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A Novel Organometallic Re I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis
Author(s) -
Raszeja Lukasz,
Maghnouj Abdelouahid,
Hahn Stephan,
MetzlerNolte Nils
Publication year - 2011
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201000576
Subject(s) - solid phase synthesis , peptide , peptide synthesis , phase (matter) , combinatorial chemistry , nanotechnology , chemistry , materials science , organic chemistry , biochemistry
Organometallic complexes possess great potential for imaging applications in biology, due to their kinetic stability and often favourable intrinsic properties. In this work we present a new class of Re I ‐tricarbonyl complexes with a substituted bis(phenanthridinylmethyl)amine (bpm) ligand. The complex Re(CO) 3 (R‐bpm) could be conveniently prepared by microwave synthesis from [Re(CO) 3 (H 2 O) 3 ]Br and a suitably substituted bis(phenanthridinylmethyl)amine (R‐bpm). Complex 5 , with R=CH 2 ‐CO 2 ‐CH 3 , was characterized by a single‐crystal X‐ray structure. Complex 6 (R=CH 2 ‐C 6 H 4 ‐CO 2 H) was used in solid‐phase peptide synthesis (SPPS) to label the neurotensin(8–13) (NT) fragment N‐terminally. The complexes show luminescence emission with large Stokes shifts ( λ ex =350 nm, λ em =570 nm). Cellular uptake and intracellular localization studies in several cell lines demonstrate the utility of the new Re(CO) 3 (R‐bpm) complexes for fluorescence imaging and reveal significant differences between the simple methyl ester 5 and the NT bioconjugate 7 .