Polyfluorophores on a DNA Backbone: A Multicolor Set of Labels Excited at One Wavelength
- 2 March 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (11), 3923-3933
- https://doi.org/10.1021/ja805502k
Abstract
We recently described the assembly of fluorescent deoxyriboside monomers (“fluorosides”) into DNA-like phosphodiester oligomers (oligodeoxyfluorosides or ODFs) in which hydrocarbon and heterocyclic aromatic fluorophores interact both physically and electronically. Here we report the identification of a multicolor set of water-soluble ODF dyes that display emission colors across the visible spectrum, and all of which can be simultaneously excited by long-wavelength UV light at 340−380 nm. Multispectral dye candidates were chosen from a library of 4096 tetramer ODFs constructed on PEG-polystyrene beads using a simple long-pass filter to observe all visible colors at the same time. We resynthesized and characterized a set of 23 ODFs containing one to four individual chromophores and included 2−3 spacer monomers to increase aqueous solubility and minimize aggregation. Emission maxima of this set range from 376 to 633 nm, yielding apparent colors from violet to red, all of which can be visualized directly. The spectra of virtually all ODFs in this set varied considerably from the simple combination of monomer components, revealing extensive electronic interactions between the presumably stacked monomers. In addition, comparisons of anagrams in the set (isomers having the same components in a different sequence) reveal the importance of nearest-neighbor interactions in the emissive behavior. Preliminary experiments with human tumor (HeLa) cells, observing two ODFs by laser confocal microscopy, showed that they can penetrate the outer cellular membrane, yielding cytoplasmic localization. In addition, a set of four distinctly colored ODFs was incubated with live zebrafish embryos, showing tissue penetration, apparent biostability, and no apparent toxicity. The results suggest that ODF dyes may be broadly useful as labels in biological systems, allowing the simultaneous tracking of multiple species by color, and allowing visualization in moving systems where classical fluorophores fail.Keywords
This publication has 54 references indexed in Scilit:
- UV excitation of single DNA and RNA strands produces high yields of exciplex states between two stacked basesProceedings of the National Academy of Sciences of the United States of America, 2008
- Efficient Quenching of Oligomeric Fluorophores on a DNA BackboneJournal of the American Chemical Society, 2007
- Oligodeoxyfluorosides: strong sequence dependence of fluorescence emissionTetrahedron, 2007
- Fluorescent DNA Nanotags: Supramolecular Fluorescent Labels Based on Intercalating Dye Arrays Assembled on Nanostructured DNA TemplatesJournal of the American Chemical Society, 2007
- Syntheses, Photophysical Properties, and Application of Through‐Bond Energy‐Transfer Cassettes for BiotechnologyChemistry – A European Journal, 2006
- Optical molecular imaging for systems biology: from molecule to organismAnalytical and Bioanalytical Chemistry, 2006
- The Fluorescent Toolbox for Assessing Protein Location and FunctionScience, 2006
- Sensing Metal Ions with DNA Building Blocks: Fluorescent Pyridobenzimidazole NucleosidesJournal of the American Chemical Society, 2006
- Base stacking controls excited-state dynamics in A·T DNANature, 2005
- The Preparation of α- and β-Gentiobiose OctaacetatesJournal of the American Chemical Society, 1938