Bisphenol Design and Prediction of Some Bisphenol A Analogs’ Estrogen Activities
Main Article Content
Abstract
Abstract: The article presents the results of research and application of QSAR model (Estrogen active -structural relationship) of bisphenol A (BPA) and its derivatives using quantum chemical calculation and artificial neural network (ANN). On the basis of the QSAR model and the results of quantum computation, the article assesses the influence of the structure - quantum parameters on the biological activity of the surveyed substances. Accordingly, the parameters C12, EHOMO, C3, µ, C13 and C6 have the most significant impact on the estrogenic activity of the surveyed substances. By analyzing the expression of toxicity and the change in parameters of the molecules related to the change of one or several "fragments" of molecular structure associated with the active-structural models, the article establishes a new molecular design to optimize the biological response of compounds in applied sciences. The newly designed molecules have significantly lower estrogen activity than that of the molecules in the 23 surveyed substances.
Keywords: QSAR, bisphenol A, artificial neural network.
References
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[10] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, et al.. Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2009.
[11] Vũ Văn Đạt, Lâm Ngọc Thiềm, Lê Kim Long, Đoàn Văn Phúc, Nguyễn Hoàng Trang. Xây dựng mô hình QSAR mô tả hoạt tính Estrogen của Bisphenol A và các dẫn xuất sử dụng lý thuyết hóa lượng tử và phép hồi quy đa biến tuyến tính Tạp chí Khoa học Đại học Quốc gia Hà Nội (Khoa học tự nhiên và công nghệ) 34 (2018) 3.
[12] Vu Van Dat, Le Kim Long, Doan Van Phuc, Nguyen Hoang Trang, Nguyen Van Trang, Nguyen Thi Thu Ha. Predicting estrogen activities of bisphenol A and its analogs using quantum chemistry calculations and artificial neural networks. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 62 (5) (2019) 31-37. https://doi. org 10.6060/ivkkt.20196205.5933.
References
[2] D. Melzer, N.E. Rice, C. Lewis, W.E. Henley, T.S. Galloway. Association of Urinary Bisphenol a Concentration with Heart Disease: Evidence from NHANES 2003/06. PLoS ONE 6 (2010) 5(1): e8673. http://doi.org/ 10.1371/journal.pone.0008673.
[3] M. Manikkam, R. Tracey, C. Guerrero-Bosagna, M.K Skinner. (January 24, 2013). Plastics derived endocrine disruptors (BPA, DEHP and DBP) induce epigenetic transgenerational inheritance of obesity, reproductive disease and sperm epimutations. PLoS ONE 8 (2013) 1-16. http:// doi.org/ 10.1371/journal.pone.0055387.
[4] D.R. Doerge, N.C. Twaddle, M. Vanlandingham, R.P. Brown, J.W. Fisher. Distribution of bisphenol A into tissues of adult, neonatal, and fetal Sprague -Dawley rats. Toxicol Appl Pharmacol (2011) 255 (3) 261-70. http://doi.rog/ 10.1016/j.taap.2011.07.009.
[5] S.M. Ho, W.Y Tang, J. Belmonte de Frausto, G.S. Prins. Developmental exposure to estradiol and bisphenol A increases susceptibility to prostate carcinogenesis and epigenetically regulates phosphodiesterase type 4 variant 4 (2006). Cancer Res. 66 (11) 5624-32. http://doi.org/10.1158/0008-5472. CAN-06-0516.
[6] J.R. Rochester, A.L. Bolden. Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes. Environ Health Perspect 123 (7) 643-50. Environ Health Perspect. 123 (7) (2015) 643-50. https://doi.org/10.1289/ehp.1408989.
[7] P.C. Kelly, A.T. William, E.W. Thomas. QSAR models of thein vitro estrogen activity of bisphenol A analogs. QSAR & Combinatorial Science 22 (1) (2003) 78-88. https://doi.org/ 10.1002/qsar.200390008.
[8] Cui Shihai, Liu Shushen, Yang Jing, Wang Xiaodong, Wang Liansheng. Quantitative structure-activity relationship of estrogen activities of bisphenol A analogs. Chinese Science Bulletin, 51 (3) (2006) 287-292. https://doi.org/ 10.1002/tox.22539.
[9] Keisuke Maruyama, Masaharu Nakamura and ets. Structure-activity relationships of bisphenol A analogs at estrogen receptors (ERs): Discovery of an ERa-selective antagonist. Bioorganic & Medicinal Chemistry Letters 23 (2013) 4031-4036. http://doi.org/ 10.1016/j.bmcl.2013.05.067.
[10] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, et al.. Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2009.
[11] Vũ Văn Đạt, Lâm Ngọc Thiềm, Lê Kim Long, Đoàn Văn Phúc, Nguyễn Hoàng Trang. Xây dựng mô hình QSAR mô tả hoạt tính Estrogen của Bisphenol A và các dẫn xuất sử dụng lý thuyết hóa lượng tử và phép hồi quy đa biến tuyến tính Tạp chí Khoa học Đại học Quốc gia Hà Nội (Khoa học tự nhiên và công nghệ) 34 (2018) 3.
[12] Vu Van Dat, Le Kim Long, Doan Van Phuc, Nguyen Hoang Trang, Nguyen Van Trang, Nguyen Thi Thu Ha. Predicting estrogen activities of bisphenol A and its analogs using quantum chemistry calculations and artificial neural networks. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 62 (5) (2019) 31-37. https://doi. org 10.6060/ivkkt.20196205.5933.