Synthesis and characterization of a pegylated derivative of 3-(1,2,3,6-tetrahydro-pyridin-4yl)-1H-indole (IDT199): A high affinity SERT ligand for conjugation to quantum dots

Quantum dots consisting of a cadmium selenide core encapsulated in a shell of cadmium doped zinc sulfide have the potential to revolutionize fluorescent imaging of live cell cultures. In order to utilize these fluorescent probes it is necessary to functionalize them with biologically active ligands. In this paper we report the design and synthesis of a ligand that has a high affinity for the serotonin transporter (SERT) that may be conjugated to quantum dots.

Graphical abstract(i) 3-(1,2,3,6-Tetrahydro-pyridin-4yl)-1H-indole, cesium carbonate, 37.5%; (ii) hydrazine monohydrate, 34.6%; (iii) Boc-NH-PEG-NHS-3400, 100%; (iv) TFA, 100%.Figure optionsDownload full-size imageDownload as PowerPoint slide