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Synthesis of Gold Glyconanoparticles Based on Thiol-Containing d-Hexose Acylhydrazones and Their Modification by Thiolated Poly(2-deoxy-2-methacryloylamino-D-glucose)

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Abstract

A procedure has been developed for the synthesis of gold glyconanoparticles with an average particle size of 15–30 nm and a low polydispersity index on the basis of natural hexose (d-glucose, d-galactose, d-mannose) sulfanylacetyl-, 3-sulfanylpropanoyl-, and 2-sulfanylbenzoylhydrazones and thiolated poly(2-deoxy-2-methacryloylamino-d-glucose).

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References

  1. Thygesen, M.B. and Jensen, K.J., Carbohydrate Nanotechnology, Stine, K.J., Ed., Hoboken, NJ: Wiley, 2016, chap. 3, p. 79. doi 10.1002/9781118860212.ch3

    Google Scholar 

  2. Adak, A.K., Yu, C.-C., and Lin, C.-C., Glycochemical Synthesis: Strategies and Applications, Hung, S.-C. and Zulueta, M.M.L., Eds., Hoboken, NJ: Wiley, 2016, chap. 16, p. 425. doi 10.1002/978111 9006435.ch16

  3. García, I., Gallo, J., Marradi, M., and Penadés, S., Engineered Carbohydrate-Based Materials for Biomedical Applications: Polymers, Surfaces, Dendrimers, Nanoparticles, and Hydrogels, Narain, R., Ed., Hoboken, NJ: Wiley, 2011, chap. 6, p. 213. doi 10.1002/9780470944349.ch6

    Google Scholar 

  4. Bhattarai, J.K., Neupane, D., Mikhaylov, V., Demchenko, A.V., and Stine, K.J., Carbohydrate, Caliskan, M., Kavakli, I.H., and Öz, G.C., Eds., Istanbul: InTech, 2017, chap. 3. doi 10.5772/66194

  5. Nanobiomaterials in Cancer Therapy: Applications of Nanobiomaterials, Grumezescu, A.M., Ed., Oxford: Elsevier, 2016. doi 10.1016 /B978-0-323-42863-7.00002-5

  6. Marin, M.J., Schofield, C.L., Field, R.A., and Russell, D.A., Analyst, 2015, vol. 140, p. 59. doi 10.1039/C4AN01466A

    Article  CAS  PubMed  Google Scholar 

  7. de la Fuente, J.M. and Penades, S., Biochim. Biophys. Acta, 2006, vol. 1760, no. 4, p. 636. doi 10.1016/j.bbagen.2005.12.001

    Article  CAS  PubMed  Google Scholar 

  8. Barrientos, A.G., de la Fuente, J.M., Rojas, T.C., Fernandez, A., and Penades, S., Chem. Eur. J., 2003, vol. 9, no. 9, p. 1909. doi 10.1002/CHEM.200204544

    Article  CAS  PubMed  Google Scholar 

  9. Vetro, M., Safari, D., Fallarini, S., Salsabila, K., Lahmann, M., Penades, S., Lay, L., Marradi, M., and Compostella, F., Nanomedicine, 2017, vol. 12, no. 1, p. 13. doi 10.2217/nnm-2016-0306

    Article  CAS  PubMed  Google Scholar 

  10. Bogart, L.K., Pourroy, G., Murphy, C. J., Puntes, V., Pellegrino, T., Rosenblum, D., Peer, D., and Lévy, R., ACS Nano, 2014, vol. 8, no. 4, p. 3107. doi 10.1021/nn500962q

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Fedotcheva, T.A., Olenin, A.Yu., Starostin, K.M., Lisichkin, G.V., Banin, V.V., and Shimanovskii, N.L., Pharm. Chem. J., 2015, vol. 49, no. 4, p. 220. doi 10.1007/s11094-015-1260-6

    Article  CAS  Google Scholar 

  12. Jazayeri, M.H., Amani, H., Pourfatollah, A.A., Avan, A., Ferns, G.A., and Pazoki-Toroudi, H., Cancer Gene Ther., 2016, vol. 23, p. 365. doi 10.1038/cgt.2016.42

    Article  CAS  PubMed  Google Scholar 

  13. Veerapandian, M., Lim, S.K., Nam, H.M., Kuppannan, G., and Yun, K.S., Anal. Bioanal. Chem., 2010, vol. 398, p. 867. doi 10.1007/s00216-010-3964-5

    Article  CAS  PubMed  Google Scholar 

  14. Perfezou, M., Turner, A., and Merkoci, A., Chem. Soc. Rev., 2012, vol. 41, p. 2606. doi 10.1039/C1CS15134G

    Article  CAS  PubMed  Google Scholar 

  15. Love, J.C., Estroff, L.A., Kriebel, J.K., Nuzzo, R.G., and Whitesides, G.M., Chem. Rev., 2005, vol. 105, p. 1103. doi 10.1021/cr0300789

    Article  CAS  PubMed  Google Scholar 

  16. Pourceau, G., del Valle-Carrandi, L., Di Gianvincenzo, P., Michelena, O., and Penades, S., RSC Adv., 2014, vol. 4, p. 59284. doi 10. 1039/C4RA11741G

    Article  CAS  Google Scholar 

  17. Wang, C., Adv. Mater. Res., 2013, vol. 643, p. 153. doi 10.4028/www.scientific.net/AMR.643.153

    Article  CAS  Google Scholar 

  18. Vasileva, M.Yu., Ershov, A.Yu., Baygildin, V.A., Shabsel’s, B.M., Lagoda, I.V., and Yakimansky, A.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 6, p. 1205. doi 10.1134/S1070 36321806027

    Article  CAS  Google Scholar 

  19. Ershov, A.Yu., Vasileva, M.Yu., Lagoda, I.V., and Yakimansky, A.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 6, p. 1199. doi 10.1134/S1070363218060245

    Article  CAS  Google Scholar 

  20. Ershov, A.Yu., Vasil’eva, M.Yu., Lagoda, I.V., Baigil’din, V.A., Nasledov, D.G., Kuleshova, L.Yu., and Yakimanskii, A.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 103. doi 10.1134/S1070363218010164

    Article  CAS  Google Scholar 

  21. Vasileva, M.Yu., Ershov, A.Yu., Baigildin, V.A., Lagoda, I.V., Kuleshova, L.Yu., Shtro, A.A., Zarubaev, V.V., and Yakimanskii, A.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 109. doi 10.1134/S1070363218010176

    Article  CAS  Google Scholar 

  22. Ershov, A.Yu., Lagoda, I.V., Yakimovich, S.I., Zerova, I.V., Pakal’nis, V.V., Mokeev, M.V., and Shamanin, V.V., Russ. J. Org. Chem., 2009, vol. 45, no. 5, p. 740. doi 10.1002/chin. 201008197

    Article  CAS  Google Scholar 

  23. Ershov, A.Yu., Lagoda, I.V., Yakimovich, S.I., Zerova, I.V., Pakal’nis, V.V., and Shamanin, V.V., Russ. J. Org. Chem., 2009, vol. 45, no. 10, p. 1488. doi 10.1134/S107042800910011X

    Article  CAS  Google Scholar 

  24. Alekseev, V.V., Ershov, A.Yu., Chernitsa, B.V., Doroshenko, V.A., Lagoda, I.V., Yakimovich, S.I., Zerova, I.V., Pakal’nis, V.V., and Shamanin, V.V., Russ. J. Org. Chem., 2010, vol. 46, no. 6, p. 860. doi 10.1134/S1070428010060138

    Article  CAS  Google Scholar 

  25. Ershov, A.Yu., Lagoda, I.V., Yakimovich, S.I., Kuleshova, L.Yu., Vasileva, M.Yu., Korovina, I.S., and Shamanin, V.V., Open Access Libr. J., 2016, vol. 3, article no. e2646. doi 10.4236/oalib.1102646

  26. Turkevich, J., Gold Bull., 1985, vol. 18, p. 125. doi 10.1007/BF03214694

    Article  CAS  Google Scholar 

  27. Toyoshima, M., Oura, T., Fukuda, T., Matsumoto, E., and Miura, Y., Polym. J., 2010, vol. 42, p. 172. doi 10.1038/pj.2009.321

    Article  CAS  Google Scholar 

  28. Li, X., Bao, M., Weng, Y., Yang, K., Zhang, W., and Chen, G., J. Mater. Chem. B, 2014, vol. 2, p. 5569. doi 10.1039/c4tb00852a

    Article  CAS  Google Scholar 

  29. Parry, A.L., Clemson, N.A., Ellis, J., Bernhard, S.S.R., and Davis, B.G., J. Am. Chem. Soc., 2013, vol. 135, no. 25, p. 9362. doi 10.1021/ja4046857

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Housni, A., Cai, H., Liu, S., Suzie, H., Pun, S.H., and Narain, R., Langmuir, 2007, vol. 23, no. 9, p. 5056. doi 10.1021/la070089n

    Article  CAS  PubMed  Google Scholar 

  31. Spain, S.G., Albertin, L., and Cameron, N.R., Chem. Commun., 2006, p. 4198. doi 10.1039/b608383h

    Google Scholar 

  32. Shan, J. and Tenhu, H., Chem. Commun., 2007, p. 4580. doi 10.1039/b707740h

    Google Scholar 

  33. Luan, B., Friedrich, T., Zhai, J., Streltsov, V.A., Lindsey, B.W., Kaslin, J., de Jonge, M.D., Zhu, J., Hughes, T.C., and Hao, X., RSC Adv., 2016, vol. 6, p. 23 550. doi 10.1039/c6ra02801b

    Article  CAS  Google Scholar 

  34. Lu, W., Ma, W., Lu, J., Li, X., Zhao, Y., and Chen, G., Macromol. Rapid Commun., 2014, vol. 35, p. 827. doi 10.1002/marc.201300905

    Article  CAS  PubMed  Google Scholar 

  35. Willcock, H. and O’Reilly, R.K., Polym. Chem., 2010, no. 1, p. 149. doi 10.1039/b9py00340a

    Article  CAS  Google Scholar 

  36. Lowe, A.B., Polym. Chem., 2010, no. 1, p. 17. doi 10.1039/b9py 00216b

    Article  CAS  Google Scholar 

  37. Hoyle, S.E. and Bowman, C.N., Angew. Chem., Int. Ed., 2010, vol. 49, p. 1540. doi 10.1002/anie.200903924

    Article  CAS  Google Scholar 

  38. Johnke, R.M., Sattler, J.A., and Allison, R.R., Future Oncol., 2014, vol. 10, no. 15, p. 2345. doi 10.2217/FON.14.175

    Article  CAS  PubMed  Google Scholar 

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Correspondence to A. Yu. Ershov.

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Russian Text © A.Yu. Ershov, M.Yu. Vasilyeva, M.L. Levit, I.V. Lagoda, V.A. Baygildin, B.M. Shabsels, A.A. Martynenkov, A. V. Yakimansky, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 2, pp. 309–318.

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Ershov, A.Y., Vasilyeva, M.Y., Levit, M.L. et al. Synthesis of Gold Glyconanoparticles Based on Thiol-Containing d-Hexose Acylhydrazones and Their Modification by Thiolated Poly(2-deoxy-2-methacryloylamino-D-glucose). Russ J Gen Chem 89, 300–308 (2019). https://doi.org/10.1134/S107036321902021X

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