Computational screening of FDA-approved drugs to identify potential aromatase receptor inhibitors for polycystic ovary syndrome

References

• Abraham, M. J., Murtola, T., Schulz, R., Páll, S., Smith, J. C., Hess, B., & Lindahl, E. (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX, 1, 19–25.
   Google Scholar
• Acar Çevik, U., Kaya Çavuşoğlu, B., Sağlık, B. N., Osmaniye, D., Levent, S., Ilgın, S., Özkay, Y., & Kaplancıklı, Z. A. (2020). Synthesis, docking studies and biological activity of new benzimidazole-triazolothiadiazine derivatives as aromatase inhibitor. Molecules, 25(7), 1642. https://doi.org/10.3390/molecules25071642
   PubMed Web of Science ®Google Scholar
• Aghajanian, P., Hall, S., Wongworawat, M. D., & Mohan, S. (2015). The roles and mechanisms of actions of vitamin C in bone: New developments. Journal of Bone and Mineral Research, 30(11), 1945–1955. https://doi.org/10.1002/jbmr.2709
   PubMed Web of Science ®Google Scholar
• Amet, N., Lee, H.-F., & Shen, W.-C. (2009). Insertion of the designed helical linker led to increased expression of tf-based fusion proteins. Pharmaceutical Research, 26(3), 523–528. https://doi.org/10.1007/s11095-008-9767-0
   PubMed Web of Science ®Google Scholar
• Arai, R., Ueda, H., Kitayama, A., Kamiya, N., & Nagamune, T. (2001). Design of the linkers which effectively separate domains of a bifunctional fusion protein. Protein Engineering Design and Selection, 14(8), 529–532. https://doi.org/10.1093/protein/14.8.529
   Web of Science ®Google Scholar
• Aziz, S., et al. (2022). Contriving multi-epitope vaccine ensemble for monkeypox disease using an immunoinformatics approach. Frontiers in Immunology, 13, 1004804.
   Web of Science ®Google Scholar
• Behmard, E., Abdulabbas, H. T., Abdalkareem Jasim, S., Najafipour, S., Ghasemian, A., Farjadfar, A., Barzegari, E., Kouhpayeh, A., & Abdolmaleki, P. (2022). Design of a novel multi-epitope vaccine candidate against hepatitis C virus using structural and nonstructural proteins: An immunoinformatics approach. PLoS One, 17(8), e0272582. https://doi.org/10.1371/journal.pone.0272582
   PubMed Web of Science ®Google Scholar
• Borumandnia, N., Alavi Majd, H., Khadembashi, N., & Alaii, H. (2022). Worldwide trend analysis of primary and secondary infertility rates over past decades: A cross-sectional study. International Journal of Reproductive Biomedicine, 20(1), 37–46. https://doi.org/10.18502/ijrm.v20i1.10407
   PubMed Web of Science ®Google Scholar
• Casper, R. F., & Mitwally, M. F. (2006). Aromatase inhibitors for ovulation induction. The Journal of Clinical Endocrinology and Metabolism, 91(3), 760–771. https://doi.org/10.1210/jc.2005-1923
   PubMed Web of Science ®Google Scholar
• Casper, R. F., & Mitwally, M. F. (2011). Use of the aromatase inhibitor letrozole for ovulation induction in women with polycystic ovarian syndrome. Clinical Obstetrics and Gynecology, 54(4), 685–695. https://doi.org/10.1097/GRF.0b013e3182353d0f
   PubMed Web of Science ®Google Scholar
• Cruzat, V., Macedo Rogero, M., Noel Keane, K., Curi, R., & Newsholme, P. (2018). Glutamine: metabolism and immune function, supplementation and clinical translation. Nutrients, 10(11), 1564. https://doi.org/10.3390/nu10111564
   PubMed Web of Science ®Google Scholar
• De Luca, M., Occhiuzzi, M. A., Rizzuti, B., Ioele, G., Ragno, G., Garofalo, A., & Grande, F. (2022). Interaction of letrozole and its degradation products with aromatase: Chemometric assessment of kinetics and structure-based binding validation. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 1600–1609. https://doi.org/10.1080/14756366.2022.2081845
   PubMed Web of Science ®Google Scholar
• Dehghan, Z., Mohammadi-Yeganeh, S., Sameni, M., Mirmotalebisohi, S. A., Zali, H., & Salehi, M. (2021). Repurposing new drug candidates and identifying crucial molecules underlying PCOS pathogenesis based on bioinformatics analysis. DARU Journal of Pharmaceutical Sciences, 29(2), 353–366. https://doi.org/10.1007/s40199-021-00413-9
   Google Scholar
• DeLano, W. L. (2002). Pymol: An open-source molecular graphics tool. CCP4 Newsletter on Protein Crystallography, 40(1), 82–92.
   Google Scholar
• Ghosh, D., Griswold, J., Erman, M., & Pangborn, W. (2009). Structural basis for androgen specificity and oestrogen synthesis in human aromatase. Nature, 457(7226), 219–223. https://doi.org/10.1038/nature07614
   PubMed Web of Science ®Google Scholar
• Ghosh, D., Griswold, J., Erman, M., & Pangborn, W. (2010). X-ray structure of human aromatase reveals an androgen-specific active site. The Journal of Steroid Biochemistry and Molecular Biology, 118(4–5), 197–202. https://doi.org/10.1016/j.jsbmb.2009.09.012
   PubMed Web of Science ®Google Scholar
• Głowacka, K., & Wiela-Hojeńska, A. (2021). Pseudoephedrine—benefits and risks. International Journal of Molecular Sciences, 22(10), 5146. https://doi.org/10.3390/ijms22105146
   PubMed Web of Science ®Google Scholar
• Guang, H-j., Li, F., & Shi, J. (2018). Letrozole for patients with polycystic ovary syndrome: A retrospective study. Medicine, 97(44), e13038. https://doi.org/10.1097/MD.0000000000013038
   PubMed Web of Science ®Google Scholar
• Habel, J. R., Nguyen, A. T., Rowntree, L. C., Szeto, C., Mifsud, N. A., Clemens, E. B., Loh, L., Chen, W., Rockman, S., Nelson, J., Davies, J., Miller, A., Tong, S. Y. C., Rossjohn, J., Gras, S., Purcell, A. W., Hensen, L., Kedzierska, K., & Illing, P. T. (2022). HLA-A* 11: 01-restricted CD8+ T cell immunity against influenza A and influenza B viruses in Indigenous and non-Indigenous people. PLOS Pathogens, 18(3), e1010337. https://doi.org/10.1371/journal.ppat.1010337
   PubMed Web of Science ®Google Scholar
• Hammed-Akanmu, M., Mim, M., Osman, A. Y., Sheikh, A. M., Behmard, E., Rabaan, A. A., Suppain, R., & Hajissa, K. (2022). Designing a multi-epitope vaccine against Toxoplasma gondii: An immunoinformatics approach. Vaccines, 10(9), 1389. https://doi.org/10.3390/vaccines10091389
   Web of Science ®Google Scholar
• Homburg, R., Hendriks, M. L., König, T. E., Anderson, R. A., Balen, A. H., Brincat, M., Child, T., Davies, M., D'Hooghe, T., Martinez, A., Rajkhowa, M., Rueda-Saenz, R., Hompes, P., & Lambalk, C. B. (2012). Clomifene citrate or low-dose FSH for the first-line treatment of infertile women with anovulation associated with polycystic ovary syndrome: A prospective randomized multinational study. Human Reproduction (Oxford, England), 27(2), 468–473. https://doi.org/10.1093/humrep/der401
   PubMed Web of Science ®Google Scholar
• Jahantigh, H., et al. (2022). Repurposing antiviral drugs against HTLV-1 protease by molecular docking and molecular dynamics simulation. Journal of Biomolecular Structure and Dynamics, 25, 1–10.
   Web of Science ®Google Scholar
• Jørgensen, C. K., & Reisfeld, R. (1983). Judd-Ofelt parameters and chemical bonding. Journal of the Less Common Metals, 93(1), 107–112. https://doi.org/10.1016/0022-5088(83)90454-X
   Google Scholar
• Kaminski, G., & Jorgensen, W. L. (1996). Performance of the AMBER94, MMFF94, and OPLS-AA force fields for modeling organic liquids. The Journal of Physical Chemistry, 100(46), 18010–18013. https://doi.org/10.1021/jp9624257
   Web of Science ®Google Scholar
• Knowles, H. J., Tian, Y.-M., Mole, D. R., & Harris, A. L. (2004). Novel mechanism of action for hydralazine: Induction of hypoxia-inducible factor-1 α, vascular endothelial growth factor, and angiogenesis by inhibition of prolyl hydroxylases. Circulation Research, 95(2), 162–169.
   PubMed Web of Science ®Google Scholar
• Koes, D. R., Baumgartner, M. P., & Camacho, C. J. (2013). Lessons learned in empirical scoring with smina from the CSAR 2011 benchmarking exercise. Journal of Chemical Information and Modeling, 53(8), 1893–1904. https://doi.org/10.1021/ci300604z
   PubMed Web of Science ®Google Scholar
• Kollman, P. A., Massova, I., Reyes, C., Kuhn, B., Huo, S., Chong, L., Lee, M., Lee, T., Duan, Y., Wang, W., Donini, O., Cieplak, P., Srinivasan, J., Case, D. A., & Cheatham, T. E. (2000). Calculating structures and free energies of complex molecules: Combining molecular mechanics and continuum models. Accounts of Chemical Research, 33(12), 889–897.
   PubMed Web of Science ®Google Scholar
• Krishnamurthy, N., Grimshaw, A. A., Axson, S. A., Choe, S. H., & Miller, J. E. (2022). Drug repurposing: A systematic review on root causes, barriers and facilitators. BMC Health Services Research, 22(1), 1–17. https://doi.org/10.1186/s12913-022-08272-z
   PubMed Web of Science ®Google Scholar
• Kumari, R., Kumar, R., & Lynn, A. (2014). g_mmpbsa– A GROMACS tool for high-throughput MM-PBSA calculations. Journal of Chemical Information and Modeling, 54(7), 1951–1962. https://doi.org/10.1021/ci500020m
   PubMed Web of Science ®Google Scholar
• Louwers, Y. V., & Laven, J. S. (2020). Characteristics of polycystic ovary syndrome throughout life. Therapeutic Advances in Reproductive Health, 14, 2633494120911038. https://doi.org/10.1177/2633494120911038
   Google Scholar
• Low, Z. Y., Farouk, I. A., & Lal, S. K. (2020). Drug repositioning: New approaches and future prospects for life-debilitating diseases and the COVID-19 pandemic outbreak. Viruses, 12(9), 1058. https://doi.org/10.3390/v12091058
   PubMed Web of Science ®Google Scholar
• Mitwally, M. F., & Casper, R. F. (2001). Use of an aromatase inhibitor for induction of ovulation in patients with an inadequate response to clomiphene citrate. Fertility and Sterility, 75(2), 305–309.
   PubMed Web of Science ®Google Scholar
• Mojaddami, A., Sakhteman, A., Fereidoonnezhad, M., Faghih, Z., Najdian, A., Khabnadideh, S., Sadeghpour, H., & Rezaei, Z. (2017). Binding mode of triazole derivatives as aromatase inhibitors based on docking, protein ligand interaction fingerprinting, and molecular dynamics simulation studies. Research in Pharmaceutical Sciences, 12(1), 21–30. https://doi.org/10.4103/1735-5362.199043
   PubMedGoogle Scholar
• Pavone, M. E., & Bulun, S. E. (2013). The use of aromatase inhibitors for ovulation induction and superovulation. The Journal of Clinical Endocrinology & Metabolism, 98(5), 1838–1844. https://doi.org/10.1210/jc.2013-1328
   PubMed Web of Science ®Google Scholar
• Pushpakom, S., Iorio, F., Eyers, P. A., Escott, K. J., Hopper, S., Wells, A., Doig, A., Guilliams, T., Latimer, J., McNamee, C., Norris, A., Sanseau, P., Cavalla, D., & Pirmohamed, M. (2019). Drug repurposing: Progress, challenges and recommendations. Nature Reviews Drug Discovery, 18(1), 41–58. https://doi.org/10.1038/nrd.2018.168
   PubMed Web of Science ®Google Scholar
• Rampogu, S., Park, C., Son, M., Baek, A., Zeb, A., Lee, G., & Lee, K. W. (2019). Modulation of aromatase by natural compounds—A pharmacophore guided molecular modelling simulations. South African Journal of Botany, 120, 230–240. https://doi.org/10.1016/j.sajb.2018.06.019
   Web of Science ®Google Scholar
• Rashid, R., Mir, S. A., Kareem, O., Ali, T., Ara, R., Malik, A., Amin, F., & Bader, G. N. (2022). Polycystic ovarian syndrome-current pharmacotherapy and clinical implications. Taiwanese Journal of Obstetrics & Gynecology, 61(1), 40–50.
   PubMed Web of Science ®Google Scholar
• Requena, A., Herrero, J., Landeras, J., Navarro, E., Neyro, J. L., Salvador, C., Tur, R., Callejo, J., Checa, M. A., Farré, M., Espinós, J. J., Fábregues, F., & Graña-Barcia, M. (2008). Use of letrozole in assisted reproduction: A systematic review and meta-analysis. Human Reproduction Update, 14(6), 571–582. https://doi.org/10.1093/humupd/dmn033
   PubMed Web of Science ®Google Scholar
• Russell, R. G. G., Watts, N. B., Ebetino, F. H., & Rogers, M. J. (2008). Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporosis International, 19(6), 733–759. https://doi.org/10.1007/s00198-007-0540-8
   PubMed Web of Science ®Google Scholar
• Shim, J. S., & Liu, J. O. (2014). Recent advances in drug repositioning for the discovery of new anticancer drugs. International Journal of Biological Sciences, 10(7), 654–663. https://doi.org/10.7150/ijbs.9224
   PubMed Web of Science ®Google Scholar
• Suvannang, N., Nantasenamat, C., Isarankura-Na-Ayudhya, C., & Prachayasittikul, V. (2011). Molecular docking of aromatase inhibitors. Molecules, 16(5), 3597–3617. https://doi.org/10.3390/molecules16053597
   Web of Science ®Google Scholar
• Usluogullari, B., Duvan, C. Z., & Usluogullari, C. A. (2015). Use of aromatase inhibitors in practice of gynecology. Journal of Ovarian Research, 8(1), 1–7. https://doi.org/10.1186/s13048-015-0131-9
   PubMedGoogle Scholar
• Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Protein Engineering, Design and Selection, 8(2), 127–134. https://doi.org/10.1093/protein/8.2.127
   Web of Science ®Google Scholar
• Witchel, S. F., Oberfield, S. E., & Peña, A. S. (2019). Polycystic ovary syndrome: pathophysiology, presentation, and treatment with emphasis on adolescent girls. Journal of the Endocrine Society, 3(8), 1545–1573. https://doi.org/10.1210/js.2019-00078
   PubMed Web of Science ®Google Scholar
• Wu, P., Feng, Q., Kerchberger, V. E., Nelson, S. D., Chen, Q., Li, B., Edwards, T. L., Cox, N. J., Phillips, E. J., Stein, C. M., Roden, D. M., Denny, J. C., & Wei, W.-Q. (2022). Integrating gene expression and clinical data to identify drug repurposing candidates for hyperlipidemia and hypertension. Nature Communications, 13(1), 1–12. https://doi.org/10.1038/s41467-021-27751-1
   PubMedGoogle Scholar
• Wu, Y., Tepper, H. L., & Voth, G. A. (2006). Flexible simple point-charge water model with improved liquid-state properties. The Journal of Chemical Physics, 124(2), 024503. https://doi.org/10.1063/1.2136877
   PubMed Web of Science ®Google Scholar
• Yang, A.-M., Cui, N., Sun, Y.-F., & Hao, G.-M. (2021). Letrozole for female infertility. Frontiers in Endocrinology, 12, 676133. https://doi.org/10.3389/fendo.2021.676133
   PubMed Web of Science ®Google Scholar