STEARIN AS A STARTING MATERIAL FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE IONIC LIQUIDS

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

For the first time, the possibility of using widely available stearin for the production of fatty acid-derived ionic liquids (ILs) has been shown. New amphiphilic ILs based on imidazolium, pyridinium, and quaternary ammonium cations containing long-chain alkyl substituents were obtained. The synthesized compounds are shown to have biological activity comparable to known antimicrobial compounds. ILs with one alkyl substituent have higher cytotoxicity and antimicrobial activity compared to disubstituted derivatives.

About the authors

M. M. Seitkalieva

N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences

Author for correspondence.
Email: s_marina@ioc.ac.ru
Russian Federation, 119991, Moscow

A. V. Vavina

N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences

Email: s_marina@ioc.ac.ru
Russian Federation, 119991, Moscow

E. N. Strukova

Gause Institute of New Antibiotics, Russian Academy of Sciences

Email: s_marina@ioc.ac.ru
Russian Federation, 119021, Moscow

References

  1. Welton T. // Biophys. Rev. 2018. V. 10. № 3. P. 691–706. https://doi.org/10.1007/s12551-018-0419-2
  2. Koroleva M.Yu., Yurtov E.V. // Russ. Chem. Rev. 2022. V. 91. № 5. P. RCR5024. https://doi.org/10.1070/rcr5024
  3. Arzhakova O.V., Arzhakov M.S., Badamshina E.R., Bryuzgina E.B., Bryuzgin E.V., Bystrova A.V., Vaganov G.V., Vasilevskaya V.V., Vdovichenko A.Yu., Gallyamov M.O., Gumerov R.A., Didenko A.L., Zefirov V.V., Karpov S.V., Komarov P.V., Kulichikhin V.G., Kurochkin S.A., Larin S.V., Malkin A.Ya., Milenin S.A., Muzafarov A.M., Molcha-nov V.S., Navrotskiy A.V., Novakov I.A., Panarin E.F., Panova I.G., Potemkin I.I., Svetlichny V.M., Sedush N.G., Serenko O.A., Uspenskii S.A., Philippova O.E., Khokh-lov A.R., Chvalun S.N., Sheiko S.S., Shibaev A.V., Elmanovich I.V., Yudin V.E., Yakimansky A.V., Yarosla-vov A.A. // Russ. Chem. Rev. 2022. V. 91. № 12. RCR5062. https://doi.org/10.57634/RCR5062
  4. Antipin I.S., Alfimov M.V., Arslanov V.V., Burilov V.A., Vatsadze S.Z., Voloshin Ya.Z., Volcho K.P., Gorbatchuk V.V., Gorbunova Yu.G., Gromov S.P., Dudkin S.V., Zaitsev S.Yu., Zakharova L.Ya., Ziganshin M.A., Zolotukhina A.V., Kalinina M.A., Karakhanov E.A., Kashapov R.R., Koifman O.I., Konovalov A.I., Korenev V.S., Maksi-mov A.L., Mamardashvili N.Zh., Mamardashvili G.M., Martynov A.G., Mustafina A.R., Nugmanov R.I., Ovsyannikov A.S., Padnya P.L., Potapov A.S., Selek-tor S.L., Sokolov M.N., Solovieva S.E., Stoikov I.I., Stuzhin P.A., Suslov E.V., Ushakov E.N., Fedin V.P., Fedorenko S.V., Fedorova O.A., Fedorov Yu.V., Chvalun S.N., Tsivadze A.Yu., Shtykov S.N., Shurpik D.N., Shcherbi-na M.A., Yakimova L.S. // Russ. Chem. Rev. 2021. V. 90. № 8. P. 895–1107. https://doi.org/10.1070/RCR5011
  5. Azov V.A., Egorova K.S., Seitkalieva M.M., Kashin A.S., Ananikov V.P. // Chem. Soc. Rev. 2018. V. 47. № 4. P. 1250–1284. https://doi.org/10.1039/c7cs00547d
  6. Ohno H., Yoshizawa-Fujita M., Kohno Y. // Bull. Chem. Soc. Jpn. 2019. V. 92. № 4. P. 852–868. https://doi.org/10.1246/bcsj.20180401
  7. Wang H., Gurau G., Rogers R.D. // Chem. Soc. Rev. 2012. V. 41. № 4. P. 1519–1537. https://doi.org/10.1039/c2cs15311d
  8. Welton T. // Coord. Chem. Rev. 2004. V. 248. № 21–24. P. 2459–2477. https://doi.org/10.1016/j.ccr.2004.04.015
  9. MacFarlane D.R., Tachikawa N., Forsyth M., Pringle J.M., Howlett P.C., Elliott G.D., Davis J.H., Watanabe M., Simon P., Angell C.A. // Energy Environ. Sci. 2014. V. 7. № 1. P. 232–250. https://doi.org/10.1039/c3ee42099j
  10. Antuganov D.O., Nadporojskii M.A., Kondratenko Yu.A. // Mendeleev Commun. 2022. V. 32. № 3. P. 408–410. https://doi.org/10.1016/j.mencom.2022.05.040
  11. Krasovskiy V.G., Gorbatsevich O.B., Talalaeva E.V., Glukhov L.M., Chernikova E.A., Kustov L.M. // Mendeleev Commun. 2022. V. 32. № 4. P. 551–553. https://doi.org/10.1016/j.mencom.2022.07.039
  12. Marrucho I.M., Branco L.C., Rebelo L.P.N. // Annu. Rev. Chem. Biomol. Eng. 2014. V. 5. № 1. P. 527–546. https://doi.org/10.1146/annurev-chembioeng-060713-040024
  13. Egorova K.S., Gordeev E.G., Ananikov V.P. // Chem. Rev. 2017. V. 117. № 10. P. 7132–7189. https://doi.org/10.1021/acs.chemrev.6b00562
  14. Simoes M., Pereira A.R., Simoes L.C., Cagide F., Bor-ges F. // Drug Discov. Today. 2021. V. 26. № 6. P. 1340–1346. https://doi.org/10.1016/j.drudis.2021.01.031
  15. Vereshchagin A.N., Frolov N.A., Egorova K.S., Seitkalieva M.M., Ananikov V.P. // Int. J. Mol. Sci. 2021. V. 22. № 13. P. 6793. https://doi.org/10.3390/ijms22136793
  16. Ali M.K., Moshikur R.M., Wakabayashi R., Tahara Y., Moniruzzaman M., Kamiya N., Goto M. // J. Colloid. Interface Sci. 2019. V. 551. P. 72–80. https://doi.org/10.1016/j.jcis.2019.04.095
  17. Raj T., Chandrasekhar K., Park J., Varjani S., Sharma P., Kumar D., Yoon J.J., Pandey A., Kim S.H. // Chemosphere. 2022. V. 307. Part 2. P. 135787. https://doi.org/10.1016/j.chemosphere.2022.135787
  18. Gusain R., Khatri O.P. // RSC Adv. 2016. V. 6. № 5. P. 3462–3469. https://doi.org/10.1039/c5ra25001c
  19. Oulego P., Faes J., González R., Viesca J.L., Blanco D., Battez A.H. // J. Mol. Liq. 2019. V. 292. P. 111451. https://doi.org/10.1016/j.molliq.2019.111451
  20. Gundolf T., Weyhing-Zerrer N., Sommer J., Kalb R., Schoder D., Rossmanith P., Mester P. // ACS Sustainable Chem. Eng. 2019. V. 7. № 19. P. 15865–15873. https://doi.org/10.1021/acssuschemeng.8b06201
  21. Dzhemileva L.U., D’yakonov V.A., Seitkalieva M.M., Kulikovskaya N.S., Egorova K.S., Ananikov V.P. // Green Chem. 2021. V. 23. № 17. P. 6414–6430. https://doi.org/10.1039/d1gc01520f
  22. Gal N., Malferrari D., Kolusheva S., Galletti P., Tagliavini E., Jelinek R. // Biochim. Biophys. Acta 2012. V. 1818. № 12. P. 2967–2974. https://doi.org/10.1016/j.bbamem.2012.07.025
  23. Wu S., Zeng L., Wang C., Yang Y., Zhou W., Li F., Tan Z. // J. Hazard. Mater. 2018. V. 348. P. 1–9. https://doi.org/10.1016/j.jhazmat.2018.01.028
  24. Egorova K.S., Seitkalieva M.M., Kashin A.S., Gordeev E.G., Vavina A.V., Posvyatenko A.V., Ananikov V.P. // J. Mol. Liq. 2022. V. 367. Part A. P. 120450. https://doi.org/10.1016/j.molliq.2022.120450
  25. Soller F., Roy L.A., Davis D.A. // J. World Aquac. Soc. 2019. V. 50. № 1. P. 186–203. https://doi.org/10.1111/jwas.12571
  26. Gunstone F.D., Herslöf B.G. Lipid glossary 2. Bridgwater, Oily press, 2000. 262 p.
  27. Wanasundara U.N., Wanasundara P.K. J.P.D., Shahidi F., Novel Separation Techniques for Isolation and Purification of Fatty Acids and Oil By-Products. In: Bailey’s Industrial Oil and Fat Products. Shahidi F. (Ed.). 7th Edn. John Wiley & Sons, Ltd., 2020. https://doi.org/10.1002/047167849x.bio065.pub2
  28. Brown J.B., Kolb D.K. // Prog. Chem. Fats Other Lipds. 1955. V. 3. P. 57–94. https://doi.org/10.1016/0079-6832(55)90004-5
  29. Maddikeri G.L., Pandit A.B., Gogate P.R. // Ind. Eng. Chem. Res. 2012. V. 51. № 19 P. 6869–6876. https://doi.org/10.1021/ie3000562
  30. Martins P.F., Ito V.M., Batistella C.B., Maciel M.R.W. // Sep. Purif. Technol. 2006. V. 48. № 1. P. 78–84. https://doi.org/10.1016/j.seppur.2005.07.028
  31. Steinigeweg S., Gmehling J. // Ind. Eng. Chem. Res. 2003. V. 42. № 15. P. 3612–3619. https://doi.org/10.1021/ie020925i
  32. Ni J., Meunier F.C. // Appl. Catal. A: Gen. 2007. V. 333. № 1. P. 122–130. https://doi.org/10.1016/j.apcata.2007.09.019
  33. Nakai Y., Moriyama K., Togo H. // Eur. J. Org. Chem. 2016. V. 2016. № 4. P. 768–772. https://doi.org/10.1002/ejoc.201501315
  34. Frolov N.A., Fedoseeva K.A., Hansford K.A., Vereshchagin A.N. // ChemMedChem. 2021. V. 16. № 19. P. 2954–2959. https://doi.org/10.1002/cmdc.202100284
  35. Xia X., Wan R., Wang P., Huo W., Dong H., Du Q. // Ecotoxicol. Environ. Saf. 2018. V. 162. P. 408–414. https://doi.org/10.1016/j.ecoenv.2018.07.022
  36. Arcau J., Andermark V., Rodrigues M., Giannicchi I., Pérez-Garcia L., Ott I., Rodríguez L. // Eur. J. Inorg. Chem. 2014. V. 2014. № 35. P. 6117–6125. https://doi.org/10.1002/ejic.201402819
  37. Carson L., Chau P.K W., Earle M.J., Gilea M.A., Gil-more B.F., Gorman S.P., McCann M.T., Seddon K.R. // Green Chem. 2009. V. 11. № 4. P. 492–497. https://doi.org/10.1039/b821842k
  38. Demberelnyamba D., Kim K.S., Choi S., Park S.Y., Lee H., Kim C.J., Yoo I.D. // Bioorg. Med. Chem. 2004. V. 12. № 5. P. 853–857. https://doi.org/10.1016/j.bmc.2004.01.003
  39. Thorsteinsson T., Masson M., Kristinsson K.G., Hjalmarsdottir M.A., Hilmarsson H., Loftsson T. // J. Med. Chem. 2003. V. 46. № 19. P. 4173–4181. https://doi.org/10.1021/jm030829z
  40. Cole M.R., Li M., El-Zahab B., Janes M.E., Hayes D., Warner I.M. // Chem. Biol. Drug Des. 2011. V. 78. № 1. P. 33–41. https://doi.org/10.1111/j.1747-0285.2011.01114.x
  41. Siopa F., Figueiredo T., Frade R.F.M., Neto I., Meirinhos A., Reis C.P., Sobral R.G., Afonso C.A.M., Rijo P. // ChemistrySelect. 2016. V. 1. № 18. P. 5909–5916. https://doi.org/10.1002/slct.201600864
  42. Łuczak J., Jungnickel C., Łącka I., Stolte S., Hupka J. // Green Chem. 2010. V. 12. № 4 P. 593–601. https://doi.org/10.1039/b921805j
  43. Vavina A.V., Seitkalieva M.M., Posvyatenko A.V., Gordeev E.G., Strukova E.N., Egorova K.S., Anani-kov V.P. // J. Mol. Liq. 2022. V. 352. P. 118673. https://doi.org/10.1016/j.molliq.2022.118673
  44. Seitkalieva M.M., Vavina A.V., Posvyatenko A.V., Egorova K.S., Kashin A.S., Gordeev E.G., Strukova E.N., Romashov L.V., Ananikov V.P. // ACS Sustain. Chem. Eng. 2021. V. 9. № 9. P. 3552–3570. https://doi.org/10.1021/acssuschemeng.0c08790

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2.

Download (103KB)
Indexing metadata

Copyright (c) 2023 М.М. Сейткалиева, А.В. Вавина, Е.Н. Струкова