Book of Abstracts - Ruhr-Universität Bochum

P-13
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Synthesis, Characterization, and Biological Study of Functionalized
Cyclopentadienylmanganese and Rhenium Tricarbonyl Complexes
and Their Peptide Bioconjugates
Wanning Hu, a Katrin Splith, b Ines Neundorf, b and Ulrich Schatzschneider *a
a Ruhr-Universität Bochum, Lehrstuhl für Anorganische Chemie I - Bioanorganische Chemie,
Universitätsstr. 150, D-44801 Bochum, Germany.
b Institut für Biochemie, Universität Leipzig, Brüderstr. 34, D-04103 Leipzig, Germany.
wanning.hu@rub.de
rel. cell viability [%]
125
100
75
50
25
0
0 50 100 150 200 250
csubstance [�mol]
Cym1-sC18
Cyr1-sC18
Cyr5-sC18
71
OC
M
CO CO
O
M = Mn, Re
L
COOH
Several functionalized cyclopentadienyl manganese and rhenium tricarbonyl half-sandwich complexes
were prepared and coupled to the sC18 carrier peptide to investigate whether the structural
modification of the linker and the change of the metal center would influence the biological properties
of the metal-peptide-bioconjugates. Two new cymantrene complexes with a 1,3- and 1,4-phenylene
linker were prepared and were fully characterized with 1 H-NMR, 13 C-NMR, IR, ESI-MS, elemental
analysis, and X-ray crystallography. 1 In addition, three novel related CpRe(CO)3 complexes showed
good purity in 1 H-NMR, IR and ESI-MS. Four of the compounds were successfully coupled to the
sC18 peptide and the cytotoxicity of the conjugates was studied with the resazurin assay on MCF-7
human breast cancer cells. The CpMn(CO)3 conjugates showed IC50 values of about 55 µM on MCF-7
human breast cancer cells, which is comparable to other cymantrene-sC18 conjugates already studied. 2
In contrast, the rhenium analogue of the cymantrene complex with the 1,2-phenylene linker is inactive
at up to 150 µM. However, a CpRe(CO)3 complex with the 1,4-phenylene linker but a methylene
group between the Cp and phenyl rings gave a bioconjugate with an activity very similar to the
cymantrene- sC18-bioconjugates. The cellular internalization of these conjugates was studied with
confocal fluorescence microscopy on MCF-7 cells.
References
1. K. Splith, I. Neundorf, W. Hu, H. W. Peindy N'Dongo, V. Vasylyeva, K. Merz, U. Schatzschneider,
Dalton Trans. 2010, 39, 2536-2545.
2. I. Neundorf, J. Hoyer, K. Splith, R. Rennert, H. W. Peindy N'dongo, U. Schatzschneider, Chem.
Commun. 2008, 5604-5606.