Synthesis and Biological Evaluation of Oxindole Sulfonamide Derivatives as Bruton's Tyrosine Kinase Inhibitors

. 2024 Jan 02 ; 19 (1) : e202300511. [epub] 20231122

Jazyk angličtina Země Německo Médium print-electronic

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/pmid37916435

Grantová podpora
DST-SERB-EDCR/2016/000288 Department of Science and Technology, India
LM2023052 CZ-OPENSCREEN
LM2023053 EATRIS-CZ
LX22NPO5102 National Institute for Cancer Research
LX22NPO5107 National Institute for Neurological Research
Ministry of Education, Youth and Sports of the Czech Republic (MEYS)

Bruton's tyrosine kinase (BTK) is a promising molecular target for several human B-cell-related autoimmune disorders, inflammation, and haematological malignancies. The pathogenic alterations in various cancer tissues depend on mutant BTK for cell proliferation and survival, and BTK is also overexpressed in a range of hematopoietic cells. Due to this, BTK is emerging as a potential drug target to treat various human diseases, and several reversible and irreversible inhibitors have been developed and are being developed. As a result, BTK inhibition, clinically validated as an anticancer treatment, is finding great interest in B-cell malignancies and solid tumours. This study focuses on the design and synthesis of new oxindole sulfonamide derivatives as promising inhibitors of BTK with negligible off-target effects. The most cytotoxic compounds with greater basicity were PID-4 (2.29±0.52 μM), PID-6 (9.37±2.47 μM), and PID-19 (2.64±0.88 μM). These compounds caused a selective inhibition of Burkitt's lymphoma RAMOS cells without significant cytotoxicity in non-BTK cancerous and non-cancerous cell lines. Further, PID-4 showed promising activity in inhibiting BTK and downstream signalling cascades. As a potent inhibitor of Burkitt's lymphoma cells, PID-4 is a promising lead for developing novel chemotherapeutics.

Zobrazit více v PubMed

X. Wang, L. Kokabee, M. Kokabee, D. S. Conklin, Frontiers in Cell and Developmental Biology 2021, 9, 668996, DOI 10.3389/fcell.2021.668996.

T. Seiler, M. Dreyling, Expert Opin. Invest. Drugs 2017, 26, 909-915.

S. Middendorp, G. M. Dingjan, A. Maas, K. Dahlenborg, R. W. Hendriks, J. Immunol. 2003, 171, 5988-5996.

J. Lee, M. Rhee, T. K. Min, H. I. Bang, M.-A. Jang, E.-S. Kang, H.-J. Kim, H.-J. Yang, B. Y. Pyun, Korean J. Pediatr. 2016, 59, S49-S52.

H. Sung, J. Ferlay, R. L. Siegel, M. Laversanne, I. Soerjomataram, A. Jemal, F. Bray, CA Cancer J. Clin. 2021, 71, 209-249.

U. Anand, A. Dey, A. K. S. Chandel, R. Sanyal, A. Mishra, D. K. Pandey, V. De Falco, A. Upadhyay, R. Kandimalla, A. Chaudhary, J. K. Dhanjal, S. Dewanjee, J. Vallamkondu, J. M. Pérez de la Lastra, Genes Dis. 2023, 10, 1367-1401.

L. A. Garraway, P. A. Jänne, Cancer Dis. 2012, 2, 214-226.

S. Srivastava, E. J. Koay, A. D. Borowsky, A. M. De Marzo, S. Ghosh, P. D. Wagner, B. S. Kramer, Nat. Rev. Cancer 2019, 19, 349-358.

D. Hanahan, R. A. Weinberg, Cell 2011, 144, DOI 10.1016/j.cell.2011.02.013.

E. M. Ammann, T. D. Shanafelt, K. B. Wright, B. D. McDowell, B. K. Link, E. A. Chrischilles, Leuk. Lymphoma 2018, 59, 643-649.

C. Y. Cheah, J. F. Seymour, M. L. Wang, JCO 2016, 34, 1256-1269.

B. Y. Chang, M. Francesco, M. F. M. De Rooij, P. Magadala, S. M. Steggerda, M. M. Huang, A. Kuil, S. E. M. Herman, S. Chang, S. T. Pals, W. Wilson, A. Wiestner, M. Spaargaren, J. J. Buggy, L. Elias, Blood 2013, 122, 2412-2424.

S. P. Treon, L. Xu, G. Yang, Y. Zhou, X. Liu, Y. Cao, P. Sheehy, R. J. Manning, C. J. Patterson, C. Tripsas, L. Arcaini, G. S. Pinkus, S. J. Rodig, A. R. Sohani, N. L. Harris, J. M. Laramie, D. A. Skifter, S. E. Lincoln, Z. R. Hunter, N. Engl. J. Med. 2012, 367, 826-833.

K. Krysiak, F. Gomez, B. S. White, M. Matlock, C. A. Miller, L. Trani, C. C. Fronick, R. S. Fulton, F. Kreisel, A. F. Cashen, K. R. Carson, M. M. Berrien-Elliott, N. L. Bartlett, M. Griffith, O. L. Griffith, T. A. Fehniger, Blood 2017, 129, 473-483.

D. Vetrie, I. Vořechovský, P. Sideras, J. Holland, A. Davies, F. Flinter, L. Hammarström, C. Kinnon, R. Levinsky, M. Bobrow, C. I. E. Smith, D. R. Bentley, Nature 1993, 361, 226-233.

S. Tsukada, D. C. Saffran, D. J. Rawlings, O. Parolini, R. C. Allen, I. Klisak, R. S. Sparkes, H. Kubagawa, T. Mohandas, S. Quan, J. W. Belmont, M. D. Cooper, M. E. Conley, O. N. Witte, Cell 1993, 72, 279-290.

S. Pal Singh, F. Dammeijer, R. W. Hendriks, Mol. Cancer 2018, 17, 57.

B. Tasso, A. Spallarossa, E. Russo, C. Brullo, Molecules 2021, 26, DOI 10.3390/molecules26237411.

P. Jain, M. Keating, W. Wierda, Z. Estrov, A. Ferrajoli, N. Jain, B. George, D. James, H. Kantarjian, J. Burger, S. O′Brien, Blood 2015, 125, 2062-2067.

J. Molina-Cerrillo, T. Alonso-Gordoa, P. Gajate, E. Grande, Cancer Treat. Rev. 2017, 58, 41-50.

S. De Cesco, J. Kurian, C. Dufresne, A. K. Mittermaier, N. Moitessier, Eur. J. Med. Chem. 2017, 138, 96-114.

A. Alu, H. Lei, X. Han, Y. Wei, X. Wei, J. Hematol. Oncol. 2022, 15, 138.

A. T. Bender, A. Gardberg, A. Pereira, T. Johnson, Y. Wu, R. Grenningloh, J. Head, F. Morandi, P. Haselmayer, L. Liu-Bujalski, Mol. Pharmacol. 2017, 91, 208.

Y. Guo, Y. Liu, N. Hu, D. Yu, C. Zhou, G. Shi, B. Zhang, M. Wei, J. Liu, L. Luo, Z. Tang, H. Song, Y. Guo, X. Liu, D. Su, S. Zhang, X. Song, X. Zhou, Y. Hong, S. Chen, Z. Cheng, S. Young, Q. Wei, H. Wang, Q. Wang, L. Lv, F. Wang, H. Xu, H. Sun, H. Xing, N. Li, W. Zhang, Z. Wang, G. Liu, Z. Sun, D. Zhou, W. Li, L. Liu, L. Wang, Z. Wang, J. Med. Chem. 2019, 62, 7923-7940.

A. R. Johnson, P. B. Kohli, A. Katewa, E. Gogol, L. D. Belmont, R. Choy, E. Penuel, L. Burton, C. Eigenbrot, C. Yu, D. F. Ortwine, K. Bowman, Y. Franke, C. Tam, A. Estevez, K. Mortara, J. Wu, H. Li, M. Lin, P. Bergeron, J. J. Crawford, W. B. Young, ACS Chem. Biol. 2016, 11, 2897-2907.

Y. Chu, S. Lee, T. Shah, C. Yin, M. Barth, R. R. Miles, J. Ayello, E. Morris, L. Harrison, C. Van de Ven, P. Galardy, S. C. Goldman, M. S. Lim, M. Hermiston, L. M. McAllister-Lucas, L. Giulino-Roth, S. L. Perkins, M. S. Cairo, Oncoimmunology 2019, 8, e1512455.

A. Turetsky, E. Kim, R. H. Kohler, M. A. Miller, R. Weissleder, Sci. Rep. 2014, 4, 4782.

E. Pastwa, R. I. Somiari, M. Malinowski, S. B. Somiari, T. A. Winters, Int. J. Biochem. Cell Biol. 2009, 41, 1254-1260.

L. Ping, N. Ding, Y. Shi, L. Feng, J. Li, Y. Liu, Y. Lin, C. Shi, X. Wang, Z. Pan, Y. Song, J. Zhu, Oncotarget 2017, 8, 24.

G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem. 2009, 30, 2785-2791.

A. D. Hunter, J. Chem. Educ. 1997, 74, 905.

E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, J. Comput. Chem. 2004, 25, 1605-1612.

J. Hodoň, I. Frydrych, Z. Trhlíková, J. Pokorný, L. Borková, S. Benická, M. Vlk, B. Lišková, A. Kubíčková, M. Medvedíková, M. Pisár, J. Šarek, V. Das, A. Ligasová, K. Koberna, P. Džubák, M. Hajdúch, M. Urban, Eur. J. Med. Chem. 2022, 243, 114777.

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