Abstract
In vitro cytotoxic activities of 24 quaternary protoberberine alkaloids related to berberine have been evaluated using a human cancer cell line panel coupled with a drug sensitivity database. Extending the alkyl chain at position 8 or 13 strongly influenced the cytotoxic activity, that is, relative lipophilicity as well as the size of the substituent affects cytotoxicity. The highest level of activity was observed in 8- or 13-hexyl-substituted derivatives of berberine. Structure-activity relationships are described.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / pharmacology
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Berberine / analogs & derivatives*
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Berberine / chemical synthesis*
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Berberine / chemistry
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Berberine / pharmacology
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Berberine Alkaloids / chemical synthesis*
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Berberine Alkaloids / chemistry
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Berberine Alkaloids / pharmacology
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Brain Neoplasms / metabolism
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Breast Neoplasms / metabolism
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Colonic Neoplasms / metabolism
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Crystallography, X-Ray
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Databases, Factual
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Doxorubicin / pharmacology
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Female
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Humans
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Lung Neoplasms / metabolism
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Magnetic Resonance Spectroscopy
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Mice
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Mitomycin / pharmacology
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Molecular Structure
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Ovarian Neoplasms / metabolism
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Papaver / chemistry
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Plants, Medicinal
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Stomach Neoplasms / metabolism
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Structure-Activity Relationship
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Tumor Cells, Cultured / drug effects
Substances
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Antineoplastic Agents, Phytogenic
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Berberine Alkaloids
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coptisine
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Berberine
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Mitomycin
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Doxorubicin
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palmatine