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The [(Cp)M(CO) 3 ] (M=Re, 99m Tc) Building Block for Imaging Agents and Bioinorganic Probes: Perspectives and Limitations
Author(s) -
Can Daniel,
Peindy N'Dongo Harmel W.,
Spingler Bernhard,
Schmutz Paul,
Raposinho Paula,
Santos Isabel,
Alberto Roger
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201200076
Subject(s) - chemistry , hydroxamic acid , bioinorganic chemistry , substrate (aquarium) , stereochemistry , histone deacetylase , combinatorial chemistry , histone , biochemistry , dna , oceanography , geology
Starting from asymmetric Thiele 's acid derivatives, two different imaging probes [ 99m Tc(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‐DielsAlder 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 IC 50 values [μ M ] for these compounds, comparable to their purely organic congeners.