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Accelerated Synthesis of Surface Functionalized Mannosylated Dendrimers Built on Cyclotriphosphazene Core

Published online by Cambridge University Press:  11 October 2019

Lamyaa M. Sallam ,
Tze Chieh Shiao ,
Celia Sehad ,
Abdelkrim Azzouz  and
René Roy
Lamyaa M. Sallam
Affiliation:
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada
Tze Chieh Shiao
Affiliation:
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada
Celia Sehad
Affiliation:
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada
Abdelkrim Azzouz
Affiliation:
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada
René Roy*
Affiliation:
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada INRS-Institut Armand-Frappier, Université du Québec, 531 boul. des Prairies, Laval, Québec, H7V 1B7, Canada Glycovax Pharma Inc., 424 Guy, Suite 202, Montreal, Quebec, H3J 1S6, Canada
*
*Corresponding author: [email protected] ; Tel.: +1 438-393-5009
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Abstract

The syntheses of five propargylated dendrimer scaffolds ranging from 2, 3, 4, 6, and 12 surface groups are described together with a 2-azidoethyl α-D-mannopyranoside. The former is appended to the core structure using highly efficient copper-catalysed azide-alkyne cycloaddition (CuAAC) (“click reaction”) to provide glycodendrimers in an accelerated approach. Two of the core structures are based on cyclotrisphosphazene, thus expanding the scope of the “onion-peel” strategy to build dendritic architectures with a large number of surface groups at the G1 generation only.

Keywords

biomaterialchemical synthesisnanostructure
Type
Articles
Information
MRS Advances , Volume 4 , Issue 59-60: International Materials Research Congress XXVIII , 2019 , pp. 3187 - 3198
Copyright
Copyright © Materials Research Society 2019 

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References

REFERENCES

Mousavifar, L., Touaibia, M., and Roy, R., Acc. Chem. Res. 51, 2937 (2018).CrossRefGoogle Scholar
Roy, R., Curr. Opin. Struct. Biol. 6, 692 (1996).CrossRefGoogle Scholar
Roy, R., Topics Curr. Chem. 187, 241 (1997).CrossRefGoogle Scholar
Roy, R., "The Chemistry of Neoglycoconjugates". Carbohydrate Chemistry, ed. Boons, G. J. (Chapman & Hall, UK, 1998), Chap. 7, pp. 243-321.Google Scholar
Hu, J., Wei, P., Seeberger, P. H., and Yin, J., Chem. Asian J. 13, 3448 (2018).CrossRefGoogle Scholar
Roy, R., Trends Glycosci. Glycotechnol. (TIGGS) 8, 79 (1996).CrossRefGoogle Scholar
Roy, R., Polymer News 21, 226(1996).Google Scholar
Roy, R., Trends Glycosci, R.. Glycotecnol. (TIGGS) 15, 289 (2003).Google Scholar
Chabre, Y. M. and Roy, R., Adv. Carbohydr. Chem. Biochem. 63, 165 (2010).CrossRefGoogle Scholar
Pozsgay, V., ACS Symp. Ser. 989, 36 (2008).CrossRefGoogle Scholar
Chabre, Y. M. and Roy, R., “Solving promiscuous protein carbohydrate recognition domains with multivalent glycofullerenes”, Synthesis and Biological Applications of Glycoconjugates , ed. Renaudet, O. and Spinelli, N. (Bentham Science Publishers, 2011), Chap. 4, pp. 64-77.Google Scholar
Kottari, N., Chabre, Y. M., Sharma, R., and Roy, R., “Applications of Glyconanoparticles as “Sweet” Glycobiological Therapeutics and Diagnostics”, Advances in Polymer Science, Nanoparticles for advancement of Biopolymers: Preparation, Properties, and Applications toward Biology, Catalysis, and Nanotechnology, ed. Dutta, P. K. (Springer, 2013), 254, 297-342.Google Scholar
Goyard, D., Shiao, T. C., Fraleigh, N. L., Vu, H.-Y., Lee, H., Diaz-Mitoma, F., Le, H.-T., and Roy, R., J. Mater. Chem. B, 4, 4227 (2016).CrossRefGoogle Scholar
Percec, V., Leowanawat, P., Sun, H.-J., Kulikov, O., Nusbaum, C. D., Tran, T. M., Bertin, A., Wilson, D. A., Peterca, M., Zhang, S., Kamat, N. P., Vargo, K., Moock, D., Johnston, E. D., Hammer, D. A., Pochan, D. J., Chen, Y., Chabre, Y. M., Shiao, T. C., Bergeron-Brlek, M., André, S., Roy, R., Gabius, H.-J., and Heiney, P. A., J. Am. Chem. Soc. 2013, 135, 9055 (2013).CrossRefGoogle Scholar
Zhang, S., Moussodia, R.-O., Sun, H.-J., Leowanawat, P., Muncan, A., Nusbaum, C. D., Chelling, K. M., Heiney, P. A., Klein, M. L., André, S., Roy, R., Gabius, H.-J., and Percec, V., Angew. Chem Int. Ed. 53, 10899 (2014).CrossRefGoogle Scholar
Zhang, S., MoussodiaR,-O. R,-O., Murzeau, C., Sun, H.-J., Klein, M. L., Vértesy, S., André, S., Roy, R., Gabius, H.-J., and Percec, V., Angew. Chem. Int. Ed. 54, 4036 (2015).CrossRefGoogle Scholar
de la Fuente, J. M. and Penadés, S., Biochim. Biophys. Acta 1760, 636 (2006).CrossRefGoogle Scholar
Roy, R., Drug Discovery Today: Technologies 1, 327 (2004).CrossRefGoogle Scholar
Roy, R. and Shiao, T. C., Chimia, 2011, 65, 24 (2011).CrossRefGoogle Scholar
Roy, R. and Shiao, T. C., New J. Chem. 2012, 36, 324 (2012).Google Scholar
Roy, R., Shiao, T. C., and Rittenhouse-Olson, K., Braz. J. Pharm. Sci. 49, 85 (2013).CrossRefGoogle Scholar
Shivatare, S. V. S., Shivatare, S. S., Lee, C.-C. D., Liang, C.-H., Liao, K.-S., Cheng, Y.-Y., Saidachary, G., Wu, C.-Y., Lin, N.-H., Kwong, P. D., Burton, D. R., Wu, C.-Y., and Wong, C.-H., J. Am. Chem. Soc., 140, 5202 (2018).CrossRefGoogle Scholar
Sally, S. L. Y., Alonso, S., Nguyen-Khuong, T., Rudd, P. M., Frontiers Microbiol. 8, 1415 (2017).Google Scholar
Rojo, J. and Delgado, R., J. Antimicrob. Chemother. 54, 579 (2004).CrossRefGoogle Scholar
Zhou, G., Mo, W.-J., Sebbel, P., Min, G., Neubert, T. A., Glockshuber, R., Wu, X.-R., Sun, T.-T., Kong, X.-P., J. Cell Sci. 114, 4095 (2001).Google Scholar
Chabre, Y. M. and Roy, R., “Dendrimer-coated carbohydrate residues as drug delivery Trojan horses in glycosciences”, Dendrimer-based Drug delivery Systems: From Theory to Practice , ed. Cheng, Y. Y. (Wiley-VCH, Weinheim, 2012), Chap. 11, 407-438.CrossRefGoogle Scholar
Chabre, Y. M. and Roy, R., Chem. Soc. Rev. 42, 4657 (2013).CrossRefGoogle Scholar
Tomalia, D. A. and Khanna, S. N., Chem. Rev. 116, 2705 (2016).CrossRefGoogle Scholar
Appelhans, D., Klajnert-Maculewicz, B., Janaszewska, A., Lazniewskab, J., and Voit, B., Chem. Soc. Rev. 44, 3968 (2015).CrossRefGoogle Scholar
Malström, E., Johansson, M., and Hult, A., Macromolecules, 28, 1695 (1995).Google Scholar
Newkome, G. R. and Shreiner, C., Chem. Rev. 110, 6338, (2010).CrossRefGoogle Scholar
Caminade, A.-M., Ouali, A., Hameau, A., Laurent, R., Rebout, C., Delavaux-Nicot, B., Turrin, C.-O., Moineau, K., Ching, C., and Majoral, J.-P., Pure Appl. Chem. 88, 919 (2016).CrossRefGoogle Scholar
Astruc, D., Boisselier, E., and Ornelas, C., Chem. Rev. 110, 1857 (2010).CrossRefGoogle Scholar
Carlmark, A., Hawker, C., Hult, A., and Malkoch, M., Chem. Soc. Rev. 38, 352 (2009).CrossRefGoogle Scholar
Roy, R. and Shiao, T. C., Chem Soc. Rev., 2015, 44, 3924 (2015).CrossRefGoogle Scholar
Shiao, T. C., Rej, R., Rose, M., Pavan, G. M., and Roy, R., Molecules 21, 448 (2016).CrossRefGoogle Scholar
Touaibia, M. and Roy, R., J. Org. Chem. 73, 9292 (2008).CrossRefGoogle Scholar
Naresh, K., Shiao, T. C., Chabre, Y. M., and Roy, R., Chem. Commun. 50, 1983 (2014).Google Scholar
Sharma, R., Kottari, N., Chabre, Y. M., Abbassi, L., Shiao, T. C., and Roy, R., Chem Commun . 50, 13300 (2014).CrossRefGoogle Scholar
Sharma, R., Naresh, K., Chabre, Y. M., Rej, R., Saadeh, N. K., and Roy, R., Polym. Chem. 5, 4321 (2014).CrossRefGoogle Scholar
Sharma, R., Zhang, I., Abbassi, L., Rej, R., Maysinger, D., and Roy, R., Polym. Chem. 6, 1436 (2015).CrossRefGoogle Scholar
Bagul, R. S., Hosseini, M., Shiao, T. C., and Roy, R., Can. J. Chem. 95, 975 (2017).CrossRefGoogle Scholar
Bagul, R. S., Hosseini, M., Shiao, T. C., Saadeh, N. K., and Roy, R., Polymer Chem. 8, 5354 (2017).CrossRefGoogle Scholar
Abbassi, L., Chabre, Y. M., Kottari, N., Arnold, A. A., André, S., Josserand, J., Gabius, H.-J., and Roy, R., Polym.Chem. 6, 7666 (2015).CrossRefGoogle Scholar
Kolb, H. C., Finn, M. G., and Sharpless, K. B., Angew. Chem. Int. Ed. 40, 2004 (2001).3.0.CO;2-5>CrossRefGoogle Scholar
Sehad, C., Shiao, T. C., Sallam, L. M., Azzouz, A., and Roy, R., Molecules 23, 1890 (2018).CrossRefGoogle Scholar
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