Abstract
Installation of a nitrogen at the C6 position of artemisinin facilitates the addition of a functional unit on the cyclohexane moiety (C-ring). In this study, conjugation of an amphiphilic chain, composed of sequentially connected hydrophilic oligoethylene glycol, hydrophobic alkyl chain, urea, and 4,4'-disubstituted biphenyl linker, imparted self-assembling properties. The fully synthetic mid-molecular weight 6-aza-artemisinin 6 bearing the amphiphilic moiety formed aggregates (approx. 200 nm) at ambient temperature and exhibited increased in vitro anti-cancer activities compared to the N-benzylated aza-artemisinin 5.
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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Artemisinins / chemistry
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Artemisinins / pharmacology*
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Biphenyl Compounds / chemistry
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Biphenyl Compounds / pharmacology
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Drug Screening Assays, Antitumor
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Ethylene Glycol / chemistry
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Ethylene Glycol / pharmacology
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Humans
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Hydrophobic and Hydrophilic Interactions
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Molecular Structure
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Particle Size
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Surface Properties
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Surface-Active Agents / chemistry
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Surface-Active Agents / pharmacology*
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Urea / chemistry
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Urea / pharmacology
Substances
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Antineoplastic Agents
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Artemisinins
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Biphenyl Compounds
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Surface-Active Agents
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diphenyl
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Urea
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artemisinin
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Ethylene Glycol