Phthalocyanine photosensitizer in polyethylene glycol-block-poly(lactide-co-benzyl glycidyl ether) nanocarriers: Probing the contribution of aromatic donor-acceptor interactions in polymeric nanospheres

For best photosensitizer activity phthalocyanine dyes used in photodynamic therapy should be molecularly dispersed. Polyethylene glycol-block-polylactide derivatives presenting benzyl side-groups were synthesized to encapsulate a highly lipophilic phthalocyanine dye (AlClPc) and evaluate the effect...

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Bibliographic Details
Published in:Materials Science & Engineering C 2019-01, Vol.94, p.220-233
Main Authors: Pound-Lana, Gwenaelle E.N., Garcia, Giani M., Trindade, Izabel C., Capelari-Oliveira, Patrícia, Pontifice, Thais Godinho, Vilela, José Mário C., Andrade, Margareth S., Nottelet, Benjamin, Postacchini, Bruna B., Mosqueira, Vanessa C.F.
Format: Article
Language:English
Subjects:
Amphiphilic block copolymer
Animals
Biodegradable polymer
Block copolymers
Cell Death
Cell Death - drug effects
Cell Survival
Cell Survival - drug effects
Cercopithecus aethiops
Chemical Sciences
Chlorocebus aethiops
Copolymerization
Copolymers
Cytotoxicity
Derivatives
Dispersion
Drug Carriers
Drug Carriers - chemistry
Drug nanocarrier
Dye dispersion
Dye releases
Dyes
Encapsulation
Field flow fractionation
Fractionation
Indoles
Indoles - chemistry
Indoles - pharmacology
Isoindoles
Kinetics
Lipophilic
Macrophages
Macrophages - cytology
Macrophages - drug effects
Macrophages - metabolism
Material chemistry
Materials science
Mice
Molecular Weight
Nanospheres
Nanospheres - chemistry
Octanols - chemistry
Octonols
Particle Size
Photodynamic therapy
Photosensitizer
Photosensitizing Agents
Photosensitizing Agents - chemistry
Photosensitizing Agents - pharmacology
Phthalocyanine
Physical properties
Polyesters
Polyesters - chemical synthesis
Polyesters - chemistry
Polyethylene glycol
Polyethylene Glycols
Polyethylene Glycols - chemical synthesis
Polyethylene Glycols - chemistry
Polylactic acid
Proton Magnetic Resonance Spectroscopy
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Stability analysis
Static Electricity
Studies
Toxicity
Vero Cells
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Summary:For best photosensitizer activity phthalocyanine dyes used in photodynamic therapy should be molecularly dispersed. Polyethylene glycol-block-polylactide derivatives presenting benzyl side-groups were synthesized to encapsulate a highly lipophilic phthalocyanine dye (AlClPc) and evaluate the effect of π-π interactions on the nanocarrier colloidal stability and dye dispersion. Copolymers with 0, 1, 2 and 6 mol% of benzyl glycidyl ether (BGE) were obtained via polyethylene glycol initiated ring-opening copolymerization of D,l-lactide with BGE. The block copolymers formed stable, monodisperse nanospheres with low in vitro cytotoxicity. AlClPc loading increased the nanosphere size and affected their colloidal stability. The photo-physical properties of the encapsulated dye, studied in batch and after separation by field flow fractionation, demonstrated the superiority of plain PEG-PLA over BGE-containing copolymers in maintaining the dye in its monomeric (non-aggregated) form in aqueous suspension. High dye encapsulation and sustained dye release suggest that these nanocarriers are good candidates for photodynamic therapy. [Display omitted] •Polyethylene glycol-block-poly(lactide-co-benzyl glycidyl ether) were obtained.•The copolymers form stable non-cytotoxic nanospheres below 100 nm.•Less benzylated copolymer meant better chloroaluminum phthalocyanine dispersion.•Controlled release, stable and bright phthalocyanine nanocarriers were achieved.
ISSN:0928-4931
1873-0191
DOI:10.1016/j.msec.2018.09.022