References
- Alaa-Eldin, E. A., El-Shafei, D. A., & Abouhashem, N. S. (2017). Individual and combined effect of chlorpyrifos and cypermethrin on reproductive system of adult male albino rats. Environmental Science and Pollution Research International, 24(2), 1532–1543. https://doi.org/https://doi.org/10.1007/s11356-016-7912-6
- Bastos, A. M. X., Souza, M. d C. B., de, A., Filho, G. L. d., Krauss, T. M., Pavesi, T., Silva, L. E. & da, (2013). Organochlorine compound levels in fertile and infertile women from Rio de Janeiro, Brazil. Arquivos Brasileiros de Endocrinologia & Metabologia, 57, 346–353.
- Beg, M. A., & Sheikh, I. A. (2020). Endocrine disruption: Structural interactions of androgen receptor against di(2-ethylhexyl) phthalate and its metabolites. Toxics, 8(4), 115. https://doi.org/https://doi.org/10.3390/toxics8040115
- Bohl, C. E., Miller, D. D., Chen, J., Bell, C. E., & Dalton, J. T. (2005). Structural basis for accommodation of nonsteroidal ligands in the androgen receptor. Journal of Biological Chemistry, 280(45), 37747–37754. https://doi.org/https://doi.org/10.1074/jbc.M507464200
- Bretveld, R., Brouwers, M., Ebisch, I., & Roeleveld, N. (2007). Influence of pesticides on male fertility. Scandinavian Journal of Work, Environment and Health, 33, 13–28. https://doi.org/https://doi.org/10.5271/sjweh.1060.
- Case, D. A., Ben-Shalom, I. Y., Brozell, S. R., Cerutti, D. S., Cheatham, T. E., III, Cruzeiro, V. W. D., Darden, T. A., Duke, R. E., Ghoreishi, D., & Gilson, M. K. (2018). Amber 2018. University of California.
- Clamp, M., Cuff, J., Searle, S. M., & Barton, G. J. (2004). The Jalview Java alignment editor. Bioinformatics (Oxford, England), 20(3), 426–427. https://doi.org/https://doi.org/10.1093/bioinformatics/btg430
- Cremonese, C., Piccoli, C., Pasqualotto, F., Clapauch, R., Koifman, R. J., Koifman, S., & Freire, C. (2017). Occupational exposure to pesticides, reproductive hormone levels and sperm quality in young Brazilian men. Reproductive Toxicology (Elmsford, N.Y.), 67, 174–185. https://doi.org/https://doi.org/10.1016/j.reprotox.2017.01.001
- Delfosse, V., Grimaldi, M., Pons, J. L., Boulahtouf, A., Le Maire, A., Cavailles, V., Labesse, G., Bourguet, W., & Balaguer, P. (2012). Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes. Proceedings of the National Academy of Sciences of the United States of America, 109(37), 14930–14935. https://doi.org/https://doi.org/10.1073/pnas.1203574109
- Duan, M., Liu, N., Zhou, W., Li, D., Yang, M., & Hou, T. (2016). Structural diversity of ligand-binding androgen receptors revealed by microsecond long molecular dynamics simulations and enhanced sampling. Journal of Chemical Theory and Computation, 12(9), 4611–4619. https://doi.org/https://doi.org/10.1021/acs.jctc.6b00424
- Duke, C. B., Jones, A., Bohl, C. E., Dalton, J. T., & Miller, D. D. (2011). Unexpected binding orientation of bulky-B-ring anti-androgens and implications for future drug targets. Journal of Medicinal Chemistry, 54(11), 3973–3976. https://doi.org/https://doi.org/10.1021/jm2000097
- Essmann, U., Perera, L., Berkowitz, M. L., Darden, T., Lee, H., & Pedersen, L. G. (1995). A smooth particle mesh Ewald method. The Journal of Chemical Physics, 103(19), 8577–8593. https://doi.org/https://doi.org/10.1063/1.470117
- González, J. G., Miranda, M. I. V., Mullor, M. R., Jerez, A. F. H., Carreño, T. P., & Rodriguez, R. A. (2017). Association of reproductive disorders and male congenital anomalies with environmental exposure to endocrine active pesticides. Reproductive Toxicology, 71, 95–100. https://doi.org/https://doi.org/10.1016/j.reprotox.2017.04.011.
- Hazarika, J., Ganguly, M., Borgohain, G., Baruah, I., Sarma, S., Bhuyan, P., & Mahanta, R. (2020). Endocrine disruption: Molecular interactions of chlorpyrifos and its degradation products with estrogen receptor. Structural Chemistry 31, 2011–2021. https://doi.org/https://doi.org/10.1007/s11224-020-01562-4
- Hazarika, J., Ganguly, M., & Mahanta, R. (2019). Molecular interactions of chlorpyrifos and its environmental degradation products with human sex hormone-binding globulin: An in silico study. Journal of Applied Toxicology, 39(7), 1002–1011. https://doi.org/https://doi.org/10.1002/jat.3789
- Hazarika, J., Ganguly, M., & Mahanta, R. (2020). A computational insight into the molecular interactions of chlorpyrifos and its degradation products with the human progesterone receptor leading to endocrine disruption. Journal of Applied Toxicology, 40(3), 434–443. https://doi.org/https://doi.org/10.1002/jat.3916
- Joshi, S. C., Mathur, R., & Gulati, N. (2007). Testicular toxicity of chlorpyrifos (an organophosphate pesticide) in albino rat. Toxicology and Industrial Health, 23(7), 439–444. https://doi.org/https://doi.org/10.1177/0748233707080908
- Kolšek, K., Gobec, M., Mlinarič Raščan, I., & Sollner Dolenc, M. (2015). Screening of bisphenol A, triclosan and paraben analogues as modulators of the glucocorticoid and androgen receptor activities. Toxicology in Vitro: An International Journal Published in Association with Bibra, 29(1), 8–15. https://doi.org/https://doi.org/10.1016/j.tiv.2014.08.009
- Lill, M. A., Winiger, F., Vedani, A., & Ernst, B. (2005). Impact of induced fit on ligand binding to the androgen receptor: A multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals. Journal of Medicinal Chemistry, 48(18), 5666–5674. https://doi.org/https://doi.org/10.1021/jm050403f
- Liu, H., Han, R., Li, J., Liu, H., & Zheng, L. (2016). Molecular mechanism of R-bicalutamide switching from androgen receptor antagonist to agonist induced by amino acid mutations using molecular dynamics simulations and free energy calculation. Journal of Computer-Aided Molecular Design, 30(12), 1189–1200. https://doi.org/https://doi.org/10.1007/s10822-016-9992-2
- Liu, H. L., Zhong, H. Y., Song, T. Q., & Li, J. Z. (2017). A molecular modeling study of the hydroxyflutamide resistance mechanism induced by androgen receptor mutations. International Journal of Molecular Sciences, 18(9), 1823. https://doi.org/https://doi.org/10.3390/ijms18091823
- Lu, N. Z., Wardell, S. E., Burnstein, K. L., Defranco, D., Fuller, P. J., Giguere, V., Hochberg, R. B., Mckay, L., Renoir, J. M., Weigel, N. L., Wilson, E. M., Mcdonnell, D. P., & Cidlowski, J. A. (2006). International union of pharmacology. LXV. The pharmacology and classification of the nuclear receptor superfamily: Glucocorticoid, mineralocorticoid, progesterone, and androgen receptors. In. Pharmacological Reviews, 58(4), 782–797. https://doi.org/https://doi.org/10.1124/pr.58.4.9
- Luccio-Camelo, D. C., & Prins, G. S. (2011). Disruption of androgen receptor signaling in males by environmental chemicals. Journal of Steroid Biochemistry and Molecular Biology, 127(1–2): 74–82.
- Maier, J. A., Martinez, C., Kasavajhala, K., Wickstrom, L., Hauser, K. E., & Simmerling, C. (2015). ff14SB: Improving the accuracy of protein side chain and backbone parameters from ff99SB. Journal of Chemical Theory and Computation, 11(8), 3696–3713. https://doi.org/https://doi.org/10.1021/acs.jctc.5b00255
- McGinley, P. L., & Koh, J. T. (2007). Circumventing anti-androgen resistance by molecular design. Journal of the American Chemical Society, 129(13), 3822–3823. https://doi.org/https://doi.org/10.1021/ja0701154
- Mehrpour, O., Karrari, P., Zamani, N., Tsatsakis, A. M., & Abdollahi, M. (2014). Occupational exposure to pesticides and consequences on male semen and fertility: A review. Toxicology Letters, 230(2), 146–156. https://doi.org/https://doi.org/10.1016/j.toxlet.2014.01.029
- Miranda-Contreras, L., Gómez-Pérez, R., Rojas, G., Cruz, I., Berrueta, L., Salmen, S., Colmenares, M., Barreto, S., Balza, A., Zavala, L., Morales, Y., Molina, Y., Valeri, L., Contreras, C. A., & Osuna, J. A. (2013). Occupational exposure to organophosphate and carbamate pesticides affects sperm chromatin integrity and reproductive hormone levels among venezuelan farm workers. Journal of Occupational Health, 55(3), 195–203. https://doi.org/https://doi.org/10.1539/joh.12-0144-FS
- Mnif, W., Hassine, A. I. H., Bouaziz, A., Bartegi, A., Thomas, O., & Roig, B. (2011). Effect of endocrine disruptor pesticides: A review. International Journal of Environmental Research and Public Health, 8(6), 2265–2303. https://doi.org/https://doi.org/10.3390/ijerph8062265
- Oliva, A., Spira, A., & Multigner, L. (2001). Contribution of environmental factors to the risk of male infertility. Human Reproduction (Oxford, England)), 16(8), 1768–1776. https://doi.org/https://doi.org/10.1093/humrep/16.8.1768
- Osguthorpe, D. J., & Hagler, A. T. (2011). Mechanism of androgen receptor antagonism by bicalutamide in the treatment of prostate cancer. Biochemistry, 50(19), 4105–4113. https://doi.org/https://doi.org/10.1021/bi102059z
- Padungtod, C., Savitz, D. A., Overstreet, J. W., Christiani, D. C., Ryan, L. M., & Xu, X. (2000). Occupational pesticide exposure and semen quality among Chinese workers. Journal of Occupational and Environmental Medicine, 42(10), 982–992.
- Peiris, D. C., & Dhanushka, T. (2017). Low doses of chlorpyrifos interfere with spermatogenesis of rats through reduction of sex hormones. Environmental Science and Pollution Research, 24(26), 20859–20867. https://doi.org/https://doi.org/10.1007/s11356-017-9617-x
- Rehan, M., Ahmad, E., Sheikh, I. A., Abuzenadah, A. M., Damanhouri, G. A., Bajouh, O. S., Al Basri, S. F., Assiri, M. M., & Beg, M. A. (2015). Androgen and progesterone receptors are targets for bisphenol a (BPA), 4-methyl-2,4-bis-(p-hydroxyphenyl)pent-1-ene-A potent metabolite of BPA, and 4-tert-octylphenol: A computational insight. PLoS One, 10(9), e0138438. https://doi.org/https://doi.org/10.1371/journal.pone.0138438
- Roe, D. R., & Cheatham, T. E. (2013). PTRAJ and CPPTRAJ: Software for processing and analysis of molecular dynamics trajectory data. Journal of Chemical Theory and Computation, 9(7), 3084–3095. https://doi.org/https://doi.org/10.1021/ct400341p
- Sakkiah, S., Wang, T., Zou, W., Wang, Y., Pan, B., Tong, W., & Hong, H. (2017). Endocrine disrupting chemicals mediated through binding androgen receptor are associated with diabetes mellitus. International Journal of Environmental Research and Public Health, 15(1), 25. https://doi.org/https://doi.org/10.3390/ijerph15010025
- Sengupta, P., & Banerjee, R. (2014). Environmental toxins: Alarming impacts of pesticides on male fertility. Human & Experimental Toxicology, 33(10), 1017–1039. https://doi.org/https://doi.org/10.1177/0960327113515504
- Sheikh, I. A., & Beg, M. A. (2017). Endocrine disruption: In silico interactions between phthalate plasticizers and corticosteroid binding globulin. Journal of Applied Toxicology, 37(12), 1471–1480. https://doi.org/https://doi.org/10.1002/jat.3497
- Sifakis, S., Androutsopoulos, V. P., Tsatsakis, A. M., & Spandidos, D. A. (2017). Human exposure to endocrine disrupting chemicals: Effects on the male and female reproductive systems. Environmental Toxicology and Pharmacology, 51, 56–70. https://doi.org/https://doi.org/10.1016/j.etap.2017.02.024
- Song, C. H., Yang, S. H., Park, E., Cho, S. H., Gong, E. Y., Khadka, D. B., Cho, W. J., & Lee, K. (2012). Structure-based virtual screening and identification of a novel androgen receptor antagonist. The Journal of Biological Chemistry, 287(36), 30769–30780. https://doi.org/https://doi.org/10.1074/jbc.M112.379107
- Swan, S. H., Kruse, R. L., Liu, F., Barr, D. B., Drobnis, E. Z., Redmon, B., Wang, C., Brazil, C., & Overstreet, J. W, Study for Future Families Research Group (2003). Semen quality relation to biomarkers of pesticide exposure. Environmental Health Perspectives, 111(12), 1478–1484. https://doi.org/https://doi.org/10.1289/ehp.6417
- Swan, S. H., & Sharpe, R. M. (2006). Semen quality in fertile US men in relation to geographical area and pesticide exposure. International Journal of Andrology, 29(1), 62–68. https://doi.org/https://doi.org/10.1111/j.1365-2605.2005.00620.x
- Tan, M. E., Li, J., Xu, H. E., Melcher, K., & Yong, E. L. (2015). Androgen receptor: Structure, role in prostate cancer and drug discovery. Acta Pharmacologica Sinica, 36(1), 3–23. https://doi.org/https://doi.org/10.1038/aps.2014.18
- Vedani, A., Dobler, M., Hu, Z., & Smieško, M. (2015). OpenVirtualToxLab – A platform for generating and exchanging in silico toxicity data. Toxicology Letters, 232(2), 519–532. https://doi.org/https://doi.org/10.1016/j.toxlet.2014.09.004
- Vedani, A., Dobler, M., & Lill, M. A. (2006). The challenge of predicting drug toxicity in silico. In Basic and Clinical Pharmacology and Toxicology. https://doi.org/https://doi.org/10.1111/j.1742-7843.2006.pto_471.x
- Vedani, A., & Smiesko, M. (2009). In silico toxicology in drug discovery – Concepts based on three-dimensional models. Alternatives to Laboratory Animals, 37(5), 477–496. https://doi.org/https://doi.org/10.1177/026119290903700506
- Wang, H., Li, J., Gao, Y., Xu, Y., Pan, Y., Tsuji, I., Sun, Z. J., & Li, X. M. (2010). Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor. Asian Journal of Andrology, 12(4), 535–547. https://doi.org/https://doi.org/10.1038/aja.2010.14
- Wang, J., Wolf, R. M., Caldwell, J. W., Kollman, P. A., & Case, D. A. (2004). Development and testing of a general Amber force field. Journal of Computational Chemistry, 25(9), 1157–1174. https://doi.org/https://doi.org/10.1002/jcc.20035
- Wang, X., Li, X., Shi, W., Wei, S., Giesy, J. P., Yu, H., & Wang, Y. (2013). Docking and CoMSIA studies on steroids and non-steroidal chemicals as androgen receptor ligands. Ecotoxicology and Environmental Safety, 89, 143–149. https://doi.org/https://doi.org/10.1016/j.ecoenv.2012.11.020
- Waterhouse, A. M., Procter, J. B., Martin, D. M. A., Clamp, M., & Barton, G. J. (2009). Jalview Version 2-A multiple sequence alignment editor and analysis workbench. Bioinformatics (Oxford, England), 25(9), 1189–1191. https://doi.org/https://doi.org/10.1093/bioinformatics/btp033
- Yucra, S., Rubio, J., Gasco, M., Gonzales, C., Steenland, K., & Gonzales, G. F. (2006). Semen quality and reproductive sex hormone levels in Peruvian pesticide sprayers. International Journal of Occupational and Environmental Health, 12(4), 355–361. https://doi.org/https://doi.org/10.1179/oeh.2006.12.4.355
- Zawatski, W., & Lee, M. M. (2013). Male pubertal development: Are endocrine-disrupting compounds shifting the norms. ?Journal of Endocrinology, 218(2), R1–R12. https://doi.org/https://doi.org/10.1530/JOE-12-0449
- Zhou, J., Liu, B., Geng, G., & Wu, J. H. (2010). Study of the impact of the TB77A mutation on ligand-induced helix-12 positioning of the androgen receptor resulted in design and synthesis of novel antiandrogens. Proteins: Structure, Function, and Bioinformatics, 78(3), 623–637. https://doi.org/https://doi.org/10.1002/prot.22592
- Zhou, W., Duan, M., Fu, W., Pang, J., Tang, Q., Sun, H., Xu, L., Chang, S., Li, D., & Hou, T. (2018). Discovery of novel androgen receptor ligands by structure-based virtual screening and bioassays. Genomics, Proteomics and Bioinformatics, 16(6), 416–427. https://doi.org/https://doi.org/10.1016/j.gpb.2018.03.007.