Biologically Active Palladium(II), Zinc(II), and Copper(II) Complexes with Terpene Ligands as Potential Pharmaceutical Drugs

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

A final review of the results of studies of versatile biological activities (in vitro) of chiral metal complexes with benzylamine and ethylenediamine derivatives of terpenes is presented. The cytotoxic profiles of palladacycles containing a Pd–C bond and palladium and zinc chelate complexes were determined. For a number of compounds, the possible mechanisms of potential anticancer action were analyzed, such as modulation of mitochondrial functioning and effect on the parameters of glycolytic function of tumor cells. The antibacterial and antifungal activities of palladium complexes of different types and copper chelate complexes were investigated. A correlation between high antimicrobial activity and antioxidant properties was found for a number of copper complexes. The material is supplemented by an extended analysis of publications in relevant subjects.

Sobre autores

Ya. Gur’eva

Institute of Chemistry, Komi Science Center, Ural Branch, Russian Academy of Sciences, Syktyvkar, Russia

Email: jana.aleksandrovna@yandex.ru
Россия, Сыктывкар

O. Zalevskaya

Institute of Chemistry, Komi Science Center, Ural Branch, Russian Academy of Sciences, Syktyvkar, Russia

Email: jana.aleksandrovna@yandex.ru
Россия, Сыктывкар

A. Kuchin

Institute of Chemistry, Komi Science Center, Ural Branch, Russian Academy of Sciences, Syktyvkar, Russia

Autor responsável pela correspondência
Email: jana.aleksandrovna@yandex.ru
Россия, Сыктывкар

Bibliografia

  1. Medina-Franco J.L., López-López E., Andrade E. et al. // Drug Discov. Today. 2022. V. 27. P. 1420. https://doi.org/10.1016/j.drudis.2022.02.021
  2. Miranda V.M. // Rev. Inorg. Chem. 2022. V. 42. P. 29. https://doi.org/10.1515/revic-2020-0030
  3. Mjos K.D., Orvig C. // Chem. Rev. 2014. V. 114. P. 4540. https://doi.org/10.1021/cr400460s
  4. Binding, Transport and Storage of Metal Ions in Biological Cells / Eds. Maret W., Wedd A. (Cambridge, UK): RSC, 2014. https://doi.org/10.1039/9781849739979
  5. Garoufis A., Hadjikakou S.K., Hadjiliadis N. // Coord. Chem. Rev. 2009. V. 253. P. 1384. https://doi.org/10.1016/j.ccr.2008.09.011
  6. Medici S., Peana M., Nurchi V.M. et al. // Coord. Chem. Rev. 2015. V. 284. P. 329. https://doi.org/10.1016/j.ccr.2014.08.002
  7. Alam M.N., Huq F. // Coord. Chem. Rev. 2016. V. 316. P. 36. https://doi.org/10.1016/j.ccr.2016.02.001
  8. Cirri D., Pratesi A., Marzo T., Messori L. // Expert Opinion Drug Disc. 2021. V. 16. P. 39. https://doi.org/10.1080/17460441.2020.1819236
  9. Frei A., Elliott A.G., Kan A. et al. // JACS Au. 2022. V. 2. № 10. P. 2277. https://doi.org/10.1021/jacsau.2c00308
  10. Carneiro T.J., Martins A.S., Marques M.P.M., Gil A.M. // Frontiers Oncology. 2020. V. 10. e590970. https://doi.org/10.3389/fonc.2020.590970
  11. Omae I. // Coord. Chem. Rev. 2014. V. 280. P. 84. https://doi.org/10.1016/j.ccr.2014.07.019
  12. Mahdy A.H.S., Salem E.Z., Ahmed M.A.B., Entesar A.H. // Tetrahedron. 2022. V. 121. Art. e132913. https://doi.org/10.1016/j.tet.2022.132913
  13. Zielińska-Błajet M., Feder-Kubis J. // Int. J. Mol. Sci. 2020. V. 21. P. 7078. https://doi.org/10.3390/ijms21197078
  14. Яровая О.И., Салахутдинов Н.Ф. // Успехи химии. 2021. Т. 90. С. 488 (Yarovaya O.I., Salakhutdinov N.F. // Russ. Chem. Rev. (Engl. Transl.) 2021. V. 90. P. 488). https://doi.org/10.1070/RCR4969
  15. Ateba S.B., Mvondo M.A., Ngeu S.T. et al. // Curr. Med. Chem. 2018. V. 25. P. 3162. https://doi.org/10.2174/0929867325666180214110932
  16. Kumar A., Jaitak V. // Eur. J. Med. Chem. 2019. V. 176. P. 268. https://doi.org/10.1016/j.ejmech.2019.05.027
  17. Mahizan N.A., Yang S.K., Moo C.L. et al. // Molecules. 2019. V. 24. P. 2631. https://doi.org/10.3390/molecules24142631
  18. Silva E.A.P., Carvalho J.S., Guimarães A.G. et al. // Expert Opin. Ther. Pat. 2019. V. 29. P. 43. https://doi.org/10.1080/13543776.2019.1558211
  19. Залевская О.А., Гурьева Я.А., Кучин А.В. // Успехи химии. 2019. Т. 88. С. 979 (Zalevskaya O.A., Gur’eva Y.A., Kutchin A.V. // Russ. Chem. Rev. (Engl. Transl.) 2019. V. 88. P. 979). https://doi.org/10.1070/RCR4880
  20. Гурьева Я.А., Залевская О.А., Фролова Л.Л. и др. // Хим. природ. соед. 2010. № 6. С. 783 (Gur’eva Y.A., Zalevskaya O.A., Frolova L.L. et al. // Chem. Nat. Comp. 2011. V. 46. № 6. P. 920). https://doi.org/10.1007/S10600-011-9783-X
  21. Кучин А.В., Гурьева Я.А., Фролова Л.Л. и др. // Изв. АН. Сер. хим. 2013. № 3. С. 745 (Kuchin A.V., Gur’eva Ya.A., Frolova L.L. et al. // Russ. Chem. Bull. (Int. Ed.). 2013. V. 62. № 3. P. 745). https://doi.org/10.1007/s11172-013-0101-6
  22. Гурьева Я.А., Залевская О.А., Алексеев И.Н. и др. // Изв. АН. Сер. хим. 2014. № 7. С. 1543 (Gur’eva Y.A., Zalevskaya O.A., Alekseev I.N. et al. // Russ. Chem. Bull. (Int. Ed.). 2014. V. 63. № 7. P. 1543). https://doi.org/10.1007/s11172-014-0633-4
  23. Дворникова И.А., Буравлев Е.В., Супонитский К.Ю. и др. // Журн. орган. химии. 2015. Т. 51. С. 498 (Dvornikova I.A., Buravlev E.V., Chukicheva I.Y. et al. // Russ. J. Org. Chem. 2015. V. 51. P. 480). https://doi.org/10.1134/S1070428015040041
  24. Гурьева Я.А., Залевская О.А., Алексеев И.Н. и др. // Журн. орган. химии. 2018. V. 54. P. 1274 (Gur’eva Y.A., Zalevskaya O.A., Alekseev I.N. et al. // Russ. J. Org. Chem. 2018. V. 54. P. 1285). https://doi.org/10.1134/S1070428018090026
  25. Gur’eva Y.A., Alekseev I.N., Dvornikova I.A. et al. // Inorg. Chim. Acta. 2018. V. 477. P. 300. https://doi.org/10.1016/j.ica.2018.03.015
  26. Гурьева Я.А., Алексеев И.Н., Залевская О.А. и др. // Журн. орган. химии. 2016. Т. 52. С. 796 (Gur’eva Y.A., Alekseev I.N., Zalevskaya O.A. et al. // Russ. J. Org. Chem. 2016. V. 52. P. 781). https://doi.org/10.1134/S107042801606004X
  27. Gur’eva Y.A., Slepukhin P.A., Kutchin A.V. // Inorg. Chim. Acta. 2019. V. 486. P. 602. https://doi.org/10.1016/j.ica.2018.11.016
  28. Zalevskaya O.A., Gur’eva Y.A., Kutchin A.V. et al. // Inorg. Chim. Acta. 2021. V. 527. e120593 https://doi.org/10.1016/j.ica.2021.120593
  29. Frei A., Zuegg J., Elliott A.G. et al. // Chem. Sci. 2020. V. 11. P. 2627. https://doi.org/10.1039/C9SC06460E
  30. Zalevskaya O.A., Gur’eva Y.A., Frolova L.L. et al. // Natural Science. 2010. V. 2. № 11. P. 1189. https://doi.org/10.4236/ns.2010.211147
  31. Гурьева Я.А., Залевская О.А., Алексеев И.Н. и др. // Хим. природ. cоед. 2014. № 4. С. 562 (Gureva Y.A., Zalevskaya O.A., Alekseev I.N. et al. // Chem. Nat. Comp. 2014. V. 50. № 4. P. 648. https://doi.org/10.1007/s10600-014-1044-3
  32. Zalevskaya O., Gur’eva Y., Kutchin A., Hansford K. // Antibiotics. 2020. V. 9. № 5. Art. e277. https://doi.org/10.3390/antibiotics9050277
  33. Fanelli M., Mauro F., Vieri F. et al. // Coord. Chem. Rev. 2016. V. 310. P. 41. https://doi.org/10.1016/j.ccr.2015.11.004
  34. Vojtek M., Marques M.P.M., Ferreira I.M.P.L.V.O. et al. // Drug Discov. Today. 2019. V. 24. P. 1044. https://doi.org/10.1016/j.drudis.2019.02.012
  35. Kapdi A.R., Fairlamb I.J.S. // Chem. Soc. Rev. 2014. V. 43. P. 4751. https://doi.org/10.1039/C4CS00063C
  36. Michelakis E.D., Webster L., Mackey J.R. // Brit. J. Cancer. 2008. V. 99. P. 989. https://doi.org/10.1038/sj.bjc.6604554
  37. Štarha P., Trávníček Z. // Coord. Chem. Rev. 2019. V. 395. P. 130. https://doi.org/10.1016/j.ccr.2019.06.001
  38. Omondi R.O., Ojwach S.O., Jaganyi D. // Inorg. Chim. Acta. 2020. V. 512. Art. e119883. https://doi.org/10.1016/j.ica.2020.119883
  39. Albert J., García S., Granell J. et al. // J. Organomet. Chem. 2013. V. 724. P. 289. https://doi.org/10.1016/j.jorganchem.2012.11.034
  40. Albert J., Bosque R., Crespo M. et al. // Eur. J. Med. Chem. 2014. V. 84. P. 530. https://doi.org/10.1016/j.ejmech.2014.07.046
  41. Albert J., D’Andrea L., Granell J. et al. // J. Inorg. Biochem. 2014. V. 140. P. 80. https://doi.org/10.1016/j.jinorgbio.2014.07.001
  42. Albert J., Granell J., Qadir R. et al. // Organometallics. 2014. V. 33. P. 7284. https://doi.org/10.1021/om501060f
  43. Karami K., Hosseini-Kharat M., Sadeghi-Aliabadi H. et al. // Polyhedron. 2012. V. 50. P. 187. https://doi.org/10.1016/j.poly.2012.11.002
  44. Karami K., Hosseini-Kharat M., Sadeghi-Aliabadi H. et al. // Eur. J. Med. Chem. 2014. V. 73. P. 8. https://doi.org/10.1016/j.ejmech.2013.11.042
  45. Karami K., Ramezanpour A., Zakariazadeh M. et al. // ChemSelect. 2019. V. 4. P. 5126. https://doi.org/10.1002/slct.201900707
  46. Zmejkovski B.B., Savić A., Poljarević J. et al. // Polyhedron. 2014. V. 80. P. 106. https://doi.org/10.1016/j.poly.2014.02.026
  47. Stojković D.L., Jevtić V.V., Radić G.P. et al. // J. Inorg. Biochem. 2015. V. 143. P. 111. https://doi.org/10.1016/j.jinorgbio.2014.12.001
  48. Franich A.A., Živković M.D., Milovanović J. et al. // J. Inorg. Biochem. 2020. V. 210. e111158. https://doi.org/10.1016/j.jinorgbio.2020.111158
  49. Bošković M., Franich A.A, Rajković S. et al. // ChemSelect. 2020. V. 5. P. Art. e10549. https://doi.org/10.1002/slct.202002350
  50. Misirlic-Dencic S., Poljarevic J., Isakovic A.M. et al. // Curr. Med. Chem. 2020. V. 27. P. 380. https://doi.org/10.2174/0929867325666181031114306
  51. Srinivasan S., Guha M., Kashina A., Avadhani N.G. // Biochim. Biophys. Acta Bioenerg. 2017. V. 1858. P. 602. https://doi.org/10.1016/j.bbabio.2017.01.004
  52. Li W., Zhang C., Sun X. // J. Vis. Exp. 2018. V. 135. Art. e56236. https://doi.org/10.3791/56236
  53. Warburg O. // Science. 1956. V. 124. P. 269.
  54. Wallace D.C. // Nat. Rev. Cancer. 2012. V. 12. P. 685. https://doi.org/10.1038/nrc3365
  55. Zheng Y., Liu P., Wang N. et al. // Oxid. Med. Cell Longev. 2019. V. 2019. Art. e8781690. https://doi.org/10.1155/2019/8781690
  56. Korga A., Ostrowska M., Iwan M. et al. // FEBS Open Bio. 2019. V. 9. P. 959. https://doi.org/10.1002/2211-5463.12628
  57. Zhang J., Zhang Q. Methods in Molecular Biology. N.Y.: Humana Press, 2019. V. 1928. P. 353. https://doi.org/10.1007/978-1-4939-9027-618
  58. Hashemi S., Karami K., Dehkordi Z.S. et al. // J. Biomolec. Struct. Dynam. 2022. V. 40. P. 5000. https://doi.org/10.1080/07391102.2020.1865202
  59. Abedanzadeh S., Karami K., Rahimi M. et al. // Dalton Trans. 2020. V. 49. Art. e14891. https://doi.org/10.1039/D0DT02304C
  60. Гурьева Я.А., Залевская О.А., Николаева Н.С. и др. // Изв. АН. Сер. хим. 2023. № 3. С. 793.
  61. Pellei M., Del Bello F., Porchia M., Santini C. // Coord. Chem. Rev. 2021. V. 445. Art. e214088. https://doi.org/10.1016/j.ccr.2021.214088
  62. Abendrot M., Chęcińska L., Kusz J. et al. // Molecules. 2020. V. 25. P. 951. https://doi.org/10.3390/molecules25040951
  63. Кипрова Н.С., Кондратенко Ю.А., Уголков В.Л. и др. // Изв. АН. Сер. хим. 2020. Т. 69. С. 1789 (Kiprova N.S., Kondratenko Y.A., Ugolkov V.L. et al. // Russ. Chem. Bull. (Int. Ed.). 2020. V. 69. P. 1789). https://doi.org/10.1007/s11172-020-2963-8
  64. Basu Baul T.S., Nongsiej K., Lamin Ka-Ot A. et al. // Appl. Organomet. Chem. 2019. V. 33. Art. e4905. https://doi.org/10.1002/aoc.4905
  65. Mastrolorenzo A., Scozzafava A., Supuran C.T. // Eur. J. Pharm. Sci. 2000. V. 11. P. 99. https://doi.org/10.1016/s0928-0987(00)00093-2
  66. Azevedo-França J.A., Borba-Santos L.P., Almeida Pimentel G. et al. // J. Inorg. Biochem. 2021. V. 219. Art. e111401. https://doi.org/10.1016/j.jinorgbio.2021.111401
  67. Matiadis D., Tsironis D., Stefanou V. et al. // J. Inorg. Biochem. 2019. V. 194. P. 65. https://doi.org/10.1016/j.jinorgbio.2019.02.008
  68. Zaltariov V.-F., Cazacu M., Avadanei M. et al. // Polyhedron. 2015. V. 100. P. 121. https://doi.org/10.1016/j.poly.2015.07.030
  69. Porchia M., Pellei M., Del Bello F., Santini C. // Molecules. 2020. V. 9. Art. e5814. https://doi.org/10.3390/molecules25245814
  70. Рукк Н.С., Кузьмина Л.Г., Давыдова Г.А. и др. // Изв. АН. Сер. хим. 2020. Т. 69. С. 1394 (Rukk N.S., Kuzmina L.G., Davydova G.A. et al. // Russ. Chem. Bull. (Int. Ed.). 2020. V. 69. P. 1394). https://doi.org/10.1007/s11172-020-2914-4
  71. Yu P., Deng J., Cai J. et al. // Metallomics. 2019. V. 11. P. 1372. https://doi.org/10.1039/c9mt00124g
  72. Garufi A., Giorno E., Gilardini Montani M.S. et al. // Biomolecules. 2021. V. 11. P. 348. https://doi.org/10.3390/biom11030348
  73. Shahraki S., Majd M.H., Heydari A. // J. Mol. Struct. 2019. V. 1177. 536. https://doi.org/10.1016/j.molstruc.2018.10.005
  74. Chukwuma C.I., Mashele S.S., Eze K.C. et al. // Pharmacol. Res. 2020. V. 155. Art. e104744. https://doi.org/10.1016/j.phrs.2020.104744
  75. Motloung D.M., Mashele S.S., Matowane G.R. et al. // J. Pharm. Pharmacol. 2020. V. 72. P. 1412. https://doi.org/10.1111/jphp.13322
  76. Rice D.R., Mendiola M.D.L.B., Murillo-Solano C. et al. // Bioorg. Med. Chem. 2017. V. 25. P. 2754. https://doi.org/10.1016/j.bmc.2017.03.050
  77. Гурьева Я.А., Залевская О.А., Николаева Н.С. и др. // Изв. АН. Сер. хим. 2022. № 12. С. 2612.
  78. Fang D., Maldonado E.N. // Adv. Cancer Res. 2018. V. 138. P. 41. https://doi.org/10.1016/bs.acr.2018.02.002
  79. Zhao Y., Liu J., Liu L. // Mol. Med. Rep. 2020. V. 22. P. 3017. https://doi.org/10.3892/mmr.2020.11341
  80. Quinlan C.L., Orr A.L., Perevoshchikova I.V. et al. // J. Biol. Chem. 2012. V. 287. Art. e27255. https://doi.org/10.1074/jbc.M112.374629
  81. Sciacovelli M., Guzzo G., Morello V. et al. // Cell Metab. 2013. V. 17. P. 988. https://doi.org/10.1016/j.cmet.2013.04.019
  82. Guzzo G., Sciacovelli M., Bernardi P., Rasola A. // Oncotarget. 2014. V. 5. Art. e11897. https://doi.org/10.18632/oncotarget.2472
  83. Moog S., Lussey-Lepoutre C., Favier J. // Endocr. Relat. Cancer. 2020. V. 27. P. 451. https://doi.org/10.1530/ERC-20-0346
  84. Withey S.J., Perrio S., Christodoulou D. et al. // Radiographics. 2019. V. 39. P. 1393. https://doi.org/10.1148/rg.2019180151
  85. Ibrahim A., Chopra S. // Arch. Pathol. Lab. Med. 2020. V. 144. P. 655. https://doi.org/10.5858/arpa.2018-0370-RS
  86. Gill A.J. // Histopathology. 2018. V. 72. P. 106. https://doi.org/10.1111/his.13277
  87. Stocks P.A., Barton V., Antoine T. et al. // Parasitology. 2014. V. 141. P. 50. https://doi.org/10.1017/S0031182013001571
  88. Onwudiwe D.C., Ekennia A.C. // Res. Chem. Intermed. 2017. V. 43. P. 1465. https://doi.org/10.1007/s11164-016-2709-2
  89. Ganji N., Aveli R., Narendrula V., Sreenu D.S. // J. Mol. Struct. 2018. V. 1173. P. 173. https://doi.org/10.1016/j.molstruc.2018.06.100
  90. Oladipo S.D., Omondi B., Mocktar C. // Polyhedron. 2019. V. 170. P. 712. https://doi.org/10.1016/j.poly.2019.06.038
  91. El-Medani S.M., Abdelmoneim A.M., Hussein M. et al. // J. Mol. Struct. 2020. V. 1208. Art. e127860. https://doi.org/10.1016/j.molstruc.2020.127860
  92. Ramesh G., Daravath S., Ganji N. et al. // J. Mol. Struct. 2020. V. 1202. 127338. https://doi.org/10.1016/j.molstruc.2019.127338
  93. Psomas G. // Coord. Chem. Rev. 2020. V. 412. 213259. https://doi.org/10.1016/j.ccr.2020.213259
  94. Boussadia A., Beghidja A., Gali L. et al. // Inorg. Chim. Acta. 2020. V. 508. Art. e119656. https://doi.org/10.1016/j.ica.2020.119656
  95. Guerreiro J.F., Gomes M.A.G.B., Pagliari F. et al. // RSC Adv. 2020. V. 10. Art. e12699. https://doi.org/10.1039/d0ra00166j
  96. Said M. A., Al-unizi A., Al-Mamary M. et al. // Inorg. Chim. Acta. 2020. V. 505. Art. e119434. https://doi.org/10.1016/j.ica.2020.119434
  97. Boulguemha I.-E., Beghidjaa A., Khattabib L. et al. // Inorg. Chim. Acta. 2020. V. 507. e119519. https://doi.org/10.1016/j.ica.2020.119519
  98. Patel A.K., Jadeja R.N., Roy H. et al. // Polyhedron. 2020. V. 186. Art. e114624. https://doi.org/10.1007/s11164-016-2709-2
  99. Sakthivel A., Thangagiri B., Raman N. et al. // J. Biomol. Struct. Dyn. 2020. V. 39. P. 6500. https://doi.org/10.1080/07391102.2020.1801508
  100. Mo D., Shi J., Zhao D. et al. // J. Mol. Struct. 2021. V. 1223. Art. e129229. https://doi.org/10.1016/j.molstruc.2020.129229
  101. Simunkova M., Lauro P., Jomova K. et al. // J. Inorg. Biochem. 2019. V. 194. P. 97. https://doi.org/10.1016/j.jinorgbio.2019.02.010
  102. Singh Y.P., Patel S.K. // J. Mol. Struct. 2021. V. 1228. Art. e129457. https://doi.org/10.1016/j.molstruc.2020.129457
  103. Siqueira J.D., de Pellegrin S.F., dos Santos S.S. // J. Inorg. Biochem. 2020. V. 204. Art. e110950. https://doi.org/10.1016/j.jinorgbio.2019.110950
  104. Riley D.P. // Chem. Rev. 1999. V. 99. P. 2573. https://doi.org/10.1021/cr980432g
  105. Hordyjewska A., Popiołek L., Kocot J. // Biometals. 2014. V. 27. P. 611. https://doi.org/10.1007/s10534-014-9736-5
  106. Balsano C., Sideri S. // Metallomics. 2018. V. 10. P. 1712. https://doi.org/10.1039/c8mt00219c
  107. Santini C., Pellei M., Gandin V. et al. // Chem. Rev. 2014. V. 114. P. 815. https://doi.org/10.1021/cr400135x
  108. Zalevskaya O.A, Gur’eva Y.A. // Russ. J. Coord. Chem. 2021. V. 47. P. 861. https://doi.org/10.1134/S1070328421120046
  109. Gur’eva Y.A., Zalevskaya O.A., Shevchenko O.G. et al. // RSC Advances. 2022. V. 12. P. 8841. https://doi.org/10.1039/d2ra00223j
  110. Davis W.W., Stout T.R. // Appl. Microbiology. 1971. V. 22. P. 659. https://doi.org/10.1128/am.22.4.659-665.1971
  111. Davis W.W., Stout T.R. // Appl. Microbiology. 1971. V. 22. P. 666. https://doi.org/10.1128/am.22.4.666-670.1971
  112. Santiago P.H.O., Tiago F.S., Castro M.S. et al. // J. Inorg. Biochem. 2020. V. 204. Art. e110949. https://doi.org/10.1016/j.jinorgbio.2019.110949
  113. Gordon A.T., Abosede O.O., Ntsimango S., et al. // Inorg. Chim. Acta. 2020. V. 510. e119744. https://doi.org/10.1016/j.ica.2020.119744
  114. Takebayashi J., Chen A., Tai A.A. // Advanced Protocols in Oxidative Stress II. Totowa (NJ, USA): Humana Press, 2010. P. 287. https://doi.org/10.1007/978-1-60761-411-1_20
  115. Niki E. // Free Radical Biology Medicine. 2010. V. 49. P. 503. https://doi.org/10.1016/j.freeradbiomed.2010.04.016
  116. Zou C.G., Agar N.S., Jones G.L. // Life Sciences. 2001. V. 69. P. 75. https://doi.org/10.1016/S0024-3205(01)01112-2
  117. Shiva Shankar Reddy C.S., Subramanyam M.V.V., Vani R., Asha Devi S. // Toxicol. Vitr. 2007. V. 21. P. 1355. https://doi.org/10.1016/j.tiv.2007.06.010
  118. Ajila C.M., Rao P.U.J.S. // Food Chem. Tox. 2008. V. 46. P. 303. https://doi.org/10.1016/j.fct.2007.08.024
  119. Rocha S., Costa E., Coimbra S. et al. // Blood Cells Molecules Diseases. 2009. V. 43. P. 68. https://doi.org/10.1021/cr980432g
  120. Ko F.N., Hsiao G., Kuo Y.H. // Free Radical Biol. Med. 1997. V. 22. P. 215. https://doi.org/10.1016/S0891-5849(96)00295-X

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
2.

Baixar (44KB)
3.

Baixar (100KB)
4.

Baixar (96KB)
5.

Baixar (86KB)
6.

Baixar (109KB)
7.

Baixar (180KB)
8.

Baixar (102KB)
9.

Baixar (219KB)
10.

Baixar (45KB)
11.

Baixar (439KB)
12.

Baixar (300KB)
13.

Baixar (35KB)
14.

Baixar (182KB)
15.

Baixar (166KB)
16.

Baixar (45KB)
17.

Baixar (25KB)


Este site utiliza cookies

Ao continuar usando nosso site, você concorda com o procedimento de cookies que mantêm o site funcionando normalmente.

Informação sobre cookies