Self-assembly behavior of thermoresponsive difunctionalized γ-amide polycaprolactone amphiphilic diblock copolymers

Stefan, Mihaela C.; Wang, Hanghang; Calubaquib, Erika L.; Bhadran, Abhi; Ma, Ziyuan; Miller, Justin T.; Zhang, Anyue

doi:10.1039/d2py01444k

Cited by 3 publications

(5 citation statements)

References 52 publications

(92 reference statements)

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“… Examples of recently reported functional CL monomers [ 32 , 34 , 36 , 57 , 64 , 70 , 71 , 72 , 73 ]. …”

Section: Functional Pclmentioning

confidence: 99%

“…For example, Stefan et al reported TBD-catalyzed ROP of γ-amide functionalized ε-CL monomers. Their work demonstrated that TBD could initiate the synthesis of amphiphilic homopolymers as well as amphiphilic block copolymers ( Figure 7 ) [ 32 , 70 ].…”

Section: Functional Pclmentioning

confidence: 99%

“…Thermo-responsive polymers reported as DDS are known to undergo phase transition between a hydrated state and a dehydrated state above or below their critical solution temperature (CST) [ 170 ], as represented in Figure 16 . These thermo-responsive polymers become globular in a hydrated state and coil-like once dehydrated [ 13 , 70 , 171 ]. The temperature above which thermo-responsive polymers are insoluble in aqueous solution is termed lower critical solution temperature (LCST) and is often determined as the temperature at which there is a 50% drop in the transmittance as the polymer solution is heated [ 12 , 13 , 160 , 161 ].…”

Section: Stimuli-responsive Pcl For Drug Releasementioning

confidence: 99%

“… Synthesis of ( a ) amphiphilic homopolymer, ( b ) amphiphilic block copolymer based on amide functionalized PCL [ 32 , 70 ]. …”

Section: Figurementioning

confidence: 99%

See 3 more Smart Citations

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Bhadran,

Shah,

Babanyinah

et al. 2023

Pharmaceutics

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Poly(ε-Caprolactone)s are biodegradable and biocompatible polyesters that have gained considerable attention for drug delivery applications due to their slow degradation and ease of functionalization. One of the significant advantages of polycaprolactone is its ability to attach various functionalities to its backbone, which is commonly accomplished through ring-opening polymerization (ROP) of functionalized caprolactone monomer. In this review, we aim to summarize some of the most recent advances in polycaprolactones and their potential application in drug delivery. We will discuss different types of polycaprolactone-based drug delivery systems and their behavior in response to different stimuli, their ability to target specific locations, morphology, as well as their drug loading and release capabilities.

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“… Examples of recently reported functional CL monomers [ 32 , 34 , 36 , 57 , 64 , 70 , 71 , 72 , 73 ]. …”

Section: Functional Pclmentioning

confidence: 99%

Section: Functional Pclmentioning

confidence: 99%

Section: Stimuli-responsive Pcl For Drug Releasementioning

confidence: 99%

“… Synthesis of ( a ) amphiphilic homopolymer, ( b ) amphiphilic block copolymer based on amide functionalized PCL [ 32 , 70 ]. …”

Section: Figurementioning

confidence: 99%

See 2 more Smart Citations

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Bhadran,

Shah,

Babanyinah

et al. 2023

Pharmaceutics

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“…Thermoresponsive carriers having a lower critical solution temperature (LCST) can preserve their cargo below the LCST and undergo phase transition upon application of heat, which leads to a burst release of the drug into the tumor tissue. ,,,, Polymers with LCSTs in the range of 38–42 °C are desired for drug delivery, such that the exterior block remains water-soluble at a physiological temperature (37 °C) but dehydrates upon gentle heating (achieved by localized ultrasound or mild hyperthermia). ,− We previously demonstrated that the tri(ethylene glycol)-substituted PCLs (PME 3 CL) are hydrophilic and thermoresponsive and their amphiphilic block copolymers have tunable LCST. ,,, PME 3 CL-based amphiphilic block copolymers have an LCST in the range of 31–43 °C, which is highly dependent on the substituents attached to the hydrophobic block and the ratio of the hydrophobic to hydrophilic blocks. , The polymeric micelles formed from these polymers are utilized for the delivery of anticancer drugs such as doxorubicin (DOX), and thermally controlled drug release can also be achieved. ,, …”

Section: Introductionmentioning

confidence: 99%

Reversible Cross-linked Thermoresponsive Polycaprolactone Micelles for Enhanced Stability and Controlled Release

Bhadran,

Polara,

Calubaquib

et al. 2023

Biomacromolecules

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Thermoresponsive amphiphilic poly(ε-caprolactone)s (PCL)s are excellent candidates for drug delivery due to their biodegradability, biocompatibility, and controlled release. However, the thermoresponsivity of modified PCL can often lead to premature drug release because their lower critical solution temperature (LCST) is close to physiological temperature conditions. To address this issue, we developed a novel approach that involves functionalizing redox-responsive lipoic acid to the hydrophobic block of PCL. Lipoic acid has disulfide bonds that undergo reversible cross-linking after encapsulating the drug. Herein, we synthesized an ether-linked propargyl-substituted PCL as the hydrophobic block of an amphiphilic copolymer along with unsubstituted PCL. The propargyl group was used to attach lipoic acid through a postpolymerization modification reaction. The hydrophilic block is composed of an ether-linked, thermoresponsive tri(ethylene glycol)-substituted PCL. Anticancer drug doxorubicin (DOX) was encapsulated within the core of the micelles and induced cross-linking in the presence of a reducing agent, dithiothreitol. The developed micelles are thermodynamically stable and demonstrated thermoresponsivity with an LCST value of 37.5 °C but shifted to 40.5 °C after cross-linking. The stability and release of both uncross-linked (LA-PCL) and cross-linked (CLA-PCL) micelles were studied at physiological temperatures. The results indicated that CLA-PCL was stable, and only 35% release was observed after 46 h at 37 °C while LA-PCL released more than 70% drug at the same condition. Furthermore, CLA-PCL was able to release a higher amount of DOX in the presence of glutathione and above the LCST condition (42 °C). Cytotoxicity experiments revealed that CLA-PCL micelles are more toxic toward MDA-MB-231 breast cancer cells at 42 °C than at 37 °C, which supported the thermoresponsive release of the drug. These results indicate that the use of reversible cross-linking is a great approach toward synthesizing stable thermoresponsive micelles with reduced premature drug leakage.

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Fabrication and characterization of strontium- and copper-doped bioactive glasses modified biodegradable MgO-PCL coated magnesium biomaterials

Amukarimi,

Zadshakoyan,

Mobasherpour

2024

Appl. Phys. A

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Self-assembly behavior of thermoresponsive difunctionalized γ-amide polycaprolactone amphiphilic diblock copolymers

Abstract: Polycaprolactone (PCL)-based polymeric micelles are extensively used as drug delivery carriers to improve the bioavailability of poorly water soluble drugs due to their convenient tunability by varying functional groups on...

Cited by 3 publications

References 52 publications

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Reversible Cross-linked Thermoresponsive Polycaprolactone Micelles for Enhanced Stability and Controlled Release

Fabrication and characterization of strontium- and copper-doped bioactive glasses modified biodegradable MgO-PCL coated magnesium biomaterials

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