A novel organometallic ReI complex with favourable properties for bioimaging and applicability in solid-phase peptide synthesis.

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.