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Research Article

Click estradiol dimers with novel aromatic bridging units: synthesis and anticancer evaluation

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Article: 2367139 | Received 17 Nov 2023, Accepted 06 Jun 2024, Published online: 21 Jun 2024

References

  • Brouhard GJ, Rice LM. Microtubule dynamics: an interplay of biochemistry and mechanics. Nat Rev Mol Cell Biol. 2018;19(7):1–16.
  • Lafanechère L. The microtubule cytoskeleton: an old validated target for novel therapeutic drugs. Front Pharmacol. 2022;13:969183.
  • Serrano-del Valle A, Reina-Ortiz C, Benedi A, Anel A, Naval J, Marzo I. Future prospects for mitosis-targeted antitumor therapies. Biochem Pharmacol. 2021;190:114655.
  • Čermák V, Dostál V, Jelínek M, Libusová L, Kovář J, Rösel D, Brábek J. Microtubule-targeting agents and their impact on cancer treatment. Eur J Cell Biol. 2020;99(4):151075.
  • Wordeman L, Vicente JJ. Microtubule targeting agents in disease: classic drugs, novel roles. Cancers. 2021;13(22):5650.
  • Verenich S, Gerk PM. Therapeutic promises of 2-methoxyestradiol and its drug disposition challenges. Mol Pharm. 2010;7(6):2030–2039.
  • Pertegal M, Fenoy FJ, Bonacasa B, Mendiola J, Delgado JL, Hernández M, Salom MG, Bosch V, Hernández I. 2-Methoxyestradiol plasma levels are associated with clinical severity indices and biomarkers of preeclampsia. Reprod Sci. 2015;22(2):198–206.
  • Nahar L, Sarker SD. A review on steroid dimers: 2011–2019. Steroids. 2020;164:108736.
  • Jurášek M, Černohorská M, Řehulka J, Spiwok V, Sulimenko T, Dráberová E, Darmostuk M, Gurská S, Frydrych I, Buriánová R, et al. Estradiol dimer inhibits tubulin polymerization and microtubule dynamics. J Steroid Biochem Mol Biol. 2018;183:68–79.
  • Jurášek M, Řehulka J, Hrubá L, Ivanová A, Gurská S, Mokshyna O, Trousil P, Huml L, Polishchuk P, Hajdúch M, et al. Triazole-based estradiol dimers prepared via CuAAC from 17α-ethinyl estradiol with five-atom linkers causing G2/M arrest and tubulin inhibition. Bioorg Chem. 2023;131:106334.
  • Bouysset C, Fiorucci S. Prolif: a library to encode molecular interactions as fingerprints. J Cheminform. 2021;13(1):72.
  • Thomas JR, Liu XJ, Hergenrother PJ. Size-specific ligands for RNA hairpin loops. J Am Chem Soc. 2005;127(36):12434–12435.
  • Rasheed OK, Lawrence A, Quayle P, Bailey PD. A modular approach to functionalised dyes. Synlett. 2015;27(6):905–911.
  • Shtyrlin NV, Vafina RM, Pugachev MV, Khaziev RM, Nikitina EV, Zeldi MI, Iksanova AG, Shtyrlin YG. Synthesis and biological activity of quaternary phosphonium salts based on 3-hydroxypyridine and 4-deoxypyridoxine. Russ Chem Bull. 2016;65(2):537–545.
  • Sali A, Blundell T. Comparative protein modeling by satisfaction of spatial restraints. J Mol Biol. 1993;234:64–86.
  • Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. UCSF chimera – a visualization system for exploratory research and analysis. J Comput Chem. 2004;25(13):1605–1612.
  • Trott O, Olson AJ. Autodock vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem. 2010;31(2):455–461.
  • Landrum G. RDkit: open-source cheminformatics software; 2021. Available from: https://www.rdkit.org
  • Cxcalc utility was used for ligand protonation, Cxcalc version 19.22.0. ChemAxon. Available from: https://www.chemaxon.com
  • Hess B, Kutzner C, van der Spoel D, Lindahl E. GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation. J Chem Theory Comput. 2008;4(3):435–447.
  • Lindorff-Larsen K, Piana S, Palmo K, Maragakis P, Klepeis JL, Dror RO, Shaw DE. Improved side-chain torsion potentials for the amber ff99sb protein force field. Proteins. 2010;78(8):1950–1958.
  • Case DA, Aktulga HM, Belfon K, Ben-Shalom IY, Berryman JT, Brozell SR, Cerutti DS, Cheatham TE, III, Cisneros GA, Cruzeiro VWD, et al. Amber 2023. San Francisco: University of California; 2023.