Polymerizable near-IR dyes
Inventors
Gamsey, Soya • KUTYAVIN, Alex • CLARY, Jacob William
Assignees
Publication Number
US-11866588-B2
Publication Date
2024-01-09
Expiration Date
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Abstract
The present invention is directed, in certain embodiments, to polymerizable near-IR dyes and polymers comprising said dyes as monomeric residues. In other embodiments, the present invention also relates to methods for the preparation of polymerizable near-IR dyes, and to the use of polymerizable near-IR dyes in the preparation of fluorescent polymers.
Core Innovation
The present invention is directed, in certain embodiments, to polymerizable near-IR dyes and polymers comprising said dyes as monomeric residues. In other embodiments, the present invention also relates to methods for the preparation of polymerizable near-IR dyes, and to the use of polymerizable near-IR dyes in the preparation of fluorescent polymers. The disclosure features a compound having a structure of formula (I) and, in a second aspect, a polymer comprising the residue of the compound of any of formulas (I), (IA), (IB), (IC), (ID), (IE), (IF), or (IG) as a monomeric unit.
Fluorescent polymers are functionalized macromolecules that find numerous applications in the fields of materials and life sciences and can be used as fluorescent probes, smart polymeric sensors, drug delivery carriers, and the like. Traditionally, fluorescent polymers are synthesized by chemical conjugation between activated fluorescent dye compounds and polymers bearing modifiable or reactive groups, and this approach has several drawbacks: the activated dye derivatives are usually unstable and are prone to decomposition or side reactions, and the degree of polymer modification could be hard to control. Although methods of fluorescent polymer synthesis via direct polymerization of fluorescent functional monomers or fluorescent chain transfer agents have certain advantages, they cannot be used to synthesize polymers bearing fluorescent groups that are incompatible with the polymerization conditions; for example, cyanine dyes are incompatible with radical polymerization conditions. Thus, until the present disclosure there remains a clear need in the art to provide near-IR, e.g., cyanine dye monomers, that are compatible with radical polymerization conditions and can form polymers, e.g., hydrogels, with fluorescent properties substantially similar to those of the monomers.
Claims Coverage
Overview: three inventive features are claimed covering a polymerizable near-IR dye, polymers of defined formulae, and polymers comprising the dye and a monomer.
Polymerizable near-IR dye of formula (I)
A polymerizable near-IR dye having a structure according to formula (I):
Polymer having structure of formula (II)
A polymer having a structure according to formula (II):
Polymer comprising a polymerizable near-IR dye and a monomer
A polymer comprising a polymerizable near-IR dye and a monomer, said polymer having a repeating unit according to formula (III):
The independent claims principally cover: a polymerizable near-IR dye defined by formula (I); polymers defined by formula (II); and polymers comprising a polymerizable near-IR dye and a monomer with a repeating unit defined by formula (III).
Stated Advantages
Excitation and emission wavelengths in the near-IR region (approximately 550 nm to 1000 nm) allowing detection of analytes deep within a tissue or an organ.
High signal-to-noise ratio.
Compatibility with polymerization conditions used to produce polymers with ethylenic backbones.
Documented Applications
Fluorescent probes.
Smart polymeric sensors.
Drug delivery carriers.
Sensing and imaging applications.
Accurate and optionally long term measurements of pH both in vivo and in vitro.
Detection of an analyte in vitro and diagnostic applications in vitro and in vivo.
Incorporation into a tissue-integrating scaffold and formation of a tissue-integrating sensor.
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