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Preparation of photocrosslinked fish elastin polypeptide/microfibrillated cellulose composite gels with elastic properties for biomaterial applications.

Yano S, Mori M, Teramoto N, Iisaka M, Suzuki N, Noto M, Kaimoto Y, Kakimoto M, Yamada M, Shiratsuchi E, Shimasaki T, Shibata M - Mar Drugs (2015)

Bottom Line: We obtained hydrogels successfully by substitution of DMSO with water.The tensile test of the composite gels revealed that the addition of MFC improved the tensile properties, and the shape of the stress-strain curve of the composite gel became more similar to the typical shape of an elastic material with an increase of MFC content.The cell proliferation test on the composite gel showed no toxicity.

View Article: PubMed Central - PubMed

Affiliation: Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. shinya.y08232@gmail.com.

ABSTRACT
Photocrosslinked hydrogels reinforced by microfibrillated cellulose (MFC) were prepared from a methacrylate-functionalized fish elastin polypeptide and MFC dispersed in dimethylsulfoxide (DMSO). First, a water-soluble elastin peptide with a molecular weight of ca. 500 g/mol from the fish bulbus arteriosus was polymerized by N,N'-dicyclohexylcarbodiimide (DCC), a condensation reagent, and then modified with 2-isocyanatoethyl methacrylate (MOI) to yield a photocrosslinkable fish elastin polypeptide. The product was dissolved in DMSO and irradiated with UV light in the presence of a radical photoinitiator. We obtained hydrogels successfully by substitution of DMSO with water. The composite gel with MFC was prepared by UV irradiation of the photocrosslinkable elastin polypeptide mixed with dispersed MFC in DMSO, followed by substitution of DMSO with water. The tensile test of the composite gels revealed that the addition of MFC improved the tensile properties, and the shape of the stress-strain curve of the composite gel became more similar to the typical shape of an elastic material with an increase of MFC content. The rheology measurement showed that the elastic modulus of the composite gel increased with an increase of MFC content. The cell proliferation test on the composite gel showed no toxicity.

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FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly.
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marinedrugs-13-00338-f001: FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly.

Mentions: After purification of ElaPoly, the modification reaction with 2-methacryloyloxyethylisocyanate (MOI) was carried out in dimethylsulfoxide (DMSO). The reaction product (ME-ElaPoly) was soluble in DMSO and N,N-dimethylformamide (DMF) but slightly soluble in water. Since ElaPep and ElaPoly are soluble in DMSO and water but insoluble in DMF, ME-ElaPoly is more hydrophobic than ElaPep and ElaPoly. Figure 1 shows the FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly, and Figure 2 shows the 1H NMR spectra of ElaPep, ElaPoly, and ME-ElaPoly. It is known that a peptide bond has two absorption bands of amide I at 1680–1620 cm−1 and amide II at 1510–1580 cm−1 in FT-IR spectroscopy. Though these two absorption peaks did not split clearly in the spectrum of ElaPep, they split clearly at 1650 cm−1 (amide I) and 1540 cm−1 (amide II) in that of ElaPoly. This result indicates the formation of peptide bonds. After the reaction of ElaPoly with MOI, the increase in the absorbance related with methacrylate groups and urethane bonds was expected. However, the increase was not observed clearly, because the modification with MOI only partially occurred. The modification was confirmed clearly by the NMR spectral changes. In the NMR spectrum of ME-ElaPoly, four signals appeared. Two signals corresponding to the unsaturated methacrylate groups were observed at 6.1 ppm and 5.6 ppm, and a signal corresponding to the methyl protons of the methacrylate group was observed at 1.8 ppm. A signal corresponding to the methylene protons of –O–CH2– was observed at 4.1 and 4.2 ppm. A signal corresponding to the methylene protons of –CH2–N< was not observed, because the signal overlaps the signal of water at 3.4 ppm. These results confirmed the synthesis of ME-ElaPoly. The isocyanate groups of MOI react with hydroxyl groups, amino groups, mercapto groups, and carboxyl groups. Since the content of amino acids that react with isocyanate groups—that is Asp, Cys, Glu, Hyp, Lys, Ser, Thr, and Tyr—is obtained from the amino acid composition of ElaPep, the degree of conversion can be calculated using signal integral values of the 1H NMR spectra. We calculated the degree of conversion, and found that the degree of conversion for ME-ElaPoly was 26%.


Preparation of photocrosslinked fish elastin polypeptide/microfibrillated cellulose composite gels with elastic properties for biomaterial applications.

Yano S, Mori M, Teramoto N, Iisaka M, Suzuki N, Noto M, Kaimoto Y, Kakimoto M, Yamada M, Shiratsuchi E, Shimasaki T, Shibata M - Mar Drugs (2015)

FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306940&req=5

marinedrugs-13-00338-f001: FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly.
Mentions: After purification of ElaPoly, the modification reaction with 2-methacryloyloxyethylisocyanate (MOI) was carried out in dimethylsulfoxide (DMSO). The reaction product (ME-ElaPoly) was soluble in DMSO and N,N-dimethylformamide (DMF) but slightly soluble in water. Since ElaPep and ElaPoly are soluble in DMSO and water but insoluble in DMF, ME-ElaPoly is more hydrophobic than ElaPep and ElaPoly. Figure 1 shows the FT-IR spectra of ElaPep, ElaPoly, and ME-ElaPoly, and Figure 2 shows the 1H NMR spectra of ElaPep, ElaPoly, and ME-ElaPoly. It is known that a peptide bond has two absorption bands of amide I at 1680–1620 cm−1 and amide II at 1510–1580 cm−1 in FT-IR spectroscopy. Though these two absorption peaks did not split clearly in the spectrum of ElaPep, they split clearly at 1650 cm−1 (amide I) and 1540 cm−1 (amide II) in that of ElaPoly. This result indicates the formation of peptide bonds. After the reaction of ElaPoly with MOI, the increase in the absorbance related with methacrylate groups and urethane bonds was expected. However, the increase was not observed clearly, because the modification with MOI only partially occurred. The modification was confirmed clearly by the NMR spectral changes. In the NMR spectrum of ME-ElaPoly, four signals appeared. Two signals corresponding to the unsaturated methacrylate groups were observed at 6.1 ppm and 5.6 ppm, and a signal corresponding to the methyl protons of the methacrylate group was observed at 1.8 ppm. A signal corresponding to the methylene protons of –O–CH2– was observed at 4.1 and 4.2 ppm. A signal corresponding to the methylene protons of –CH2–N< was not observed, because the signal overlaps the signal of water at 3.4 ppm. These results confirmed the synthesis of ME-ElaPoly. The isocyanate groups of MOI react with hydroxyl groups, amino groups, mercapto groups, and carboxyl groups. Since the content of amino acids that react with isocyanate groups—that is Asp, Cys, Glu, Hyp, Lys, Ser, Thr, and Tyr—is obtained from the amino acid composition of ElaPep, the degree of conversion can be calculated using signal integral values of the 1H NMR spectra. We calculated the degree of conversion, and found that the degree of conversion for ME-ElaPoly was 26%.

Bottom Line: We obtained hydrogels successfully by substitution of DMSO with water.The tensile test of the composite gels revealed that the addition of MFC improved the tensile properties, and the shape of the stress-strain curve of the composite gel became more similar to the typical shape of an elastic material with an increase of MFC content.The cell proliferation test on the composite gel showed no toxicity.

View Article: PubMed Central - PubMed

Affiliation: Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. shinya.y08232@gmail.com.

ABSTRACT
Photocrosslinked hydrogels reinforced by microfibrillated cellulose (MFC) were prepared from a methacrylate-functionalized fish elastin polypeptide and MFC dispersed in dimethylsulfoxide (DMSO). First, a water-soluble elastin peptide with a molecular weight of ca. 500 g/mol from the fish bulbus arteriosus was polymerized by N,N'-dicyclohexylcarbodiimide (DCC), a condensation reagent, and then modified with 2-isocyanatoethyl methacrylate (MOI) to yield a photocrosslinkable fish elastin polypeptide. The product was dissolved in DMSO and irradiated with UV light in the presence of a radical photoinitiator. We obtained hydrogels successfully by substitution of DMSO with water. The composite gel with MFC was prepared by UV irradiation of the photocrosslinkable elastin polypeptide mixed with dispersed MFC in DMSO, followed by substitution of DMSO with water. The tensile test of the composite gels revealed that the addition of MFC improved the tensile properties, and the shape of the stress-strain curve of the composite gel became more similar to the typical shape of an elastic material with an increase of MFC content. The rheology measurement showed that the elastic modulus of the composite gel increased with an increase of MFC content. The cell proliferation test on the composite gel showed no toxicity.

Show MeSH
Related in: MedlinePlus