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Depsipeptides / pharmacology*
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Drug Design
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Drug Discovery*
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HEK293 Cells
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Hepatocytes / drug effects*
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Hepatocytes / metabolism
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Humans
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Liver Neoplasms / drug therapy*
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Liver Neoplasms / metabolism
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Lyngbya Toxins / chemical synthesis
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Lyngbya Toxins / chemistry
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Lyngbya Toxins / pharmacology*
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Molecular Structure
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Oligopeptides / chemical synthesis
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Oligopeptides / chemistry
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Oligopeptides / toxicity
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Osmolar Concentration
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Peptide Fragments / chemical synthesis
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Peptide Fragments / chemistry
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Peptide Fragments / toxicity
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Protein Conformation
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Antineoplastic Agents
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Depsipeptides
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Lyngbya Toxins
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Oligopeptides
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Peptide Fragments
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itralamide B