Open AccessSynthesis, Characterization, and Biological Affinity of a Near-Infrared-Emitting Conjugated Oligoelectrolyte
Author(s) -
Alexander W. Thomas,
Zachary B. Henson,
Jenny Du,
Carol A. Vandenberg,
Guillermo C. Bazan
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja412695w
Subject(s) - chemistry , staining , propidium iodide , internalization , biophysics , negative stain , conjugated system , colocalization , membrane , stain , lipid bilayer , biochemistry , microbiology and biotechnology , cell , electron microscope , organic chemistry , apoptosis , physics , programmed cell death , biology , optics , polymer , medicine , pathology
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.
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