title: 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.
authors.affiliation: Department of Chemistry & Biochemistry, and ‡Department of Molecular, Cellular and Developmental Biology, University of California , Santa Barbara, California 93106, United States.
authors.forename: Alexander W
authors.initials: AW
authors.lastname: Thomas
authors.forename: Zachary B
authors.initials: ZB
authors.lastname: Henson
authors.forename: Jenny
authors.initials: J
authors.lastname: Du
authors.forename: Carol A
authors.initials: CA
authors.lastname: Vandenberg
authors.forename: Guillermo C
authors.initials: GC
authors.lastname: Bazan
mesh_terms: D000818:Animals; D019556:COS Cells / Q000166:cytology; D002470:Cell Survival; D002522:Chlorocebus aethiops; D004573:Electrolytes / Q000032:analysis* / Q000138:chemical synthesis / Q000378:metabolism; D004705:Endocytosis; D004926:Escherichia coli / Q000166:cytology; D018613:Microscopy, Confocal / Q000379:methods; D061848:Optical Imaging / Q000379:methods*; D013194:Staining and Labeling / Q000379:methods*; D015003:Yeasts / Q000166:cytology
chemical_list: D004573:Electrolytes