An in silico investigation of the toxicological effects and biological activities of 3-phenoxybenzoic acid and its metabolite products

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 1-2, 19-25. doi: 10.1016/j.softx.2015.06.001.
   Google Scholar
• Agu, P.C., Afiukwa, C.A., Orji, O.U., Ezeh, E.M., Ofoke, I.H., Ogbu, C.O., Ugwuja, E.I., Aja, P.M., 2023. Molecular docking as a tool for the discovery of molecular targets of nutraceuticals in diseases management. Sci. Rep. 13(1), 13398. doi: 10.1038/s41598-023-40160-2.
   Google Scholar
• Ahamad, A., Kumar, J., 2023. Pyrethroid pesticides: An overview on classification, toxicological assessment and monitoring. Journal of Hazardous Materials Advances 10, 100284. doi: 10.1016/j.hazadv.2023.100284.
   Google Scholar
• Akter, N., Bourougaa, L., Ouassaf, M., Bhowmic, R.C., Uddin, K.M., Bhat, A.R., Ahmed, S., Kawsar, S.M.A., 2024. Molecular docking, ADME-Tox, DFT and molecular dynamics simulation of butyroyl glucopyranoside derivatives against DNA gyrase inhibitors as antimicrobial agents. J. Mol. Struct. 1307, 137930. doi: 10.1016/j.molstruc.2024.137930.
   Google Scholar
• Amin, M.R., Yasmin, F., Dey, S., Mahmud, S., Saleh, M.A., Emran, T.B., Hasan, I., Rajia, S., Ogawa, Y., Fujii, Y., Yamada, M., Ozeki, Y., Kawsar, S.M.A., 2022. Methyl β-D-galactopyranoside esters as potential inhibitors for SARS-CoV-2 protease enzyme: synthesis, antimicrobial, PASS, molecular docking, molecular dynamics simulations and quantum computations. Glycoconj. J. 39(2), 261-290. doi: 10.1007/s10719-021-10039-3.
   Google Scholar
• Amin, M.R., Yasmin, F., Hosen, M.A., Dey, S., Mahmud, S., Saleh, M.A., Emran, T.B., Hasan, I., Fujii, Y., Yamada, M., Ozeki, Y., Kawsar, S.M.A., 2021. Synthesis, Antimicrobial, Anticancer, PASS, Molecular Docking, Molecular Dynamic Simulations & Pharmacokinetic Predictions of Some Methyl β-D-Galactopyranoside Analogs. Molecules 26(22). doi: 10.3390/molecules26227016.
   Google Scholar
• Anowar Hosen, M., Sultana Munia, N., Al-Ghorbani, M., Baashen, M., Almalki, F.A., Ben Hadda, T., Ali, F., Mahmud, S., Abu Saleh, M., Laaroussi, H., Kawsar, S.M.A., 2022. Synthesis, antimicrobial, molecular docking and molecular dynamics studies of lauroyl thymidine analogs against SARS-CoV-2: POM study and identification of the pharmacophore sites. Bioorg. Chem. 125, 105850. doi: 10.1016/j.bioorg.2022.105850.
   Google Scholar
• Aylward, L.L., Irwin, K., St-Amand, A., Nong, A., Hays, S.M.J.R.T., Pharmacology, 2018. Screening-level biomonitoring equivalents for tiered interpretation of urinary 3-phenoxybenzoic acid (3-PBA) in a risk assessment context. 92, 29-38
   Google Scholar
• Barr, D.B., Olsson, A.O., Wong, L.Y., Udunka, S., Baker, S.E., Whitehead, R.D., Magsumbol, M.S., Williams, B.L., Needham, L.L., 2010. Urinary concentrations of metabolites of pyrethroid insecticides in the general U.S. population: National Health and Nutrition Examination Survey 1999-2002. Environ. Health Perspect. 118(6), 742-748. doi: 10.1289/ehp.0901275.
   Google Scholar
• Baskin, I.I., 2018 Machine learning methods in computational toxicology, Computational Toxicology. Springer, pp. 119-139.
   Google Scholar
• Bin Deng, Z.Z., Jialing Zheng,Wanlin Yang,Yu Huang,Yuqi Luo,Dana Jin,Lu Shen,Kunlin Jin,Qing Wang, FTD-PSP is an Unusual Clinical Phenotype in A Frontotemporal Dementia Patient with A Novel Progranulin Mutation. 0-. doi: 10.14336/ad.2021.0309.
   Google Scholar
• Bussi, G., Donadio, D., Parrinello, M., 2007. Canonical sampling through velocity rescaling. J. Chem. Phys. 126(1), 014101. doi: 10.1063/1.2408420.
   Google Scholar
• Choi, Y.H., Lee, J.Y., Huh, D.A., Moon, K.W., 2022. Urinary 3-phenoxybenzoic acid (3-PBA) levels and changes in hematological parameters in Korean adult population: A Korean National Environmental Health Survey (KoNEHS) 2012-2014 analysis. Int. J. Hyg. Environ. Health 243, 113988. doi: 10.1016/j.ijheh.2022.113988.
   Google Scholar
• Croom, E.J.P.i.m.b., science, t., 2012. Metabolism of xenobiotics of human environments. 112, 31-88
   Google Scholar
• Daina, A., Michielin, O., Zoete, V., 2017. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep. 7(1), 42717. doi: 10.1038/srep42717.
   Google Scholar
• de Bruyn Kops, C., Šícho, M., Mazzolari, A., Kirchmair, J., 2021. GLORYx: Prediction of the Metabolites Resulting from Phase 1 and Phase 2 Biotransformations of Xenobiotics. Chem. Res. Toxicol. 34(2), 286-299. doi: 10.1021/acs.chemrestox.0c00224.
   Google Scholar
• EFSA, 2024 Scientific opinion on toxicity of pyrethroid common metabolites. Available at: https://www.efsa.europa.eu/en/efsajournal/pub/7582. (Accessed Accessed on April 6th, 2024.
   Google Scholar
• Esteves, F., Rueff, J., Kranendonk, M., 2021. The Central Role of Cytochrome P450 in Xenobiotic Metabolism-A Brief Review on a Fascinating Enzyme Family. Journal of xenobiotics 11(3), 94-114. doi: 10.3390/jox11030007.
   Google Scholar
• Favaloro, B., Allocati, N., Graziano, V., Di Ilio, C., De Laurenzi, V., 2012. Role of apoptosis in disease. Aging (Albany N. Y.) 4(5), 330-349. doi: 10.18632/aging.100459.
   Google Scholar
• Gan, J., Spurlock, F., Hendley, P., Weston, D.P., 2008 Synthetic pyrethroids: occurrence and behavior in aquatic environments. ACS Publications.
   Google Scholar
• Guengerich, F.P., 2021. A history of the roles of cytochrome P450 enzymes in the toxicity of drugs. Toxicological research 37(1), 1-23. doi: 10.1007/s43188-020-00056-z.
   Google Scholar
• Guvenc, D., Inal, S., Kuruca, N., Gokmen, S., Guvenc, T., 2021. Synthetic pyrethroids common metabolite 3-phenoxybenzoic acid induces caspase-3 and Bcl-2 mediated apoptosis in human hepatocyte cells. Drug Chem. Toxicol., 1-7. doi: 10.1080/01480545.2021.1894720.
   Google Scholar
• Han, Y., Xia, Y., Han, J., Zhou, J., Wang, S., Zhu, P., Zhao, R., Jin, N., Song, L., Wang, X., 2008. The relationship of 3-PBA pyrethroids metabolite and male reproductive hormones among non-occupational exposure males. Chemosphere 72(5), 785-790. doi: 10.1016/j.chemosphere.2008.03.058.
   Google Scholar
• Hanwell, M.D., Curtis, D.E., Lonie, D.C., Vandermeersch, T., Zurek, E., Hutchison, G.R., 2012. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J. Cheminform. 4(1), 17. doi: 10.1186/1758-2946-4-17.
   Google Scholar
• Hemmerich, J., Ecker, G.F., 2020. In silico toxicology: From structure–activity relationships towards deep learning and adverse outcome pathways. WIREs Computational Molecular Science 10(4), e1475. doi: 10.1002/wcms.1475.
   Google Scholar
• Hołyńska-Iwan, I., Szewczyk-Golec, K., 2020. Pyrethroids: How They Affect Human and Animal Health? Medicina (Kaunas) 56(11). doi: 10.3390/medicina56110582.
   Google Scholar
• Hu, X., li, J., Fu, M., Zhao, X., Wang, W., 2021. The JAK/STAT signaling pathway: from bench to clinic. Signal Transduction and Targeted Therapy 6(1), 402. doi: 10.1038/s41392-021-00791-1.
   Google Scholar
• Huckle, K.R., Chipman, J.K., Hutson, D.H., Millburn, P., 1981. Metabolism of 3-phenoxybenzoic acid and the enterohepatorenal disposition of its metabolites in the rat. Drug Metab. Disposition 9(4), 360
   Google Scholar
• Hwang, M., Lee, Y., Choi, K., Park, C., 2019. Urinary 3-phenoxybenzoic acid levels and the association with thyroid hormones in adults: Korean National Environmental Health Survey 2012-2014. Sci. Total Environ. 696, 133920. doi: 10.1016/j.scitotenv.2019.133920.
   Google Scholar
• Ji, G., Xia, Y., Gu, A., Shi, X., Long, Y., Song, L., Wang, S., Wang, X., 2011. Effects of non-occupational environmental exposure to pyrethroids on semen quality and sperm DNA integrity in Chinese men. Reprod. Toxicol. 31(2), 171-176. doi: 10.1016/j.reprotox.2010.10.005.
   Google Scholar
• Joshi, U., Pearson, A., Evans, J.E., Langlois, H., Saltiel, N., Ojo, J., Klimas, N., Sullivan, K., Keegan, A.P., Oberlin, S., Darcey, T., Cseresznye, A., Raya, B., Paris, D., Hammock, B., Vasylieva, N., Hongsibsong, S., Stern, L.J., Crawford, F., Mullan, M., Abdullah, L., 2019. A permethrin metabolite is associated with adaptive immune responses in Gulf War Illness. Brain. Behav. Immun. 81, 545-559. doi: 10.1016/j.bbi.2019.07.015.
   Google Scholar
• Kaneko, H., 2010 Pyrethroid chemistry and metabolism, Hayes' Handbook of Pesticide Toxicology. Elsevier, pp. 1635-1663.
   Google Scholar
• Kim, B., Jung, A., Yun, D., Lee, M., Lee, M.-R., Choi, Y.-H., Kim, Y., Park, C., Hong, Y.-C., Kim, S., 2015. Association of urinary 3-phenoxybenzoic acid levels with self-reported depression symptoms in a rural elderly population in Asan, South Korea. Environ. Health Toxicol. 30, e2015002-e2015002. doi: 10.5620/eht.e2015002.
   Google Scholar
• Kim, J.H., Lee, S., Kim, K.N., Hong, Y.C., 2019. Association of urinary 3-phenoxybenzoic acid level with pulmonary function reduction in an urban elderly population with repeated measures data. Environ. Pollut. 246, 811-818. doi: 10.1016/j.envpol.2018.12.078.
   Google Scholar
• Kim, M.K., Kim, K.S., Chung, J.H., Kim, J.H., Kim, J.R., Chung, H.Y., Kim, M.S., 2007. Environmental metabolite, 1,2-diacetylbenzene, produces cytotoxicity through ROS generation in HUVEC cells. J. Toxicol. Environ. Health A 70(15-16), 1336-1343. doi: 10.1080/15287390701428895.
   Google Scholar
• Kim, M.S., Kim, M.K., Kim, K.S., Chung, J.H., Kim, S.J., Kim, J.H., Kim, J.R., Lee, J., Yu, B.P., Chung, H.Y., 2008. Cytotoxicity of 1,2-diacetylbenzene in human neuroblastoma SHSY5Y cells is mediated by oxidative stress. Toxicology 243(1-2), 216-223. doi: 10.1016/j.tox.2007.10.012.
   Google Scholar
• Kim, U.J., Hong, M., Choi, Y.H., 2021. Environmental Pyrethroid Exposure and Cognitive Dysfunction in U.S. Older Adults: The NHANES 2001-2002. Int. J. Environ. Res. Public Health 18(22). doi: 10.3390/ijerph182212005.
   Google Scholar
• Krasnov, L., Khokhlov, I., Fedorov, M.V., Sosnin, S., 2021. Transformer-based artificial neural networks for the conversion between chemical notations. Sci. Rep. 11(1), 14798. doi: 10.1038/s41598-021-94082-y.
   Google Scholar
• Krieger, R., 2010 Hayes' handbook of pesticide toxicology. Academic press.
   Google Scholar
• Lagunin, A., Stepanchikova, A., Filimonov, D., Poroikov, V.J.B., 2000. PASS: prediction of activity spectra for biologically active substances. 16(8), 747-748
   Google Scholar
• Lee, S.Y., Lee, D.Y., Kang, J.H., Jeong, J.W., Kim, J.H., Kim, H.W., Oh, D.H., Kim, J.-M., Rhim, S.-J., Kim, G.-D., Kim, H.S., Jang, Y.D., Park, Y., Hur, S.J., 2022. Alternative experimental approaches to reduce animal use in biomedical studies. J. Drug Deliv. Sci. Technol. 68, 103131. doi: 10.1016/j.jddst.2022.103131.
   Google Scholar
• Lee, W.S., Lim, Y.H., Kim, B.N., Shin, C.H., Lee, Y.A., Kim, J.I., Hong, Y.C., Kim, K.N., 2020. Residential pyrethroid insecticide use, urinary 3-phenoxybenzoic acid levels, and attention-deficit/hyperactivity disorder-like symptoms in preschool-age children: The Environment and Development of Children study. Environ. Res. 188, 109739. doi: 10.1016/j.envres.2020.109739.
   Google Scholar
• M. A. Kawsar, S., Hosen, M.A., Ahmad, S., El Bakri, Y., Laaroussi, H., Ben Hadda, T., Almalki, F.A., Ozeki, Y., Goumri-Said, S., 2022. Potential SARS-CoV-2 RdRp inhibitors of cytidine derivatives: Molecular docking, molecular dynamic simulations, ADMET, and POM analyses for the identification of pharmacophore sites. PLoS One 17(11), e0273256. doi: 10.1371/journal.pone.0273256.
   Google Scholar
• Morgan, M.K., 2012. Children's exposures to pyrethroid insecticides at home: a review of data collected in published exposure measurement studies conducted in the United States. Int. J. Environ. Res. Public Health 9(8), 2964-2985. doi: 10.3390/ijerph9082964.
   Google Scholar
• Nayeem, A., Sitkoff, D., Krystek, S., Jr., 2006. A comparative study of available software for high-accuracy homology modeling: from sequence alignments to structural models. Protein Sci. 15(4), 808-824. doi: 10.1110/ps.051892906.
   Google Scholar
• Neta, G., Goldman, L.R., Barr, D., Apelberg, B.J., Witter, F.R., Halden, R.U., 2011. Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes. Environ. Sci. Technol. 45(4), 1680-1687. doi: 10.1021/es103417j.
   Google Scholar
• Nguyen, H.D., Kim, M.-S., 2022a. The Effects of a Mixture of Cadmium, Lead, and Mercury on Metabolic Syndrome and Its Components, as well as Cognitive Impairment: Genes, MicroRNAs, Transcription Factors, and Sponge Relationships. Biol. Trace Elem. Res. doi: 10.1007/s12011-022-03343-y.
   Google Scholar
• Nguyen, H.D., Kim, M.-S., 2022b. Exposure to a mixture of heavy metals induces cognitive impairment: genes and microRNAs involved. Toxicology 15(471), 153164. doi: 10.1016/j.tox.2022.153164.
   Google Scholar
• Nguyen, H.D., Kim, M.-S., 2022c. The protective effects of curcumin on metabolic syndrome and its components: In-silico analysis for genes, transcription factors, and microRNAs involved. Arch. Biochem. Biophys. 727, 109326. doi: 10.1016/j.abb.2022.109326.
   Google Scholar
• Nguyen, H.D., Oh, H., Jo, W.H., Hoang, N.H.M., Kim, M.S., 2021. Mixtures modeling identifies heavy metals and pyrethroid insecticide metabolites associated with obesity. Environ. Sci. Pollut. Res. Int. doi: 10.1007/s11356-021-16936-2.
   Google Scholar
• Park, J., Kim, C., Jeon, H.-J., Kim, K., Kim, M.-J., Moon, J.-K., Lee, S.-E., 2021. Developmental toxicity of 3-phenoxybenzoic acid (3-PBA) and endosulfan sulfate derived from insecticidal active ingredients: Abnormal heart formation by 3-PBA in zebrafish embryos. Ecotoxicol. Environ. Saf. 224, 112689. doi: 10.1016/j.ecoenv.2021.112689.
   Google Scholar
• Parrinello, M., Rahman, A., 1981. Polymorphic transitions in single crystals: A new molecular dynamics method. Journal of Applied Physics 52(12), 7182-7190. doi: 10.1063/1.328693.
   Google Scholar
• Poroikov, V.V., Filimonov, D.A., Ihlenfeldt, W.-D., Gloriozova, T.A., Lagunin, A.A., Borodina, Y.V., Stepanchikova, A.V., Nicklaus, M.C., 2003. PASS Biological Activity Spectrum Predictions in the Enhanced Open NCI Database Browser. J. Chem. Inf. Comput. Sci. 43(1), 228-236. doi: 10.1021/ci020048r.
   Google Scholar
• Pratama, R.A., Astina, J., Parikesit, A.A., 2023. In silico Screening of Potential Antidiabetic Phenolic Compounds from Banana (Musa spp.) Peel Against PTP1B Protein. 2023 8(3). doi: 10.22146/jtbb.83124.
   Google Scholar
• Raunio, H., Kuusisto, M., Juvonen, R.O., Pentikäinen, O.T., 2015. Modeling of interactions between xenobiotics and cytochrome P450 (CYP) enzymes. Front. Pharmacol. 6, 123-123. doi: 10.3389/fphar.2015.00123.
   Google Scholar
• Rudik, A.V., Bezhentsev, V.M., Dmitriev, A.V., Druzhilovskiy, D.S., Lagunin, A.A., Filimonov, D.A., Poroikov, V.V.J.J.o.c.i., modeling, 2017. MetaTox: web application for predicting structure and toxicity of xenobiotics’ metabolites. 57(4), 638-642
   Google Scholar
• Saillenfait, A.-M., Ndiaye, D., Sabaté, J.-P., 2015. Pyrethroids: Exposure and health effects – An update. Int. J. Hyg. Environ. Health 218(3), 281-292. doi: 10.1016/j.ijheh.2015.01.002.
   Google Scholar
• Shelton Janie, F., Geraghty Estella, M., Tancredi Daniel, J., Delwiche Lora, D., Schmidt Rebecca, J., Ritz, B., Hansen Robin, L., Hertz-Picciotto, I., 2014. Neurodevelopmental Disorders and Prenatal Residential Proximity to Agricultural Pesticides: The CHARGE Study. Environ. Health Perspect. 122(10), 1103-1109. doi: 10.1289/ehp.1307044.
   Google Scholar
• Stasevych, M., Zvarych, V., Novikov, V., 2020 A Computational Approach in the Search of New Biologically Active 9, 10-Anthraquinone Derivatives, IDDM. pp. 178-185.
   Google Scholar
• Sudakin, D.L., 2006. Pyrethroid Insecticides: Advances and Challenges in Biomonitoring. Clin. Toxicol. 44(1), 31-37. doi: 10.1080/15563650500394647.
   Google Scholar
• Testa, B., Pedretti, A., Vistoli, G.J.D.d.t., 2012. Reactions and enzymes in the metabolism of drugs and other xenobiotics. 17(11-12), 549-560
   Google Scholar
• Trott, O., Olson, A.J.J.J.o.c.c., 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. 31(2), 455-461
   Google Scholar
• Tyzack, J.D., Kirchmair, J.J.C.b., design, d., 2019. Computational methods and tools to predict cytochrome P450 metabolism for drug discovery. 93(4), 377-386
   Google Scholar
• US_EPA, 2022 Pyrethrins and Pyrethroids. Available at: https://www.epa.gov/sites/default/files/documents/rmpp_6thed_ch4_pyrethrinspyrethroids.pdf. (Accessed Accessed on June 11th 2022.
   Google Scholar
• Wan, F., 2020 The Influence of 3-Phenoxybenzoic Acid in Dopaminergic Degeneration, Mov. Disord. WILEY 111 RIVER ST, HOBOKEN 07030-5774, NJ USA, pp. S233-S233.
   Google Scholar
• Wan, F., Yu, T., Hu, J., Yin, S., Li, Y., Kou, L., Chi, X., Wu, J., Sun, Y., Zhou, Q., Zou, W., Zhang, Z., Wang, T., 2022. The pyrethroids metabolite 3-phenoxybenzoic acid induces dopaminergic degeneration. Sci. Total Environ. 838(Pt 2), 156027. doi: 10.1016/j.scitotenv.2022.156027.
   Google Scholar
• Wan, F., Yu, T., Hu, J., Yin, S., Li, Y., Kou, L., Chi, X., Wu, J., Sun, Y., Zhou, Q., Zou, W., Zhang, Z., Wang, T., 2022. The pyrethroids metabolite 3-phenoxybenzoic acid induces dopaminergic degeneration. Sci. Total Environ. 838, 156027. doi: 10.1016/j.scitotenv.2022.156027.
   Google Scholar
• Watkins, D.J., Fortenberry, G.Z., Sánchez, B.N., Barr, D.B., Panuwet, P., Schnaas, L., Osorio-Valencia, E., Solano-González, M., Ettinger, A.S., Hernández-Ávila, M., Hu, H., Téllez-Rojo, M.M., Meeker, J.D., 2016. Urinary 3-phenoxybenzoic acid (3-PBA) levels among pregnant women in Mexico City: Distribution and relationships with child neurodevelopment. Environ. Res. 147, 307-313. doi: 10.1016/j.envres.2016.02.025.
   Google Scholar
• Weinshilboum, R.M., Otterness, D.M., Szumlanski, C.L.J.A.r.o.p., toxicology, 1999. Methylation pharmacogenetics: catechol O-methyltransferase, thiopurine methyltransferase, and histamine N-methyltransferase. 39, 19
   Google Scholar
• Xia, Y., Han, Y., Wu, B., Wang, S., Gu, A., Lu, N., Bo, J., Song, L., Jin, N., Wang, X., 2008. The relation between urinary metabolite of pyrethroid insecticides and semen quality in humans. Fertil. Steril. 89(6), 1743-1750. doi: 10.1016/j.fertnstert.2007.05.049.
   Google Scholar
• Xiong, G., Wu, Z., Yi, J., Fu, L., Yang, Z., Hsieh, C., Yin, M., Zeng, X., Wu, C., Lu, A., Chen, X., Hou, T., Cao, D., 2021. ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Res. 49(W1), W5-w14. doi: 10.1093/nar/gkab255.
   Google Scholar
• Xu, H., Mao, Y., Xu, B., 2020. Association between pyrethroid pesticide exposure and hearing loss in adolescents. Environ. Res. 187, 109640. doi: 10.1016/j.envres.2020.109640.
   Google Scholar
• Xue, Q., Pan, A., Wen, Y., Huang, Y., Chen, D., Yang, C.-X., Hy Wu, J., Yang, J., Pan, J., Pan, X.-F., 2021. Association between pyrethroid exposure and cardiovascular disease: A national population-based cross-sectional study in the US. Environ. Int. 153, 106545. doi: 10.1016/j.envint.2021.106545.
   Google Scholar
• Xue, Z., Li, X., Su, Q., Xu, L., Zhang, P., Kong, Z., Xu, J., Teng, J., 2013. Effect of Synthetic Pyrethroid Pesticide Exposure During Pregnancy on the Growth and Development of Infants. Asia Pacific Journal of Public Health 25(4_suppl), 72S-79S. doi: 10.1177/1010539513496267.
   Google Scholar
• Zoete, V., Cuendet, M.A., Grosdidier, A., Michielin, O., 2011. SwissParam: a fast force field generation tool for small organic molecules. J. Comput. Chem. 32(11), 2359-2368. doi: 10.1002/jcc.21816.
   Google Scholar