{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T01:34:03Z","timestamp":1778808843724,"version":"3.51.4"},"reference-count":80,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2024,12,11]],"date-time":"2024-12-11T00:00:00Z","timestamp":1733875200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005888","name":"Medical University of Lodz","doi-asserted-by":"publisher","award":["503\/3-016-03\/503-31-001"],"award-info":[{"award-number":["503\/3-016-03\/503-31-001"]}],"id":[{"id":"10.13039\/501100005888","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>One of the functions of placenta is to protect the fetus against harmful xenobiotics. Protective mechanisms of placenta are based on enzymes, e.g., antioxidant enzymes from the glutathione S-transferases group (GST) or human N-acetyltransferase 2 (NAT2). Many organic sunscreens are known to cross biological barriers\u2014they are detected in mother\u2019s milk, semen, umbilical cord blood or placental tissues. Some organic sunscreens are able to cross the placenta and to interfere with fetal development; they are known or suspected endocrine disruptors or neurotoxins. In this study, 16 organic sunscreens were investigated in the context of their placenta permeability and interactions with gluthatione S-transferase and human N-acetyltransferase 2 enzymes present in the human placenta. Binary permeability models based on discriminant analysis and artificial neural networks proved that the majority of studied compounds are likely to cross the placenta by passive diffusion. Molecular docking analysis suggested that some sunscreens show stronger affinity for glutathione S-transferase and human N-acetyltransferase 2 that native ligands (glutathione and Coenzyme A for GST and NAT2, respectively)\u2014it is therefore possible that they are able to reduce the enzyme\u2019s protective activity. It was established that sunscreens bind to the studied enzymes mainly by alkyl, hydrogen bonds, van der Waals, \u03c0-\u03c0, \u03c0-alkyl and \u03c0-sulfur interactions. To conclude, sunscreens may become stressors affecting humans by different mechanisms and at different stages of development.<\/jats:p>","DOI":"10.3390\/molecules29245836","type":"journal-article","created":{"date-parts":[[2024,12,11]],"date-time":"2024-12-11T03:14:58Z","timestamp":1733886898000},"page":"5836","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Organic Sunscreens\u2014Is Their Placenta Permeability the Only Issue Associated with Exposure During Pregnancy? In Silico Studies of Sunscreens\u2019 Placenta Permeability and Interactions with Selected Placental Enzymes"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1846-9240","authenticated-orcid":false,"given":"Anna W.","family":"Soba\u0144ska","sequence":"first","affiliation":[{"name":"Department of Analytical Chemistry, Medical University of Lodz, Muszy\u0144skiego 1, 90-151 Lodz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrzej M.","family":"Soba\u0144ski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.watres.2014.09.013","article-title":"Occurrence, distribution and ecological risk assessment of multiple classes of UV filters in surface waters from different countries","volume":"67","author":"Tsui","year":"2014","journal-title":"Water Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"708","DOI":"10.1016\/j.trac.2009.03.010","article-title":"Chemical analysis and ecotoxicological effects of organic UV-absorbing compounds in aquatic ecosystems","volume":"28","year":"2009","journal-title":"TrAC\u2014Trends Anal. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.chemosphere.2013.10.053","article-title":"Ecotoxicological evaluation of four UV filters using marine organisms from different trophic levels Isochrysis galbana, Mytilus galloprovincialis, Paracentrotus lividus, and Siriella armata","volume":"104","author":"Paredes","year":"2014","journal-title":"Chemosphere"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5619","DOI":"10.1021\/es400675y","article-title":"First determination of UV filters in marine mammals. Octocrylene levels in Franciscana dolphins","volume":"47","author":"Alonso","year":"2013","journal-title":"Environ. Sci. Technol."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Soba\u0144ska, A.W. (2021). Evaluation of drug-likeness and ADME properties of sunscreens and preservatives using reversed-phase thin layer chromatographic retention data and calculated descriptors. J. Pharm. Biomed. Anal., 201.","DOI":"10.1016\/j.jpba.2021.114126"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"142486","DOI":"10.1016\/j.scitotenv.2020.142486","article-title":"Risks of organic UV filters: A review of environmental and human health concern studies","volume":"755","author":"Huang","year":"2021","journal-title":"Sci. Total Environ."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1007\/s00216-010-3947-6","article-title":"Solid-phase extraction liquid chromatography-tandem mass spectrometry analytical method for the determination of 2-hydroxy-4-methoxybenzophenone and its metabolites in both human urine and semen","volume":"398","author":"Chisvert","year":"2010","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1016\/j.chemosphere.2010.09.079","article-title":"Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: Correlation of UV filters with use of cosmetics","volume":"81","author":"Schlumpf","year":"2010","journal-title":"Chemosphere"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"101307","DOI":"10.1016\/j.mex.2021.101307","article-title":"Development of a sensitive analytical method for the simultaneous analysis of Benzophenone-type UV filters and paraben preservatives in umbilical cord blood","volume":"8","author":"Peiro","year":"2021","journal-title":"MethodsX"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"107834","DOI":"10.1016\/j.envint.2023.107834","article-title":"Target analysis and suspect screening of UV filters, parabens and other chemicals used in personal care products in human cord blood: Prenatal exposure by mother-fetus transfer","volume":"173","year":"2023","journal-title":"Environ. Int."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"80","DOI":"10.1016\/j.jchromb.2013.08.006","article-title":"Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS\/MS. Assessment of their in vitro endocrine activity","volume":"936","author":"Ballesteros","year":"2013","journal-title":"J. Chromatogr. B Anal. Technol. Biomed. Life Sci."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1111\/j.1365-4632.2008.03957.x","article-title":"Photoallergic contact dermatitis caused by ultraviolet filters in different sunscreens","volume":"47","author":"Collaris","year":"2008","journal-title":"Int. J. Dermatol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1615\/JEnvironPatholToxicolOncol.2020033188","article-title":"Safety Concerns of Organic Ultraviolet Filters: Special Focus on Endocrine-Disrupting Properties","volume":"39","author":"Oral","year":"2020","journal-title":"J. Environ. Pathol. Toxicol. Oncol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2833","DOI":"10.1002\/etc.3129","article-title":"Endocrine-disrupting effect of the ultraviolet filter benzophenone-3 in zebrafish, Danio rerio","volume":"34","author":"Kinnberg","year":"2015","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"128495","DOI":"10.1016\/j.jhazmat.2022.128495","article-title":"Structure-related endocrine-disrupting potential of environmental transformation products of benzophenone-type UV filters: A review","volume":"430","author":"Carstensen","year":"2022","journal-title":"J. Hazard. Mater."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.taap.2014.12.002","article-title":"Metabolism of UV-filter benzophenone-3 by rat and human liver microsomes and its effect on endocrine-disrupting activity","volume":"282","author":"Watanabe","year":"2015","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1007\/s10304-016-0086-y","article-title":"UV filters and the endocrine system","volume":"14","author":"Birkhauser","year":"2016","journal-title":"Gynakol. Endokrinol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1007\/s11154-016-9329-4","article-title":"Cosmetics as endocrine disruptors: Are they a health risk?","volume":"16","author":"Hens","year":"2015","journal-title":"Rev. Endocr. Metab. Disord."},{"key":"ref_19","first-page":"32","article-title":"Sun lotion chemicals as endocrine disruptors","volume":"14","author":"Maipas","year":"2015","journal-title":"Horm.-Int. J. Endocrinol. Metab."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Wang, J., Pan, L., Wu, S., Lu, L., Xu, Y., Zhu, Y., Guo, M., and Zhuang, S. (2016). Recent Advances on Endocrine Disrupting Effects of UV Filters. Int. J. Environ. Res. Public Health, 13.","DOI":"10.3390\/ijerph13080782"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"345","DOI":"10.2533\/chimia.2008.345","article-title":"Endocrine active UV filters: Developmental toxicity and exposure through breast milk","volume":"62","author":"Schlumpf","year":"2008","journal-title":"Chimia"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.tox.2004.06.043","article-title":"Endocrine activity and developmental toxicity of cosmetic UV filters\u2014An update","volume":"205","author":"Schlumpf","year":"2004","journal-title":"Toxicology"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1016\/j.steroids.2018.01.006","article-title":"Photoprotection of ultraviolet-B filters: Updated review of endocrine disrupting properties","volume":"131","author":"Lorigo","year":"2018","journal-title":"Steroids"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Passamani, F., Santos, B.A.M.C., and Gon\u00e7alves, A.S. (2023). Endocrine disruption study of active sunscreens\u2019s compounds by docking and molecular dynamics simulations. Preprint.","DOI":"10.21203\/rs.3.rs-3254244\/v1"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1111\/j.1365-2605.2012.01280.x","article-title":"Sunscreens: Are they beneficial for health? An overview of endocrine disrupting properties of UV-filters","volume":"35","author":"Krause","year":"2012","journal-title":"Int. J. Androl."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"940","DOI":"10.1002\/ieam.4449","article-title":"Occurrence of major organic UV filters in aquatic environments and their endocrine disruption potentials: A mini-review","volume":"17","author":"Kwon","year":"2021","journal-title":"Integr. Environ. Assess. Manag."},{"key":"ref_27","first-page":"240","article-title":"Ultraviolet filters differentially impact the expression of key endocrine and stress genes in embryos and larvae of Chironomus riparius","volume":"557","author":"Morcillo","year":"2016","journal-title":"Sci. Total Environ."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1016\/j.aquatox.2014.07.004","article-title":"Effects of benzophenone-3 exposure on endocrine disruption and reproduction of Japanese medaka (Oryzias latipes)\u2014A two generation exposure study","volume":"155","author":"Kim","year":"2014","journal-title":"Aquat. Toxicol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"948","DOI":"10.1007\/s10646-022-02555-1","article-title":"Waterborne exposure to avobenzone and octinoxate induces thyroid endocrine disruption in wild-type and thr alphaa\u2212\/\u2212 zebrafish larvae","volume":"31","author":"Ka","year":"2022","journal-title":"Ecotoxicology"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.neuro.2008.12.008","article-title":"Female sexual behavior, estrous cycle and gene expression in sexually dimorphic brain regions after pre- and postnatal exposure to endocrine active UV filters","volume":"30","author":"Faass","year":"2009","journal-title":"Neurotoxicology"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1189","DOI":"10.1016\/j.bcp.2009.12.005","article-title":"The UV-filter benzophenone-1 inhibits 17\u03b2-hydroxysteroid dehydrogenase type 3: Virtual screening as a strategy to identify potential endocrine disrupting chemicals","volume":"79","author":"Nashev","year":"2010","journal-title":"Biochem. Pharmacol."},{"key":"ref_32","first-page":"120","article-title":"Effects of in vivo exposure to UV filters (4-MBC, OMC, BP-3, 4-HB, OC, OD-PABA) on endocrine signaling genes in the insect Chironomus riparius","volume":"456","author":"Morcillo","year":"2013","journal-title":"Sci. Total Environ."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"334","DOI":"10.1530\/EC-17-0375","article-title":"Maternal exposure to UV filters: Associations with maternal thyroid hormones, IGF-I\/IGFBP3 and birth outcomes","volume":"7","author":"Krause","year":"2018","journal-title":"Endocr. Connect."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1530\/EC-17-0156","article-title":"EDC IMPACT: Chemical UV filters can affect human sperm function in a progesterone-like manner","volume":"7","author":"Rehfeld","year":"2018","journal-title":"Endocr. Connect."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1210\/js.2018-00024","article-title":"Oxybenzone Alters Mammary Gland Morphology in Mice Exposed During Pregnancy and Lactation","volume":"2","author":"LaPlante","year":"2018","journal-title":"J. Endocr. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.toxrep.2017.05.006","article-title":"Neurotoxic effect of active ingredients in sunscreen products, a contemporary review","volume":"4","author":"Ruszkiewicz","year":"2017","journal-title":"Toxicol. Rep."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/j.marenvres.2004.03.027","article-title":"Assessment of hormonal activity of UV filters in tadpoles of frog Xenopus laevis at environmental concentrations","volume":"58","author":"Kunz","year":"2004","journal-title":"Mar. Environ. Res."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1093\/toxsci\/kfj082","article-title":"Comparison of in vitro and in vivo estrogenic activity of UV filters in fish","volume":"90","author":"Kunz","year":"2006","journal-title":"Toxicol. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/j.taap.2007.08.004","article-title":"Effects of the UV filter benzophenone-2 on reproduction in fish","volume":"225","author":"Weisbrod","year":"2007","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"325","DOI":"10.2533\/000942904777677795","article-title":"Chemical analysis and ecotoxicological effects of UV absorbing organic chemicals in aquatic environments","volume":"58","author":"Fent","year":"2004","journal-title":"Chimia"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1080\/17512433.2020.1733412","article-title":"The role of xenobiotic-metabolizing enzymes in the placenta: A growing research field","volume":"13","author":"Souto","year":"2020","journal-title":"Expert. Rev. Clin. Pharmacol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"100274","DOI":"10.1016\/j.comtox.2023.100274","article-title":"Forever chemicals could expose the human fetus to xenobiotics by binding to placental enzymes: Prescience from molecular docking, DFT, and machine learning","volume":"26","author":"Duru","year":"2023","journal-title":"Comput. Toxicol."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"130600","DOI":"10.1016\/j.jhazmat.2022.130600","article-title":"Evaluation of nanoplastics toxicity to the human placenta in systems","volume":"446","author":"Enyoh","year":"2023","journal-title":"J. Hazard. Mater."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Soba\u0144ska, A.W., Banerjee, A., and Roy, K. (2024). Organic Sunscreens and Their Products of Degradation in Biotic and Abiotic Conditions\u2014In Silico Studies of Drug-Likeness and Human Placental Transport. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms252212373"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Pirotta, G. (2020). Sunscreen Regulation in the World, Springer.","DOI":"10.1007\/698_2019_440"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Mazari, A.M.A., Zhang, L., Ye, Z.-W., Zhang, J., Tew, K.D., and Townsend, D.M. (2023). The Multifaceted Role of Glutathione S-Transferases in Health and Disease. Biomolecules, 13.","DOI":"10.3390\/biom13040688"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2705","DOI":"10.1111\/bph.12598","article-title":"Arylamine N-acetyltransferases: From drug metabolism and pharmacogenetics to drug discovery","volume":"171","author":"Sim","year":"2014","journal-title":"Br. J. Pharmacol."},{"key":"ref_48","unstructured":"(2011). Neural Network Architecture. Encyclopedia of Machine Learning, Springer Science & Business Media."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Miikkulainen, R. (2011). Topology of a Neural Network. Encyclopedia of Machine Learning, Springer.","DOI":"10.1007\/978-0-387-30164-8_837"},{"key":"ref_50","first-page":"86","article-title":"Creativity of Neural Networks","volume":"Volume 4029","author":"Czeczot","year":"2006","journal-title":"Lecture Notes in Computer Science (Including Subseries Lecture Notes in Artificial Intelligence and Lecture Notes in Bioinformatics)"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1021\/ci00028a014","article-title":"Electrotopological State Indices for Atom Types: A Novel Combination of Electronic, Topological, and Valence State Information","volume":"35","author":"Hall","year":"1995","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1074","DOI":"10.1021\/ci00028a019","article-title":"Molecular Similarity Based on Novel Atom-Type Electrotopological State Indices","volume":"35","author":"Hall","year":"1995","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1517\/13543776.16.4.431","article-title":"Glutathione S-transferase (GST) inhibitors","volume":"16","author":"Mathew","year":"2006","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/S0169-409X(97)00029-X","article-title":"Inhibitors of glutathione S-transferases as therapeutic agents","volume":"26","author":"Schultz","year":"1997","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"20230159","DOI":"10.1515\/chem-2023-0159","article-title":"Some anticancer agents as effective glutathione S-transferase (GST) inhibitors","volume":"21","year":"2023","journal-title":"Open Chem."},{"key":"ref_56","first-page":"308","article-title":"Antibiotics as Inhibitor of Glutathione S-transferase: Biological Evaluation and Molecular Structure Studies","volume":"22","author":"Ayna","year":"2021","journal-title":"Curr. Drug Metab."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Alqarni, M.H., Foudah, A.I., Muharram, M.M., Alam, A., and Labrou, N.E. (2022). Myricetin as a Potential Adjuvant in Chemotherapy: Studies on the Inhibition of Human Glutathione Transferase A1\u20131. Biomolecules, 12.","DOI":"10.3390\/biom12101364"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"601","DOI":"10.21608\/ejchem.2024.325338.10562","article-title":"Dual Action of Resveratrol: Inhibition of Human Glutathione Transferase and its Antagonism with Tamoxifen on Breast Cancer Cell Viability","volume":"67","author":"Shokeer","year":"2024","journal-title":"Egypt. J. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Kobzar, O., Shulha, Y., Buldenko, V., Cherenok, S., and Silenko, O. (2022). Inhibition of glutathione S-transferases by photoactive calix[4]arene \u03b1-ketophosphonic acids. Bioorganic Med. Chem. Lett., 77.","DOI":"10.1016\/j.bmcl.2022.129019"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1021\/js9803205","article-title":"MDCK (Madin-Darby canine kidney) cells: A tool for membrane permeability screening","volume":"88","author":"Irvine","year":"1999","journal-title":"J. Pharm. Sci."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1098\/rsif.2009.0170","article-title":"Prospective virtual screening with ultrafast shape recognition: The identification of novel inhibitors of arylamine N-acetyltransferases","volume":"7","author":"Ballester","year":"2010","journal-title":"J. R. Soc. Interface"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1097\/00008571-199812000-00012","article-title":"Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo","volume":"8","author":"Rothen","year":"1998","journal-title":"Pharmacogenetics"},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Abuhammad, A., Fullam, E., Lowe, E.D., Staunton, D., Kawamura, A., Westwood, I.M., Bhakta, S., Garner, A.C., Wilson, D.L., and Seden, P.T. (2012). Piperidinols That Show Anti-Tubercular Activity as Inhibitors of Arylamine N-Acetyltransferase: An Essential Enzyme for Mycobacterial Survival Inside Macrophages. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0052790"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1080\/00498250500489901","article-title":"Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2","volume":"36","author":"Kukongviriyapan","year":"2006","journal-title":"Xenobiotica"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1","DOI":"10.4236\/cmb.2017.71001","article-title":"Molecular Docking and ADMET Study of Emodin Derivatives as Anticancer Inhibitors of NAT2, COX2 and TOP1 Enzymes","volume":"7","author":"Shadrack","year":"2017","journal-title":"Comput. Mol. Biosci."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"e9562","DOI":"10.7717\/peerj.9562","article-title":"Prediction of human fetal-maternal blood concentration ratio of chemicals","volume":"8","author":"Wang","year":"2020","journal-title":"PeerJ"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"138649","DOI":"10.1016\/j.chemosphere.2023.138649","article-title":"In silico assessment of risks associated with pesticides exposure during pregnancy","volume":"329","year":"2023","journal-title":"Chemosphere"},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Daina, A., Michielin, O., and Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep., 7.","DOI":"10.1038\/srep42717"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1186\/s13321-018-0258-y","article-title":"Mordred: A molecular descriptor calculator","volume":"10","author":"Moriwaki","year":"2018","journal-title":"J. Cheminform."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1007\/s10822-011-9440-2","article-title":"Online chemical modeling environment (OCHEM): Web platform for data storage, model development and publishing of chemical information","volume":"25","author":"Sushko","year":"2011","journal-title":"J. Comput. Aided Mol. Des."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"e3226","DOI":"10.1002\/cem.3226","article-title":"Comparison of variable selection methods in partial least squares regression","volume":"34","author":"Mehmood","year":"2020","journal-title":"J. Chemom."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1007\/978-1-4939-2269-7_19","article-title":"Small-Molecule Library Screening by Docking with PyRx","volume":"1263","author":"Dallakyan","year":"2015","journal-title":"Methods Mol. Biol."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1007\/978-1-62703-059-5_21","article-title":"On the development and validation of QSAR models","volume":"930","author":"Gramatica","year":"2013","journal-title":"Methods Mol. Biol."},{"key":"ref_74","doi-asserted-by":"crossref","unstructured":"Marie, C., Cabut, S., Vendittelli, F., and Sauvant-Rochat, M.P. (2016). Changes in cosmetics use during pregnancy and risk perception by women. Int. J. Environ. Res. Public Health, 13.","DOI":"10.3390\/ijerph13040383"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"e018","DOI":"10.1097\/JW9.0000000000000018","article-title":"Assessing public interest in sunscreen safety during pregnancy and lactation","volume":"8","author":"Shareef","year":"2022","journal-title":"Int. J. Womens Dermatol."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"140271","DOI":"10.1016\/j.chemosphere.2023.140271","article-title":"Single and mixture toxicity evaluation of avobenzone and homosalate to male zebrafish and H295R cells","volume":"343","author":"Lee","year":"2023","journal-title":"Chemosphere"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"26","DOI":"10.5114\/ada.2022.113617","article-title":"Benzophenone-3, a chemical UV-filter in cosmetics: Is it really safe for children and pregnant women?","volume":"39","author":"Wnuk","year":"2022","journal-title":"Post\u0119py Dermatol. Alergol."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1055\/s-0028-1112153","article-title":"Impact of 4-methylbenzylidene-camphor (4-MBC) during embryonic and fetal development in the neuroendocrine regulation of testicular axis in prepubertal and peripubertal male rats","volume":"117","author":"Carou","year":"2009","journal-title":"Exp. Clin. Endocrinol. Diabetes"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1016\/j.reprotox.2019.02.014","article-title":"Can oxybenzone cause Hirschsprung\u2019s disease?","volume":"86","author":"DiNardo","year":"2019","journal-title":"Reprod. Toxicol."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1016\/j.chemosphere.2015.09.019","article-title":"The relationship between prenatal exposure to BP-3 and Hirschsprung\u2019s disease","volume":"144","author":"Huo","year":"2016","journal-title":"Chemosphere"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/24\/5836\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:52:04Z","timestamp":1760115124000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/24\/5836"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,12,11]]},"references-count":80,"journal-issue":{"issue":"24","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["molecules29245836"],"URL":"https:\/\/doi.org\/10.3390\/molecules29245836","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,12,11]]}}}