Modulating Neuronal Responses by Controlled Integration of Acetylcholine‐like Functionalities in Biomimetic Polymers

Gumera, C. B.; Wang, Yadong

doi:10.1002/adma.200701747

Cited by 25 publications

(41 citation statements)

References 35 publications

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“…Due to the high reactivity of the epoxide groups, our preliminary attempts, including Tl(OAc) 3 -catalyzed transesterification, DCC/DMAP-mediated condensation, and the reaction between sodium sebacate and epichlorohydrin [35], led to complex reaction mixture and very low yields, and were therefore considered to be failures. Later, we prepared diglycidyl sebacate by epoxidation of diallyl sebacate, which was prepared via esterification of allyl alcohol and sebacic acid [33]. The yield was only approximately 60%, however, despite attempts to vary conditions such as reaction temperature, reaction time, and reactant ratio.…”

Section: Resultsmentioning

confidence: 99%

“…Glycerol-based polyesters prepared using direct chemical (Scheme 1) or lipase-catalyzed polycondensation are usually compromised by premature crosslinking, large polydispersity index (PDI), or low molecular weight [1, 30, 31]. We recently reported the application of epoxide ring-opening polymerization between biomolecules with primary amines and diglycidyl esters that led to polymers with free -OH groups [32, 33]. We reasoned that a similar polymerization between a diacid and a diglycidyl ester would produce a useful PSeD polyester (Fig.…”

Section: Introductionmentioning

confidence: 99%

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A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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Polyesters with free functional groups allow facile modifications with biomolecules, which can lead to versatile biomaterials that afford controlled interactions with cells and tissues. Efficient synthesis of functionalizable polyesters is still a challenge that greatly limits the availability and widespread applications of biofunctionalized synthetic polymers. Here we report a simple route to prepare a functionalizable polyester, poly(sebacoyl diglyceride) (PSeD) bearing free hydroxyl groups. The key synthetic step is an epoxide ring-opening polymerization, instead of the traditional polycondensation, that produces poly(glycerol sebacate) (PGS) [1]. PSeD has a more defined structure with mostly linear backbone, more free hydroxyl groups, higher molecular weight, and lower polydispersity than PGS. Crosslinking PSeD with sebacic acid yields a polymer five times tougher and more elastic than cured PGS. PSeD exhibits good cytocompatibility in vitro. Furthermore, functionalization by glycine proceeds with high efficiency. This versatile synthetic platform can offer a large family of biodegradable, functionalized polymers with tunable physiochemical and biological properties useful for a wide range of biomedical applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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“…For example, synthetic elastomers may also benefit from incorporating bioactive small molecules into the bulk material. [121] The utilization of naturally occurring molecules as monomers is compatible with established synthesis and processing techniques and could have substantial impact on improving the degree of cell-biomaterial interaction in tissue engineering scaffolds. Incorporating electronic and photonic capabilities within biodegradable elastomers may also be explored through careful monomer selection and efficient synthetic routes.…”

Section: Resultsmentioning

confidence: 99%

Biodegradable Elastomers for Tissue Engineering and Cell–Biomaterial Interactions

Bettinger¹

2011

Macromolecular Bioscience

118

101

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Synthetic biomaterials serve as a cornerstone in the development of clinically focused regenerative medicine therapies that aim to reduce suffering and prolong life. Recent improvements in biodegradable elastomeric materials utilize natural extracellular matrix proteins as inspiration to yield a new class of materials with superior degradation kinetics, desirable biocompatibility profiles, and mechanical properties that closely match those of soft tissues. This review describes several classes of synthetic biodegradable elastomers and associated fabrication techniques that are relevant to scaffold development. The application of these materials to select tissue engineering models is also discussed.

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“…The polymer surface prepared with 1:60 (mol/mol) of MePEG-GMA to DMAEMA induced neuronal growth response similar to that on poly-L-lysine. Christiane et al [37] have also incorporated ACh-like functionalities (ALFs) in a series of linear polymers based on diglycidylsebacate, leucine ethyl ester, and aminoethyl acetate. The polymers were also coated onto glass coverslips, and results showed that ALFs had a profound impact on sprouting and neurite extension of dorsal root ganglia (DRG) cells in a concentration-dependent manner, the polymer with 70% ALF induced regenerative responses similar to laminin.…”

Section: Discussionmentioning

confidence: 99%

The role of hydrogels with tethered acetylcholine functionality on the adhesion and viability of hippocampal neurons and glial cells

Zhou

Geller

et al. 2012

Biomaterials

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In neural tissue engineering, designing materials with the right chemical cues is crucial in providing a permissive microenvironment to encourage and guide neuronal cell attachment and differentiation. Modifying synthetic hydrogels with biologically active molecules has become an increasingly important route in this field to provide a successful biomaterial and cell interaction. This study presents a strategy of using the monomer 2-methacryloxyethyl trimethylammonium chloride (MAETAC) to provide tethered neurotransmitter acetylcholine-like functionality with a complete 2-acetoxy-N,N,N-trimethylethanaminium segment, thereby modifying the properties of commonly used, non-adhesive PEG-based hydrogels. The effect of the functional monomer concentration on the physical properties of the hydrogels was systematically studied, and the resulting hydrogels were also evaluated for mice hippocampal neural cell attachment and growth. Results from this study showed that MAETAC in the hydrogels promotes neuronal cell attachment and differentiation in a concentration-dependent manner, different proportions of MAETAC monomer in the reaction mixture produce hydrogels with different porous structures, swollen states, and mechanical strengths. Growth of mice hippocampal cells cultured on the hydrogels showed differences in number, length of processes and exhibited different survival rates. Our results indicate that chemical composition of the biomaterials is a key factor in neural cell attachment and growth, and integration of the appropriate amount of tethered neurotransmitter functionalities can be a simple and effective way to optimize existing biomaterials for neuronal tissue engineering applications.

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Modulating Neuronal Responses by Controlled Integration of Acetylcholine‐like Functionalities in Biomimetic Polymers

Cited by 25 publications

References 35 publications

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

Biodegradable Elastomers for Tissue Engineering and Cell–Biomaterial Interactions

The role of hydrogels with tethered acetylcholine functionality on the adhesion and viability of hippocampal neurons and glial cells

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