Novel semisynthetic spin-labeled derivatives of podophyllotoxin with cytotoxic and antioxidative activity

https://doi.org/10.1016/j.bmcl.2009.12.048Get rights and content

Abstract

A series of novel spin-labeled podophyllotoxin derivatives were synthesized by reacting the corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyloxy carbonyl)-amino acids with 4β-amino-4′-demethylepipodophyllotoxin. The synthesized derivatives 12a–g were evaluated for the partition coefficients, cytotoxicities in vitro against three tumor cell lines (A-549, HL-60, and RPMI-8226) and antioxidative activities in tissues of SD rats by the TBA method. The vast majority of target compounds have shown superior or comparable activities against A-549, HL-60, and RPMI-8226 compared to VP-16, and they have shown more significant antioxidative activities and superior water solubility than VP-16.

Graphical abstract

The synthesized compounds showed superior or comparable cytotoxicities and pronounced antioxidative activity compared to VP-16.

  1. Download : Download full-size image

Section snippets

Acknowledgment

We thank State Key Laboratory of Applied Organic Chemistry of Lanzhou University for financial support.

References and notes (23)

  • E.S. Garcia et al.

    Toxicon

    (2004)
  • T. Imbert

    Biochimie

    (1998)
  • M. Gordaliza et al.

    Eur. J. Med. Chem.

    (2000)
    M.A. Castro et al.

    J. Med. Chem.

    (2004)
  • Y.-Q. Liu et al.

    Synth. Commun.

    (2005)
  • X. Tian et al.

    Life Sci.

    (1997)
  • J.-Z. Wang et al.

    Anti-Cancer Drug Des.

    (1993)
  • S.-W. Chen et al.

    Bioorg. Med. Chem.

    (2009)
  • S.-W. Chen et al.

    Bioorg. Med. Chem. Lett.

    (2007)
  • S.-W. Chen et al.

    Helv. Chim. Acta

    (2009)
  • H. Ohkawa et al.

    Anal. Biochem.

    (1979)
  • G. Sosnovsky

    Pure. Appl. Chem.

    (1990)

    • Cited by (0)

    View full text
    Copyright © 2009 Elsevier Ltd. All rights reserved.