A biostable, anti-fouling zwitterionic polyurethane-urea based on PDMS for use in blood-contacting medical devices

Kim, Seungil; Ye, Sang‐Ho; Adamo, Arianna; Orizondo, Ryan A.; Jo, J.; Cho, Sung Kwon; Wagner, William R.

doi:10.1039/d0tb01220c

Cited by 46 publications

(38 citation statements)

References 31 publications

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“…Naphthalimide has been popularly known as an excellent chromophore with high molar absorption, high photostability, and low toxicity for developing fluorescent probes and clinical drugs but has been rarely reported as singlet oxygen sensitizers. On the other hand, several conventional approaches have been explored to enhance the ISC of organic chromophores such as heavy-atom effect (1), π–π* ↔ n−π* transition (2), charge transfer for D–A dyad based on radical-pair mechanism (3), exciton coupling (4), energy-matched S 1 ↔ T n states (5), and electron spin converter (6). − However, these typical methods have shown drawbacks such as often inefficient in large chromophores and dark toxicity in PDT treatment (1), short wavelength absorption (2), or the energy matching of S 1 ↔ T n states is difficult to predict. Additionally, the synthesis process is a challenge whereas the obtained ISC efficiency is not always satisfactory.…”

Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

“…In another approach, Zhao et al developed a Troger’s base derived from naphthalimide moieties ( 310 ) with spin–orbital charge-transfer (SOCT)-enhanced ISC (Figure ). − In contrast to conventional D–A dyads containing semirigid linkers, the linker between two chromophores is rigid and its rotation is fully inhibited. 310 exhibited absorption peak at 369 nm, strong fluorescence emission at 431 nm (Φ F = 0.84), and long-lived triplet state (τ T = 46 μs).…”

Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

“…However, orthogonal geometry and even photoinduced charge separation and charge recombination are not completely sufficient to obtain efficient SOCT-enhanced ISC. 563 To clear this challenge, Zhao et al synthesized a series of D−A dyads conjugated between perylene moieties and naphthalimide (314), 557,559 phenothiazine (315), 564 and carbazole (316) 565 units with SOCTenhanced ISC process (Figure 138). increased by the increasing electron-donating ability from phenyl to methoxyphenyl and then to methylthioxyphenyl (Figure 138).…”

Section: Metal Complexesmentioning

confidence: 99%

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Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

et al. 2021

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This review presents a robust strategy to design photosensitizers (PSs) for various species. Photodynamic therapy (PDT) is a photochemical-based treatment approach that involves the use of light combined with a light-activated chemical, referred to as a PS. Attractively, PDT is one of the alternatives to conventional cancer treatment due to its noninvasive nature, high cure rates, and low side effects. PSs play an important factor in photoinduced reactive oxygen species (ROS) generation. Although the concept of photosensitizer-based photodynamic therapy has been widely adopted for clinical trials and bioimaging, until now, to our surprise, there has been no relevant review article on rational designs of organic PSs for PDT. Furthermore, most of published review articles in PDT focused on nanomaterials and nanotechnology based on traditional PSs. Therefore, this review aimed at reporting recent strategies to develop innovative organic photosensitizers for enhanced photodynamic therapy, with each example described in detail instead of providing only a general overview, as is typically done in previous reviews of PDT, to provide intuitive, vivid, and specific insights to the readers.

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Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

Section: Metal Complexesmentioning

confidence: 99%

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Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

et al. 2021

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“…Recent research validates that the toxicity of PDMS coatings is dependent on the concentration [ 36 ] and that the increase in the molecular weight of PDMS can improve the cell survival rate [ 37 ]. Additionally, special anti-fouling properties of PDMS products have been achieved for elastomers with polyurethane urea [ 38 ], as well as for PEGMA brushes obtained via the surface-initiated ATRP technique on roller-casted multiple PDMS layers [ 39 ]. Cosmetic products containing PDMS create a film on the surface of the skin, which protects against microbes and moisture loss without interfering with the skin’s physiological functions, while improving its appearance and condition [ 40 ].…”

Section: Introductionmentioning

confidence: 99%

Micellar Carriers of Active Substances Based on Amphiphilic PEG/PDMS Heterograft Copolymers: Synthesis and Biological Evaluation of Safe Use on Skin

Odrobińska

Skonieczna

Neugebauer

2021

IJMS

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Amphiphilic copolymers containing polydimethylsiloxane (PDMS) and polyethylene glycol methyl ether (MPEG) were obtained via an azide-alkyne cycloaddition reaction between alkyne-functionalized copolymer of MPEG methacrylate and azide-functionalized PDMS. “Click” reactions were carried out with an efficiency of 33–47% increasing grafting degrees. The grafted copolymers were able to carry out the micellization and encapsulation of active substances, such as vitamin C (VitC), ferulic acid (FA) and arginine (ARG) with drug loading content (DLC) in the range of 2–68% (VitC), and 51–89% (FA or ARG). In vitro release studies (phosphate buffer saline, PBS; pH = 7.4 or 5.5) demonstrated that the maximum release of active substances was mainly after 1–2 h. The permeability of released active substances through membrane mimicking skin evaluated by transdermal tests in Franz diffusion cells indicated slight diffusion into the solution (2–16%) and their remaining in the membrane. Studies on the selected carrier with FA showed no negative effect on cell viability, proliferation capacity or senescence, as well as cell apoptosis/necrosis differences or cell cycle interruption in comparison with control cells. These results indicated that the presented micellar systems are good candidates for carriers of cosmetic substances according to physicochemical characterization and biological studies.

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“…PUs can be categorized as biodegradable or biostable based on stability against hydrolysis or oxidation in aqueous conditions or due to biological actors such as enzymes and phagocytes. Biostable PUs can be prepared using biodegradation‐resistant soft segments (e.g., polydimethylsiloxane‐diol) 2,3 and frequently employ aromatic diisocyanates which provide stronger van der Waals and hydrophobic intermolecular interaction than aliphatic diisocyanates 4 . Both the hard and soft segments can be modified to increase the glass transition temperature ( T g ), enhance mechanical strength, and alter other critical properties 5 .…”

Section: Chemistry Of Biodegradable Polyurethanesmentioning

confidence: 99%

Biodegradable polyurethane scaffolds in regenerative medicine: Clinical translation review

Pedersen

Kim

Wagner

2022

J Biomedical Materials Res

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Early explorations of tissue engineering and regenerative medicine concepts commonly utilized simple polyesters such as polyglycolide, polylactide, and their copolymers as scaffolds. These biomaterials were deemed clinically acceptable, readily accessible, and provided processability and a generally known biological response. With experience and refinement of approaches, greater control of material properties and integrated bioactivity has received emphasis and a broadened palette of synthetic biomaterials has been employed. Biodegradable polyurethanes (PUs) have emerged as an attractive option for synthetic scaffolds in a variety of tissue applications because of their flexibility in molecular design and ability to fulfill mechanical property objectives, particularly in soft tissue applications. Biodegradable PUs are highly customizable based on their composition and processability to impart tailored mechanical and degradation behavior. Additionally, bioactive agents can be readily incorporated into these scaffolds to drive a desired biological response. Enthusiasm for biodegradable PU scaffolds has soared in recent years, leading to rapid growth in the literature documenting novel PU chemistries, scaffold designs, mechanical properties, and aspects of biocompatibility. Despite the enthusiasm in the field, there are still few examples of biodegradable PU scaffolds that have achieved regulatory approval and routine clinical use. However, there is a growing literature where biodegradable PU scaffolds are being specifically developed for a wide range of pathologies and where relevant pre‐clinical models are being employed. The purpose of this review is first to highlight examples of clinically used biodegradable PU scaffolds, and then to summarize the growing body of reports on pre‐clinical applications of biodegradable PU scaffolds.

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A biostable, anti-fouling zwitterionic polyurethane-urea based on PDMS for use in blood-contacting medical devices

Abstract: Polydimethylsiloxane (PDMS) is commonly used in medical devices because it is non-toxic and stable against oxidative stress. Relatively high blood platelet adhesion and the need for chemical crosslinking through curing,...

Cited by 46 publications

References 31 publications

Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

Micellar Carriers of Active Substances Based on Amphiphilic PEG/PDMS Heterograft Copolymers: Synthesis and Biological Evaluation of Safe Use on Skin

Biodegradable polyurethane scaffolds in regenerative medicine: Clinical translation review

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