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The (Cp)M(CO)3] (M=Re, 99mTc) building block for imaging agents and bioinorganic probes: Perspectives and limitations


Can, Daniel; N'Dongo, Harmel W Peindy; Spingler, Bernhard; Schmutz, Paul; Raposinho, Paula; Santos, Isabel; Alberto, Roger (2012). The (Cp)M(CO)3] (M=Re, 99mTc) building block for imaging agents and bioinorganic probes: Perspectives and limitations. Chemistry & Biodiversity, 9(9):1849-1866.

Abstract

Starting from asymmetric Thiele's acid derivatives, two different imaging probes 99mTc(CO)3(CpR)] (R=potential targeting vector) are generated simultaneously in one-pot and from one substrate. This extends the previously introduced labeling strategy of metal-mediated retro-Diels?Alder reaction with HCp-R dimers. We demonstrate that chemically active functionalities such as hydroxamic acids are not following this labeling strategy. Adopting the principle of replacing phenyl rings by Re(CO)3(Cp)] entities, potent histone deacetylase (HDAC)-inhibiting Re analogs of suberoylanlilide hydroxamic acid (SAHA; N-hydroxy-N'-phenyloctanediamide) were synthesized and characterized. Cytotoxic evaluation on different tumor cell lines revealed low IC50 values mu M] for these compounds, comparable to their purely organic congeners.

Abstract

Starting from asymmetric Thiele's acid derivatives, two different imaging probes 99mTc(CO)3(CpR)] (R=potential targeting vector) are generated simultaneously in one-pot and from one substrate. This extends the previously introduced labeling strategy of metal-mediated retro-Diels?Alder reaction with HCp-R dimers. We demonstrate that chemically active functionalities such as hydroxamic acids are not following this labeling strategy. Adopting the principle of replacing phenyl rings by Re(CO)3(Cp)] entities, potent histone deacetylase (HDAC)-inhibiting Re analogs of suberoylanlilide hydroxamic acid (SAHA; N-hydroxy-N'-phenyloctanediamide) were synthesized and characterized. Cytotoxic evaluation on different tumor cell lines revealed low IC50 values mu M] for these compounds, comparable to their purely organic congeners.

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17 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2012
Deposited On:01 Mar 2013 10:22
Last Modified:07 Dec 2017 20:09
Publisher:Wiley-VCH Verlag Berlin
ISSN:1612-1872
Publisher DOI:https://doi.org/10.1002/cbdv.201200076
PubMed ID:22976975

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