Synthesis and cellular uptake of neutral rhenium() morpholine complexes
Morpholine motifs have been used extensively as targeting moieties for lysosomes, primarily in fluorescence imaging agents. Traditionally these imaging agents are based on organic molecules which have several shortcomings including small Stokes shifts, short emission lifetimes, and susceptibility to...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2024-02, Vol.53 (7), p.347-3413 |
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| creator | Bader, Christie A Simpson, Peter V Dallerba, Elena Stagni, Stefano Johnson, Ian R. D Hickey, Shane M Sorvina, Alexandra Hackett, Mark Sobolev, Alexandre N Brooks, Doug A Massi, Massimiliano Plush, Sally E |
| description | Morpholine motifs have been used extensively as targeting moieties for lysosomes, primarily in fluorescence imaging agents. Traditionally these imaging agents are based on organic molecules which have several shortcomings including small Stokes shifts, short emission lifetimes, and susceptibility to photobleaching. To explore alternative lysosome targeting imaging agents we have used a rhenium based phosphorescent platform which has been previously demonstrated to have an improved Stokes shift, a long lifetime emission, and is highly photostable. Rhenium complexes containing morpholine substituted ligands were designed to accumulate in acidic compartments. Two of the three complexes prepared exhibited bright emission in cells, when incubated at low concentrations (20 μM) and were non-toxic at concentrations as high as 100 μM, making them suitable for live cell imaging. We show that the rhenium complexes are amenable to chemical modification and that the morpholine targeted derivatives can be used for live cell confocal fluorescence imaging of endosomes-lysosomes.
Neutral Re(I) morpholine complexes exhibiting long emission lifetimes, high photo- and pH stability and low cytotoxicity for imaging endosome-lysosome compartments. |
| doi_str_mv | 10.1039/d3dt03067a |
| format | Article |
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Neutral Re(I) morpholine complexes exhibiting long emission lifetimes, high photo- and pH stability and low cytotoxicity for imaging endosome-lysosome compartments.</description><subject>Cell Line, Tumor</subject><subject>Emission</subject><subject>Endosomes</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Imaging</subject><subject>Low concentrations</subject><subject>Lysosomes</subject><subject>Morpholine</subject><subject>Morpholines</subject><subject>Organic chemistry</subject><subject>Phosphorescence</subject><subject>Rhenium</subject><subject>Rhenium - chemistry</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0U1Lw0AQBuBFFFurF-9KwEsVors7STZ7LK1WoeDBeg6T7Iam5svdLNh_b2prBU8zMA_D8A4hl4zeMwryQYHqKNBI4BEZskAIX3IIjg89jwbkzNo1pZzTkJ-SAcQ8koGgQzJ_29TdStvCelgrL9Nl6Uo0nms7_NBek3u1dp3B0jMrXReuGt96VWPaVVMWtfaypmpL_aXtOTnJsbT6Yl9H5P3pcTl99hev85fpZOFnAKLz05BixhEiSLXKkAdCYkpjJZAjY0GeU1SYSoh4P1JKITApcsm1opLygMGIjHd7W9N8Om27pCrs9mqsdeNswiWLQwaSRj29-UfXjTN1f12veAgxsFj06m6nMtNYa3SetKao0GwSRpNtvMkMZsufeCc9vt6vdGml1YH-5tmDqx0wNjtM__4D3yRzfog</recordid><startdate>20240213</startdate><enddate>20240213</enddate><creator>Bader, Christie A</creator><creator>Simpson, Peter V</creator><creator>Dallerba, Elena</creator><creator>Stagni, Stefano</creator><creator>Johnson, Ian R. 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To explore alternative lysosome targeting imaging agents we have used a rhenium based phosphorescent platform which has been previously demonstrated to have an improved Stokes shift, a long lifetime emission, and is highly photostable. Rhenium complexes containing morpholine substituted ligands were designed to accumulate in acidic compartments. Two of the three complexes prepared exhibited bright emission in cells, when incubated at low concentrations (20 μM) and were non-toxic at concentrations as high as 100 μM, making them suitable for live cell imaging. We show that the rhenium complexes are amenable to chemical modification and that the morpholine targeted derivatives can be used for live cell confocal fluorescence imaging of endosomes-lysosomes.
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| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2024-02, Vol.53 (7), p.347-3413 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_rsc_primary_d3dt03067a |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Cell Line, Tumor Emission Endosomes Fluorescence Fluorescent Dyes - chemistry Imaging Low concentrations Lysosomes Morpholine Morpholines Organic chemistry Phosphorescence Rhenium Rhenium - chemistry |
| title | Synthesis and cellular uptake of neutral rhenium() morpholine complexes |
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