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Crystal engineering as a scientific basis for modification of physicochemical properties of bioflavonoids

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Russian Chemical Bulletin Aims and scope

Abstract

Flavonoids are of interest for pharmacy and medicinal chemistry due to a wide range of biological activities. The major goal for the design of new drugs based on flavonoids is to increase bioavailability of pharmaceutical substances. Crystal engineering is a useful tool for this purpose. This review presents a systematic analysis of the publications on crystal engineering of flavonoids published between 2000 and 2019. The data on objects, methods of supramolecular synthesis, analysis, and preclinical studies of its products are summarized. The trends in crystal engineering of flavonoids are considered and promising areas for further research are identified. The review may be of interest for researchers engaged in the design of drugs with low bioavailability, including bioflavonoids.

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References

  1. A. M. De Silva, R. W. Manville, G. W. Abbott, Science Adv., 2018, 4, eaav0824.

    Article  CAS  Google Scholar 

  2. M. Liu, E. M. El-Hassary, T. A. Oelschlaeger, M. S. Donia, R. J. Quinn, U. R. Abdelmohsen, Lancet Infect. Dis., 2019, 19, e237.

    Article  PubMed  Google Scholar 

  3. T. Rodrigues, D. Reker, P. Schneider, G. Schneider, Nature Chem., 2016, 8, 531.

    Article  CAS  Google Scholar 

  4. S. Andrieu, N. Coley, S. Lovestone, P. S. Aisen, B. Vellas, Lancet Neurol., 2015, 14, 926.

    Article  PubMed  Google Scholar 

  5. S. Kim, L. Li, Z. Maliga, Q. Yin, H. Wu, T. J. Mitchison, ASC Chem. Biol., 2013, 8, 1396.

    CAS  Google Scholar 

  6. M. B. Plotnikov, N. A. Tyukavkina, T. M. Plotnikova, Lekarstvennye preparaty na osnove dikvertina [Drugs Based on Diquertine], Izd-vo Tomskogo un-ta, Tomsk, 2005, 228 pp. (in Russian).

    Google Scholar 

  7. J. Zhao, J. Yang, Y. Xie, Int. J. Pharm., 2019, 118642.

  8. R. P. Terekhov, I. A. Selivanova, N. A. Tyukavkina, G. V. Shylov, A. N. Utenishev, Yu. B. Porozov, Acta Crystalogr. Sect. B, 2019, 75, 175.

    Article  CAS  Google Scholar 

  9. J. Li, J. Dong, J. Ouyang, J. Cui, F. Wanf, J. Wang, MedChemComm, 2017, 8, 353.

    Article  CAS  PubMed  Google Scholar 

  10. S. Zu, L. Yang, J. Huang, C. Ma, W. Wang, C. Zhao, Y. Zu, Int. J. Mol. Sci., 2012, 13, 8869.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. H. Uchiyama, Y. Wada, M. Takamatsu, K. Kadota, Y. Tozuka, Environ. Control Biol., 2018, 56, 161.

    Article  CAS  Google Scholar 

  12. A. N. Shikov, O. N. Pozharitskaya, I. Myroshnyk, S. Mirza, I. N. Urakova, S. Hirjarvi, V. G. Makarov, J. Heinamaki, J. Yliruusi, R. Hiltunen, Int. J. Pharm., 2009, 337, 148.

    Article  CAS  Google Scholar 

  13. A. Karagianni, M. Malamatari, K. Kachrimanis, Pharmaceutics, 2018, 10, E18.

    Article  PubMed  CAS  Google Scholar 

  14. A. Kumar, S. Kumar, A. Nanda, Adv. Pharm. Bull., 2018, 8, 355.

    Article  PubMed  PubMed Central  Google Scholar 

  15. S. Z. Vatsadze, A. V. Dolganov, A. V. Yakimanskii, M. Ya. Goikhman, I. V. Podeshvo, K. A. Lyssenko, A. L. Maksimov, T. V. Magdesieva, Russ. Chem. Bull., 2010, 59, 724.

    Article  CAS  Google Scholar 

  16. T. A. Vaganova, Yu. V. Gatilov, E. V. Malykhin, Russ. Chem. Bull., 2015, 64, 1746.

    Article  CAS  Google Scholar 

  17. Yu. S. Tarakhovskii, Yu. A. Kim, B. S. Abdrasilov, E. N. Muzafarov, Flavonoids: biokhimiya, biofizika, meditsina [Flavonoids: Biochemistry, Biophysics, Medicine], Synchrobook, Pushchino, 2013, 310 pp. (in Russian).

    Google Scholar 

  18. I. R. Ilyasov, V. L. Beloborodov, I. A. Selivanova, Chem. Pap., 2018, 72, 1917.

    Article  CAS  Google Scholar 

  19. J. Bernatoniene, D. M. Kopustinskiene, Molecules, 2018, 23, E965.

    Article  PubMed  CAS  Google Scholar 

  20. L. Wen, Y. Jiang, J. Yang, Y. Zhao, M. Tian, B. Yang, Ann. NY Acad. Sci., 2017, 1398, 120.

    Article  CAS  PubMed  Google Scholar 

  21. S. Miltonprabu, M. Tomczyk, K. Skalicka-Wozniak, L. Rastrelli, M. Daglia, S. F. Nabavi, S. M. Alavian, S. M. Nabavi, Food Chem. Toxicol., 2017, 108(B), 365.

    Article  CAS  Google Scholar 

  22. W Sianglum, K. Muangngam, N. Joycharat, S. P. Vorayuth-kunchai, Microb. Drug Resist., 2019; DOI:10.1089/mdr.2018.0391.

    Google Scholar 

  23. A. Salritabar, B. Darvishi, F Hadjiakhoondi, A. Manayi, A. Sureda, S. F Nabavi, L. R. Fitzpatrick, S. M. Nabavi, A. Bishayee, World J. Gastroenterol., 2017, 23, 5097.

    Article  CAS  Google Scholar 

  24. X. Yan, M. Qi, P. Li, Y. Zhan, H. Shao, Cell Biosci., 2017, 7, 50.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  25. U. Raj, P. K. Varadwaj, Interdiscip. Sci., 2016, 8, 132.

    Article  CAS  PubMed  Google Scholar 

  26. B. K. Park, J. H. Lee, H. W Seo, K. S. Oh, J. H. Lee, B. H. Lee, Int. J. Radial Biol, 2019, 95, 1094.

    Article  CAS  Google Scholar 

  27. X. Su, Y. Zhang, H. Yin, L. Liu, Y. Zhang, L. Wu, Q. Zhang, C. Wang, L. Zhang, Y. Zhang, Y. Zhang, J. Mol. Struct, 2019, 1177, 107.

    Article  CAS  Google Scholar 

  28. D. Setyawan, S. A. Permata, A. Zainul, M. L. A. D. Lestari, Indones. J. Chem., 2018, 18, 531.

    Article  CAS  Google Scholar 

  29. S. Patil, K. Chaudhari, R. Kamble, J. King Saud Univ. Sci., 2018, 30, 138.

    Article  Google Scholar 

  30. F Liu, L.-Y Wang, Y.-T. Li, Z.-Y Wu, C.-W Yan, Cryst. Growth Des., 2018, 18, 3729.

    Article  CAS  Google Scholar 

  31. U. Athiyah, P. A. Kusuma, T. Tutik, M. L. A. D. Lestari, D. Isadiartuti, D. P. Paramita, D. Setyawan, Jurnal Teknologi, 2018, 81, 39.

    Article  Google Scholar 

  32. D. Setyawan, I. P. Oktavia, R. Farizaka, R. Sari, Turk. J. Pharm. Sci., 2017, 14, 280.

    Article  CAS  Google Scholar 

  33. K. Vasisht, K. Chadha, M. Karan, Y. Bhalla, A. Jena, R. Chadha, CrystEngComm, 2016, 18, 1403.

    Article  CAS  Google Scholar 

  34. H. He, Y. Huang, Q. Zhang, J.-R. Wang, X. Mei, Cryst. Growth Des., 2016, 16, 2348.

    Article  CAS  Google Scholar 

  35. M. Veverka, T. Dubaj, J. Gallovie, V. Jorik, E. Vevekova, M. Danihelova, P. Simon, Monathsh. Chem., 2014, 146, 99.

    Article  CAS  Google Scholar 

  36. L. N. Kuleshova, D. W. M. Hofmann, R. Boese, Chem. Phys. Lett., 2013, 564, 26.

    Article  CAS  Google Scholar 

  37. A. J. Smith, PhD Dissertation, University of South Florida, 2012, 120 pp.

    Google Scholar 

  38. G. S. Borghetti, J. P. Carini, S. B. Honorato, A. P. Ayala, J. C. F Moreira, V. L. Bassani, Thermochim. Acta, 2012, 539, 112.

    Article  CAS  Google Scholar 

  39. A. J. Smith, P. Kavuru, L. Woijtas, M. J. Zaworotko, R. D. Shytle, Mol. Pharm., 2011, 8, 1867.

    Article  CAS  PubMed  Google Scholar 

  40. D. J. Timmons, M. R. Pacheco, K. A. Fricke, C. Slebodnick, Cryst. Growth Des., 2008, 8, 2765.

    Article  CAS  Google Scholar 

  41. S. Kesani, Master Degree Dissertation, University of South Florida, 2007, 80 pp.

    Google Scholar 

  42. Y Luo, S. Chen, J. Zhuo, J. Chen, L. Tian, W Gao, Y. Zhang, A. Ma, L. Li, Z. Zhou, J. Drug Deliv. Sci. Technol., 2019, 50, 248.

    Article  CAS  Google Scholar 

  43. M. Sowa, K. Slepokura, E. Matczak-Jon, CrystEngComm, 2013, 15, 7696.

    Article  CAS  Google Scholar 

  44. I. Sathisaran, S. V. Dalvi, Pharmaceutics, 2018, 10, E108.

    Article  PubMed  CAS  Google Scholar 

  45. S. Ren, M. Liu, C. Hong, G. Li, J. Sun, J. Wang, L. Zhang, Y. Xie, Acta Pharm. Sin. B, 2019, 9, 59.

    Article  PubMed  Google Scholar 

  46. R. Terekhov, I. Selivanova, J. Pharm. Innov., 2018, 13, 313.

    Article  Google Scholar 

  47. C. Luo, W. Liang, X. Chen, J. Wang, Z. Deng, H. Zhang, CrystEngComm, 2018, 20, 3025.

    Article  CAS  Google Scholar 

  48. K. Vasisht, K. Chadha, M. Karan, Y. Bhalla, R. Chadha, S. Khullar, S. Mandal, Cryst. Growth Des., 2017, 17, 2386.

    Article  CAS  Google Scholar 

  49. R. Terekhov, M. Buchholz, D. Ramsbeck, I. Selivanova, Arch. ISANH, 2017, 5, 13.

    Google Scholar 

  50. J. Xu, Y. Huang, S. Ruana, Z. Chi, K. Qin, B. Cai, T. Cai, CrystEngComm, 2016, 18, 8776.

    Article  CAS  Google Scholar 

  51. M. Liu, C. Hong, G. Li, P. Ma, Y. Xie, Nanotechnology, 2016, 27, 395601.

    Article  PubMed  CAS  Google Scholar 

  52. C. Hong, Y. Xie, Y. Yao, G. Li, X. Yuan, H. Shen, Pharm. Res., 2015, 32, 47.

    Article  CAS  PubMed  Google Scholar 

  53. M. Sowa, K. Slepokura, E. Matczak-Jon, CrystEngComm, 2014, 16, 10592.

    Article  CAS  Google Scholar 

  54. Y. Huang, B. Zhang, Y. Gao, J. Zhang, L. Shi, J. Pharm. Sci., 2014, 103, 2330.

    Article  CAS  PubMed  Google Scholar 

  55. A. J. Smith, P. Kavuru, K. K. Arora, S. Kesani, J. Tan, M. J. Zaworotko, R. D. Shytle, Mol. Pharm., 2013, 10, 2948.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. M. Sowa, K. Slepokura, E. Matczak-Jon, Acta Crystalogr. Sect. C, 2012, 68, o262.

    Article  CAS  Google Scholar 

  57. P. Kavuru, Master Degree Dissertation, University of South Florida, 2008, 87 pp.

    Google Scholar 

  58. W. Li, J. Pi, Y. Zhang, X. Ma, B. Zhang, S. Wang, D. Qi, N. Li, P. Guo, Z. Liu, Fitoterapia, 2018, 129, 85.

    Article  PubMed  CAS  Google Scholar 

  59. C. Wang, Q. Tong, X. Hou, S. Hu, J. Fang, C. C. Sun, Cryst. Growth Des., 2016, 16, 5030.

    Article  CAS  Google Scholar 

  60. M. Sowa, K. Slepokura, E. Matczak-Jon, J. Mol. Struct., 2014, 1076, 80.

    Article  CAS  Google Scholar 

  61. S. J. Franklin, P. B. Myrdal, AAPS Pharm. Sci. Technol., 2015, 16, 1400.

    Article  CAS  Google Scholar 

  62. C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Cryst. Sect. B, 2016, 72, 171.

    Article  CAS  Google Scholar 

  63. R. Chadha, Y. Bhalla, M. K. Vashisht, K. Chadha, in Recrystallization in Materials Processing, Ed. V. Glebovsky, IntechOpen, London, 2015.

  64. R. Chadha, Y. Bhalla, K. Chadha, M. Karan, J. Phar. Biomed. Anal., 2017, 134, 361.

    Article  CAS  Google Scholar 

  65. M. Muresan-Pop, L. B. Chiriac, F. Martin, S. Simon, Compos. Part B, 2016, 89, 60.

    Article  CAS  Google Scholar 

  66. M. Sowa, K. Slepokura, E. Matczak-Jon, J. Mol. Struct., 2014, 1058, 114.

    Article  CAS  Google Scholar 

  67. A. N. Streletskii, M. V. Sivak, A. Yu. Dolgoborodov, J. Mater. Sci., 2017, 52, 11810.

    Article  CAS  Google Scholar 

  68. Y.-N. Zhang, H.-M. Yin, Y. Zhang, D.-J. Zhang, X. Su, H.-X. Kuang, J. Cryst. Growth, 2016, 458, 103.

    Article  CAS  Google Scholar 

  69. J.-Y Shin, Y.-T. Sohn, J. Therm. Anal. Calorim., 2014, 115, 2457.

    Article  CAS  Google Scholar 

  70. R. P. Terekhov, I. A. Selivanova, A. K. Zhelvakova, Yu. B. Porozov, A. V. Dzuban, Biomed. Khim. [Biomed. Chem.], 2019, 65, 152 (in Russian).

    Article  CAS  Google Scholar 

  71. P. H. Karpinski, Chem. Eng. Technol, 2006, 29, 233.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Pharmacy, I. M. Sechenov First Moscow State Medical University (Sechenov University), Ministry of Healthcare of the Russian Federation, Build. 2, 8 ul. Trubetskaya, 119991, Moscow, Russian Federation

    I. A. Selivanova & R. P. Terekhov

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  1. I. A. Selivanova
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  2. R. P. Terekhov
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Correspondence to R. P. Terekhov.

Additional information

This review was prepared with the financial support of the Russian Academic Excellence Project 5–100.

Based on the materials of the 4th Russian Conference on Medicinal Chemistry with International participation (June 9–14, 2019, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2155–2162, December, 2019.

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Selivanova, I.A., Terekhov, R.P. Crystal engineering as a scientific basis for modification of physicochemical properties of bioflavonoids. Russ Chem Bull 68, 2155–2162 (2019). https://doi.org/10.1007/s11172-019-2684-z

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  • DOI: https://doi.org/10.1007/s11172-019-2684-z

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