Influence of methoxy groups on the antiproliferative effects of [Fe(III)(salophene-OMe)Cl] complexes.

Abstract

We synthesized methoxy-substituted iron(III)-salophene complexes ([Fe(III)(OMe-salophene)Cl] with salophene = N,N'-bis(salicylidene)-1,2-phenylenediamine) and analyzed their biological activity in MCF-7 and MDA-MB-231 breast cancer as well as in HT-29 colon carcinoma cells. The results obtained in a time-dependent chemosensitivity test clearly demonstrated the correlation between the cytotoxicity of the complexes and the position of methoxy substituents in the salicylidene moieties: 3-OCH(3) (4) < 5-OCH(3) (8) < H (2) < 4-OCH(3) (6) = 6-OCH(3) (10). Compounds 6 and 10 caused cytocidal effects already at a concentration of 0.5 μM. Both lead compound 2 and complex 8 showed similar time response curves, however, with a 5-fold lower activity compared to 6 and 10, respectively. Referring to [Fe(III)(salophene)Cl] (2), methoxy substitution was accompanied with the loss of tumor cell selectivity. Moreover, the free ligands (1, 3, 5, 7, and 9) were inactive.

• Authors: Annegret Hille, Ronald Gust
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 45 Issue 11 Pg. 5486-92 (Nov 2010) ISSN: 1768-3254 [Electronic] France
• PMID: 20828884 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2010 Elsevier Masson SAS. All rights reserved.

Chemical References

• Ferric Compounds
• Salicylates
• salophen

Topics

• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Ferric Compounds (chemistry, pharmacology)
• Humans
• Magnetic Resonance Spectroscopy
• Salicylates (chemistry, pharmacology)