Chromophoric and Dendritic Phosphoramidites Enable Construction of Functional Dendrimers with Exceptional Brightness and Water Solubility

Abstract

The fluorescence brightness of a molecular probe determines whether it can be effectively measured and its water solubility dictates if it can be applied in real-world biological systems. However, molecules brighter than the most efficient fluorescent dyes or particles brighter than quantum dots are hard to come by, especially when they must also be soluble in water. In this report, chromophoric phosphoramidites are used in a solid-state synthesis to construct functional dendrimers. When highly twisted chromophores are chosen and the proper spacers and dendrons are introduced, the resultant dendrimers emit exceptionally bright fluorescence. Chromophores, spacers, and dendrons are stitched together by efficient phosphoramidite reagents, which afford high-yield water-soluble phosphodiester linkages after deprotection. The resulting water-soluble dendrimers are exceptionally bright.

Fluorescent Polymer Nanoparticles Based on Dyes: Seeking Brighter Tools for Bioimaging

“…Emulsifier‐free methods have also been applied, as well as approaches with emulsifier concentrations below the cmc . A co‐monomer with two polymerizable bonds, such as divinylbenzene, can be used to obtain crosslinking of the polymer NPs . In emulsion polymerization approaches, the dye is most often incorporated during the polymerization in the form of a dye monomer, though physical trapping is also possible.…”

High definition polyphosphoesters: between nucleic acids and plastics

“…The products showed excellent water solubility due to the phosphate charges, and exceptional brightness -providing a far better probe than the ubiquitous fluorescein for single molecule studies. 123 An adjoining area of chemical space had been reached by polymer scientists, bringing with them a different set of ideas about the types and applications of sequence-defined polyphosphoesters produced by the phosphoramidite method. Sleiman has a longstanding interest in the confluence of polymer self-assembly and DNA nanotechnology.…”

Multivalent dendritic DNA aptamer molecules for the enhancement of therapeutic effects

“…This was followed by the substitution of bromide groups at the 5′-end with azido groups and cleavage from the solid support. 23,24 3′-Amine modified AS1411 DNA was synthesized through solid-phase synthesis, which was then conjugated with dibenzocyclooctyne (DBCO) via amide bond formation in solution to obtain AS1411-DBCO. Subsequently, the stem region modified with azide groups at the 5′-end was coupled with branched DNA modified with DBCO via SPAAC, resulting in trivalent 3-Branched AS1411, hexavalent 6-Branched AS1411, nonavalent 9-Branched AS1411, and their FAM-labeled counterparts (3-Branched AS1411-FAM, 6-Branched AS1411-FAM, and 9-Branched AS1411-FAM, Table S1, ESI†).…”