Installing an additional emission quenching pathway in the design of iridium(III)-based phosphorogenic biomaterials for bioorthogonal labelling and imaging. (October 2016)

• Record Type: Journal Article
• Authors: Li, Steve Po-Yam; Yip, Alex Man-Hei; Liu, Hua-Wei; Lo, Kenneth Kam-Wing
• Is Part Of: Biomaterials. Volume 103(2016)
• Page Start: 305
• Page End: 313
• Publication Date: 2016-10
• Subjects: Bioorthogonal labelling -- FRET -- Iridium -- Molecular imaging -- PET -- Tetrazine; Biomedical materials -- Periodicals; Biocompatible Materials -- Periodicals; Biomatériaux -- Périodiques; 610.28
• DOI: 10.1016/j.biomaterials.2016.06.065
• Languages: English
• ISSNs: 0142-9612

Abstract

Abstract: We report the synthesis, characterization, photophysical and electrochemical behaviour and biological labelling applications of new phosphorogenic bioorthogonal probes derived from iridium(III) polypyridine complexes containing a 1, 2, 4, 5-tetrazine moiety. In contrast to common luminescent cyclometallated iridium(III) polypyridine complexes, these tetrazine complexes are almost non-emissive due to effective Förster resonance energy transfer (FRET) and/or photoinduced electron transfer (PET) from the excited iridium(III) polypyridine unit to the appended tetrazine moiety. However, they exhibited significant emission enhancement upon reacting with (1 R, 8 S, 9 s )-bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN-OH) ( ca . 19.5–121.9 fold) and BCN-modified bovine serum albumin (BCN-BSA) ( ca . 140.8–1133.7 fold) as a result of the conversion of the tetrazine unit to a non-quenching pyridazine derivative. The complexes were applied to image azide-modified glycans in live cells using a homobifunctional crosslinker, 1, 13-bis((1 R, 8 S, 9 s )-bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonylamino)-4, 7, 10-trioxatridecane ( bis -BCN).