A polymer–drug conjugate for doxorubicin: Synthesis and biological evaluation of pluronic F127‐doxorubicin amide conjugates

Gao, Qihe; Han, Xuelian; Zhu, Jin; Chen, Renjie; Sun, Bai‐Wang

doi:10.1002/app.35613

Cited by 9 publications

(9 citation statements)

References 32 publications

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“…In vitro cytotoxicity of these prodrugs for murine leukemia cell lines P388/O and L1210/O was studied (Table 10). The cytotoxicitiy of prodrugs 1−3, having an ester linkage between Ptx and PEG, were very close to the cytotoxicity of 60 (c) Doxpoly(lactic-co-glycolic acid) (Dox-PLGA), 251 (d) folic acid-polyethylene glycol-Dox (Fol-PEG-Dox), 214 (e) polyethylene glycol-block-peptide-Dox (PEG-b-peptide-Dox), 256 (f) folic acid-polyethylene glycol-block-polycaprolactone-Dox (Fol-PEG-b-PCL-Dox), 11 (g) polyethylene glycol-Dox (PEG-Dox), 12 (h) pluronic F127-Dox (F127-Dox), 47 (i) Dox-aconitic acid linker-polyethylene glycol (Dox-CA-PEG), 45 (j) Dox-succinic acid linkerpolyethylene glycol (Dox-SA-PEG). free Ptx, which implies the release of Ptx by hydrolysis of the ester bond.…”

Section: End-functionalization Of Polymers With Drugsmentioning

confidence: 99%

Designing Smart Polymer Conjugates for Controlled Release of Payloads

2018

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Incorporating labile bonds inside polymer backbone and side chains yields interesting polymer materials that are responsive to change of environmental stimuli. Drugs can be conjugated to various polymers through different conjugation linkages and spacers. One of the key factors influencing the release profile of conjugated drugs is the hydrolytic stability of the conjugated linkage. Generally, the hydrolysis of acid-labile linkages, including acetal, imine, hydrazone, and to some extent β-thiopropionate, are relatively fast and the conjugated drug can be completely released in the range of several hours to a few days. The cleavage of ester linkages are usually slow, which is beneficial for continuous and prolonged release. Another key structural factor is the water solubility of polymer-drug conjugates. Generally, the release rate from highly water-soluble prodrugs is fast. In prodrugs with large hydrophobic segments, the hydrophobic drugs are usually located in the hydrophobic core of micelles and nanoparticles, which limits the access to the water, hence lowering significantly the hydrolysis rate. Finally, self-immolative polymers are also an intriguing new class of materials. New synthetic pathways are needed to overcome the fact that much of the small molecules produced upon degradation are not active molecules useful for biomedical applications.

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Section: End-functionalization Of Polymers With Drugsmentioning

confidence: 99%

Designing Smart Polymer Conjugates for Controlled Release of Payloads

2018

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“…Unfortunately, most anticancer drugs show systemic side effects due to nonspecific uptake by the healthy noncancerous tissue. Side effects associated with chemotherapy limit the dose or cumulative doses that can be administered to the patients, which can lead to relapse of tumors as well as development of drug resistance [17]. In order to reduce the harm to normal cells and effectively kill the cancer cells, it is crucial to target the release of drugs.…”

Section: Introductionmentioning

confidence: 99%

A pH-sensitive theranostics system based on doxorubicin conjugated with the comb-shaped polymer coating of quantum dots

Wang

Zhang

et al. 2014

J Mater Sci

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A two-phase route was developed to form a new theranostics-based system. The comb polymer poly (glycidyl methacrylate)-graft-ethane diamine-graft-polyethylene glycol (PGMA-g-EDA-g-PEG) was used to modify the quantum dots (QDs) by the method of ligand exchange. Subsequently, due to a large amount of amino groups on the surface of QDs, the doxorubicin (DOX) was conjugated by amine bonds to form pH-sensitive drug release system. UV-vis transmission spectra and PL spectra showed that the nanoparticles maintained the optical properties of QDs and DOX. The transmission electron microscopy analysis indicated that QDs were well dispersed in water and still had small sizes (7 nm) after ligand exchange and conjugated with DOX. Then the thermogravimetric analysis (TGA) revealed that about 80 wt% comb-shaped polymers coated on the surface of QDs, and about 10 wt% QDs was in nanoparticles PGMAg-EDA-g-PEG-QDs-DOX. In vitro release studies showed that PGMA-g-EDA-g-PEG -DOX and PGMA-g-EDA-g-PEG-QDs-DOX were pH sensitive. Findings from this study suggested that nanoparticles PGMA-g-EDA-g-PEGQDs-DOX can be used in a new field combined both imaging and targeted therapy.

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“…Because of the unique polymorphism character of Pluronic and biocompatibility, they are used as drug carriers. Drug delivery systems for doxorubicin based on the Pluronic F127 have been prepared for target specific drug delivery [24,25], bio-imaging [26] and for activity against multidrug-resistant cells [27]. Similarly, drug delivery systems comprising of P123 have also been used for targetspecific drug delivery [28] and nano-sized drug delivery systems [29] of doxorubicin.…”

Section: Introductionmentioning

confidence: 99%

“…Earlier studies on fluorescence quenching of DOX by the nucleotide, adenosine-5′-monophosphate revealed that DOX exists in two conformations having a difference in hydrogen bonding [30]. The concentration of DOX used in different Pluronic/ DOX systems ranges from 10 −3 to 10 −5 M [23,24,31]. However, DOX self-associates to form dimers in aqueous solutions at higher concentrations, and in the nanosecond timescales the dimers are reportedly non-fluorescent and have no significant pharmaceutical importance [1].…”

Section: Introductionmentioning

confidence: 99%

A Fluorescence Study of the Interaction of Anticancer Drug Molecule Doxorubicin Hydrochloride in Pluronic P123 and F127 Micelles

2020

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Drug delivery systems for the sustained and target delivery of doxorubicin to tumor cells are a topic of interest due to the efficacy of the doxorubicin in cancer treatment. The use of polymers such as Pluronic is being studied widely for the formulation of doxorubicin hydrochloride. However, the basic understanding of the physicochemical properties of pluronic micelles in presence of doxorubicin hydrochloride is a very essential topic of study. Doxorubicin hydrochloride is fluorescent; this helped us to study its sensitivity towards the Pluronic microenvironment using the fluorescence technique. In this work, the interaction and place of location of doxorubicin hydrochloride in Pluronic F127 and P123 micelles has been studied extensively using steady-state fluorescence intensity, dynamic fluorescence lifetime, quenching studies, dynamic light scattering, and zeta potential measurements, at different Pluronic concentrations. Using a fluorescence quenching experiment, doxorubicin hydrochloride was found to reside near the hydrophilic PEO corona region of the Pluronic micelles. For both the Pluronic, in the concentration range of study, the micellar size was found to be below 30 nm; this may have a greater advantage for various applications.

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A polymer–drug conjugate for doxorubicin: Synthesis and biological evaluation of pluronic F127‐doxorubicin amide conjugates

Cited by 9 publications

References 32 publications

Designing Smart Polymer Conjugates for Controlled Release of Payloads

Designing Smart Polymer Conjugates for Controlled Release of Payloads

A pH-sensitive theranostics system based on doxorubicin conjugated with the comb-shaped polymer coating of quantum dots

A Fluorescence Study of the Interaction of Anticancer Drug Molecule Doxorubicin Hydrochloride in Pluronic P123 and F127 Micelles

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