Preparation and Characterization of Novel Dopamine-based Bioadhesive Hydrogels†

doi:10.7503/cjcu20160443

Abstract

Abstract:

In order to replace conventional sutures in wound closing applications, a favorable bioadhesive that has strong bonding strength, good biocompatibility and appropriate biodegradability is extremely needed. In this study, periodate oxidized alginate was modified by dopamine to obtain catechol-based oxidized alginate(COA) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide/N-hydroxysuccinimide(EDC/NHS) as catalyst. Then COA was crosslinked with collagen to further obtain a novel COA-collagen bioadhesive hydrogel. The microstructure of COA was characterized by ultraviolet-visible(UV-Vis), Fourier transform infrared spectrophotometer(FTIR) and proton nuclear magnetic resonance(¹H NMR) spectroscopy. Meanwhile, the structure, equilibrium swelling ratio, degradation rate, bonding strength and cytotoxicity of the hydrogel were also evaluated. The results showed that the grafting-copolymerization of dopamine to oxidized alginate happened successfully and the degree of the substitution(DS) of dopamine was 12.5%, 18% and 22%, respectively. The hydrogels exhibited typical porous network. The equilibrium swelling ratio of the hydrogels decreased firstly and increased with the substitution ratio of dopamine increasing at last. The degradation rate of the hydrogels became lower with the increase of dopamine substitution ratio. The bonding strength of the hydrogel increased from (20.43±4.21) kPa to (29.91±6.10) kPa after modified with dopamine. Moreover, the results obtained in the methyltetrazolium(MTT) study showed that no extra cytotoxicity, which was of importance to develop a kind of biomaterials. In conclusion, the results suggest that the COA-COL bioadhesive hydrogel can potentially be a promising alternative for use in wound closing applications.

Key words: Dopamine, Periodate oxidized alginate, Collagen, Hydrogel, Bioadhesion

CLC Number:

O636.9

TrendMD:

CUI Guolian, DAN Nianhua, DAN Weihua. Preparation and Characterization of Novel Dopamine-based Bioadhesive Hydrogels^†[J]. Chem. J. Chinese Universities, 2017, 38(2): 318.

Figures/Tables 8

Fig.1 UV-Vis spectra of dopamine(a), COA-0(b), COA-12.5%(c), COA-18%(d) and COA-22%(e)

Fig.2 FTIR spectra of dopamine(a), alginate(b), COA-0(c), COA-12.5%(d), COA-18%(e) and COA-22%(f)

Fig.3 1H NMR spectra of COA-0(a), COA-12.5%(b), COA-18%(c) and COA-22%(d)

Fig.4 SEM images of COA-COL-0(A), COA-COL-12.5%(B), COA-COL-18%(C) and COA-COL-22%(D)

Fig.5 Equilibrium swelling ratio(A) and degradation(B) of COA-COL hydrogelsa. COA-COL-0; b. COA-COL-12.5%; c. COA-COL-18%; d. COA-COL-22%.

Fig.6 Lap shear strength of COA-COL hydrogelsa. Alg-dopa-col-20%; b. COA-COL-0; c. COA-COL-12.5%; d. COA-COL-18%; e. COA-COL-22%.

Scheme 1 Schematic illustration of the application of COA-COL bioadhesive hydrogels

Fig.7 Cell proliferation test by MTT assay on the 1st, 3rd and 5th day after seedinga. COA-COL-0; b. COA-COL-12.5%; c. COA-COL-18%; d. COA-COL-22%.

References 35

[1]	Mehdizadeh M., Yang J., Macromol. Biosci., 2013, 13(3), 271—288
[2]	Vernengo J., Fussell G. W., Smith N. G., LowmanA. M., J. Biomed. Mater. Res. B Appl. Biomater., 2010, 93B(2), 309—317
[3]	Hoffmann B., Volkmer E., Kokott A., Augat P., Ohnmacht M., Sedlmayr N., Schieker M., Claes L., Mutschler W., Ziegler G., J. Mater. Sci. Mater. Med., 2009, 20(10), 2001—2009
[4]	Cohen B., Pinkas O., Foox M., Zilberman M., Acta Biomater,2013, 9(11), 9004—9011
[5]	Shefy-Peleg A., Foox M., Cohen B., Zilberman M., Int. J. Polymer. Mate., 2014, 63(63), 699—707
[6]	Balakrishnan B., Joshi N., Jayakrishnan A., Banerjee R., Acta Biomater., 2014, 10(8), 3650—3663
[7]	Hou J., Li C., Guan Y., Zhang Y., Zhu X. X., Polym. Chem., 2015, 6(12), 2204—2213
[8]	Zhang H., BreL. P., Zhao T., Zheng Y., Newland B., Wang W., Biomaterials,2014, 35(2), 711—719
[9]	Lee H., Lee B. P., Messersmith P. B., Nature,2007, 448(7151), 338—341
[10]	Lee H., Scherer N. F., Messersmith P. B., Proc. Natl. Acad. Sci. USA,2006, 103(35), 12999—13003
[11]	Zhang D. L., Huang Y. B., Li X. Y., Chem. J. Chinese Universities,2015, 36(6), 1236—1242
	(张栋梁, 黄宇彬, 李晓媛. 高等学校化学学报, 2015, 36(6), 1236—1242)
[12]	Taguchi T., Saito H., Aoki H., Uchida Y., Sakane M., Kobayashi H., Tanaka J., Materials Science and Engineering: C,2006, 26(1), 9—13
[13]	Kim B. J., Oh D. X., Kim S., Seo J. H., Hwang D. S., Masic A., Han D. K., Cha H. J., Biomacromolecules,2014, 15(5), 1579—1585
[14]	Manju S., Muraleedharan C. V., Rajeev A., Jayakrishnan A., Joseph R., J. Biomed. Mater. Res. B Appl. Biomater,2011, 98(1), 139—149
[15]	Cui L., Jia J.F., Xiong Z. R., Zhang C. J., Ye Z. T., Zhu P.,Acta Polym. Sin., 2014, (3), 361—368
	(崔莉, 贾军芳, 熊子豪, 张传杰, 叶正涛, 朱平. 高分子学报, 2014, (3), 361—368)
[16]	Lee B. P., Dalsin J. L., Messersmith P. B., Biomacromolecules,2002, 3(5), 1038—1047
[17]	Lin S., Chen C. T., Bdikin I., Ball V., Grácio J., Buehler M. J., Soft Matter., 2014, 10(3), 457—464
[18]	Kan Y., Danner E. W., Israelachvili J. N., Chen Y. F., Waite J. H., PloS One,2014, 9(10), 1—7
[19]	Ho C. C., Ding S. J., J. Mater. Sci. Mater. Med., 2013, 24(10), 2381—2390
[20]	Hou C., Qi Z., Zhu H., Colloids Surf. B Biointerfaces,2015, 128, 544—551
[21]	Dahlmann J., Krause A., Moller L., Kensah G., Mowes M., Diekmann A., Martin U., Kirschning A., Gruh I., Drager G., Biomaterials,2013, 34(4), 940—951
[22]	Sun X. H., Tao Y., Liu Y. F., Jia Y. Q., Chen B., Acta Chimica Sin., 2008, 66(2), 234—238
	(孙晓红, 陶燕, 刘源发, 贾婴琦, 陈邦. 化学学报, 2008, 66(2):234—238)
[23]	Zhang H., Hu X.T., Yang N., Chen L.,Acta Polym. Sin., 2016, (3), 300—306
	(张浩, 胡晓婷, 杨宁, 陈莉. 高分子学报, 2016, (3), 300—306)
[24]	Ji C., Khademhosseini A., Dehghani F., Biomaterials,2011, 32(36), 9719—9729
[25]	Wang Y., Zhao Q., Luo Y., Xu Z., Zhang H., Yang S., Wei Y., Jia X., Chem. Commun., 2015, 51(94), 16786—16789
[26]	Yang X., Guo L., Fan Y. , Zhang X., Int. J. Biol. Macromol., 2013, 61(2), 487—493
[27]	Boontheekul T., Kong H. J., Mooney D. J., Biomaterials,2005, 26(15), 2455—2465
[28]	Jeon O., Alt D. S., Ahmed S. M., Alsberg E., Biomaterials,2012, 33(13), 3503—3514
[29]	Shin J., Lee J. S., Lee C., Park H. J., Yang K., Jin Y., Ryu J. H., Hong K. S., Moon S. H., Chung H. M., Yang H. S., Um S. H., Oh J. W., Kim D. I., Lee H., Cho S. W., Adv. Funct. Mater., 2015, 25, 3814—3824
30	Ryu J. H. , Lee Y. , Kong W. H. , Kim T. G. , Park T. G., Lee H., Biomacromolecules,2011, 12(7), 2653—2659
[31]	Ai Y. , Wei Y., Nie J., Yang D., J. Photochem. Photobiol. B,2013, 120(2), 183—190
[32]	Wilker J. J., Nat. Chem. Biol., 2011, 7(9), 579—580
[33]	Zhang F., Liu S., Zhang Y., Wei Y., Xu J., RSC Advances,2012, 2(24), 8919
[34]	Wang G. X., Lan H. L., Wang Y., Yin T. Y., Wang Y. Z., Liu Q., Wang Z. X., Functional Materials,2014, 45(14), 14013—14020
	(王贵学, 兰华林, 王溢, 尹铁英, 王亚洲, 刘茜, 王召旭. 功能材料, 2014, 45(14), 14013—14020)
[35]	Perikamana S. K. M., Lee J., Lee Y. B., Shin Y. M., Lee E. J., Mikos A. G., Shin H., Biomacromolecules,2015, 16(9), 2541—2555