In Vivo Degradation Mechanisms of Aliphatic Polycarbonates and Functionalized Aliphatic Polycarbonates

Amsden, Brian G.

doi:10.1002/mabi.202100085

Cited by 25 publications

(17 citation statements)

References 116 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Oligocarbonates, in contrast to oligoesters, degrade without the formation of carboxylic acids-only CO 2 and diols are produced. In the case of using aliphatic polyesters as biomaterials, a high local concentration of carboxylic acids leads to the harmful acidification of organisms [31]. Moreover, the hydrolysis of the carbonate linkage is accompanied by a much lower inflammatory reaction in the tissues surrounding the implemented material [32].…”

Section: Poly(urea-urethane)s Derived From Oligo(ester-carbonate) Dio...mentioning

confidence: 99%

Polymeric Materials Based on Carbon Dioxide: A Brief Review of Studies Carried Out at the Faculty of Chemistry, Warsaw University of Technology

et al. 2022

View full text Add to dashboard Cite

Carbon dioxide is an important raw material in many industrial technologies, but it is also one of the greenhouse gases that has to be effectively removed from the environment. This contribution provides a brief overview of carbon dioxide-based polymers developed in the laboratories of the Faculty of Chemistry at Warsaw University of Technology. We present some simple and versatile synthetic approaches that can be used to prepare a library of oligocarbonate diols, polycarbonates, poly(ester-carbonates), poly(ether-carbonates) and various types of polyurethanes, including the newly emerging family of environmentally friendly non-isocyanate polyurethanes. The main synthesis strategy involves the reaction of CO2 with oxiranes to form five-membered cyclic carbonates, which can be utilized as a source of carbonate bonds in polymeric materials obtained by the ester exchange reactions and/or step-growth polyaddition. We also show that cyclic carbonates are valuable starting materials in the synthesis of hyperbranched polymers and polymer networks. The properties of several CO2-based polymers are presented and their potential application as biomaterials, smart materials, and absorbers with a high CO2 capture capacity is discussed.

show abstract

Section: Poly(urea-urethane)s Derived From Oligo(ester-carbonate) Dio...mentioning

confidence: 99%

Polymeric Materials Based on Carbon Dioxide: A Brief Review of Studies Carried Out at the Faculty of Chemistry, Warsaw University of Technology

et al. 2022

View full text Add to dashboard Cite

show abstract

“…[24] Due to their hydrolytic biodegradability and biocompatibility, these features strongly suggest their translatability into clinical applications. [25][26][27] The carbonate motif has already been employed for degradable systems carrying carbonate moieties in the side chain [28,29] and, more significantly, as backbone in aliphatic polycarbonates. [30][31][32] Using amphiphilic polycarbonate block copolymers, nanoparticular systems can be selfassembled and applied for various therapeutic applications.…”

Section: Introductionmentioning

confidence: 99%

End Group Dye‐Labeled Polycarbonate Block Copolymers for Micellar (Immuno‐)Drug Delivery

Czysch

Medina‐Montano

Dal

et al. 2022

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Defined conjugation of functional molecules to block copolymer end groups is a powerful strategy to enhance the scope of micellar carriers for drug delivery. In this study, an approach to access well-defined polycarbonate-based block copolymers by labeling their end groups with single fluorescent dye molecules is established. Following controlled polymerization conditions, the block copolymers' primary hydroxy end group can be converted into activated pentafluorophenyl ester carbonates and subsequently aminolyzed with fluorescent dyes that are equipped with primary amines. During a solvent-evaporation process, the resulting end group dye-labeled block copolymers self-assemble into narrowly dispersed ∼25 nm-sized micelles and simultaneously encapsulate hydrophobic (immuno-)drugs. The covalently attached fluorescent tracer can be used to monitor both uptake into cells and stability under biologically relevant conditions, including incubation with blood plasma or during blood circulation in zebrafish embryos. By encapsulation of the toll-like receptor 7/8 (TLR7/8) agonist CL075, immune stimulatory polymeric micelles are generated that get internalized by various antigen-presenting dendritic cells and promote their maturation. Generally, such end group dye-labeled polycarbonate block copolymers display ideal features to permit targeted delivery of hydrophobic drugs to key immune cells for vaccination and cancer immunotherapy.

show abstract

“…[35] To enhance chemical translatability, materials with a broader range of degradability and an intrinsically limited lifetime are needed to prevent long-term toxicities. [36,37] These criteria could, for instance, be met by nanocarrier systems that gradually hydrolyze in aqueous environment.…”

Section: Introductionmentioning

confidence: 99%

“…In their case, degradation results in diols and the weak acid carbon dioxide which is unlikely to cause acidification and similar adverse effects. [36,45] Especially, the archetypal poly(trimethylene carbonate) (PTMC) was explored in this regard as a biodegradable and biocompatible implant material. [46][47][48] However, PTMC is lacking chemical moieties to introduce functionalities.…”

Section: Introductionmentioning

confidence: 99%

“…Notable examples of hydrolysable architectures are aliphatic polyesters and aliphatic polycarbonates. [36,[38][39][40][41] Unfortunately, as polyesters degrade, they acidify the surrounding media, which can lead to local tissue irritation and toxicity, limiting their applicability. [42][43][44] In contrast to that, aliphatic polycarbonates are more promising due to their favorable degradation products.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Transient Lymph Node Immune Activation by Hydrolysable Polycarbonate Nanogels

Czysch

Medina‐Montano

Zhong

et al. 2022

Adv Funct Materials

View full text Add to dashboard Cite

The development of controlled biodegradable materials is of fundamental importance in immunodrug delivery to spatiotemporally controlled immune stimulation but avoid systemic inflammatory side effects. Based on this, polycarbonate nanogels are developed as degradable micellar carriers for transient immunoactivation of lymph nodes. An imidazoquinoline-type TLR7/8 agonist is covalently conjugated via reactive ester chemistry to these nanocarriers. The nanogels not only provide access to complete disintegration by the hydrolysable polymer backbone, but also demonstrate a gradual disintegration within several days at physiological conditions (PBS, pH 6.4-7.4, 37 °C). These intrinsic properties limit the lifetime of the carriers but their payload can still be successfully leveraged for immunological studies in vitro on primary immune cells as well as in vitro. For the latter, a spatiotemporal control of immune cell activation in the draining lymph node is found after subcutaneous injection. Overall, these features render polycarbonate nanogels a promising delivery system for transient activation of the immune system in lymph nodes and may consequently become very attractive for further development toward vaccination or cancer immunotherapy. Due to the intrinsic biodegradability combined with the high chemical control during the manufacturing process, these polycarbonate-based nanogels may also be of great importance for clinical translation.

show abstract

In Vivo Degradation Mechanisms of Aliphatic Polycarbonates and Functionalized Aliphatic Polycarbonates

Cited by 25 publications

References 116 publications

Polymeric Materials Based on Carbon Dioxide: A Brief Review of Studies Carried Out at the Faculty of Chemistry, Warsaw University of Technology

Polymeric Materials Based on Carbon Dioxide: A Brief Review of Studies Carried Out at the Faculty of Chemistry, Warsaw University of Technology

End Group Dye‐Labeled Polycarbonate Block Copolymers for Micellar (Immuno‐)Drug Delivery

Transient Lymph Node Immune Activation by Hydrolysable Polycarbonate Nanogels

Contact Info

Product

Resources

About