Synthesis, thermal properties and cell-compatibility of photocrosslinked cinnamoyl-modified hydroxypropyl cellulose

Yano, Shinya; Iwase, Takumi; Teramoto, Naozumi; Shimasaki, Toshiaki; Shibata, Mitsuhiro

doi:10.1016/j.carbpol.2017.12.087

Cited by 17 publications

(12 citation statements)

References 48 publications

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“…Therefore, the surface wettability of poly(HEMA-co-CEMA) decreased with an increase of CEMA component and with photocrosslinking. This tendency was previously observed as we reported in our previous study [27,38].…”

Section: Surface Wettability Of Poly(hema-co-cema)supporting

confidence: 91%

“…These results are similar to the cell proliferation results on trehalose cinnamate and cinnamoyl-modified HPC, which we previously reported [27,38]. These studies revealed that the fibroblast cell adhesion and proliferation on crosslinked polymers were promoted most on thin films of photocrosslinked polymers carrying most cinnamoyl groups.…”

Section: Surface Wettability Of Poly(hema-co-cema)supporting

confidence: 90%

“…The T g of poly(HEMA-co-CEMA) decreased with an increase of the contents of CEMA components in the copolymer. As we previously reported for HPC [38], T g is considered to be influenced by the intermolecular interaction between hydroxyl groups. A decrease of hydroxy groups leads to a decrease of intermolecular interaction and subsequently to a decrease of T g .…”

Section: Synthesis Of Poly(hema-co-cema)mentioning

confidence: 92%

“…The unirradiated poly(HEMA-co-CEMA) had a main absorption peak at 283 nm attributed to the ethenylbenzene unit of cinnamoyl groups. This absorption decreased in the time course of UV irradiation, suggesting the occurrence of photo-dimerization [13][14][15]17,29,30,33,34,38,44]. The rate of this absorption decline of P(H60/C40) was higher than that of P(H25/C75) and that of P(H0/C100).…”

Section: Photocrosslinking Of Poly(hema-co-cema)mentioning

confidence: 96%

“…In order to investigate the necessity of trehalose, we synthesized hydroxypropyl cellulose (HPC) cinnamate (HPC-C) with different DS and carried out the cell growth assay. The assay revealed that the number of adherent cells slightly increased on the photocrosslinked HPC-C with highest DS compared to that with lower DS [38]. Therefore, as the next step, we subsequently planned to investigate the effect of cinnamoyl groups on cell adhesion and proliferation using polymers without carbohydrate backbone.…”

Section: Scheme 1 Dimerization Reaction Of Cinnamate Esters By Uv Irmentioning

confidence: 99%

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Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Yano

Iwase

Shibata

et al. 2020

J. Photopol. Sci. Technol.

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Cinnamoyl-modified methacrylate, 2-cinnamoyloxyethyl methacrylate (CEMA), was synthesized from 2-hydroxyethyl methacrylate (HEMA) and cinnamoyl chloride. Copolymers with various cinnamoyl contents were synthesized by random copolymerization of HEMA and CEMA at different feed ratios. Thus three copolymers with different CEMA contents were synthesized, and the monomer composition ([HEMA]:[CEMA]) in the copolymers ranged from 75:25 to 0:100. The coating films of copolymers on glass plates were prepared by the dip-coating method. Photo-induced dimerization of the cinnamoyl groups in the copolymers was confirmed by the ultraviolet-visible (UV-Vis) spectral changes. The cell proliferation on the photocrosslinked copolymers was tested using 3T3 Swiss albino mouse embryo fibroblasts. The results of the cell proliferation assay revealed that the photocrosslinked copolymers carrying more cinnamoyl groups promoted the cell proliferation compared with the photocrosslinked copolymers carrying less cinnamoyl groups. According to the results in the present study and our previous studies on cinnamoyl-modified trehalose and cinnamoyl-modified hydroxypropyl cellulose, it is presumable that the photodimerized cinnamoyl groups existing on the surface of materials at high density have some preferable effect on promoting fibroblast cell adhesion.

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Section: Surface Wettability Of Poly(hema-co-cema)supporting

confidence: 91%

Section: Surface Wettability Of Poly(hema-co-cema)supporting

confidence: 90%

Section: Synthesis Of Poly(hema-co-cema)mentioning

confidence: 92%

Section: Photocrosslinking Of Poly(hema-co-cema)mentioning

confidence: 96%

Section: Scheme 1 Dimerization Reaction Of Cinnamate Esters By Uv Irmentioning

confidence: 99%

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Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Yano

Iwase

Shibata

et al. 2020

J. Photopol. Sci. Technol.

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Cyclodextrin ‘Chaperones’ Enable Quasi‐Ideal Supramolecular Network Formation and Enhanced Photodimerization of Hydrophobic, Red‐shifted Photoswitches in Water

Hoenders,

Ludwanowski,

Barner‐Kowollik

et al. 2024

Angewandte Chemie

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Precision‐engineered light‐triggered hydrogels are important for a diversity of applications. However, fields such as biomaterials require wavelength outside the harsh UV regime to prevent photodamage, typically requiring chromophores with extended p‐conjugation that suffer from poor water solubility. Herein, we demonstrate how cyclodextrins can be used as auxiliary agents to not only solubilize such chromophores, but even to preorganize them in a 2:2 host‐guest inclusion complex to facilitate photodimerization. We apply our concept to styrylpyrene‐end‐functionalized star‐shaped polyethylene glycols (sPEGs). We initially unravel details of the host‐guest inclusion complex using spectroscopy and mass spectrometry to give clear evidence of a 2:2 complex formation. Subsequently, we show that the resultant supramolecularly linked hydrogels conform to theories of supramolecular quasi‐ideal model networks, and derive details on their association dynamics using in‐depth rheological measurements and kinetic models. By comparing sPEGs of different arm length, we further elucidate the model network topology and the accessible mechanical property space. The photo‐mediated dimerization proceeds smoothly, allowing to transform the supramolecular model networks into covalent ones. We believe that our strategy opens new avenues for executing hydrophobic photochemistry in aqueous environments with enhanced control over reactivity, hydrogel topology or programmable mechanical properties.

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Cyclodextrin ‘Chaperones’ Enable Quasi‐Ideal Supramolecular Network Formation and Enhanced Photodimerization of Hydrophobic, Red‐shifted Photoswitches in Water

Hoenders,

Ludwanowski,

Barner‐Kowollik

et al. 2024

Angew Chem Int Ed

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Synthesis, thermal properties and cell-compatibility of photocrosslinked cinnamoyl-modified hydroxypropyl cellulose

Cited by 17 publications

References 48 publications

Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Cyclodextrin ‘Chaperones’ Enable Quasi‐Ideal Supramolecular Network Formation and Enhanced Photodimerization of Hydrophobic, Red‐shifted Photoswitches in Water

Cyclodextrin ‘Chaperones’ Enable Quasi‐Ideal Supramolecular Network Formation and Enhanced Photodimerization of Hydrophobic, Red‐shifted Photoswitches in Water

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