Preparation and Characterization of Biodegradable Adhesive Based on Catechol†

doi:10.7503/cjcu20140812

Chem. J. Chinese Universities ›› 2015, Vol. 36 ›› Issue (6): 1236.doi: 10.7503/cjcu20140812

• Polymer Chemistry • Previous Articles

Preparation and Characterization of Biodegradable Adhesive Based on Catechol^†

ZHANG Dongliang^1,^*(), HUANG Yubin², LI Xiaoyuan^2,^*()

1. Beijing Stomatological Hospital, Capital Medical University, Beijing 100006, China
2. State Key Laboratory of Polymer Physics and Chemistry, Chang Chun Institute of Applied Chemistry,Chinese Academy of Sciences, Changchun 130022, China

Received:2014-09-05 Online:2015-06-10 Published:2015-04-21
Contact: ZHANG Dongliang,LI Xiaoyuan E-mail:zhangdongliang@hotmail.com;xiaoyuanli@ciac.ac.cn
Supported by:
† Supported by the Beijing Natural Science Foundation, China(No.3122018)

Abstract

Abstract:

Macromolecular initiator aminated monomethoxy poly(ethylene glycol)(abbreviated as mPEG-NH₂) was synthesized to get mimic bioadhesives mPEG-b-P(LL-g-DHPPA) and mPEG-b-P(LG-g-Dopamine). The structures of target products were confirmed by nuclear magnetic resonance(NMR), Fourier transform infrared spectroscopy(FTIR) and gel permeation chromatography(GPC), and the degree of the catechol moiety grafting density of these two polymers were tested to be 30% and 28.6%, respectively. The results of tensile stripping experiments demonstrated that the mimic bioadhesive that bearing amino groups on its side chain[i.e., mPEG-b-P(LL-g-DHPPA)] exhibited higher adhesive strength and faster curing speed.

Key words: Bioadhesive, mPEG-b-P(LL-g-DHPPA), mPEG-b-P(LG-g-Dopamine), o-Dihydroxybenzene, Degradable adhesive

CLC Number:

O633.22

TrendMD:

ZHANG Dongliang, HUANG Yubin, LI Xiaoyuan. Preparation and Characterization of Biodegradable Adhesive Based on Catechol^†[J]. Chem. J. Chinese Universities, 2015, 36(6): 1236.

Figures/Tables 13

Scheme 1 Synthesis of macromolecular initiator mPEG-NH2

Scheme 2 Synthesis of mPEG-b-PLL

Scheme 3 Synthesis of mPEG-b-P(LL-g-DHPPA)

Scheme 4 Synthesis of mPEG-b-P(LG-g-Dopamine)

Fig.1 13C NMR spectra of mPEG-OMs(A), mPEG-N3(B) and mPEG-NH2(C)

Fig.2 1H NMR spectra of mPEG-b-PZLL(A), mPEG-b-PLL(B) and mPEG-b-P(LL-g-DHPPA)(C)

Fig.3 FTIR spectra of mPEG-b-PZLL(a) and mPEG-b-ZLL(b)

Fig.4 1H NMR spectra of mPEG-b-PBLG in CDCl3/CD3COOH(A), mPEG-b-PLG in CDCl3/CD3COOH(B) and mPEG-b-P(LG-g-Dopamine)(C) in DMSO-d6

Fig.5 Standard curve of DHPPA measured at a series of concentrations

Fig.6 UV-Vis spectra of DHPPA(a), mPEG-b-P(LL-g-DHPPA)(b) and mPEG-b-PLL(c)

Fig.7 Standard curve of Dopamine measured at a series of concentrations

Fig.8 UV-Vis spectra of Dopamine(a), mPEG-b-P(LG-g-Dopamine)(b) and mPEG-b-PLG(c)

Fig.9 Changing trend of shear strength of different bioadhesives with curing timea. mPEG-b-P(LL-g-DHPPA); b. mPEG-b-P(LG-g-Dopamine); c. mPEG-b-PLL; d. mPEG-b-PLG.

References 18

[1]	Liu Y., Li K., Macromol. Rapid Comm., 2002, 2, 739—742
[2]	Yu M., Deming T. J., Macromolecules, 1998, 31, 4739—4745
[3]	Statz A. R., Meagher R. J., Barron A. E., Messersmith P. B., J. Am. Chem. Soc., 2005, 127, 7972—7973
[4]	Hu B. H., Messersmith P. B., Tetrahedron Lett., 2000, 41, 5795—5798
[5]	Ooka A. K., Garrell R. L., Biopolymers, 2000, 57, 92—102
[6]	Yamamoto H., J. Chem. Soc., Perkin Trans. 1, 1987, 1, 613—618
[7]	Yamamoto H., Kuno S., Nagai A., Nishida A., Yamauchi S., Ikeda K., Int. J. Biol. Macromol., 1990, 12, 305—310
[8]	Waite J. H., Tanzer M. L., Science, 1981, 212, 1038—1040
[9]	Waite J. H., J. Biol. Chem., 1983, 258, 2911—2915
[10]	Prakash T. P., Kraynack B., Baker B. F., Swayze E. E., Bhat B., Bioorg. Med. Chem. Lett., 2006, 16, 3238—3240
[11]	Zheng J. K., Chen Y., Karim A., Becker M. L., ACS Macro. Lett., 2014, 3, 1084—1087
[12]	Waiter J. H., Ann. N. Y. Acad. Sci., 1999, 875, 301—309
[13]	Lee H., Scherer N. F., Messersmith P. B., Proc. Natl. Acad. Sci. USA, 2006, 103, 12999—13003
[14]	Lee B. P., Dalsin J. L., Messersmith P. B., Biomacromolecules, 2002, 3, 1038—1047
[15]	Wu J. J., Long Y. H., Zhao N., Xu J., Polymer Bulletin, 2011, 10, 86—93
	(吴俊杰, 龙宇华, 赵宁, 徐坚. 高分子通报, 2011, 10, 86—93)
[16]	Ding J. X., Zhuang X. L., Xiao C. S., Cheng Y. L., Zhao L., He C. L., Tang Z. H., Chen X. S., J. Mater. Chem., 2011, 21, 11383—11391
[17]	Van Dijk-Wolthuis W. N. E., van de Water L., van de Wetering P., van Steenbergen M. J., Kettenes-van den Bosch J. J., Schuyl W. J. W., Hennink W. E., Macromol. Chem. Phys., 1997, 198, 3893—3906
[18]	Lee H., Lee Y., Statz A. R., Rho J. S., Park T. G., Messersmith P. B., Adv. Mater., 2008, 20, 1619—1623

Preparation and Characterization of Biodegradable Adhesive Based on Catechol^†

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