BIOCHEMICAL BASIS OF THE ANTIMICROBIAL ACTIVITY OF QUINAZOLINONE DERIVATIVES IN THE LIGHT OF INSIGHTS INTO THE FEATURES OF THE CHEMICAL STRUCTURE AND WAYS OF BINDING TO TARGET MOLECULES. A REVIEW
- Авторлар: Samotruyeva M.1, Starikova A.2, Bashkina O.1, Tsibizova A.1, Borisov A.2, Merezhkina D.2, Tyurenkov I.2, Ozerov A.2,3
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Мекемелер:
- Astrakhanskiy State Medical University
- Volgograd State Medical University
- Volgograd Medical Scientific Center
- Шығарылым: Том 510, № 1 (2023)
- Беттер: 3-27
- Бөлім: ХИМИЯ
- URL: https://journals.rcsi.science/2686-9535/article/view/135973
- DOI: https://doi.org/10.31857/S2686953522600672
- EDN: https://elibrary.ru/YRQTZC
- ID: 135973
Дәйексөз келтіру
Аннотация
The review characterizes the role of the main targets of antibacterial agents: “efflux pumps”; enzymes (DNA-hyruases as a subclass of topoisomerases, homoserine transacetylase, various classes of sorbitases, aromatics, lipoteichoyl synthase, polyketide synthase, pantothenate synthetase, acetyl-CoA carboxylase, sensory histidine kinase, kinase, cyclooxygenase, etc.); penicillin-binding protein; quorum signaling and adhesin systems in important biochemical processes of pathogen maintenance and virulence manifestation. The possibility of manifestation of antimicrobial effect by the substance upon its binding to the protein molecules responsible for pathogenicity of a microorganism was shown. The role of quinazolinone derivatives exhibiting high reactivity, stability in chemical processes and characterized by a wide spectrum of pharmacological activity including antimicrobial activity with respect to various gram-positive and gram-negative bacteria was determined. It has been shown that changes in the compound structure through the introduction of different substituents modify the degree of hydrophilicity and, as a result, determine a different degree of drug penetration through the cell membrane; the ability to form intermediate complex compounds stabilized by hydrogen bonds and van der Waals and stacking interactions with enzymatic targets as well as receptor-regulator proteins and signaling systems of pathogen cells. The results on prediction of the mechanism of action of the compounds synthesized by the authors of the article by methods of mathematical modeling are presented. The possibility of creating combined structures based on the quinazolinone core with various heterocyclic derivatives as a product with a pronounced antimicrobial activity is assessed. The considered regularities are of practical importance for the specialists in the field of medicinal chemistry, organic synthesis, biotechnology, clinical pharmacology, pharmaceutical chemistry and technology whose efforts are aimed at obtaining a new drug substance.
Авторлар туралы
M. Samotruyeva
Astrakhanskiy State Medical University
Email: alhimik.83@mail.ru
Russian, 414000, Astrakhan
A. Starikova
Volgograd State Medical University
Хат алмасуға жауапты Автор.
Email: alhimik.83@mail.ru
Russian, 400131, Volgograd
O. Bashkina
Astrakhanskiy State Medical University
Email: alhimik.83@mail.ru
Russian, 414000, Astrakhan
A. Tsibizova
Astrakhanskiy State Medical University
Email: alhimik.83@mail.ru
Russian, 414000, Astrakhan
A. Borisov
Volgograd State Medical University
Email: alhimik.83@mail.ru
Russian, 400131, Volgograd
D. Merezhkina
Volgograd State Medical University
Email: alhimik.83@mail.ru
Russian, 400131, Volgograd
I. Tyurenkov
Volgograd State Medical University
Email: alhimik.83@mail.ru
Russian, 400131, Volgograd
A. Ozerov
Volgograd State Medical University; Volgograd Medical Scientific Center
Email: alhimik.83@mail.ru
Russian, 400131, Volgograd; Russian, 400131, Volgograd
Әдебиет тізімі
- Desai N.C., Dodiya A., Shihory N. // J. Saudi Chem. Soc. 2013. V. 17. P. 259–267. https://doi.org/10.1016/j.jscs.2011.04.001
- Шемякин И.Г., Фирстова В.В., Фурсова Н.К., Абаев И.В., Филиппович С.Ю., Игнатов С.Г., Дятлов И.А. // Биохимия. 2020. Т. 85. № 11. С. 1615–1632. https://doi.org/10.31857/S0320972520110081
- Borges A., Saavedra M.J., Simoes M.// Curr. Med. Chem. 2015. V. 22. P. 2590–2614. https://doi.org/10.2174/0929867322666150530210522
- Гординская Н.А., Борискина Е.В., Кряжев Д.В. // Здоровье населения и среда обитания. 2021. № 4. С. 50–56. https://doi.org/10.35627/2219-5238/2021-337-4-50-56
- Карева Е.Н., Сереброва С.Ю., Лазарева Н.Б., Шипилова С.Ю., Булгакова В.А., Козаева Л.П., Кононова И.Н., Яровой С.К., Дроздов В.Н., Стародубцев А.К. // Экспериментальная и клиническая фармакология. 2018. Т. 81. № 9. С. 26–32. https://doi.org/10.30906/0869-2092-2018-81-9-26-32
- Путилина А.Д., Коменкова Т.С., Зайцева Е.А. // Медико-фармацевтический журнал “Пульс”. 2019. Т. 21. № 10. С. 125–130. https://doi.org/10.26787/nydha-2686-6838-2019-21-10-125-130
- Du D., Wang-Kan X., Neuberger A., Veen H.W., Pos K.M., Piddock L.J.V., Luisi B.F. // Nat. Rev. Microbiol. 2018. V. 16. № 9. P. 523–539. https://doi.org/10.1038/s41579-018-0048-6
- Иванов М.Э., Фурсова Н.К., Потапов В.Д. // Клиническая лабораторная диагностика. 2022. Т. 67. № 1. С. 53–58. https://doi.org/10.51620/0869-2084-2022-67-1-53-58
- Карпова Е.В., Тапальский Д.В. // Лабораторная диагностика. Восточная Европа. 2022. Т. 11. № 2. С. 214–223. https://doi.org/10.34883/PI.2022.11.2.018
- Pagès J.M., Amaral L., Fanning S. // Curr. Med. Chem. 2011. V. 18. P. 2969–2680. https://doi.org/10.2174/092986711796150469
- Henderson P.J., Maher C., Elbourne L.D.H., Eijkel-kamp B.A., Paulsen I.T., Hassan K.A. // Chem. Rev. 2021. V. 121. № 9. P. 5417–5478. https://doi.org/10.1021/acs.chemrev.0c01226
- Alav I., Sutton J.M., Rahman K.M. // J. Antimicrob. Chemother. 2018. V. 73. № 8. P. 2003–2020. https://doi.org/10.1093/jac/dky042
- Hassan K.M., Datta D., Nguyen A.N. // Antibiotics. 2021. V. 11. № 1. P. 40. https://doi.org/10.3390/antibiotics11010040
- Liu J., Takiff H.E., Nikaido H. // J. Bacteriol. 1996. V. 178. № 13. P. 3791–3795. https://doi.org/10.1128/jb.178.13.3791-3795.1996
- Kumar S., Lekshmi M., Parvathi A., Ojha M., Wenzel N., Varela M.F. // Microorganisms. 2020. V. 8. № 2. P. 266–286. https://doi.org/10.3390/microorganisms8020266
- Takiff H.E., Cimino M., Musso M.C., Weisbrodi T., Martinez R., Delgado M.B., Salazar L., Bloom B.R., Jacobs W.R. // Proc. Natl. Acad. Sci. USA. 1996. № 93. 362–367. https://doi.org/10.1073/pnas.93.1.362
- Costa S.S., Sobkowiak B., Parreira R., Edgeworth J.D., Viveiros M., Clark T.G., Couto I. // Front. Genet. 2019. № 9. P. 710. https://doi.org/10.3389/fgene.2018.00710
- Туницкая В.Л., Хомутов А.Р., Кочетков С.Н., Котовская С.К., Чарушин В.Н. // Acta Naturae. 2011. Т. 3. № 4. С. 98–104.
- Aguirre A.L., Chheda P.R., Lentz S.R.C., Held H.A., Groves N.P., Hiasa H., Kerns R.J. // Bioorg. Med. Chem. 2020. V. 28. № 10. P. 115439. https://doi.org/10.1016/j.bmc.2020.115439
- Федорчук В.В., Грудинина С.А., Кротова Л.А., Черкашин Е.А., Сидоренко С.В., Тишков В.И. // Вестник Московского университета. Серия 2. Химия. 2002. Т. 43. № 6. С. 349–352.
- Barančoková M., Kikelj D., Ilaš J. // Future Med. Chem. 2018. V. 10. № 10. P. 1207–1227. https://doi.org/10.4155/fmc-2017-0257
- Kolarič A., Germe T., Hrast M., Stevenson C.E., Law-son D.M., Burton N.P., Vörös J., Maxwell A., Minovski N., Anderluh M. // Nat. Commun. 2021. V. 12. № 1. P. 150–163. https://doi.org/10.1038/s41467-020-20405-8
- Khan T., Sankhe K., Suvarna V., Sherje A., Patel K., Dravyakar B. // Biomed. Pharmacotherapy. 2018. V. 103. P. 923–938. https://doi.org/10.1016/j.biopha.2018.04.021
- Champoux J.J. // Annu. Rev. Biochem. 2001. V. 70. P. 369–413. https://doi.org/10.1146/annurev.biochem.70.1.369
- Dighe S.N., Collet T.A. // Eur. J. Med. Chem. 2020. V. 199. P. 112326. https://doi.org/10.1016/j.ejmech.2020.112326
- Asadi P., Khodarahmi G., Jahanian-Najafabadi A., Saghaie L., Hassanzadeh F. // Iran. J. Basic. Med. Sci. 2017. V. 20. № 9. P. 975–989. https://doi.org/10.22038/IJBMS.2017.9260
- Асямов К.В., Свёклина Т.С., Тюрюпов М.С., Мися-ков Е.П., Фролов Д.С. // Лечение и профилактика. 2020. Т. 10. № 4. С. 106–118.
- Fortune J.M., Osheroff N. // J. Biol. Chem. 1998. V. 273. № 28. P. 17643–17650. https://doi.org/10.1074/jbc.273.28.17643
- Сутормин Д.А., Галивонджян А.Х., Полховский А.В., Камалян С.О., Северинов К.В., Дубилей С.А. // Acta Naturae. 2021. Т. 13. № 1. С. 59–75. https://doi.org/10.32607/actanaturae.11058
- Pascale G.D., Nazi I., Harrison P.H., Wright G.D. // J. Antibiot. 2011. V. 64. № 7. P. 483–487. https://doi.org/10.1038/ja.2011.37
- Nazi I., Scott A., Sham A., Rossi L., Williamson P.R., Kronstad J.W., Wright G.D. // Antimicrob. Agents Chemother. 2007. V. 51. № 5. P. 1731–1736. https://doi.org/10.1128/AAC.01400-06
- Chaton C.T., Rodriguez E.S., Reed R.W., Li J., Ken-ner C.W., Korotkov K.V. // Sci. Rep. 2019. V. 9. № 1. P. 1–11. https://doi.org/10.1038/s41598-019-56722-2
- Mabkhot Y.N., Al-Har M.S., Barakat A., Aldawsari F.D., Aldalbahi A., Ul-Haq Z. // Molecules. 2014. V. 19. № 7. P. 8725–8739. https://doi.org/10.3390/molecules19078725
- Matrelov N., Kurbatskaya V., Rudevitsa Z., Leonchik A., Fridmanis D. // Antibiotics. 2021. V. 10. № 2. P. 164. https://doi.org/10.3390/antibiotics10020164
- Spirig T., Weiner E.M., Clubb R.T. // Mol. Microbiol. 2011. V. 82. № 5. P. 1044–1059. https://doi.org/10.1111/j.1365-2958.2011.07887.x
- Зигангирова Н.А., Лубенец Н.Л., Зайцев А.В., Пушкарь Д.Ю. // Клиническая микробиология и антимикробная химиотерапия. 2021. Т. 23. № 2. С. 184–194.
- Volynets G., Vyshniakova H., Nitulescu G., Nitulescu G.M., Ungurianu A., Margina D., Moshynets O., Bdzhola V., Koleiev I., Iungin O., Tarnavskiy S., Yarmoluk S. // Molecules. 2021. V. 26. № 23. P. 7095–7106. https://doi.org/10.3390/molecules26237095
- Wang J., Shi Y., Jing S., Dong H., Wang D., Wang T. // Molecules. 2019. V. 24. № 3. P. 465–475. https://doi.org/10.3390/molecules24030465
- Sapra R., Rajora A.K., Kumar P., Maurya G.P., Pant N., Haridas V. // J. Med. Chem. 2021. V. 64. № 18. P. 13097–13130. https://doi.org/10.1021/acs.jmedchem.1c00386
- Jaudzems K., Kurbatska V., Jēkabsons A., Bobrovs R., Rudevica Z., Leonchiks A. // ACS Infect. Dis. 2019. V. 6. № 2. P. 186.
- Bradshaw W.J., Davies A.H., Chambers C.J., Roberts A.K., Shone C.C., Acharya K.R. // FEBS J. 2015. V. 282. P. 2097–2114. https://doi.org/10.1111/febs.13288
- Susmitha A., Bajaj H., Nampoothiri K.M. // The Cell Surface. 2021. V. 7. P. 100055. https://doi.org/10.1016/j.tcsw.2021.100055
- Narashimamurthy N., Rao A.R., Sastry G.N. // Curr. Med. Chem. – Anti-Cancer Agents. 2004. V. 4. № 6. P. 523–534. https://doi.org/10.2174/1568011043352669
- Alfonso A.Y.C., Lagares L.M., Novic M., Benfenati E., Kumar A., Chayawan // Toxicology in Vitro. 2022. V. 81. P. 105332. https://doi.org/10.1016/j.tiv.2022.105332
- Pingaew R., Prachayasittikul V., Anuwongcharoen N., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. // Bioorg. Chem. 2018. V. 79. P. 171–178. https://doi.org/10.1016/j.bioorg.2018.05.002
- Sauvage E., Kerff F., Terrak M., Ayala J.A., Charlier P. // FEMS Microbiol. Rev. 2008. V. 32. № 2. P. 234–258. https://doi.org/10.1111/j.1574-6976.2008.00105.x
- Meroueh S.O., Bencze K.Z., Hesek D., Lee M., Fisher J.F., Stemmler T.L., Mobashery S. // PNAS. 2006. V. 13. № 12. P. 4404–4409. https://doi.org/10.1073/pnas.0510182103
- Egan A.J.F., Cleverley R.M., Peters K., Lewis R.J., Vollmer W. // FEBS J. 2017. V. 284. № 6. P. 851–867. https://doi.org/10.1111/febs.13959
- Филиппова А.А., Рубцова М.Ю., Уляшова М.М., Фурсова Н.К. // Бактериология. 2020. Т. 5. № 3. С. 34–46. https://doi.org/10.20953/2500-1027-2020-3-34-46
- Ferrer-González E., Huh H., Al-Tameemi H.M., Boyd J.M., Lee S-H., Pilch D.S. // J. Bacteriol. 2021. V. 203. № 16. P. e00204-21. https://doi.org/10.1128/JB.00204-21
- Łeski T.A., Tomasz A. // J. Bacteriol. 2005. V. 187. № 5. P. 1815–1824. https://doi.org/10.1128/JB.187.5.1815-1824.2005
- Teo A.C.K., Roper D.I. // Antibiotics. 2015. V. 4. № 4. P. 495–520. https://doi.org/10.3390/antibiotics4040495
- Kuru E., Radkov A., Meng X., Egan A., Alvarez L., Dowson A., Booher G., Breukink E., Roper D.I., Cava F., Vollmer W., Brun Y., VanNieuwenhze M.S. // ACS Chem. Biol. 2019. V. 4. № 12. P. 2745–2756. https://doi.org/10.1021/acschembio.9b00664
- Martinez de Tejada G., Sanchez-Gómez S., Razquin-Olazaran I., Kowalski I., Kaconis Y., Heinbockel L., Andrä J., Schürholz T., Hornef M., Dupont A., Garidel P., Gutsmann T., David S.A., Brandenburg K. // Curr. Drug Targets. 2012. V. 13. № 9. P. 1121–1151. https://doi.org/10.2174/138945012802002410
- Brauweiler A.M., Goleva E., Leung D.Y. // J. Invest. Dermatol. 2019. V. 139. № 8. P. 1753–1761. https://doi.org/10.1016/j.jid.2019.02.006
- Ahn K.B., Baik J.E., Yun C.H., Han S.H. // Front. Microbiol. 2018. V. 9. P. 327. https://doi.org/10.3389/fmicb.2018.00327
- Richter S.G., Elli D., Kim H.K., Hendrickx A.P.A., Sorg J.A., Schneewind O., Missiakas D. // PNAS. 2013. V. 110. № 9. P. 3531–3536. https://doi.org/10.1073/pnas.1217337110
- Zhang B., Liu X., Lambert E., Mas G., Hiller S., Veening J.W., Perez C. // Nat. Struct. Mol. Biol. 2020. V. 27. № 6. P. 561–569. https://doi.org/10.1038/s41594-020-0425-5
- Wilson R., Kumar P., Parashar V., Vilchèze C., Chur-let R.V., Freundlich J.S., Barnes S.W., Walker J.R., Szymonifka M.J., Marchiano E., Shenai S., Colangeli R., Jacobs W.R., Jr., Neiditch M.B., Kremer L., Alland D. // Nat. Chem. Biol. 2013. V. 9. № 8. P. 499–506. https://doi.org/10.1038/nchembio.1277
- Frankfather K., Jiang X., Xu F.F. // J. Am. Soc. Mass spectrum. 2018. V. 29. P. 1688–1699. https://doi.org/10.1007/s13361-018-1993-z
- Bon C., Cabantous S., Julien S., Guillet V., Chalut C., Rima J., Brison Y., Malaga W., Sanchez‑Dafun A., Gavalda S., Quémard A., Marcoux J., Waldo G.S., Guilhot C., Mourey L. // BMC Biol. 2022. V. 20. № 1. P. 147. https://doi.org/10.1186/s12915-022-01337-9
- Bhatt A., Molle V., Besra G.S., Jacobs W.R., Jr., Kre-me L. // Mol. Microbiol. 2007. V. 64. № 6. P. 1442–1454. https://doi.org/10.1111/j.1365-2958.2007.05761.x
- Von Delft F., Lewendon A., Dhanaraj V., Blundell T.L., Abell C., Smith A.G. // Structure. 2001. V. 9. № 5. P. 439–450. https://doi.org/10.1016/S0969-2126(01)00604-9
- Hamilton T.D., Papaefstathiou G.S., MacGillivray L.R. // Etter Transactions. 2005. V. 1. P. 2–5.
- Waldrop G.L., Rayment I., Holden H.M. // Biochemistry. 1994. V. 33. № 34. P. 10249–10256. https://doi.org/10.1021/bi00200a004
- Walley J.W., Kliebenstein D.J., Bostock R.M., Dehesh K. // Curr. Opin. Plant Biol. 2013. V. 16. № 4. P. 520–526. https://doi.org/10.1016/j.pbi.2013.06.011
- Hirakawa H., Kurushima J., Hashimoto Y., Tomita H. // Antibiotics. 2020. V. 9. № 10. P. 635. https://doi.org/10.3390/antibiotics9100635
- Thomas L., Cook L. // Infect. Immun. 2020. V. 88. № 7. P. e00931-19. https://doi.org/10.1128/IAI.00931-19
- Tiwari S., Jamal S.B., Hassan S.S., Carvalho P.V.S.D., Almeida S., Barh D., Ghosh P., Silva A., Castro T.L.P., Azevedo V. // Front. Microbiol. 2017. V. 8. P. 1878. https://doi.org/10.3389/fmicb.2017.01878
- Bhagirath A.Y., Li Y., Patidar R., Yerex K., Ma X., Kumar A., Duan K. // Int. J. Mol. Sci. 2019. V. 20. № 7. P. 1781. https://doi.org/10.3390/ijms20071781
- Gotoh Y., Doi A., Furuta E., Dubrac S., Ishizaki Y., Okada M., Igarashi M., Misawa N., Yoshikawa H., Okajima T., Msadek R. Utsumi T. // J. Antibiot. 2010. V. 63. P. 127–134. https://doi.org/10.1038/ja.2010.4
- Kato A., Ueda S., Oshima T., Inukai Y., Okajima T., Igarashi M., Eguchi Y., Ryutaro Utsumi. // J. Gen. Appl. Microbiol. 2017. V. 63. № 4. P. 212–221.
- Хайтович А.Б., Мурейко Е.А. // Таврический медико-биологический вестник. 2018. Т. 21. № 1. С. 214–220.
- Otto M. // FEMS Microbiol. Lett. 2004. V. 241. № 2. P. 135–141. https://doi.org/10.1016/j.femsle.2004.11.016
- Шпаков А.О. // Микробиология. 2009. Т. 78. № 2. С. 163–175. https://doi.org/10.1134/S0026261709020015
- Баженов С.В., Щеглова Е.С., Фомин В.В., Завильгельский Г.Б., Манухов И.В. // Генетика. 2022. Т. 58. № 2. С. 148–156. https://doi.org/10.31857/S0016675822020023
- Марданова А.М., Кабанов Д.А., Рудакова Н.Л., Шарипова М.Р. Биопленки: Основные принципы организации и методы исследования. Учебное пособие. Казань, 2016. С. 9.
- Chu W., McLean R.J.C. // J. Aquat. Anim. Health. 2016. V. 28. № 2. P. 91–96. https://doi.org/10.1080/08997659.2016.1150907
- Курсов С.В., Никонов В.В. // Медицина неотложных состояний. 2016. Т. 5. № 76. С. 27–35. https://doi.org/10.22141/2224-0586.5.76.2016.76430
- Alsibaee A.M., Al-Yousef H.M., Al-Salem H.S. // Molecules. 2023. V. 28. № 3. P. 978. https://doi.org/10.3390/molecules28030978
- Dogovski C., Atkinson S.C., Dommaraju S., Dobson R., Perugini M., Hor L., Hutton C., Gerrard A. // Encyclopedia of Life Support Systems. 2009. V. 11. P. 116–136.
- Jafari E., Khajouei M.R., Hassanzadeh F., Hakime-lahi G.H., Khodarahmi G.A. // Res. Pharm. Sci. 2016. V. 11. № 1. P. 1.
- Цибизова А.А., Ясенявская А.Л., Озеров А.А., Тюренков И.Н., Башкина О.А., Самотруева М.А. // Сибирский научный медицинский журнал. 2021. Т. 41. № 6. С. 56–60. https://doi.org/10.18699/SSMJ20210606
- Цибизова А.А., Самотруева М.А., Ковалев В.Б., Тюренков И.Н. // Астраханский медицинский журнал. 2017. Т. 12. № 4. С. 27–43.
- Samotrueva M.A., Ozerov A.A., Starikova A.A., Gabi-tova N.M., Merezhkina D.V., Tsibizova A.A., Tyuren-kov I.N. // Pharm. Pharmacol. 2021. V. 9. № 4. P. 318–329. https://doi.org/10.19163/2307-9266-2021-9-4-318-329
- Старикова А.А., Габитова Н.М., Цибизова А.А., Озеров А.А., Тюренков И.Н., Башкина О.А., Само-труева М.А. // Астраханский медицинский журнал. 2022. Т. 17. № 1. С. 60–71. https://doi.org/10.48612/agmu/2022.17.1.60.71
- Жарких Л.И., Смирнова Ю.А. // Вестник технологического университета. 2020. Т. 23. № 1. С. 104–111.
- Sen T., Neog K., Sarma S., Manna P., Boruah H.P.D., Gogoi P., Singh A.K. // Bioorg. Med. Chem. 2018. V. 26. № 17. P. 4942–4951. https://doi.org/10.1016/j.bmc.2018.08.034
- Rajasekar K.K., Nizamuddin N.D., Surur A.S., Mekonnen Y.T. // Research and reports on Medical Chemistry. 2016. V. 6. P. 15–26. https://doi.org/10.2147/RRMC.S91474
- Khodarakhmi G.A., Hajway M.R., Hakimelahi G.H., Abedi D., Jafari E., Hassanzadeh F. // Res. Pharm. Sci. 2012. V. 7. № 3. P. 151.
- Qian Y., Allegretta G., Janardhanan J., Peng Z., Mahasenan K.V., Lastochkin E., Gozun M.M.N., Tejera S., Schroeder V.A., Wolter W.R., Feltzer R., Mobashery S., Chang M. // J. Med. Chem. 2020. V. 63. № 10. P. 5287–5296. https://doi.org/10.1021/acs.jmedchem.0c00153
- Ibrahim M.A.A., Abdeljawaad K.A.A., Abdelrahman A.H.M., Alzahrani O.R., Alshabrmi F.M., Khalaf E., Mousta-fa M.F., Alrumaihi F., Allemailem K.S., Soliman M.E.S., Paré P.W., Hegazy M.E.F., Atia M.A.M. // Antibiotics. 2021. V. 10. № 8. P. 934.
- Norouzbahari M., Salarinejad S., Güran M., Şanlıtürk G., Emamgholipour Z., Bijanzadeh H.R., Toolabi M., Foroumadi A. // DARU J. Pharm. Sci. 2020. V. 28. № 2. P. 661–672. https://doi.org/10.1007/s40199-020-00373-6
- Patel M.B., Kumar S.P., Valand N.N., Jasrai Y.T., Menon S.K. // Mol. Model. 2013. V. 19. № 8. P. 3201–3217. https://doi.org/10.1007/s00894-013-1820-1
- Espeland L.O., Georgiou C., Klein R., Bhukya H., Haug B.E., Underhaug J., Mainkar P.S., Brenk R. // ChemMedChem. 2021. V. 16. P. 2715–2726. https://doi.org/10.1002/cmdc.202100302
- Devi P.U., Lakshmi K.A., Ramji M.T., Khan P.A.A. // J. Pharm. Res. 2010. V. 3. № 11. P. 2765–2768.
- Sharma P.C., Jane A., Jane S., Pahwa R., Yar M.S. // J. Enzyme Inhib. Med. Chem. 2010. V. 25. № 4. P. 577–589. https://doi.org/10.3109/14756360903373350
- Fedorowicz J., Saczewski J. // Monatsh. Chem. 2018. V. 149. № 7. P. 1199–1245. https://doi.org/10.1007/s00706-018-2212-0
- Jawad A.M., Aljamali N.M., Jwad S.M. // Indian J. Forensic Med. Toxicol. 2020. V. 14. № 2. P. 1115–1122. https://doi.org/10.37506/ijfmt.v14i2.3067
- Aguirre A.L., Cheda R., Lenz S.R., Held H.A., Groves N., Hiasa H., Kerns R.J. // Bioorg. Med. Chem. 2020. V. 28. № 10. P. 115439. https://doi.org/10.1016/j.bmc.2020.115439
- Mahato A.K., Srivastava B., Shanthi C.N. // Inventi Rapid: Med. Chem. 2011. V. 1. P. 1–6.
- Mahato A., Shrivastava B., Shanthi N. // Chem. Sci. Trans. 2015. V. 4. № 2. P. 595–603. https://doi.org/10.7598/cst2015.995
- Khodarahmi G., Asadi P., Hassanzadeh F., Khodarah-mi E. // J. Res. Med. Sci. 2015. V. 20. № 11. P. 1094–1104. https://doi.org/10.4103/1735-1995.172835
- Arévalo J.M.C., Amorim J.C. // Sci. Rep. 2022. V. 12. № 1. P. 4742. https://doi.org/10.1038/s41598-022-08359-x
- Ghorab M.M., Alqahtani A.S., Soliman A.M., As-kar A.A. // Int. J. Nanomedicine. 2020. V. 15. P. 3161. http://doi.org/10.2147/IJN.S241433
- Carabajal M.A., Asquith C.R.M., Laitinen T., Tiz-zard G.J., Yim L., Rial A., Chabalgoity J.A., Zuer-cher W.J., Vescovi E.G. // Antimicrob. Agents Chemother. 2019. V. 64. № 1. P. e01744–19. https://doi.org/10.1128/AAC.01744-19
- Carabajal M.A., Viarengo G., Yim L., Martínez-Sanguiné A., Mariscotti J.F., Chabalgoity J.A., Rasia R.M., Véscovi E.G. // Sci. Signal. 2020. V. 13. № 628. P. eaaz3334. https://doi.org/10.1126/scisignal.aaz3334
- Grossman S., Soukarieh F., Richardson W., Liu R., Mashabi A., Emsley J., Williams P., Camara M., Stocks M.J. // Eur. J. Med. Chem. 2020. V. 208. P. 112778. https://doi.org/10.1016/j.ejmech.2020.112778
- Schütz C., Empting M. // Beilstein J. Org. Chem. 2018. V. 14. № 1. P. 2627–2645. https://doi.org/10.3762/bjoc.14.241
- Soukarieh F., Williams P., Stocks M.J., Camara M. // J. Med. Chem. 2018. V. 61. № 23. P. 10385–10402. https://doi.org/10.1021/acs.jmedchem.8b00540
- Rasapalli S., Murphy Z.F., Sammeta V.R., Golen J.A., Weig A.W., Melander R.J., Melander C., Macha P., Vasudev M.C. // Bioorganic Med. Chem. Lett. 2020. V. 30. № 23. P. 127550. https://doi.org/10.1016/j.bmcl.2020.127550
- Pereira M.D.F., Chevrot R., Rosenfeld E., Thiery V., Besson T. // J. Enzyme Inhib. Med. Chem. 2007. V. 22. № 5. P. 225–233. https://doi.org/10.1007/s00044-012-0004-3
- Zayed M.F., Ibrahim S.R.M., Habib E.S.E., Hassan M.H., Ahmed S., Rateb H.S. // Med. Chem. 2019. V. 15. № 6. P. 659–675. https://doi.org/10.2174/1573406414666181109092944
- Poojari S., Naik P.P., Krishnamurthy G., Kumara J.K.S., Kumar N.S., Naik S. // J. Taibah. Univ. Sci. 2017. V. 11. P. 497–511. https://doi.org/10.1016/j.jtusci.2016.10.003
- Mazumdar K., Dastidar S.G., Park J.H., Dutta N.K. // Eur. J. Clin. Microbiol. Infect. Dis. 2009. V. 28. № 8. P. 881–891. https://doi.org/10.1007/s10096-009-0739-z
- Laddha S.S., Wadodkar S.G., Meghal S.K. // ARKIVOC. 2006. V. 11. P. 1–20.
- Auti P.S., George G., Paul A.T. // RSC Adv. 2020. V. 10. № 68. P. 41353–41392. https://doi.org/10.1039/D0RA06642G
- Maddali N.K., Viswanath I.V.K., Murthy Y.L.N., Bera R., Takhi M., Rao N.S., Gudla V. // Med. Chem. Res. 2019. V. 28. P. 559–629. https://doi.org/10.1007/s00044-019-02313-9
- Mason J.I., Murry B.A., Olcott M., Sheets J.J. // Biochem. Pharmacol. 1985. V. 34. № 7. P. 1087–1092. https://doi.org/10.1016/0006-2952(85)90613-6