Synthesis, Characterization, and Dynamic Behavior of Well-defined Dithiomaleimide-functionalized Maltodextrins

Author(s): Francisco J. Hidalgo, Nathan A.P. Lorentz, TinTin B. Luu, Jonathan D. Tran, Praveen D. Wickremasinghe, Olnita Martini, Peter M. Iovine, Joan G. Schellinger*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 2 , 2020

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Abstract:

Maltodextrins have an increasing number of biomedical and industrial applications due to their attractive physicochemical properties such as biodegradability and biocompatibility. Herein, we describe the development of a synthetic pathway and characterization of thiol-responsive maltodextrin conjugates with dithiomaleimide linkages. 19F NMR studies were also conducted to demonstrate the exchange dynamics of the dithiomaleimide-functionalized sugar end groups.

Keywords: Maltodextrin, dibromomaleimide, click chemistry, thiol release, sugar conjugates, 19F NMR.

[1]
Wen, Y.F.; Oh, J.K. Macromol. Rapid Commun., 2014, 35, 1819-1832.
[2]
Miao, T.; Wang, J.; Zeng, Y.; Liu, G.; Chen, X. Adv. Sci. (Weinh.), 2018, 51700513
[3]
Swierczewska, M.; Han, H.S.; Kim, K.; Park, J.H.; Lee, S. Adv. Drug Deliv. Rev., 2016, 99, 70-84.
[4]
Chronakis, I.S. Crit. Rev. Food Sci. Nutr., 1998, 38, 599-637.
[5]
Corveleyn, S.; Remon, J.P. Pharm. Res., 1996, 13, 146-150.
[6]
Wang, Y.J.; Wang, L. Starch - Stärke, 2000, 52, 296-304.
[7]
Pycia, K.; Juszczak, L.; Gałkowska, D. Starch - Stärke, 2016, 68, 611-620.
[8]
Jafari, S.M.; He, Y.; Bhandari, B. J. Food Eng., 2007, 82, 478-488.
[9]
Liu, Z.; Jiao, Y.; Wang, Y.; Zhou, C.; Zhang, Z. Adv. Drug Deliv. Rev., 2008, 60, 1650-1662.
[10]
Zhang, Y.; Chan, J.W.; Moretti, A.; Uhrich, K.E. J. Control. Release, 2015, 219, 355-368.
[11]
Jain, K.; Kesharwani, P.; Gupta, U.; Jain, N.K. Biomaterials, 2012, 33, 4166-4186.
[12]
Davis, B.G.; Robinson, M.A. Curr. Opin. Drug Discov. Devel., 2002, 5, 279-288.
[13]
Rodrigues, A.; Emeje, M. Carbohydr. Polym., 2012, 87, 987-994.
[14]
Liu, K.; Jiang, X.; Hunziker, P. Nanoscale, 2016, 8, 16091-16156.
[15]
Seidi, F.; Jenjob, R.; Phakkeeree, T.; Crespy, D. J. Control. Release, 2018, 284, 188-212.
[16]
Isono, T.; Miyachi, K.; Satoh, Y.; Nakamura, R.; Zhang, Y.; Otsuka, I.; Tajima, K.; Kakuchi, T.; Borsali, R.; Satoh, T. Macromolecules, 2016, 49, 4178-4194.
[17]
Blazek-Welsh, A.I.; Rhodes, D.G. AAPS PharmSci, 2001, 3, 1.
[18]
Korang-Yeboah, M.; Gorantla, Y.; Paulos, S.A.; Sharma, P.; Chaudhary, J.; Palaniappan, R. Int. J. Nanomedicine, 2015, 10, 4763-4781.
[19]
Korang-Yeboah, M.; Patel, D.; Morton, D.; Sharma, P.; Gorantla, Y.; Joshi, J.; Nagappan, P.; Pallaniappan, R.; Chaudhary, J. Oncotarget, 2016, 7, 68072-68085.
[20]
Gurturk, Z.; Tezcaner, A.; Dalgic, A.D.; Korkmaz, S.; Keskin, D. MedChemComm, 2017, 8, 1337-1345.
[21]
Bezem, M.T.; Johannessen, F.G.; Jung, K.C.K.; Gundersen, E.T.; Jorge-Finnigan, A.; Ying, M.; Betbeder, D.; Herfindal, L.; Martinez, A. Bioconjug. Chem., 2018, 29, 493-502.
[22]
Yoo, W.; Yoo, D.; Hong, E.; Jung, E.; Go, Y.; Singh, S.V.B.; Khang, G.; Lee, D. J. Control. Release, 2018, 269, 235-244.
[23]
Chaurasia, S.; Patel, R.R.; Chaubey, P.; Kumar, N.; Khan, G.; Mishra, B. Carbohydr. Polym., 2015, 130, 9-17.
[24]
Villadsen, K.; Martos-Maldonado, M.C.; Jensen, K.J.; Thygesen, M.B. ChemBioChem, 2017, 18, 574-612.
[25]
Morris, G.A.; Sims, I.M.; Robertson, A.J.; Furneaux, R.H. Food Hydrocoll., 2004, 18, 1007-1014.
[26]
Akhtar, M.; Dickinson, E. Food Hydrocoll., 2007, 21, 607-616.
[27]
Wang, W.; Zhong, Q. Food Hydrocoll., 2014, 41, 257-264.
[28]
Mottram, D.S.; Wedzicha, B.L.; Dodson, A.T. Nature, 2002, 419, 448-449.
[29]
Guerry, A.; Bernard, J.; Samain, E.; Fleury, E.; Cottaz, S.; Halila, S. Bioconjug. Chem., 2013, 24, 544-549.
[30]
Ryno, L.M.; Reese, C.; Tolan, M.; O’Brien, J.; Short, G.; Sorriano, G.; Nettleton, J.; Fulton, K.; Iovine, P.M. Biomacromolecules, 2014, 15, 2944-2951.
[31]
Breitenbach, B.B.; Schmid, I.; Wich, P.R. Biomacromolecules, 2017, 18, 3844-3845.
[32]
Schatz, C.; Louguet, S.; Le Meins, J.F.; Lecommandoux, S. Angew. Chem. Int. Ed. Engl., 2009, 48, 2572-2575.
[33]
Zhao, Z.W.; Zhang, Z.; Chen, L.; Cao, Y.; He, C.L.; Chen, X.S. Langmuir, 2013, 29, 13072-13080.
[34]
Otsuka, I.; Isono, T.; Rochas, C.; Halila, S.; Fort, S.; Satoh, T.; Kakuchi, T.; Borsali, R. ACS Macro Lett., 2012, 1, 1379-1382.
[35]
Mura, S.; Nicolas, J.; Couvreur, P. Nat. Mater., 2013, 12, 991-1003.
[36]
Xu, W.G.; Ding, J.X.; Xiao, C.S.; Li, L.Y.; Zhuang, X.L.; Chen, X.S. Biomaterials, 2015, 54, 72-86.
[37]
Smith, M.E.B.; Schumacher, F.F.; Ryan, C.P.; Tedaldi, L.M.; Papaioannou, D.; Waksman, G.; Caddick, S.; Baker, J.R. J. Am. Chem. Soc., 2010, 132, 1960-1965.
[38]
Tan, J.K.; Choi, J.L.; Wei, H.; Schellinger, J.G.; Pun, S.H. Biomater. Sci., 2015, 3, 112-120.
[39]
Tan, J.K.; Schellinger, J.G. Ther. Deliv., 2015, 6, 1127-1129.
[40]
Moody, P.; Smith, M.E.; Ryan, C.P.; Chudasama, V.; Baker, J.R.; Molloy, J.; Caddick, S. ChemBioChem, 2012, 13, 39-41.
[41]
Chen, H.; Viel, S.; Ziarelli, F.; Peng, L. Chem. Soc. Rev., 2013, 42, 7971-7982.
[42]
Castaneda, L.; Wright, Z.V.; Marculescu, C.; Tran, T.M.; Chudasama, V.; Maruani, A.; Hull, E.A.; Nunes, J.P.; Fitzmaurice, R.J.; Smith, M.E.; Jones, L.H.; Caddick, S.; Baker, J.R. Tetrahedron Lett., 2013, 54, 3493-3495.
[43]
Gaitzsch, J.; Chudasama, V.; Morecroft, E.; Messager, L.; Battaglia, G. ACS Macro Lett., 2016, 5, 351-354.
[44]
Cui, Y.; Yan, Y.C.; Chen, Y.M.; Wang, Z.H. Macromol. Chem. Phys., 2013, 214, 470-477.
[45]
Bryden, F.; Maruani, A.; Savoie, H.; Chudasama, V.; Smith, M.E.; Caddick, S.; Boyle, R.W. Bioconjug. Chem., 2014, 25, 611-617.
[46]
Jones, M.W.; Strickland, R.A.; Schumacher, F.F.; Caddick, S.; Baker, J.R.; Gibson, M.I.; Haddleton, D.M. J. Am. Chem. Soc., 2012, 134, 1847-1852.
[47]
Petrelli, A.; Borsali, R.; Fort, S.; Halila, S. Chem. Commun. (Camb.), 2016, 52, 12202-12205.
[48]
Yu, J.X.; Hallac, R.R.; Chiguru, S.; Mason, R.P. Prog. Nucl. Magn. Reson. Spectrosc., 2013, 70, 25-49.


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Article Details

VOLUME: 17
ISSUE: 2
Year: 2020
Page: [85 - 89]
Pages: 5
DOI: 10.2174/1570178616666190212124838
Price: $65

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