Novel poly (2-oxazoline) block copolymer with aromatic heterocyclic side chains as a drug delivery platform
Open accessAbstract
Here we report a novel poly(2-oxazoline)-based block copolymer with the aromatic heterocyclic side chains in one block, poly(2-methyl-2-oxazoline)-b-poly(2-N,N-dimethyl-1,3,5-triazine-2,4-diamine-6-ethyl-2-oxazoline) (PMeOx-PcBOx), and demonstrate its potential application as a drug delivery platform. The copolymer was synthesized via the condensation of N,N-dimethylbiguanide with the methyl ester side chain in poly(2-methoxycarboxyethyl-2-oxazoline) block (PMestOx) of the PMeOx-PMestOx diblock copolymer. We confirmed the N,N-dimethylbiguanide condensation with PMestOx and the complete conversion of the side chain to the N,N-dimethyl-1,3,5-triazine-2,4-diamine-6-ethyl moiety by NMR spectroscopy, MALDI-TOF mass spectroscopy, UV-Vis spectroscopy, and titration analysis. The PMeOx-PcBOx copolymer self-assemble into polymeric micelles in aqueous solution. Successful encapsulation into these micelles has been demonstrated for 1) several poorly soluble drugs, such as bruceantin and LY2109761, and 2) dichloro(1,2-diaminocyclohexane)platinum(II) (DachPt). The first class of drugs is incorporated possibly via hydrogen bonding and pi-pi interactions with the PcBOx side groups, while the second one is likely forms coordination bonds with the same side groups. The capability of this new copolymer to solubilize a uniquely diverse set of active pharmaceutical ingredients suggests potential applications in drug delivery.
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Before adding the triazine ring, the polymer could not form micelles in aqueous solution.
“Prior to adding the ring structure, the polymer was unable to form micelles in aqueous solution.”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
The Results section (“Self-assembly of PMeOx-PcBOx copolymer”; page unavailable) reports that the triazine-containing polymer formed particles in aqueous media. It also reports no proton correlations in a test of the precursor, PMeOx-PMestOx, but does not establish that the precursor was unable to form micelles. The claim’s assertion about the polymer before modification is therefore unsupported. (LLM, conf=0.83)
Experimental — accuracy not yet measuredOver 24 hours, paclitaxel was not completely released from the PBuOx polymer but was completely released from the triazine-ring-based polymer.
“Their work showed that over 24 hours paclitaxel was not completely released from the PBuOx polymer while it was completely released from the triazine ring-based polymer.”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
The Results (Solubilization of poorly soluble small molecules; page not available) report that after 24 hours, less than 50% of paclitaxel had been released from P2, the PBuOx-containing polymer, while most had been released from the triazine-containing PcBOx polymer. They report over 80% release from PcBOx, not complete release; the Discussion calls its release profile “more complete,” not complete. (LLM, conf=0.92)
Experimental — accuracy not yet measuredAdditional molecular interactions in the core, such as hydrogen bonding and pi-pi interactions, can strengthen polymer-drug interactions.
“Additional molecular interactions existing in the core, such as hydrogen bonding and pi-pi interactions, are no less significant as they can strengthen the molecular interactions between the polymer and the drug in the core [28, 39].”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
A POx diblock copolymer with a triazine-ring hydrophobic block exhibits hydrophobic interaction and likely pi-pi stacking capabilities.
“Also, we have recently reported a POx based diblock copolymer which has a hydrophobic block consisting of a triazine ring and exhibits both hydrophobic interaction and likely pi-pi stacking capabilities [28].”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
The triazine-ring polymer structure conferred unique solubilization characteristics, likely through increased drug-polymer interaction modalities such as hydrogen bonding and pi-pi stacking.
“This polymer structure conferred some unique solubilization characteristics likely due increased modalities of drug-polymer interaction, such as hydrogen bonding and pi-pi stacking.”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
In vitro release can give some insights into differential affinity between drugs and various polymeric micelle core structures.
“While limited in scope, this study shows that in vitro release can give some insights into the differential affinity between drugs and various polymeric micelle core structures.”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
In Hwang et al.'s study, bruceantin release rate was approximately the same from triazine-ring-based and PMeOx-b-PBuOx-b-PMeOx micelles, while paclitaxel release was drastically different.
“While the rate of release of bruceantin from both types of the micelles was approximately the same, the rate of release of paclitaxel was drastically different.”
From Polymeric micelles for the delivery of poorly soluble drugs: From nanoformulation to clinical approval. (2020) · cites this paper as [28]
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- Authors
- Hwang, D., Ramsey, J. D., Makita, N., Sachse, C., Jordan, R., Sokolsky-Papkov, M., & Kabanov, A. V.
- Affiliations
- University of North Carolina at Chapel Hill (US)
- Technische Universität Dresden (DE)
- Corresponding author
- Kabanov, Alexander V.
- ORCID
- Venue
- Journal of Controlled Release
- Publisher
- Elsevier BV
- Published
- 2019-08
- Volume
- 307
- Pages
- 261-271
- ISSN
- 0168-3659 (ISSN-L)
- PMC
- PMC7482421
- OpenAlex
- W2953999598
- Cited by
- 40
- References
- 44
- Citations by year
- 2026: 4 · 2024: 4 · 2023: 5 · 2022: 11 · 2021: 10 · 2020: 4 · 2019: 2
- FWCI
- 2.74
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Journal of Controlled Release (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill
- National Cancer Institute
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › Nanoparticle-Based Drug Delivery
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Advanced Drug Delivery Systems
- Keywords
- polymeric micelles, drug encapsulation, self-assembly, poorly water-soluble drugs, bruceantin, LY2109761, platinum(II) complexes, drug solubilization, hydrogen bonding, π-π stacking, coordination bonding
- MeSH terms
- Animals, Antineoplastic Agents, Humans, Micelles, Oxazoles, Polymers, Drug Delivery Systems, Cell Line, Tumor, Mice, Drug Liberation
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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