Abstract
Twenty-four ester analogues of renieramycin M (1m) were prepared from jorunnamycin A (3a), which was easily transformed from marine natural 1m in three steps. These analogues, along with 1m itself, cyanojorumycin (2b), and jorunnamycins A (3a) and C (3b), were evaluated in vitro for cytotoxicity by measuring IC(50) values through the 3-(4,5-dimethyltriazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay using human HCT116 colon carcinoma and MDA-MB-435 breast carcinoma cell lines. Nitrogen-containing heterocyclic ester derivatives 9a-f showed similar in vitro cytotoxicity to 1m, whereas the other derivatives were slightly less cytotoxic than 1m. 2'-Pyridinecarboxylic acid ester derivative (9c) exhibited a threefold increase in cytotoxicity relative to 1m.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemical synthesis
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Antineoplastic Agents, Phytogenic / chemistry*
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Antineoplastic Agents, Phytogenic / therapeutic use
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Antineoplastic Agents, Phytogenic / toxicity*
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Breast Neoplasms / drug therapy
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Carcinoma / drug therapy
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Cell Line, Tumor
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Cell Proliferation / drug effects*
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Colonic Neoplasms / drug therapy
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Drug Screening Assays, Antitumor
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Female
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Humans
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Inhibitory Concentration 50
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Molecular Structure
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Structure-Activity Relationship
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Tetrahydroisoquinolines / chemical synthesis
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Tetrahydroisoquinolines / chemistry*
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Tetrahydroisoquinolines / therapeutic use
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Tetrahydroisoquinolines / toxicity*
Substances
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Antineoplastic Agents, Phytogenic
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Tetrahydroisoquinolines
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renieramycin M