Skip to main content

Advertisement

Log in

Macrocycle-based oligo- and polylactides: synthesis and prospects of application

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The review considers methods for modifying oligo- and polymers of lactic acid by macrocyclic moieties (cyclodextrin, tetrapyrrole, and calixarene) and the effect of modifiers on the complexing, thermal, and aggregation properties. Analytical characteristics of oligolactide-based sensors and biosensors are discussed, with particular emphasis on the mechanism of signal generation and the contribution of modified materials to the selectivity and sensitivity of analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. Nofar, D. Sacligil, P. J. Carreau, M. R. Kamal, M.-C. Heuzey, Int. J. Biol. Macromol., 2019, 125, 307.

    Article  CAS  PubMed  Google Scholar 

  2. D. Garlotta, J. Polym. Environ., 2001, 9, 63.

    Article  CAS  Google Scholar 

  3. K. Marcincinova-Benabdillah, M. Boustta, J. Coudane, M. Vert, Biomacromolecules, 2001, 2, 1279.

    Article  CAS  PubMed  Google Scholar 

  4. S. Kumar, S. Singh, S. Senapati, A. P. Singh, B. Ray, P. Maiti, Int. J. Biol. Macromol., 2017, 104, 487.

    Article  CAS  PubMed  Google Scholar 

  5. A. Jain, K. R. Kunduru, A. Basu, B. Mizrahi, A. J. Domb, W. Khan, Adv. Drug Deliv. Rev., 2016, 107, 213.

    Article  CAS  PubMed  Google Scholar 

  6. D. Pandita, S. Kumar, V. Lather, Drug Discovery Today, 2015, 20, 95.

    Article  CAS  PubMed  Google Scholar 

  7. I. E. Nifant’ev, A. V. Shlyakhtin, V. V. Bagrov, P. D. Komarov, A. N. Tavtorkin, M. E. Minyaev, P. V. Ivchenko, Mendeleev Commun., 2018, 28, 412.

    Article  CAS  Google Scholar 

  8. A. G. Andreopoulos, E. C. Hatzi, M. Doxastakis, J. Mater. Sci.Mater. Med., 2000, 11, 393.

    Article  CAS  PubMed  Google Scholar 

  9. C. H. Kum, Y. Cho, Y. K. Joung, J. Choi, K. Park, S. H. Seo, Y. S. Park, D. J. Ahn, D. K. Han, J. Mater. Chem. B, 2013, 1, 2764.

    Article  CAS  PubMed  Google Scholar 

  10. M. Murariu, P. Dubois, Adv. Drug Deliv. Rev., 2016, 107, 17.

    Article  CAS  PubMed  Google Scholar 

  11. P. Saini, M. Arora, M. N. V. R. Kumar, Adv. Drug Deliv. Rev., 2016, 107, 47.

    Article  CAS  PubMed  Google Scholar 

  12. I. V. Averianov, M. A. Stepanova, I. V. Gofman, A. L. Nikolaeva, V. A. Korzhikov-Vlakh, M. Karttunen, E. G. Korzhikova-Vlakh, Mendeleev Commun., 2019, 29, 220.

    Article  CAS  Google Scholar 

  13. H. Moustafa, A. M. Youssef, N. A. Darwish, A. I. Abou-Kandil, Composites, Part B, 2019, 172, 16.

    Article  CAS  Google Scholar 

  14. J. Pretula, S. Slomkowski, S. Penczek, Adv. Drug Deliv. Rev., 2016, 107, 3.

    Article  CAS  PubMed  Google Scholar 

  15. J. M. Ren, T. G. McKenzie, Q. Fu, E. H. H. Wong, J. Xu, Z. An, S. Shanmugam, T. P. Davis, C. Boyer, G. G. Qiao, Chem. Rev., 2016, 116, 6743.

    Article  CAS  PubMed  Google Scholar 

  16. A. Poulsen, A. D. William, B. W. Dymock, RSC Drug Discovery Series, 2015, 40, 141.

    CAS  Google Scholar 

  17. M. Imran, M. Ramzan, A. K. Qureshi, M. A. Khan, M. Tariq, Biosensors, 2018, 8, 95; DOI: https://doi.org/10.3390/bios8040095.

    Article  CAS  PubMed Central  Google Scholar 

  18. G. Crini, Chem. Rev., 2014, 114, 10940.

    Article  CAS  PubMed  Google Scholar 

  19. F. van de Manakker, T. Vermonden, C. F. van Nostrum, W. E. Hennink, Biomacromolecules, 2009, 10, 3157.

    Article  CAS  PubMed  Google Scholar 

  20. J. Shen, A. Hao, G. Du, H. Zhang, H. Sun, Carbohydr. Res., 2008, 343, 2517.

    Article  CAS  PubMed  Google Scholar 

  21. M. Adeli, Z. Zarnegar, R. Kabiri, Eur. Polym. J., 2008, 44, 1921.

    Article  CAS  Google Scholar 

  22. H. Gao, Y. N. Wang, Y. G. Fan, J. B. Ma, J. Controlled Release, 2005, 107, 158.

    Article  CAS  Google Scholar 

  23. L. Y. Qiu, R. J. Wang, C. Zheng, Y. Jin, L. Q. Jin, Nanomedicine, 2010, 5, 193.

    Article  CAS  PubMed  Google Scholar 

  24. N. E. Sedyakina, A. F. Krivoshchepov, A. Ya. Zasypko, A. G. Demchenko, A. L. Rozofarov, V. N. Kuryakov, N. B. Feldman, S. V. Lutsenko, Mendeleev Commun., 2019, 29, 320.

    Article  CAS  Google Scholar 

  25. H. R. Kricheldorf, A. Serra, Polym. Bull., 1985, 14, 497.

    Article  CAS  Google Scholar 

  26. N. Yao, W. Lin, X. Zhang, H. Gu, L. Zhang, J. Polym. Sci., Part A: Polym. Chem., 2016, 54, 186.

    Article  CAS  Google Scholar 

  27. X. Zhang, W. Lin, L. Wen, N. Yao, S. Nie, L. Zhang, Phys. Chem. Chem. Phys., 2016, 18, 26519.

    Article  CAS  PubMed  Google Scholar 

  28. W. Lin, N. Yao, L. Qian, X. Zhang, Q. Chen, J. Wang, L. Zhang, Acta Biomaterialia, 2017, 58, 455.

    Article  CAS  PubMed  Google Scholar 

  29. W. Lin, N. Yao, H. Li, S. Hanson, W. Han, C. Wang, L. Zhang, Polymers, 2016, 8, 397; DOI: https://doi.org/10.3390/polym8110397.

    Article  PubMed Central  CAS  Google Scholar 

  30. K. Tungala, P. Adhikary, V. Azmeera, K. Kumar, K. Ramesh, S. Krishnamoorthi, RSC Adv., 2016, 6, 41594.

    Article  CAS  Google Scholar 

  31. K. Ramesh, D. S. B. Anugrah, K. T. Lim, React. Funct. Polym., 2018, 131, 12.

    Article  CAS  Google Scholar 

  32. S. Shao, V. Rajendiran, J. F. Lovell, Coord. Chem. Rev., 2019, 379, 99.

    Article  CAS  PubMed  Google Scholar 

  33. K. Wang, D. Qi, Y. Li, T. Wang, H. Liu, J. Jiang, Coord. Chem. Rev., 2019, 378, 188.

    Article  CAS  Google Scholar 

  34. M.-J. Shieh, C.-Y. Hsu, L.-Y. Huang, H.-Y. Chen, F.-H. Huang, P.-S. Lai, J. Controlled Release, 2011, 152, 418.

    Article  CAS  Google Scholar 

  35. V. Lassalle, M. L. Ferreira, Macromol. Biosci., 2007, 7, 767.

    Article  CAS  PubMed  Google Scholar 

  36. C.-Y. Hsu, M.-P. Nieh, P.-S. Lai, Chem. Commun., 2012, 48, 9343.

    Article  CAS  Google Scholar 

  37. X.-H. Dai, W. Liu, Y.-F. Huang, C.-M. Dong, Adv. Mater. Res., 2011, 239–242, 1703.

    Article  CAS  Google Scholar 

  38. D. J. Lee, G. Y. Park, K. T. Oh, N. M. Oh, D. S. Kwag, Y. S. Youn, Y. T. Oh, J. W. Park, E. S. Lee, Int. J. Pharm., 2012, 434, 257.

    Article  CAS  PubMed  Google Scholar 

  39. E. Boix-Garriga, F. Bryden, H. Savoie, M. L. Sagristá, M. Mora, R. W. Boyle, S. Nonell, J. Porphyrins Phthalocyanines, 2016, 20, 1306.

    Article  CAS  Google Scholar 

  40. X.-H. Dai, H. Jin, M.-H. Cai, H. Wang, Z.-P. Zhou, J.-M. Pan, X.-H. Wang, Y.-S. Yan, D.-M. Liu, L. Sun, Reac. Funct. Polym., 2015, 89, 9.

    Article  CAS  Google Scholar 

  41. X.-H. Dai, Z.-M. Wang, L.-Y. Gao, J.-M. Pan, X.-H. Wang, Y.-S. Yan, D.-M. Liu, New J. Chem., 2014, 38, 3569.

    Article  CAS  Google Scholar 

  42. X.-H. Dai, Z.-M. Wang, W. Liu, C.-M. Dong, J.-M. Pan, S.-S. Yuan, Y.-S. Yan, D.-M. Liu, L. Sun, Colloid. Polym. Sci., 2014, 292, 2111.

    Article  CAS  Google Scholar 

  43. X.-H. Dai, Z.-M. Wang, J.-M. Pan, S.-S. Yuan, Y.-S. Yan, D.-M. Liu, L. Sun, J. Biomater. Sci., Polym. Ed., 2014, 25, 1755.

    Article  CAS  Google Scholar 

  44. F. Seidi, R. Jenjob, T. Phakkeeree, D. Crespy, J. Controlled Release, 2018, 284, 188.

    Article  CAS  Google Scholar 

  45. T. Wang, D. Zhu, G. Liu, W. Tao, W. Cao, L. Zhang, L. Wang, H. Chen, L. Mei, L. Huang, X. Zeng, RSC Adv., 2015, 5, 50617.

    Article  CAS  Google Scholar 

  46. J. Li, Z. Song, L. Gao, H. Shan, Polym. Bull., 2016, 73, 2121.

    Article  CAS  Google Scholar 

  47. C. D. Gutsche, In Calixarenes Revisited, Monographs in Supramolecular Chemistry, Ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1998.

  48. R. Ludwig, N. T. K. Dzung, Sensors, 2002, 2, 397.

    Article  Google Scholar 

  49. D. Dria, B. A. Goudy, K. A. Moga, P. S. Corbin, Polym. Chem., 2012, 3, 2070.

    Article  CAS  Google Scholar 

  50. N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev., 2006, 106, 5291.

    Article  CAS  PubMed  Google Scholar 

  51. F. Perret, A. W. Coleman, Chem. Commun., 2011, 47, 7303.

    Article  CAS  Google Scholar 

  52. O. A. Mostovaya, P. L. Padnya, A. A. Vavilova, D. N. Shurpik, B. I. Khairutdinov, T. A. Mukhametzyanov, A. A. Khannanov, M. P. Kutyreva, I. I. Stoikov, New J. Chem., 2018, 42, 177.

    Article  CAS  Google Scholar 

  53. V. V. Gorbachuk, P. L. Padnya, I. I. Stoikov, Russ. J. Gen. Chem., 2018, 88, 1838.

    Article  CAS  Google Scholar 

  54. A. A. Vavilova, V. V. Gorbachuk, D. N. Shurpik, A. V. Gerasimov, L. S. Yakimova, P. L. Padnya, I. I. Stoikov, J. Mol. Liq., 2019, 281, 243.

    Article  CAS  Google Scholar 

  55. V. V. Gorbatchuk, A. V. Porifreva, V. B. Stepanova, Yu. I. Kuzin, V. G. Evtugyn, R. V. Shamagsumova, I. I. Stoikov, G. A. Evtugyn, Sens. Actuators, B, 2017, 246, 136.

    Article  CAS  Google Scholar 

  56. V. V. Gorbachuk, O. A. Mostovaya, V. G. Evtugyn, Yu. N. Osin, I. Kh. Rizvanov, A. V. Gerasimov, I. I. Stoikov, Macroheterocycles, 2017, 10, 174.

    Article  CAS  Google Scholar 

  57. O. A. Mostovaya, V. V. Gorbachuk, O. B. Bazanova, A. V. Gerasimov, V. G. Evtugyn, Y. N. Osin, V. D. Myakushev, I. Kh. Rizvanov, I. I. Stoikov, Mater. Chem. Front., 2019, 3, 292.

    Article  CAS  Google Scholar 

  58. L. Hlavatá, V. Vyskočil, K. Beníková, M. Borbélyová, J. Labuda, Cent. Eur. J. Chem., 2014, 12, 604.

    Article  CAS  Google Scholar 

  59. R. J. Klinger, J. K. Kochi, J. Phys. Chem., 1981, 85, 1731.

    Article  Google Scholar 

  60. R. V. Shamagsumova, O. Yu. Efimova, V. V. Gorbatchuk, V. G. Evtugyn, I. I. Stoikov, G. A. Evtugyn, Anal. Lett., 2019, 52, 1558.

    Article  CAS  Google Scholar 

  61. A. V. Porifreva, V. V. Gorbatchuk, V. G. Evtugyn, I. I. Stoikov, G. A. Evtugyn, Electroanalysis, 2018, 30, 641.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to I. I. Stoikov or P. L. Padnya.

Additional information

Based on the materials of the V International Scientific Conference “Advances in Synthesis and Complexing” (April 22–26, 2019, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1962–1982, November, 2019.

This study was financially supported by the Russian Science Foundation (Project No. 16-13-00005).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stoikov, I.I., Padnya, P.L., Mostovaya, O.A. et al. Macrocycle-based oligo- and polylactides: synthesis and prospects of application. Russ Chem Bull 68, 1962–1982 (2019). https://doi.org/10.1007/s11172-019-2655-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2655-4

Key words

Navigation