Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin

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  • Jamal Mustafa
    National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy University of Mississippi University MS 38677
  • Shabana I. Khan
    National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy University of Mississippi University MS 38677
  • Guoyi Ma
    National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy University of Mississippi University MS 38677
  • Larry A. Walker
    Department of Pharmacology School of Pharmacy, University of Mississippi University Mississippi 38677
  • Ikhlas A. Khan
    Department of Pharmacognosy School of Pharmacy, University of Mississippi University Mississippi 38677

説明

<jats:title>Abstract</jats:title><jats:p>Derivatives of podophyllotoxin were prepared by coupling 10 FA with the C<jats:sub>4</jats:sub>‐α‐hydroxy function of podophyllotoxin. The coupling reactions between FA and podophyllotoxin were carried out by dicyclohexylcarbodiimide in the presence of a catalytic amount of dimethylaminopyridine to produce quantitative yields of desired products. FA incorporated were the following: 10‐hydroxydecanoic, 12‐hydroxydodecanoic, 15‐hydroxypentadecanoic, 16‐hydroxyhexadecanoic, 12‐hydroxyoctadec‐<jats:italic>Z</jats:italic>‐9‐enoic, eicosa‐<jats:italic>Z</jats:italic>‐5,8,11,14‐tetraenoic, eicosa‐<jats:italic>Z</jats:italic>‐8,11, 14‐trienoic, eicosa‐<jats:italic>Z</jats:italic>‐11,14‐dienoic, eicosa‐<jats:italic>Z</jats:italic>‐11‐enoic, and eicosanoic acids. Spectroscopic studies confirmed the formation of the desired products. New molecules were investigated for their <jats:italic>in vitro</jats:italic> anticancer activity against a panel of human cancer cell lines including SK‐MEL, KB, BT‐549, SK‐OV‐3 (solid tumors), and HL‐60 (human leukemia) cells. Most of the analogs were cytotoxic against cancerous cells, whereas no effect was observed against normal cells, unlike the parent compound podophyllotoxin, the use of which is limited due to its severe side effects.</jats:p>

収録刊行物

  • Lipids

    Lipids 39 (2), 167-172, 2004-02

    Wiley

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