Investigation of Formation Mechanism of Polydopamine by Adding Free Radical Quencher †

doi:10.7503/cjcu20190696

Abstract

Abstract:

In this paper, by using dimethyl sulfoxide(DMSO) and edaravone as the free radical quencher, the free radical polymerization pathways of dopamine under different pH conditions were studied. Besides, the absorbance of the dopamine solutions was characterized by means of UV-Vis spectroscopy. It is found that the dopamine polymerization rate decreases with the increase of the DMSO concentration, indicating that DMSO can slow down the polymerization of dopamine. Further experiments show that edaravone can slow down the polymerization of dopamine more significantly. These results indicate that the free radical polymerization is one of the possible pathways of dopamine polymerization. Although DMSO can slow down the polymerization of dopamine, it cannot completely restrain the polymerization, which indicates that the polymerization has other reaction pathways besides the free radical polymerization. These pathways may be the main reason for the structure complexity of polydopamine. Moreover, it is found that the polymerization rate increases with the increase of pH and the final reaction products under different pH conditions are similar.

Key words: Dopamine, Mechanism of polymerization, Free radical quencher, Free radical polymerization

CLC Number:

O636.9

TrendMD:

WANG Qianying, CUI Shuxun. Investigation of Formation Mechanism of Polydopamine by Adding Free Radical Quencher ^†[J]. Chem. J. Chinese Universities, 2020, 41(6): 1378.

Figures/Tables 7

References 40

[1]	Waite J. H., Tanzer M. L., Science, 1981, 212(4498), 1038—1040
[2]	Harrington M. J., Masic A., Holten A. N., Waite J. H., Fratzl P., Science, 2010, 328(5975), 216—220
[3]	Waite J. H., Qin X. X., Biochemistry, 2001, 40(9), 2887—2893
[4]	Lin Q., Gourdon D., Sun C. J., Holten-Andersen N., Anderson T. H., Waite J. H., Israelachvili J. N., Proc. Natl. Acad. Sci. U. S. A., 2007, 104(10), 3782—3786
[5]	Burzio L. A., Waite J. H., Biochemistry, 2000, 39(36), 11147—11153
[6]	Lee B. P., Messersmith P. B., Israelachvili J. N., Waite J. H., Ann. Rev. Mater. Res., 2011, 41(1), 99—132
[7]	Han L., Yan L. W., Wang K. F., Fang L. M., Zhang H. P., Tang Y. H., Ding Y. H., Weng L. T., Xu J. l., Weng J., NPG Asia Mater., 2017, 9(4), e372
[8]	Xie B., Li G. C., Dai L., Yang P., Huang N. , Chem. J. Chinese Universities 2012, 33(1), 90—95
	( 谢槟, 李贵才, 代璐, 杨苹, 黄楠 . 高等学校化学学报, 2012, 33(1) 90—95)
[9]	Li X., Cao Y. M., Kang G. D., Yu H. J., Liu Z. N. , Chem. J. Chinese Universities 2014, 35(9), 2026—2030
	( 李霞, 曹义鸣, 康国栋, 于海军, 刘中楠 . 高等学校化学学报, 2014, 35(9) 2026—2030)
[10]	Lee H., Dellatore S. M., Miller W. M., Messersmith P. B., Science, 2007, 318(5849), 426—430 doi: 10.1126/science.1147241 URL
[11]	Bernsmann F., Ball V., Addiego F., Ponche A., Michel M., Gracio J. J. D., Toniazzo V., Ruch D., Langmuir, 2011, 27(6), 2819—2825
[12]	Kobayashi S., Makino A., Chem. Rev., 2009, 109(11), 5288—5353 doi: 10.1021/cr900165z URL
[13]	Ouyang R. Z., Lei H. P., Ju H. X., Xue Y. D., Adv. Funct. Mater., 2007, 17(16), 3223—3230
[14]	Ball V., Del Frari D., Michel M., Buehler M. J., Toniazzo V., Singh M. K., Gracio J., Ruch D., BioNanoSci., 2012, 2(1), 16—34
[15]	Lynge M. E., van der Westen R., Postma A., Städler B., Nanoscale, 2011, 3(12), 4916—4928
[16]	Sedo J., Saiz-Poseu J., Busque F., Ruiz-Molina D., Adv. Mater., 2013, 25(5), 653—701
[17]	Ge R., Lin M., Li X., Liu S. W., Yang B., ACS Appl. Mater. Interfaces, 2017, 9(23), 19706—19716
[18]	Dang G. J., Wang M., Wang Z. B., Li H. Y., Zhang Q. S. , Chem. J. Chinese Universities 2014, 35(12), 2680—2687
	( 党国举, 王淼, 王昭勍, 李海燕, 张全生 . 高等学校化学学报, 2014, 35(12) 2680—2687)
[19]	Su B. Q., Zhang Y. Z., Du Y. L., Wang C. M. , Chem. J. Chinese Universities 2010, 31(8), 1661—1664
	( 苏碧泉, 张永珍, 杜永令, 王春明 . 高等学校化学学报, 2010, 31(8) 1661—1664)
[20]	Li W., Ma Z. Y., Bai G. Q., Hu J. M., Guo X. H., Dai B., Jia X., Appl. Catal. B-Environ., 2015, 174(1), 43—48
[21]	Zheng J. K., Chen Y., Karim A., Becker M. L., ACS Macro Lett., 2014, 3(10), 1084—1087 doi: 10.1021/mz5005162 URL
[22]	Song Y., Ye G., Lu Y. X., Chen J., Wang J. C., Matyjaszewski K., ACS Macro Lett., 2016, 5(3), 382—386 doi: 10.1021/acsmacrolett.6b00099 URL
[23]	Qiang W., Zhang F., Jie L., Li B., Zhao C., Polym. Chem., 2010, 1(9), 1430—1433
[24]	Zhang L., Wu J. J., Wang Y. X., Long Y. H., Zhao N., Xu J., J. Am. Chem. Soc., 2012, 134(24), 9879—9881
[25]	Shen H., Guo J., Wang H., Zhao N., Xu J., ACS Appl. Mater. Interfaces, 2015, 7(10), 5701—5708
[26]	Zhang W., Yang F. K., Pan Z. H., Zhang J., Zhao B. X., Macromol. Rapid Commun, 2014, 35(3), 350—354
[27]	Li Y. L., Liu M. L., Xiang C. H., Xie Q. J., Yao S. Z., Thin Solid Films, 2006, 497(1/2), 270—278
[28]	van der Leeden M. C., Langmuir, 2005, 21(24), 11373—11379 doi: 10.1021/la0515468 URL
[29]	Dreyer D. R., Miller D. J., Freeman B. D., Paul D. R., Bielawski C. W., Langmuir, 2012, 28(15), 6428—6435
[30]	Hong S., Na Y. S., Choi S., Song I. T., Kim W. Y., Lee H., Adv. Funct. Mater., 2012, 22(22), 4711—4717
[31]	Della V. N. F., Avolio R., Alfè M., Errico M. E., Napolitano A., d'Ischia M., Adv. Funct. Mater., 2013, 23(10), 1331—1340
[32]	Kang X. M., Cai W. H., Zhang S., Cui S. X., Polym. Chem., 2017, 8(5), 860—864
[33]	Kang X. M., Cai W. H., Gu H. G., Liu S. Y., Cui S. X., Chinese J. Polym. Sci., 2017, 35(7), 857—865 doi: 10.1007/s10118-017-1934-5 URL
[34]	Liu X., Kang J., Wang Y., Li W., Guo H., Xu L., Guo X., Zhou F., Jia X., Macromol. Rapid Commun., 2018, 39(12), e1800160
[35]	Kang X. M., Yu Y., Bao Y., Cai W. H., Cui S. X., Polym. Chem., 2015, 6(23), 4252—4257 doi: 10.1039/C5PY00513B URL
[36]	Brayton C. F., Cornell. Vet., 1986, 76(1), 61—90
[37]	Fujimura N., Sumita S., Aimono M., Masuda Y., Shichinohe Y., Narimatsu E., Namiki A., Am. J. Resp. Crit. Care., 2000, 162(6), 2159—2165
[38]	Pérez-González A., Galano A., J. Phys. Chem. B, 2011, 115(5), 1306—1314
[39]	Yamawaki M., Sasaki N., Shimoyama M., Miake J., Ogino K., Igawa O., Tajima F., Shigemasa C., Hisatome I., Brit. J. Pharmacol., 2004, 142(3), 618—626
[40]	Fu X. C., Shen W. X., Yao T. W., Physical Chemistry(The Fifth Edition), Higher Education Press, Beijing, 2005, 129—137
	( 傅献彩, 沈文霞, 姚天物物理化学(第五版), 北京: 高等教育出版社 2005, 129—137)