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Findings from University of Heidelberg in the Area of Biochemistry Reported (Structure-Activity Relationship of Trifluoromethyl-Containing...

July 25, 2014



Findings from University of Heidelberg in the Area of Biochemistry Reported (Structure-Activity Relationship of Trifluoromethyl-Containing Metallocenes: Electrochemistry, Lipophilicity, Cytotoxicity, and ROS Production)

By a News Reporter-Staff News Editor at Health & Medicine Week -- Researchers detail new data in Life Science Research. According to news reporting from Heidelberg, Germany, by NewsRx journalists, research stated, "We report the synthesis of trifluoromethylated metallocenes (M=Fe, Ru) and related metal-free compounds for comparison of their biological properties with the aim to establish structure-activity relationships toward the anti-proliferative activity of this compound class. All new compounds were comprehensively characterized by NMR spectroscopy (1H, 13C, 19F), mass spectrometry, IR spectroscopy, and elemental analysis."

The news correspondents obtained a quote from the research from the University of Heidelberg, "A single-crystal X-ray structure was obtained on the Ru derivative, 1-(1-hydroxy-1-hexafluoromethylethyl)ruthenocene (3). The cytotoxicity of all compounds was tested on MCF-7, HT-29, and PT-45 cells, and IC50 values as low as 12M were observed. Both the metallocene moiety and the hydroxy function are crucial for cytotoxicity. In addition, the activity decreased sharply even if only one trifluoromethyl group was replaced with a methyl group. Electrochemical investigations by cyclic voltammetry revealed that all CF3-containing compounds are harder to oxidize than the unsubstituted metallocenes. Moreover, logP determination by RP-HPLC showed the fluorinated derivatives to have higher lipophilicity, with logP values up to 4.6. At the same time, the generation of reactive oxygen species (ROS) in Jurkat cells by these compounds was investigated by flow cytometry. Strong ROS production was shown exclusively for the bis-CF3 derivative 1-(1-hydroxy-1-hexafluoromethylethyl)ferrocene (1) after 6 and 24h. Also on the Jurkat cell line, only compound 1 strongly induces necrosis after 24 and 48h, as shown by annexinV/propidium iodide staining. No induction of apoptosis was observed."

According to the news reporters, the research concluded: "We propose that compound 1 is more efficiently incorporated into cancer cells relative to all other derivatives, causing significant induction of oxidative stress within the cell, which ultimately leads to cell death."

For more information on this research see: Structure-Activity Relationship of Trifluoromethyl-Containing Metallocenes: Electrochemistry, Lipophilicity, Cytotoxicity, and ROS Production. Chemmedchem, 2014;9(6):1188-1194. Chemmedchem can be contacted at: Wiley-V C H Verlag Gmbh, Boschstrasse 12, D-69469 Weinheim, Germany. (Wiley-Blackwell - www.wiley.com/; Chemmedchem - onlinelibrary.wiley.com/journal/10.1002/(ISSN)1860-7187)

Our news journalists report that additional information may be obtained by contacting M. Maschke, Heidelberg Univ, Inst Pharm & Mol Biotechnol, D-69120 Heidelberg, Germany. Additional authors for this research include H. Alborzinia, M. Lieb, S. Wolfl and N. Metzler-Nolte (see also Life Science Research).

Keywords for this news article include: Europe, Germany, Chemicals, Heidelberg, Electrochemistry, Life Science Research

Our reports deliver fact-based news of research and discoveries from around the world. Copyright 2014, NewsRx LLC


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Source: Health & Medicine Week


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