Luminescent Difluoroboron β-Diketonate PLA-PEG Nanoparticle

Caroline Kerr; Christopher A. DeRosa; Margaret L. Daly; Hengtao Zhang; Gregory M. Palmer; Cassandra L. Fraser

doi:10.1021/acs.biomac.6b01708

Luminescent Difluoroboron β-Diketonate PLA-PEG Nanoparticle

Caroline Kerr, Christopher A. DeRosa, Margaret L. Daly, Hengtao Zhang, Gregory M. Palmer, Cassandra L. Fraser

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Luminescent difluoroboron β-diketonate poly(lactic acid) (BF₂bdkPLA) materials serve as biological imaging agents. In this study, dye structures were modified to achieve emission colors that span the visible region with potential for multiplexing applications. Four dyes with varying π-conjugation (phenyl, naphthyl) and donor groups (−OMe, −NMe₂) were coupled to PLLA-PEG block copolymers (∼11 kDa) by a postpolymerization Mitsunobu reaction. The resulting dye-polymer conjugates were fabricated as nanoparticles (∼55 nm diameter) to produce nanomaterials with a range of emission colors (420-640 nm). For increased stability, dye-PLLA-PEG conjugates were also blended with dye-free PDLA-PEG to form stereocomplex nanoparticles of smaller size (∼45 nm diameter). The decreased dye loading in the stereoblocks blue-shifted the emission, generating a broader range of fluorescence colors (410-620 nm). Tumor accumulation was confirmed in a murine model through biodistribution studies with a red emitting dimethyl amino-substituted dye-polymer analogue. The synthesis, optical properties, oxygen-sensing capabilities, and stability of these block copolymer nanoparticles are presented.

Original language	English (US)
Pages (from-to)	551-561
Number of pages	11
Journal	Biomacromolecules
Volume	18
Issue number	2
DOIs	https://doi.org/10.1021/acs.biomac.6b01708
State	Published - Feb 13 2017
Externally published	Yes

Bibliographical note

Funding Information:
We thank the National Institutes of Health (R01 CA167250) and UVA Cancer Center (P30 CA44579) for support of this work. We thank Corbion Purac for the generous donation of the D- and L-lactide monomers. We gratefully acknowledge the Beckman Foundation for a Beckman Scholarship to C.K. The Harrison Foundation is also acknowledged for an award to C.K. and M.D. We thank Prof. Kelly Dryden, at the UVA Molecular Electron Microscopy Core, which is supported by the UVA School of Medicine and the NIH (G20-RR31199). We thank Tristan Butler for helpful discussions. We also utilized the Duke Optical Molecular Imaging and Analysis shared resource at Duke, which is supported by the Duke Cancer Institute and Duke School of Medicine.

Publisher Copyright:
© 2017 American Chemical Society.

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10.1021/acs.biomac.6b01708

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6348463

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title = "Luminescent Difluoroboron β-Diketonate PLA-PEG Nanoparticle",

abstract = "Luminescent difluoroboron β-diketonate poly(lactic acid) (BF2bdkPLA) materials serve as biological imaging agents. In this study, dye structures were modified to achieve emission colors that span the visible region with potential for multiplexing applications. Four dyes with varying π-conjugation (phenyl, naphthyl) and donor groups (−OMe, −NMe2) were coupled to PLLA-PEG block copolymers (∼11 kDa) by a postpolymerization Mitsunobu reaction. The resulting dye-polymer conjugates were fabricated as nanoparticles (∼55 nm diameter) to produce nanomaterials with a range of emission colors (420-640 nm). For increased stability, dye-PLLA-PEG conjugates were also blended with dye-free PDLA-PEG to form stereocomplex nanoparticles of smaller size (∼45 nm diameter). The decreased dye loading in the stereoblocks blue-shifted the emission, generating a broader range of fluorescence colors (410-620 nm). Tumor accumulation was confirmed in a murine model through biodistribution studies with a red emitting dimethyl amino-substituted dye-polymer analogue. The synthesis, optical properties, oxygen-sensing capabilities, and stability of these block copolymer nanoparticles are presented.",

author = "Caroline Kerr and DeRosa, {Christopher A.} and Daly, {Margaret L.} and Hengtao Zhang and Palmer, {Gregory M.} and Fraser, {Cassandra L.}",

note = "Funding Information: We thank the National Institutes of Health (R01 CA167250) and UVA Cancer Center (P30 CA44579) for support of this work. We thank Corbion Purac for the generous donation of the D- and L-lactide monomers. We gratefully acknowledge the Beckman Foundation for a Beckman Scholarship to C.K. The Harrison Foundation is also acknowledged for an award to C.K. and M.D. We thank Prof. Kelly Dryden, at the UVA Molecular Electron Microscopy Core, which is supported by the UVA School of Medicine and the NIH (G20-RR31199). We thank Tristan Butler for helpful discussions. We also utilized the Duke Optical Molecular Imaging and Analysis shared resource at Duke, which is supported by the Duke Cancer Institute and Duke School of Medicine. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Fraser, Cassandra L.

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Luminescent Difluoroboron β-Diketonate PLA-PEG Nanoparticle

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