STUDYING ANTITUMOR ACTIVITY  IN VITRO  IODO-δ-LACTONES 5 Z ,9 Z -DIENOIC ACID

E. Kh. Makarova; Макарова Э. Х.; I. V. Ishbulatov; Ишбулатов И. В.; А. А. Makarov; Макаров А. А.; L. U. Dzhemileva; Джемилева Л. У.; U. M. Dzhemilev; Джемилев У. М.; V. A. D’yakonov; Дьяконов В. А.

doi:10.31857/S2686953523600277

STUDYING ANTITUMOR ACTIVITY IN VITRO IODO-δ-LACTONES 5Z,9Z-DIENOIC ACID

Авторлар: Makarova E.K.¹, Ishbulatov I.V.¹, Makarov А.А.¹, Dzhemileva L.U.², Dzhemilev U.M.², D’yakonov V.A.²
Мекемелер:
1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
2. N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Шығарылым: Том 513, № 1 (2023)
Беттер: 54-61
Бөлім: CHEMISTRY
URL: https://rjeid.com/2686-9535/article/view/651931
DOI: https://doi.org/10.31857/S2686953523600277
EDN: https://elibrary.ru/UWUBSS
ID: 651931

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Толық мәтін

Ашық рұқсат
Рұқсат жабық

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Рұқсат жабық

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Аннотация
Авторлар туралы
Әдебиет тізімі
Қосымша файлдар
Статистика

Аннотация

A previously undescribed phenyl-substituted iodo-δ-lactone of 11‑phenylundeca-5Z,9Z-dienoic acid was synthesized using the Ti-catalyzed intermolecular cross-cyclomagnesiation of an aromatic 1,2-diene with an O‑containing allene at the key stage in a 94% yield. The in vitro cytotoxic activity of the obtained alkyl- and phenyl-substituted iodo-δ-lactones 5Z,9Z-dienoic acids was studied in relation to the cell lines Jurkat, K562, U937, HL60, Hek293, and the effect on the cell cycle and the ability to induce apoptosis with using flow cytometry.

Негізгі сөздер

cross-cyclomagnesiation, 1,2-dienes, iodo-δ-lactones, Cp₂TiCl₂, cytotoxic activity, apoptosis, Jurkat, K562, U937, HL60, Hek293

Әдебиет тізімі

Wang L., Zhou X., Fredimoses M., Liao S., Liu Y. // RSC Adv. 2014. V. 4. № 101. P. 57350–57376. https://doi.org/10.1039/c4ra09833a
Dembitsky V.M. // Nat. Prod. Commun. 2006. V. 1. № 2. P. 139–175. https://doi.org/10.1177/1934578x0600100210
Kyeremeh K., Acquah K.S., Appiah-Opong R., Deng M., Jaspars H. // J. Chem. Applications. 2014. V. 1. № 1. P. 1–4.
Aiello A., Fattorusso E., Imperatore C., Menna M., Müller W. // Mar. Drugs. 2010. V. 8. № 2. P. 285–291. https://doi.org/10.3390/md8020285
Andavan G.S.B., Lemmens-Gruber R. // Mar. Drugs. 2010. V. 8. № 3. P. 810–834. https://doi.org/10.3390/md8030810
Hiroyuki I., Hiroki S., Hideo,K., Kiyoyuki Y. // Tetrahedron. 1994. V. 50. № 45. P. 12853–12882. https://doi.org/10.1016/s0040-4020(01)81206-0
Shen Y.-C., Cheng Y.-B., Lin Y.-C., Guh J.-H., Teng C.-M., Ko C.-L. // J. Nat. Prod. 2004. V. 67. № 4. P. 542–546. https://doi.org/10.1021/np030435a
Williams P.G., Yoshida W.Y., Moore R.E., Paul V.J. // Org. Lett. 2003. V. 5. P. 4167–4170. https://doi.org/10.1021/ol035620u
Kigoshi H., Kanematsu K., Yokota K., Uemura D. // Tetrahedron. 2000. V. 56. № 46. P. 9063–9070. https://doi.org/10.1016/s0040-4020(00)00759-6
Hwang B.S., Lee K., Yang C., Jeong E.J., Rho J.-R. // J. Nat. Prod. 2013. V. 76. № 12. P. 2355–2359. https://doi.org/10.1021/np400793r
Maiese W.M., Lechevalier M.P., Lechevalier H.A., Korshalla J., Kuck N., Fantini A., Wildey M.J., Thomas J., Greenstein M. // J. Antibiot. 1989. V. 42. P. 558–563.
Zhao B., Konno S., Wu J.M., Oronsky A.L. // Cancer Lett. 1990. V. 50. № 2. P. 141–147. https://doi.org/10.1016/0304-3835(90)90244-r
Nicolaou K.C., Hale C.R.H., Nilewski C. // Chem. Rec. 2012 V. 12. № 4. P. 407–441. https://doi.org/10.1002/tcr.201200005
Ricart A.D. // Clin. Cancer Res. 2011. V. 17. № 20. P. 6417–6427. https://doi.org/10.1158/1078-0432.ccr-11-0486
Gartner R., Rank P., Ander B. // Hormones. 2010. V. 9. № 1. P. 60–66.
Boeynaems J.M., Hubbard W.C. // J. Biol. Chem. 1980. V. 255. P. 9001–9004. https://doi.org/10.1016/S0021-9258(19)70513-4
Thomasz L., Oglio R., Salvarredi L., Perona M., Rossich L., Copelli S., Pisarev M., Juvenal G. // Mol. Cell Endocrinol. 2018. V. 470. P. 115–126. https://doi.org/10.1016/j.mce.2017.10.004
Nava-Villalba M., Nucez-Anita R.E., Bontempo A., Aceves C. // Mol. Cancer. 2015. V. 14. P. 168. https://doi.org/10.1186/s12943-015-0436-8
Arroyo-Helguera O., Rojas E., Delgado G., Aceves C. // Endocr. Relat. Cancer. 2008. V. 15. P. 1003–1011. https://doi.org/10.1677/ERC-08-0125
Aceves C., Mendieta I., Anguiano B., Delgado-Gonza-lez E. // J. Mol. Sci. 2021. V. 22. P. 1228. https://doi.org/10.3390/ijms22031228
D’yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.Kh., Khusnutdinova E.K., Dzhemilev U.M. // Chem. Commun. 2013. V. 49. P. 8401–8403. https://doi.org/10.1039/C3CC44926B
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M. // Bioorg. Med. Chem. Lett. 2015. V. 25. № 11. P. 2405–2408. https://doi.org/10.1016/j.bmcl.2015.04.011
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mu-lyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstiko-va T.G., Dzhemilev U.M. // Curr. Cancer Drug Targets. 2015. V. 15. № 6. P. 504–510. https://doi.org/10.2174/1568009615666150506093155
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mu-lyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstiko-va T.G., Dzhemilev U.M. // Med. Chem. Res. 2016. V. 25. № 1. P. 30–39. https://doi.org/10.1007/s00044-015-1446-1
D’yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.Kh., Ramazanov I.R., Dzhemilev U.M. // Cancers. 2021. V. 13. № 8. P. 1808. https://doi.org/10.3390/cancers13081808
Maкarov A.A., Ishbulatov I.V., Makarova E.Kh., D’yakonov V.A., Dzhemilev U.M. // Russ. J. Org. Chem. 2022. V. 58. № 12. P. 1954–1958. https://doi.org/10.1134/S1070428022120259
Tyagi R., Shimpukade B., Blattermann S., Kostenisb E., Ulven T. // Med. Chem. Commun. 2012. V. 3. P. 195–198. https://doi.org/10.1039/C1MD00231G
Kuang J., Ma S. // J. Org. Chem. 2009. V. 74. P. 1763. https://doi.org/10.1021/jo802391x