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Record W1974358760 · doi:10.1021/ja905343x

A Cascade Biodegradable Polymer Based on Alternating Cyclization and Elimination Reactions

2009· article· en· W1974358760 on OpenAlexafffund
Matthew A. DeWit, Elizabeth R. Gillies

Bibliographic record

VenueJournal of the American Chemical Society · 2009
Typearticle
Languageen
FieldMaterials Science
Topicbiodegradable polymer synthesis and properties
Canadian institutionsWestern University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryPolymerCopolymerAqueous solutionAmphiphilePolymer chemistryAmine gas treatingBiodegradable polymerDiamineCombinatorial chemistryMicelleEthylene oxideOrganic chemistry

Abstract

fetched live from OpenAlex

Polymers that depolymerize by a cascade of intramolecular reactions in response to the removal of a stabilizing end-cap can allow for an unprecedented degree of control over the polymer degradation process. Described here is the development of polymers comprising N,N'-dimethylethylenediamine and 4-hydroxybenzyl alcohol linked by carbamate linkages. The polycarbamate backbone is stable in aqueous solution, but removal of a protective end-cap from the amine terminus allows the diamine to cyclize, forming N,N'-dimethylimidazolidinone and releasing the phenol, which undergoes a 1,6-elimination followed by the release of CO(2) to reveal the next amine to continue the cascade. These polymers therefore degrade by alternating cyclization and elimination reactions. First, a tert-butylcarbamate (Boc) group was introduced as a cleavable end-cap, and the degradation kinetics and mechanism were studied by (1)H nuclear magnetic resonance (NMR) spectroscopy and size exclusion chromatography. Next, to demonstrate the degradability of these polymers under biologically relevant conditions, poly(ethylene oxide) was introduced as an end-cap via an ester linkage, to provide an amphiphilic block copolymer. This copolymer was found to assemble into cascade degradable nanoparticles that were capable of encapsulating and subsequently releasing a fluorescent dye in aqueous solution. This new class of polymers therefore provides highly promising materials that can be used for the development of medical devices, drug delivery vehicles, and tissue engineering scaffolds with unique biodegradation properties.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0010.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.015
GPT teacher head0.246
Teacher spread0.231 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations155
Published2009
Admission routes2
Has abstractyes

Explore more

Same venueJournal of the American Chemical SocietySame topicbiodegradable polymer synthesis and propertiesFrench-language works237,207