Display options
Cite
Shurpik DN, Makhmutova LI, Usachev KS, et al. Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers. Nanomaterials (Basel). 2021;11(4)doi: 10.3390/nano11040947.
Shurpik, D. N., Makhmutova, L. I., Usachev, K. S., Islamov, D. R., Mostovaya, O. A., Nazarova, A. A., Kizhnyaev, V. N., & Stoikov, I. I. (2021). Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers. Nanomaterials (Basel, Switzerland), 11(4), . https://doi.org/10.3390/nano11040947
Shurpik, Dmitriy N, et al. "Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers." Nanomaterials (Basel, Switzerland) vol. 11,4 (2021). doi: https://doi.org/10.3390/nano11040947
Shurpik DN, Makhmutova LI, Usachev KS, Islamov DR, Mostovaya OA, Nazarova AA, Kizhnyaev VN, Stoikov II. Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers. Nanomaterials (Basel). 2021 Apr 08;11(4). doi: 10.3390/nano11040947. PMID: 33917874; PMCID: PMC8068209.
Copy Download .nbib Format: NLM
Share it on

Nanomaterials (Basel). 2021 Apr 08;11(4). doi: 10.3390/nano11040947.

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers.

Nanomaterials (Basel, Switzerland)

Dmitriy N Shurpik, Lyaysan I Makhmutova, Konstantin S Usachev, Daut R Islamov, Olga A Mostovaya, Anastasia A Nazarova, Valeriy N Kizhnyaev, Ivan I Stoikov

Affiliations

  1. A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
  2. Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
  3. FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Institute of Organic and Physical Chemistry, Arbuzov St., 8, 420088 Kazan, Russia.
  4. Department of Theoretical and Applied Organic Chemistry and Polymerization Processes, Irkutsk State University, K. Marksa, 1, 664003 Irkutsk, Russia.

PMID: 33917874 PMCID: PMC8068209 DOI: 10.3390/nano11040947

Abstract

In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures-pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first synthesized and characterized. Pillar[5]arenes containing primary and tertiary amino groups, capable of interacting with tetrazole-containing polymers, were obtained with high yield by removing the tosylate and phthalimide protection. According to the fluorescence spectroscopy data, a dramatic fluorescence enhancement in the pillar[5]arene/fluorescein/polymer system was observed with decreasing pH from neutral (pH = 7) to acidic (pH = 5). This indicates the destruction of associates and the release of the dye at a pH close to 5. The presented results open a broad range of opportunities for the development of new universal stimulus-sensitive drug delivery systems containing macrocycles and nontoxic tetrazole-based polymers.

Keywords: drug delivery systems; fluorescein; pillar[5]arene; tetrazole

References

  1. Chem Commun (Camb). 2018 Dec 4;54(97):13626-13640 - PubMed
  2. Chem Commun (Camb). 2011 Dec 7;47(45):12340-2 - PubMed
  3. Chem Soc Rev. 2019 May 20;48(10):2682-2697 - PubMed
  4. Acc Chem Res. 2005 Apr;38(4):313-23 - PubMed
  5. Chemistry. 2003 Dec 5;9(23):5873-8 - PubMed
  6. Int J Pharm. 2018 Jan 15;535(1-2):253-260 - PubMed
  7. Chem Commun (Camb). 2019 Jul 4;55(55):7883-7898 - PubMed
  8. Adv Drug Deliv Rev. 2012 Aug;64(11):979-92 - PubMed
  9. Chem Commun (Camb). 2016 Oct 25;52(87):12792-12805 - PubMed
  10. Chem Rev. 2019 Feb 13;119(3):1970-2042 - PubMed
  11. Drug Dev Ind Pharm. 2017 Dec;43(12):1963-1977 - PubMed
  12. Org Lett. 2018 Aug 17;20(16):4745-4748 - PubMed
  13. J Am Chem Soc. 2020 Apr 15;142(15):6957-6961 - PubMed
  14. Biophys J. 2020 Jan 7;118(1):138-150 - PubMed
  15. J Adv Res. 2018 Jun 25;15:1-18 - PubMed
  16. Chem Commun (Camb). 2018 Sep 6;54(72):10203-10206 - PubMed
  17. J Am Chem Soc. 2020 Apr 1;142(13):6360-6364 - PubMed
  18. Bioorg Chem. 2019 Apr;85:325-336 - PubMed
  19. Nat Rev Chem. 2017 Aug;1(8): - PubMed
  20. Chem Soc Rev. 2011 Mar;40(3):1305-23 - PubMed
  21. J Control Release. 2017 Aug 28;260:46-60 - PubMed
  22. Drug Discov Today. 2019 Mar;24(3):858-866 - PubMed
  23. Dalton Trans. 2005 Jan 21;(2):359-64 - PubMed
  24. Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8 - PubMed
  25. Int J Pharm. 2019 Apr 20;561:244-264 - PubMed
  26. Biotechnol J. 2019 Jan;14(1):e1800354 - PubMed
  27. J Biomater Sci Polym Ed. 2019 Feb;30(3):202-214 - PubMed
  28. Pharmacol Res Commun. 1983 Feb;15(2):183-9 - PubMed
  29. Org Biomol Chem. 2019 Nov 27;17(46):9951-9959 - PubMed
  30. Chem Commun (Camb). 2011 Apr 28;47(16):4694-6 - PubMed
  31. Chem Soc Rev. 2018 Jul 17;47(14):5491-5528 - PubMed
  32. Chem Soc Rev. 2008 Jan;37(1):84-100 - PubMed
  33. Angew Chem Int Ed Engl. 2003 Oct 6;42(38):4640-3 - PubMed
  34. J Colloid Interface Sci. 2013 Apr 1;395:190-7 - PubMed
  35. J Am Chem Soc. 2019 Jul 31;141(30):11847-11851 - PubMed
  36. Nanoscale Horiz. 2017 Sep 1;2(5):297-302 - PubMed
  37. Org Biomol Chem. 2017 Jan 25;15(4):762-772 - PubMed
  38. Polymers (Basel). 2020 Jun 28;12(7): - PubMed
  39. Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22 - PubMed
  40. Mater Sci Eng C Mater Biol Appl. 2016 Mar;60:569-578 - PubMed

Publication Types

Grant support