Tuning the crystallinity and degradability of PCL by organocatalytic copolymerization with δ-hexalactone

Song, Qilei; Xia, Yening; Hu, Shuangyan; Zhao, Junpeng; Zhang, Guangzhao

doi:10.1016/j.polymer.2016.09.026

Cited by 26 publications

(33 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to its high durability, PεCL has found a wide range of applications mainly for implantable medical devices [ 33 , 34 ], in which degradation occurs over two to four years [ 13 ]. However, to tailor their application for drug delivery purposes, faster degradation kinetics of the P ε CL are desirable and can be achieved by copolymerization of εCL with its isomer δCL [ 9 ]. Introducing δCL repeating units to the PεCL polymer decreases its degree of crystallinity [ 17 ], and as such, it increases its rate of degradation as confirmed by investigations of films [ 35 ].…”

Section: Resultsmentioning

confidence: 99%

“…Independent investigations of the influence of the polymer crystallinity on the resulting particle characteristics (e.g., particle formation and degradation) while keeping the key properties of the system constant are rare or only provide partial conclusions typically due to influences of a third variable [ 9 ]. In particular, alterations of HHB are frequently accompanied by changes in crystallinity [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187

et al. 2021

View full text Add to dashboard Cite

Seven polycaprolactones (PCL) with constant hydrophobicity but a varying degree of crystallinity prepared from the constitutional isomers ε-caprolactone (εCL) and δ-caprolactone (δCL) were utilized to formulate nanoparticles. The aim was to investigate the effect of the crystallinity of the bulk polymers on the enzymatic degradation of the particles. Furthermore, their efficiency to encapsulate the hydrophobic anti-inflammatory drug BRP-187 and the final in vitro performance of the resulting NPs were evaluated. Initially, high-throughput nanoprecipitation was employed for the εCL and δCL homopolymers to screen and establish important formulation parameters (organic solvent, polymer and surfactant concentration). Next, BRP-187-loaded PCL nanoparticles were prepared by batch nanoprecipitation and characterized using dynamic light scattering, scanning electron microscopy and UV-Vis spectroscopy to determine and to compare particle size, polydispersity, zeta potential, drug loading as well as the apparent enzymatic degradation as a function of the copolymer composition. Ultimately, NPs were examined for their potency in vitro in human polymorphonuclear leukocytes to inhibit the BRP-187 target 5-lipoxygenase-activating protein (FLAP). It was evident by Tukey’s multi-comparison test that the degree of crystallinity of copolymers directly influenced their apparent enzymatic degradation and consequently their efficiency to inhibit the drug target.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The aim of our study was to obtain PCL with varied degrees of crystallinity. Since δCL is rarely focused on, even in academic research, ,, a broad screening of the homopolymerization conditions represented the initial step of this study. Therefore, the organobase TBD was used as a catalyst at room temperature and parameters such as [monomer] to [initiator] ratio and monomer concentration in toluene were varied (see the SI for details).…”

Section: Resultsmentioning

confidence: 99%

“…As Song et al reported that a δCL fraction in the feed f δCL,0 of 50% resulted in amorphous materials, we varied the feed ratio of εCL and δCL between 80:20 and 50:50. For this purpose, the kinetics of five different statistical copolymerizations were examined applying the conditions described above ([CL] 0 :[BnOH] 0 :[TBD] 0 = 100:1:2; [CL] 0 = 4 mol L –1 in toluene at room temperature, Figures S15–S19).…”

Section: Resultsmentioning

confidence: 99%

“…In this regard, the copolymerization of the two isomers ε-caprolactone (εCL) and δ-caprolactone (δCL) represents a useful tool to access a library of materials featuring the same HHB. To the best of our knowledge, both monomers have only been copolymerized by Song et al, who focused on the enzymatic degradation of three statistical copolymers . However, detailed insights into the copolymerization kinetics and, hence, the copolymer microstructure remain unknown to date.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copolymerization of Caprolactone Isomers to Obtain Nanoparticles with Constant Hydrophobicity and Tunable Crystallinity

et al. 2020

View full text Add to dashboard Cite

To obtain a set of polycaprolactones (PCL) with varying crystallinity, the triazabicyclodecene-catalyzed copolymerization of the two constitutional isomers ε-caprolactone (εCL) and δ-caprolactone (δCL) was carried out at room temperature in toluene. Variation of the feed fraction of εCL from 50% to 80% and the detailed kinetic studies accompanied by application of terminal as well as nonterminal kinetic models suggested the formation of random copolymers. Differential scanning calorimetry and wide-angle X-ray scattering investigations revealed the decrease of melting temperatures and degree of crystallinity with the εCL fraction in the PCL. All copolymers were suited to obtain aqueous nanoparticle dispersions by means of nanoprecipitation. Encapsulation of the fluorescent probe pyrene confirmed a constant hydrophilic/hydrophobic balance of the nanoparticles.

show abstract

Noninvasive biosensing 3D scaffold to monitor degradation: The potential of fluorescent PCL and PLGA for tissue engineering

Balaburov,

Kamaraj,

Doyle

et al. 2023

J of Applied Polymer Sci

View full text Add to dashboard Cite

The nondestructive localization and traceability of polymers by fluorescent tagging has become a valuable tool for biomedical applications. Integration of fluorescent molecule to the pristine polymers could modify polymers' degradation rate which is still unpredictable from a scaffold application standpoint. The current study focused to understand the material perspective of fluorescently tagged biodegradable polymers such as polycaprolactone (PCL) and poly (d,l‐lactide‐co‐glycolide) (PLGA) with fluorescein amine isomer I (FITC). PCL‐FITC and PLGA‐FITC were characterized using FTIR for surface chemistry analysis and rheology for their mechanical properties. The grafted materials were utilized to form 3‐dimentional scaffolds, and their degradation was monitored under accelerated degradation conditions triggered by pH. It was found that PCL and PCL‐FITC had a very slow degradation rate, when compared to PLGA and PLGA‐FITC. Both the FITC tagged materials displayed a faster degradation rate compared to their respective pristine material. Biocompatibility of the FITC conjugated polymers was tested using human‐adipose derived stem cells (hADSCs) revealing that the sub products from the degradation of the polymers over 7 days did not negatively affect the cellular metabolic activity. This work highlights the significance of initial characterization of fluorescent modified polymers for future biomedical application.

show abstract

Tuning the crystallinity and degradability of PCL by organocatalytic copolymerization with δ-hexalactone

Cited by 26 publications

References 56 publications

Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187

Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187

Copolymerization of Caprolactone Isomers to Obtain Nanoparticles with Constant Hydrophobicity and Tunable Crystallinity

Noninvasive biosensing 3D scaffold to monitor degradation: The potential of fluorescent PCL and PLGA for tissue engineering

Contact Info

Product

Resources

About