Vitamin В12 in drug delivery systems

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

Vitamin B12 is a vital biologically active compound for human and is involved in a wide range of metabolic processes. The widespread vitamin B12 deficiency and vitamin’s low penetrating ability into cells determine the urgency of delivery systems development for the design of formulations with improved biopharmaceutical properties. This work provides a brief discussion of the main chemical and biochemical properties of the vitamin B12, as well as considers oral, injectable and transdermal multicomponent dosage forms of vitamin B12 that are aimed at solving the issue. Moreover, the literature analysis of the prospects of using vitamin B12 as an auxiliary component for both passive and active delivery of other drug molecules, for example, peptide nucleic acids and antitumor drugs, is presented. The review describes in detail the types of proposed delivery systems for biologically active compounds, in which vitamin B12 is one of the components.

全文:

受限制的访问

作者简介

A. Skuredina

Lomonosov Moscow State University

编辑信件的主要联系方式.
Email: anna.skuredina@yandex.ru

Department of Chemistry

俄罗斯联邦, Leninskie Gory 1/3, Moscow, 119991

D. Ialama

Lomonosov Moscow State University

Email: anna.skuredina@yandex.ru

Department of Chemistry

俄罗斯联邦, Leninskie Gory 1/3, Moscow, 119991

I. Le-Deygen

Lomonosov Moscow State University

Email: anna.skuredina@yandex.ru

Department of Chemistry

俄罗斯联邦, Leninskie Gory 1/3, Moscow, 119991

参考

  1. Guéant J.L., Guéant-Rodriguez R.M., Alpers D.H. // Vitam. Horm. 2022. V. 119. P. 241–274. https://doi.org/10.1016/bs.vh.2022.01.016
  2. Temova Rakuša Ž., Roškar R., Hickey N., Geremia S. // Molecules. 2022. V. 28. P. 240. https://doi.org/10.3390/molecules28010240
  3. Kozyraki R., Cases O. // Biochimie. 2013. V. 95. P. 1002–1007. https://doi.org/10.1016/j.biochi.2012.11.004
  4. Tanner S.M., Li Z., Perko J.D., Öner C., Çetin M., Altay Ç., Yurtsever Z., David K.L., Faivre L., Ismail E.A., Gräsbeck R., de la Chapelle A. // Proc. Natl. Acad. Sci. USA. 2005. V. 102. P. 4130–4133. https://doi.org/10.1073/pnas.0500517102
  5. Клинические рекомендации “Железодефицитная анемия” 2021-2022-2023 (09.09.2021), разработанные Национальным гематологическим обществом, Национальным обществом детских гематологов и онкологов – Утверждены Минздравом РФ.
  6. Antoine D., Li Z., Quilliot D., Sirveaux M.A., Meyre D., Mangeon A., Brunaud L., Guéant J.L., Guéant-Rodriguez R.M. // Clin. Nutr. 2021. V. 40. P. 87–93. https://doi.org/10.1016/j.clnu.2020.04.029
  7. Montoro-Huguet M.A., Belloc B., Domínguez-Cajal M. // Nutrients. 2021. V. 13. P. 1254. https://doi.org/10.3390/nu13041254
  8. Fidaleo M., Tacconi S., Sbarigia C., Passeri D., Rossi M., Tata A.M., Dini L. // Nanomaterials. 2021. V. 11. P. 743. https://doi.org/10.3390/nano11030743
  9. Van Campen C.M.C., Riepma K., Visser F.C. // Front. Pharmacol. 2019. V. 10. P. 1102. https://doi.org/10.3389/fphar.2019.01102
  10. Bensky M.J., Ayalon-Dangur I., Ayalon-Dangur R., Naamany E., Gafter-Gvili A., Koren G., Shiber S. // Drug Deliv. Transl. Res. 2019. V. 9. P. 625–630. https://doi.org/10.1007/s13346-018-00613-y
  11. Wang X., Wei L., Kotra L.P. // Bioorg. Med. Chem. 2007. V. 15. P. 1780–1787. https://doi.org/10.1016/j.bmc.2006.11.036
  12. Smith A.D., Warren M.J., Refsum H. // Adv. Food Nutr. Res. 2018. V. 83. P. 215–279. https://doi.org/10.1016/bs.afnr.2017.11.005
  13. Bajaj S.R., Singhal R.S. // J. Food Eng. 2020. V. 272. P. 109800. https://doi.org/10.1016/j.jfoodeng.2019.109800
  14. Rizzo G., Laganà A.S. // Molecular Nutrition: Vitamins / Ed. Patel V.B. London: Academic Press, 2020. P. 105–129. https://doi.org/10.1016/B978-0-12-811907-5.00005-1
  15. Ramalho M.J., Andrade S., Coelho M.A.N., Loureiro J.A., Pereira M.C. // Colloids Surf. B. 2020. V. 194. P. 111187. https://doi.org/10.1016/j.colsurfb.2020.111187
  16. Abdelwahab O.A., Abdelaziz A., Diab S., Khazragy A., Elboraay T., Fayad T., Diab R.A., Negida A. // Ir. J. Med. Sci. 2024. V. 193. P. 1621–1639. https://doi.org/10.1007/s11845-023-03602-4
  17. Lima S., Webb C.L., Deery E., Robinson C., Zedler J.A.Z. // Biology. 2018. V. 7. P. 19. https://doi.org/10.3390/BIOLOGY7010019
  18. Estevinho B.N., Carlan I., Blaga A., Rocha F. // Powder Technol. 2016. V. 289. P. 71–78. https://doi.org/10.1016/j.powtec.2015.11.019
  19. Galdioli Pellá M.C., Simão A.R., Lima-Tenório M.K., Tenório-Neto E., Scariot D.B., Nakamura C.V., Rubira A.F. // Carbohydr. Polym. 2020. V. 239. P. 116236. https://doi.org/10.1016/j.carbpol.2020.116236
  20. Шохин И.Е., Кулинич Ю.И., Раменская Г.В., Кукес В.Г. // Биомедицина. 2012. Т. 3. С. 91–97.
  21. Sugandhi V.V., Mahajan H.S. // J. Drug Delivery Sci. Tech. 2022. V. 70. P. 103212. https://doi.org/10.1016/j.jddst.2022.103212
  22. Mendes A.C., Gorzelanny C., Halter N., Schneider S.W., Chronakis I.S. // Int. J. Pharm. 2016. V. 510. P. 48–56. https://doi.org/10.1016/j.ijpharm.2016.06.016
  23. Yekrang J., Gholam Shahbazi N., Rostami F., Ramyar M. // Int. J. Biol. Macromol. 2023. V. 230. P. 123187. https://doi.org/10.1016/j.ijbiomac.2023.123187
  24. Ramöller I.K., Tekko I.A., McCarthy H.O., Donnelly R.F. // Int. J. Pharm. 2019. V. 566. P. 299–306. https://doi.org/10.1016/j.ijpharm.2019.05.066
  25. Farzanfar S., Kouzekonan G.S., Mirjani R., Shekarchi B. // Biomed. Eng. Lett. 2020. V. 10. P. 547– 554. https://doi.org/10.1007/s13534-020-00165-6
  26. Ramalho M.J., Loureiro J.A., Pereira M.C. // ACS Appl. Nano Mater. 2021. V. 4. P. 6881–6892. https://doi.org/10.1021/acsanm.1c00954
  27. Bucolo C., Maugeri G., Giunta S., D’Agata V., Drago F., Romano G.L. // Front. Pharmacol. 2023. V. 14. P. 1109291. https://doi.org/10.3389/fphar.2023.1109291
  28. Romano M.R., Biagioni F., Carrizzo A., Lorusso M., Spadaro A., Micelli Ferrari T., Vecchione C., Zurria M., Marrazzo G., Mascio G., Sacchetti B., Madonna M., Fornai F., Nicoletti F., Lograno M.D. // Exp. Eye Res. 2014. V. 120. P. 109–117. https://doi.org/10.1016/j.exer.2014.01.017
  29. Petrus A.K., Vortherms A.R., Fairchild T.J., Doyle R.P. // ChemMedChem. 2007. V. 2. P. 1717–1721. https://doi.org/10.1002/cmdc.200700239
  30. Clardy-James S., Allis D.G., Fairchild T.J., Doyle R.P. // MedChemComm. 2012. V. 3. P. 1054–1058. https://doi.org/10.1039/c2md20040f
  31. Wierzba A.J., Hassan S., Gryko D. // Asian J. Org. Chem. 2018. V. 8. P. 6–24. https://doi.org/10.1002/ajoc.201800579
  32. Petrus A.K., Fairchild T.J., Doyle R.P. // Angew. Chem. Int. Ed. Engl. 2009. V. 48. P. 1022–1028. https://doi.org/10.1002/anie.200800865
  33. Lawrence A.D., Nemoto-Smith E., Deery E., Baker J.A., Schroeder S., Brown D.G., Tullet J.M.A., Howard M.J., Brown I.R., Smith A.G., Boshoff H.I., Barry C.E., Warren M.J. // Cell Chem. Biol. 2018. V. 25. P. 941–951.e6. https://doi.org/10.1016/j.chembiol.2018.04.012
  34. Wierzba A.J., Wojciechowska M., Trylska J., Gryko D. // Methods Mol. Biol. 2021. V. 2355. P. 65–82. https://doi.org/10.1007/978-1-0716-1617-8_7
  35. Анцыпович С.И. // Успехи химии. 2002. Т. 39. № 1. С. 81–96. https://doi.org/10.1070/RC2002v071n01ABEH000691
  36. Równicki M., Dąbrowska Z., Wojciechowska M., Wierzba A.J., Maximova K., Gryko D., Trylska J. // ACS Omega. 2019. V. 4. P. 819–824. https://doi.org/10.1021/acsomega.8b03139
  37. Wierzba A.J., Maximova K., Wincenciuk A., Równicki M., Wojciechowska M., Nexø E., Trylska J., Gryko D. // Chemistry. 2018. V. 24. P. 18772–18778. https://doi.org/10.1002/chem.201804304
  38. Pieńko T., Wierzba A.J., Wojciechowska M., Gryko D., Trylska J. // J. Phys. Chem. B. 2017. V. 121. P. 2968– 2979. https://doi.org/10.1021/acs.jpcb.7b00649
  39. Pieńko T., Czarnecki J., Równicki M., Wojciechowska M., Wierzba A.J., Gryko D., Bartosik D., Trylska J. // Biophys. J. 2021. V. 120. P. 725–737. https://doi.org/10.1016/j.bpj.2021.01.004
  40. Giedyk M., Jackowska A., Równicki M., Kolanowska M., Trylska J., Gryko D. // Chem. Commun. 2019. V. 55. P. 763–766. https://doi.org/10.1039/c8cc05064c
  41. Shell T.A., Lawrence D.S. // Acc. Chem. Res. 2015. V. 48. P. 2866–2874. https://doi.org/10.1021/acs.accounts.5b00331
  42. Gick G.G., Arora K., Sequeira J.M., Nakayama Y., Lai S.C., Quadros E.V. // Exp. Cell Res. 2020. V. 396. P. 112256. https://doi.org/10.1016/j.yexcr.2020.112256
  43. Wierzba A., Wojciechowska M., Trylska J., Gryko D. // Bioconjug. Chem. 2016. V. 27. P. 189–197. https://doi.org/10.1021/acs.bioconjchem.5b00599
  44. Liu L., Liu P. // Front. Mater. Sci. 2015. V. 9. P. 211–226. https://doi.org/10.1007/s11706-015-0283-y
  45. Ertas B., Onay I.N., Yilmaz-Goler A.M., Karademir-Yilmaz B., Aslan I., Cam M.E. // J. Drug Delivery Sci. Tech. 2023. V. 89. P. 104963. https://doi.org/10.1016/j.jddst.2023.104963
  46. Long L., Lai M., Mao X., Luo J., Yuan X., Zhang L.M., Ke Z., Yang L., Deng D.Y.B. // Int. J. Nanomedicine. 2019. V. 14. P. 7743–7758. https://doi.org/10.2147/IJN.S218944
  47. Chen Z., Liang Y., Feng X., Liang Y., Shen G., Huang H., Chen Z., Yu J., Liu H., Lin T., Chen H., Wu D., Li G., Zhao B., Guo W., Hu Y. // Mater. Sci. Eng. C. Mater. Biol. Appl. 2021. V. 120. P. 111722. https://doi.org/10.1016/j.msec.2020.111722
  48. Brito A., Habeych E., Silva-Zolezzi I., Galaffu N., Allen L.H. // Nutr. Rev. 2018. V. 76. P. 778–792. https://doi.org/10.1093/nutrit/nuy026
  49. Sarti F., Müller C., Iqbal J., Perera G., Laffleur F., Bernkop-Schnürch A. // Eur. J. Pharm. Biopharm. 2013. V. 84. P. 132–137. https://doi.org/10.1016/j.ejpb.2012.11.024
  50. Maiorova L.A., Erokhina S.I., Pisani M., Barucca G., Marcaccio M., Koifman O.I., Salnikov D.S., Gromova O.A., Astolfi P., Ricci V., Erokhin V. // Colloids Surf. B. 2019. V. 182. P. 110366. https://doi.org/10.1016/j.colsurfb.2019.110366
  51. Nath J., Saikia P.P., Handique J., Gupta K., Dolui S.K. // J. Appl. Polym. Sci. 2020. V. 137. P. 49193. https://doi.org/10.1002/app.49193
  52. Sarti F., Iqbal J., Müller C., Shahnaz G., Rahmat D., Bernkop-Schnürch A. // Anal. Biochem. 2012. V. 420. P. 13–19. https://doi.org/10.1016/j.ab.2011.08.039
  53. Ramazani Afarani Z., Sarvi M.N., Akbari Alavijeh M. // J. Taiwan Inst. Chem. Eng. 2018. V. 84. P. 19–27. https://doi.org/10.1016/j.jtice.2018.01.002
  54. Coelho S.C., Laget S., Benaut P., Rocha F., Estevinho B.N. // Powder Technol. 2021. V. 392. P. 47–57. https://doi.org/10.1016/j.powtec.2021.06.056
  55. Zhang J., Field C.J., Vine D., Chen L. // Pharm. Res. 2015. V. 32. P. 1288–1303. https://doi.org/10.1007/s11095-014-1533-x
  56. Genç L., Kutlu H.M., Güney G. // Pharm. Dev. Technol. 2015. V. 20. P. 337–344. https://doi.org/10.3109/10837450.2013.867447
  57. Andrade S., Ramalho M.J., Loureiro J.A., Pereira M.C. // Int. J. Pharm. 2022. V. 626. P. 122167. https://doi.org/10.1016/j.ijpharm.2022.122167
  58. Liu G., Yang J., Wang Y., Liu X., Guan L.L., Chen L. // Food Hydrocoll. 2019. V. 92. P. 189–197. https://doi.org/10.1016/j.foodhyd.2018.12.020
  59. Guo W., Deng L., Chen Z., Chen Z., Yu J., Liu H., Li T., Lin T., Chen H., Zhao M., Zhang L., Li G., Hu Y. // Nanomedicine. 2019. V. 14. P. 353–370. https://doi.org/10.2217/nnm-2018-0321
  60. Thepphankulngarm N., Wonganan P., Sapcharoenkun C., Tuntulani T., Leeladee P. // New J. Chem. 2017. V. 41. P. 13823–13829. https://doi.org/10.1039/c7nj02754k
  61. Wang J., Tan J., Luo J., Huang P., Zhou W., Chen L., Long L., Zhang L. ming, Zhu B., Yang L., Deng D.Y.B. // J. Nanobiotechnology. 2017. V. 15. P. 18. https://doi.org/10.1186/s12951-017-0251-z
  62. Delasoie J., Rossier J., Haeni L., Rothen-Rutishauser B., Zobi F. // Dalton Trans. 2018. V. 47. P. 17221–17232. https://doi.org/10.1039/c8dt02914h
  63. Dubashynskaya N.V., Bokatyi A.N., Sall T.S., Egorova T.S., Nashchekina Y.A., Dubrovskii Y.A., Murashko E.A., Vlasova E.N., Demyanova E.V., Skorik Y.A. // Int. J. Mol. Sci. 2023. V. 24. P. 11550. https://doi.org/10.3390/ijms241411550
  64. Singh A., Yadagiri G., Parvez S., Singh O.P., Verma A., Sundar S., Mudavath S.L. // Mater. Sci. Eng. C. Mater. Biol. Appl. 2020. V. 117. P. 111279. https://doi.org/10.1016/j.msec.2020.111279
  65. Ke Z., Guo H., Zhu X., Jin Y., Huang Y. // J. Pharm. Pharm. Sci. 2015. V. 18. P. 155–170. https://doi.org/10.18433/j3j88q
  66. Francis M.F., Cristea M., Winnik F.M. // Biomacromolecules. 2005. V. 6. P. 2462–2467. https://doi.org/10.1021/bm0503165

补充文件

附件文件
动作
1. JATS XML
2. Fig. 1. Chemical structures of cobalamins.

下载 (125KB)
3. Fig. 2. Scheme of vitamin B12 metabolism [32].

下载 (150KB)
4. Fig. 3. Schematic representation of the interaction of the PNA chain with DNA/RNA.

下载 (81KB)

版权所有 © Russian Academy of Sciences, 2024