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Synthesis, characterization, and biological affinity of a near-infrared-emitting conjugated oligoelectrolyte.

ABSTRACT: A near-IR-emitting conjugated oligoelectrolyte (COE), ZCOE, was synthesized, and its photophysical features were characterized. The biological affinity of ZCOE is compared to that of an established lipid-membrane-intercalating COE, DSSN+, which has blue-shifted optical properties making it compatible for tracking preferential sites of accumulation. ZCOE exhibits diffuse staining of E. coli cells, whereas it displays internal staining of select yeast cells which also show propidium iodide staining, indicating ZCOE is a "dead" stain for this organism. Staining of mammalian cells reveals complete internalization of ZCOE through endocytosis, as supported by colocalization with LysoTracker and late endosome markers. In all cases DSSN+ persists in the outer membranes, most likely due to its chemical structure more closely resembling a lipid bilayer.

SUBMITTER: Thomas AW

PROVIDER: S-EPMC3985452 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Synthesis, characterization, and biological affinity of a near-infrared-emitting conjugated oligoelectrolyte.

Thomas Alexander W AW Henson Zachary B ZB Du Jenny J Vandenberg Carol A CA Bazan Guillermo C GC

Journal of the American Chemical Society 20140304 10

A near-IR-emitting conjugated oligoelectrolyte (COE), ZCOE, was synthesized, and its photophysical features were characterized. The biological affinity of ZCOE is compared to that of an established lipid-membrane-intercalating COE, DSSN+, which has blue-shifted optical properties making it compatible for tracking preferential sites of accumulation. ZCOE exhibits diffuse staining of E. coli cells, whereas it displays internal staining of select yeast cells which also show propidium iodide stainin ...[more]

PMID: 24575841

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