| [1] | VANDENBERG L N, HAUSER R, MARCUS M, et al. Human exposure to bisphenol A (BPA) [J]. Reproductive Toxicology, 2007, 24(2): 139-177. doi: 10.1016/j.reprotox.2007.07.010 |
| [2] | CHEN D, KANNAN K, TAN H L, et al. Bisphenol analogues other than BPA: Environmental occurrence, human exposure, and toxicity—a review [J]. Environmental Science & Technology, 2016, 50(11): 5438-5453. |
| [3] | DODDS E C, LAWSON W. Molecular structure in relation to oestrogenic activity. Compounds without a phenanthrene nucleus [J]. Proceedings of the Royal Society of London Series B - Biological Sciences, 1938, 125(839): 222-232. |
| [4] | ROCHESTER J R. Bisphenol A and human health: A review of the literature [J]. Reproductive Toxicology, 2013, 42: 132-155. doi: 10.1016/j.reprotox.2013.08.008 |
| [5] | BEN-JONATHAN N. Endocrine disrupting chemicals and breast cancer: The saga of bisphenol A[M]. Estrogen Receptor and Breast Cancer. Cham: Humana Press, 2019: 343-377. |
| [6] | CORBEL T, GAYRARD V, PUEL S, et al. Bidirectional placental transfer of Bisphenol A and its main metabolite, Bisphenol A-Glucuronide, in the isolated perfused human placenta [J]. Reproductive Toxicology, 2014, 47: 51-58. doi: 10.1016/j.reprotox.2014.06.001 |
| [7] | CABATON N, DUMONT C, SEVERIN I, et al. Genotoxic and endocrine activities of bis(hydroxyphenyl)methane (bisphenol F) and its derivatives in the HepG2 cell line [J]. Toxicology, 2009, 255(1-2): 15-24. doi: 10.1016/j.tox.2008.09.024 |
| [8] | NADERI M, WONG M Y L, GHOLAMI F. Developmental exposure of zebrafish (Danio rerio) to bisphenol-S impairs subsequent reproduction potential and hormonal balance in adults [J]. Aquatic Toxicology, 2014, 148: 195-203. doi: 10.1016/j.aquatox.2014.01.009 |
| [9] | KONNO Y, SUZUKI H, KUDO H, et al. Synthesis and properties of fluorine-containing poly(ether)s with pendant hydroxyl groups by the polyaddition of bis(oxetane)s and bisphenol AF [J]. Polymer Journal, 2004, 36(2): 114-122. doi: 10.1295/polymj.36.114 |
| [10] | MATSUSHIMA A, LIU X H, OKADA H, et al. Bisphenol AF is a full agonist for the estrogen receptor ERα but a highly specific antagonist for ERβ [J]. Environmental Health Perspectives, 2010, 118(9): 1267-1272. doi: 10.1289/ehp.0901819 |
| [11] | LIU K, LI J, YAN S J, et al. A review of status of tetrabromobisphenol A (TBBPA) in China [J]. Chemosphere, 2016, 148: 8-20. doi: 10.1016/j.chemosphere.2016.01.023 |
| [12] | ELADAK S, GRISIN T, MOISON D, et al. A new chapter in the bisphenol A story: Bisphenol S and bisphenol F are not safe alternatives to this compound [J]. Fertility and Sterility, 2015, 103(1): 11-21. doi: 10.1016/j.fertnstert.2014.11.005 |
| [13] | ZHANG Y F, REN X M, LI Y Y, et al. Bisphenol A alternatives bisphenol S and bisphenol F interfere with thyroid hormone signaling pathway in vitro and in vivo [J]. Environmental Pollution, 2018, 237: 1072-1079. doi: 10.1016/j.envpol.2017.11.027 |
| [14] | GRAMEC SKLEDAR D, PETERLIN MAŠIČ L. Bisphenol A and its analogs: Do their metabolites have endocrine activity? [J]. Environmental Toxicology and Pharmacology, 2016, 47: 182-199. doi: 10.1016/j.etap.2016.09.014 |
| [15] | GHOSH P, ROY S S, BEGUM M, et al. Bisphenol A: Understanding its health effects from the studies performed on model organisms[M]// Bisphenol A Exposure and Health Risks. London: InTech, 2017: 2-26. |
| [16] | ASHA S, VIDYAVATHI M. Role of human liver microsomes in in vitro metabolism of drugs—a review [J]. Applied Biochemistry and Biotechnology, 2010, 160(6): 1699-1722. doi: 10.1007/s12010-009-8689-6 |
| [17] | TANG W, WANG R, LU A. Utility of recombinant cytochrome P450 enzymes: A drug metabolism perspective [J]. Current Drug Metabolism, 2005, 6(5): 503-517. doi: 10.2174/138920005774330602 |
| [18] | YOUDIM K A, SAUNDERS K C. A review of LC-MS techniques and high-throughput approaches used to investigate drug metabolism by cytochrome P450s [J]. Journal of Chromatography B, 2010, 878(17-18): 1326-1336. doi: 10.1016/j.jchromb.2010.02.013 |
| [19] | GUENGERICH F P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity [J]. Chemical Research in Toxicology, 2001, 14(6): 611-650. doi: 10.1021/tx0002583 |
| [20] | CRUCIANI G, CAROSATI E, DE BOECK B, et al. MetaSite: Understanding metabolism in human cytochromes from the perspective of the chemist [J]. Journal of Medicinal Chemistry, 2005, 48(22): 6970-6979. doi: 10.1021/jm050529c |
| [21] | RYDBERG P, GLORIAM D E, ZARETZKI J, et al. SMARTCyp: A 2D method for prediction of cytochrome P450-mediated drug metabolism [J]. ACS Medicinal Chemistry Letters, 2010, 1(3): 96-100. doi: 10.1021/ml100016x |
| [22] | ZÜHLKE M K, SCHLÜTER R, HENNING A K, et al. A novel mechanism of conjugate formation of bisphenol A and its analogues by Bacillus amyloliquefaciens: Detoxification and reduction of estrogenicity of bisphenols [J]. International Biodeterioration & Biodegradation, 2016, 109: 165-173. |
| [23] | CABATON N, ZALKO D, RATHAHAO E, et al. Biotransformation of bisphenol F by human and rat liver subcellular fractions [J]. Toxicology in Vitro, 2008, 22(7): 1697-1704. doi: 10.1016/j.tiv.2008.07.004 |
| [24] | SHAIK S, DE VISSER S P, KUMAR D. External electric field will control the selectivity of enzymatic-like bond activations [J]. Journal of the American Chemical Society, 2004, 126(37): 11746-11749. doi: 10.1021/ja047432k |
| [25] | JACOBSON M P, KALYANARAMAN C, ZHAO S W, et al. Leveraging structure for enzyme function prediction: Methods, opportunities, and challenges [J]. Trends in Biochemical Sciences, 2014, 39(8): 363-371. |
| [26] | FU T T, ZHENG Q C, ZHANG H X. Investigation of the molecular and mechanistic basis for the regioselective metabolism of midazolam by cytochrome P450 3A4 [J]. Physical Chemistry Chemical Physics, 2022, 24(14): 8104-8112. doi: 10.1039/D2CP00232A |
| [27] | HUI C G, SINGH W, QUINN D, et al. Regio- and stereoselectivity in the CYP450BM3-catalyzed hydroxylation of complex terpenoids: A QM/MM study [J]. Physical Chemistry Chemical Physics, 2020, 22(38): 21696-21706. doi: 10.1039/D0CP03083J |
| [28] | CHAI L H, ZHANG H N, GUO F J, et al. Computational investigation of the bisphenolic drug metabolism by cytochrome P450: What factors favor intramolecular phenol coupling [J]. Chemical Research in Toxicology, 2022, 35(3): 440-449. doi: 10.1021/acs.chemrestox.1c00350 |
| [29] | ZHU L D, ZHOU J, ZHANG Q Z, et al. Computational study on the metabolic activation mechanism of PeCDD by Cytochrome P450 1A1 [J]. Journal of Hazardous Materials, 2021, 405: 124276. doi: 10.1016/j.jhazmat.2020.124276 |
| [30] | HE L, HE F, BI H C, et al. Isoform-selective inhibition of chrysin towards human cytochrome P450 1A2. Kinetics analysis, molecular docking, and molecular dynamics simulations [J]. Bioorganic & Medicinal Chemistry Letters, 2010, 20(20): 6008-6012. |
| [31] | SCHRÖDINGER E. An undulatory theory of the mechanics of atoms and molecules [J]. Physical Review, 1926, 28(6): 1049-1070. doi: 10.1103/PhysRev.28.1049 |
| [32] | HARTREE D R. The wave mechanics of an atom with a non-coulomb central field. part Ⅰ. theory and methods [J]. Mathematical Proceedings of the Cambridge Philosophical Society, 1928, 24(1): 89-110. doi: 10.1017/S0305004100011919 |
| [33] | KOHN W, SHAM L J. Self-consistent equations including exchange and correlation effects [J]. Physical Review, 1965, 140(4A): A1133-A1138. doi: 10.1103/PhysRev.140.A1133 |
| [34] | TRANG B, LI Y L, XUE X S, et al. Low-temperature mineralization of perfluorocarboxylic acids [J]. Science, 2022, 377(6608): 839-845. doi: 10.1126/science.abm8868 |
| [35] | JI L, JI S J, WANG C C, et al. Molecular mechanism of alternative P450-catalyzed metabolism of environmental phenolic endocrine-disrupting chemicals [J]. Environmental Science & Technology, 2018, 52(7): 4422-4431. |
| [36] | SHAIK S, COHEN S, WANG Y, et al. P450 enzymes: Their structure, reactivity, and selectivity-Modeled by QM/MM calculations [J]. Chemical Reviews, 2010, 110(2): 949-1017. doi: 10.1021/cr900121s |
| [37] | GUIDEZ E B, GORDON M S. Dispersion correction derived from first principles for density functional theory and Hartree-Fock theory [J]. The Journal of Physical Chemistry A, 2015, 119(10): 2161-2168. doi: 10.1021/acs.jpca.5b00379 |
| [38] | GRIMME S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction [J]. Journal of Computational Chemistry, 2006, 27(15): 1787-1799. doi: 10.1002/jcc.20495 |
| [39] | RILEY K E, VONDRÁŠEK J, HOBZA P. Performance of the DFT-D method, paired with the PCM implicit solvation model, for the computation of interaction energies of solvated complexes of biological interest [J]. Physical Chemistry Chemical Physics, 2007, 9(41): 5555-5560. doi: 10.1039/b708089a |
| [40] | WANG M S, MO F, LI H B, et al. Adsorption based on weak interaction between phenolic hydroxyl, carboxyl groups and silver nanoparticles in aqueous environment: Experimental and DFT-D3 exploration [J]. Journal of Environmental Chemical Engineering, 2021, 9(6): 106816. doi: 10.1016/j.jece.2021.106816 |
| [41] | LAIDLER K J, KING M C. Development of transition-state theory [J]. The Journal of Physical Chemistry, 1983, 87(15): 2657-2664. doi: 10.1021/j100238a002 |
| [42] | MARCUS R A. Electron transfer reactions in chemistry: Theory and experiment (Nobel lecture) [J]. Angewandte Chemie International Edition in English, 1993, 32(8): 1111-1121. doi: 10.1002/anie.199311113 |
| [43] | JI L, ZHANG J, LIU W P, et al. Metabolism of halogenated alkanes by cytochrome P450 enzymes. Aerobic oxidation versus anaerobic reduction [J]. Chemistry - An Asian Journal, 2014, 9(4): 1175-1182. doi: 10.1002/asia.201301608 |
| [44] | JI L, WANG C C, JI S J, et al. Mechanism of cobalamin-mediated reductive dehalogenation of chloroethylenes [J]. ACS Catalysis, 2017, 7(8): 5294-5307. doi: 10.1021/acscatal.7b00540 |
| [45] | HIMO F. Recent trends in quantum chemical modeling of enzymatic reactions [J]. Journal of the American Chemical Society, 2017, 139(20): 6780-6786. doi: 10.1021/jacs.7b02671 |
| [46] | DENISOV I G, MAKRIS T M, SLIGAR S G, et al. Structure and chemistry of cytochrome P450 [J]. Chemical Reviews, 2005, 105(6): 2253-2278. doi: 10.1021/cr0307143 |
| [47] | VÖLKEL W, COLNOT T, CSANÁDY G A, et al. Metabolism and kinetics of bisphenol A in humans at low doses following oral administration [J]. Chemical Research in Toxicology, 2002, 15(10): 1281-1287. doi: 10.1021/tx025548t |
| [48] | HANIOKA N, NAITO T, NARIMATSU S. Human UDP-glucuronosyltransferase isoforms involved in bisphenol A glucuronidation [J]. Chemosphere, 2008, 74(1): 33-36. doi: 10.1016/j.chemosphere.2008.09.053 |
| [49] | GRAMEC SKLEDAR D, TROBERG J, LAVDAS J, et al. Differences in the glucuronidation of bisphenols F and S between two homologous human UGT enzymes, 1A9 and 1A10 [J]. Xenobiotica, 2015, 45(6): 511-519. doi: 10.3109/00498254.2014.999140 |
| [50] | STREET C M, ZHU Z H, FINEL M, et al. Bisphenol-A glucuronidation in human liver and breast: Identification of UDP-glucuronosyltransferases (UGTs) and influence of genetic polymorphisms [J]. Xenobiotica, 2017, 47(1): 1-10. doi: 10.3109/00498254.2016.1156784 |
| [51] | YE X Y, KUKLENYIK Z, NEEDHAM L L, et al. Quantification of urinary conjugates of bisphenol A, 2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry [J]. Analytical and Bioanalytical Chemistry, 2005, 383(4): 638-644. doi: 10.1007/s00216-005-0019-4 |
| [52] | SUIKO M, SAKAKIBARA Y, LIU M C. Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases [J]. Biochemical and Biophysical Research Communications, 2000, 267(1): 80-84. doi: 10.1006/bbrc.1999.1935 |
| [53] | NISHIYAMA T, OGURA K, NAKANO H, et al. Sulfation of environmental estrogens by cytosolic human sulfotransferases [J]. Drug Metabolism and Pharmacokinetics, 2002, 17(3): 221-228. doi: 10.2133/dmpk.17.221 |
| [54] | YE X Y, ZHOU X L, NEEDHAM L L, et al. In-vitro oxidation of bisphenol A: Is bisphenol A catechol a suitable biomarker for human exposure to bisphenol A? [J]. Analytical and Bioanalytical Chemistry, 2011, 399(3): 1071-1079. doi: 10.1007/s00216-010-4344-x |
| [55] | ZALKO D, SOTO A M, DOLO L, et al. Biotransformations of bisphenol A in a mammalian model: Answers and new questions raised by low-dose metabolic fate studies in pregnant CD1 mice [J]. Environmental Health Perspectives, 2003, 111(3): 309-319. doi: 10.1289/ehp.5603 |
| [56] | KNAAK J B, SULLIVAN L J. Metabolism of bisphenol A in the rat [J]. Toxicology and Applied Pharmacology, 1966, 8(2): 175-184. doi: 10.1016/S0041-008X(66)80001-7 |
| [57] | ATKINSON A, ROY D. In vivo DNA adduct formation by bisphenol A [J]. Environmental and Molecular Mutagenesis, 1995, 26(1): 60-66. doi: 10.1002/em.2850260109 |
| [58] | JAEG J P, PERDU E, DOLO L, et al. Characterization of new bisphenol A metabolites produced by CD1 mice liver microsomes and S9 fractions [J]. Journal of Agricultural and Food Chemistry, 2004, 52(15): 4935-4942. doi: 10.1021/jf049762u |
| [59] | OKUDA K, FUKUUCHI T, TAKIGUCHI M, et al. Novel pathway of metabolic activation of bisphenol A-related compounds for estrogenic activity [J]. Drug Metabolism and Disposition, 2011, 39(9): 1696-1703. doi: 10.1124/dmd.111.040121 |
| [60] | SCHMIDT J, KOTNIK P, TRONTELJ J, et al. Bioactivation of bisphenol A and its analogs (BPF, BPAF, BPZ and DMBPA) in human liver microsomes [J]. Toxicology in Vitro, 2013, 27(4): 1267-1276. doi: 10.1016/j.tiv.2013.02.016 |
| [61] | NAKAMURA S, TEZUKA Y, USHIYAMA A, et al. Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity [J]. Toxicology Letters, 2011, 203(1): 92-95. doi: 10.1016/j.toxlet.2011.03.010 |
| [62] | YOSHIHARA S, MIZUTARE T, MAKISHIMA M, et al. Potent estrogenic metabolites of bisphenol A and bisphenol B formed by rat liver S9 fraction: Their structures and estrogenic potency [J]. Toxicological Sciences, 2004, 78(1): 50-59. doi: 10.1093/toxsci/kfh047 |
| [63] | SKLEDAR D G, SCHMIDT J, FIC A, et al. Influence of metabolism on endocrine activities of bisphenol S [J]. Chemosphere, 2016, 157: 152-159. doi: 10.1016/j.chemosphere.2016.05.027 |
| [64] | ASHRAP P, ZHENG G M, WAN Y, et al. Discovery of a widespread metabolic pathway within and among phenolic xenobiotics [J]. Proceedings of the National Academy of Sciences of the United States of America, 2017, 114(23): 6062-6067. doi: 10.1073/pnas.1700558114 |
| [65] | LIU L, CUI H Y, HUANG Y X, et al. Enzyme-mediated reactions of phenolic pollutants and endogenous metabolites as an overlooked metabolic disruption pathway [J]. Environmental Science & Technology, 2022, 56(6): 3634-3644. |
| [66] | SHAIK S, KUMAR D, DE VISSER S P, et al. Theoretical perspective on the structure and mechanism of cytochrome P450 enzymes [J]. Chemical Reviews, 2005, 105(6): 2279-2328. doi: 10.1021/cr030722j |
| [67] | ASAKA M, FUJII H. Participation of electron transfer process in rate-limiting step of aromatic hydroxylation reactions by compound I models of heme enzymes [J]. Journal of the American Chemical Society, 2016, 138(26): 8048-8051. doi: 10.1021/jacs.6b03223 |
| [68] | CANTÚ REINHARD F G, SAINNA M A, UPADHYAY P, et al. A systematic account on aromatic hydroxylation by a cytochrome P450 model Compound Ⅰ: A low-pressure mass spectrometry and computational study [J]. Chemistry - A European Journal, 2016, 22(51): 18608-18619. doi: 10.1002/chem.201604361 |
| [69] | SHAIK S, FILATOV M, SCHRÖDER D, et al. Electronic structure makes a difference: Cytochrome P-450 mediated hydroxylations of hydrocarbons as a two-state reactivity paradigm [J]. Chemistry - A European Journal, 1998, 4(2): 193-199. doi: 10.1002/(SICI)1521-3765(19980210)4:2<193::AID-CHEM193>3.0.CO;2-Q |
| [70] | DIAS A H S, YADAV R, MOKKAWES T, et al. Biotransformation of bisphenol by human cytochrome P450 2C9 enzymes: A density functional theory study [J]. Inorganic Chemistry, 2023, 62(5): 2244-2256. doi: 10.1021/acs.inorgchem.2c03984 |
| [71] | DE VISSER S P, SHAIK S. A proton-shuttle mechanism mediated by the porphyrin in benzene hydroxylation by cytochrome P450 enzymes [J]. Journal of the American Chemical Society, 2003, 125(24): 7413-7424. doi: 10.1021/ja034142f |
| [72] | DE VISSER S P, OGLIARO F, SHARMA P K, et al. What factors affect the regioselectivity of oxidation by cytochrome P450? A DFT study of allylic hydroxylation and double bond epoxidation in a model reaction [J]. Journal of the American Chemical Society, 2002, 124(39): 11809-11826. doi: 10.1021/ja026872d |
| [73] | YADAV R, AWASTHI N, KUMAR D. Biotransformation of BPA via epoxidation catalyzed by Cytochrome P450 [J]. Inorganic Chemistry Communications, 2022, 139: 109321. doi: 10.1016/j.inoche.2022.109321 |
| [74] | GUO F J, CHAI L H, ZHANG S B, et al. Computational biotransformation profile of emerging phenolic pollutants by cytochromes P450: Phenol-coupling mechanism [J]. Environmental Science & Technology, 2020, 54(5): 2902-2912. |
| [75] | RIU A, LE MAIRE A, GRIMALDI M, et al. Characterization of novel ligands of ERα, Erβ, and PPARγ: The case of halogenated bisphenol A and their conjugated metabolites [J]. Toxicological Sciences, 2011, 122(2): 372-382. doi: 10.1093/toxsci/kfr132 |
| [76] | FIC A, ŽEGURA B, SOLLNER DOLENC M, et al. Mutagenicity and DNA damage of bisphenol A and its structural analogues in HepG2 cells [J]. Archives of Industrial Hygiene and Toxicology, 2013, 64(2): 189-200. doi: 10.2478/10004-1254-64-2013-2319 |