Abstract
We report the synthesis of a series of novel diphenylcarbazoles designed to interact with DNA. The compounds bearing two or three dimethylaminoalkyloxy side chains were found to bind much more tightly to DNA, preferentially at AT-rich sites, than the corresponding hydroxy compounds. The DNA binding compounds exhibit potent cytotoxic activity toward P388 leukemia cells. The 3,6-diphenylcarbazole thus represent an interesting scaffold to develop antitumor agents interacting with nucleic acids.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Animals
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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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Apoptosis / drug effects
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Benzene Derivatives / chemical synthesis*
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Benzene Derivatives / chemistry
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Benzene Derivatives / pharmacology
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Carbazoles / chemical synthesis*
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Carbazoles / chemistry
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Cell Cycle / drug effects
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Cell Division / drug effects
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Cell Line, Tumor
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DNA / chemistry*
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Flow Cytometry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Inhibitory Concentration 50
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Magnetic Resonance Spectroscopy
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Mice
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Molecular Structure
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Poly dA-dT / chemistry
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Structure-Activity Relationship
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Transition Temperature / drug effects
Substances
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Antineoplastic Agents
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Benzene Derivatives
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Carbazoles
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Heterocyclic Compounds, 4 or More Rings
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Poly dA-dT
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DNA