Organometallic cobalamin anticancer derivatives for targeted prodrug delivery via transcobalamin-mediated uptakeElectronic supplementary information (ESI) available: Detailed synthetic procedures, full characterization of the new compound and other necessary characterization studies. See DOI: 10.1039/c6dt04443c
Herein we report the synthesis of new water-soluble vitamin B 12 prodrugs bearing metal complexes at the β-upper side of the cobalt center. A total of three derivatives with the general design {Co-C&z.tbd;C-bpy-M}, where M represents a cytotoxic metal complex, were prepared and tested for their...
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Main Authors | , , , , |
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Format | Journal Article |
Language | English |
Published |
14.02.2017
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Online Access | Get full text |
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Summary: | Herein we report the synthesis of new water-soluble vitamin B
12
prodrugs bearing metal complexes at the β-upper side of the cobalt center. A total of three derivatives with the general design {Co-C&z.tbd;C-bpy-M}, where M represents a cytotoxic metal complex, were prepared and tested for their cytotoxicity against MCF-7 breast cancer cells. The choice of the metal was oriented on the eminent Pt and promising Ru and Re species to demonstrate the general applicability of the approach. The recognition of the derivatives by transcobalamin was demonstrated by competitive displacement assays using rhodamine labeled B
12
. This compound further served to prepare a dual luminescent probe by orthogonal synthesis with M = ((HCCbpy)Ru(bpy)
2
)Cl
2
and to perform
in vitro
assays. Cellular imaging experiments allowed us to observe the different compartmentalization of both dyes and thus prove that the species follow the natural cobalamin uptake as well as the self-triggered release of the β-upper complex.
We report the synthesis and study of new water-soluble vitamin B
12
prodrugs bearing metal complexes at the β-upper side of the cobalt center for targeted prodrug delivery. |
---|---|
Bibliography: | 10.1039/c6dt04443c Electronic supplementary information (ESI) available: Detailed synthetic procedures, full characterization of the new compound and other necessary characterization studies. See DOI |
ISSN: | 1477-9226 1477-9234 |
DOI: | 10.1039/c6dt04443c |