Abstract
In this study, quantitative structure–property relationship (QSPR) methodology employed for modeling of the sorption coefficient (log KCNT) of 13 polycyclic aromatic hydrocarbons (PAHs) on multiwall carbon nanotube (MWCNT) adsorbent. A molecular docking simulation used to present a reliable and accurate QSPR model with defining the distance and best orientation of PAHs structures on nano-adsorbent. A genetic algorithm-multiple linear regression method was employed for implementation of QSPR model. In this model, the square of correlation coefficients (R2) was 0.945 and 0.890, and the root mean square errors (RMSE) were 0.08 and 0.18 for the training and test sets, respectively. Also, inspection to selected descriptors indicates the electrostatic and steric parameters of PAHs are the predominant factors responsible on the log KCNT values. These results can be used for prediction of sorption coefficient of other PAHs by MWCNT and modify the surface of the adsorbent for improving the log KCNT.
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21 March 2019
The original version of the article contained mistakes in equations. The corrected equations are given below.
References
Agudelo-Castañeda, D.M., Teixeira, E.C., Schneider, I.L., Lara, S.R., Silva, L.F.: Exposure to polycyclic aromatic hydrocarbons in atmospheric PM1. 0 of urban environments: carcinogenic and mutagenic respiratory health risk by age groups. Environ. Pollut. 224, 158–170 (2017)
Ali, I.: New generation adsorbents for water treatment. Chem. Rev. 112(10), 5073–5091 (2012)
Ambure, P., Aher, R.B., Gajewicz, A., Puzyn, T., Roy, K.: “NanoBRIDGES” software: open access tools to perform QSAR and nano-QSAR modeling. Chemom. Intell. Lab. Syst. 147, 1–13 (2015)
Anjum, M., Miandad, R., Waqas, M., Gehany, F., Barakat, M.: Remediation of wastewater using various nano-materials. Arab. J. Chem. (2016). https://doi.org/10.1016/j.arabjc.2016.10.004
Atkinson, A.C.: Plots, Transformations and Regression; An Introduction to Graphical Methods of Diagnostic Regression Analysis. Clarendon Press, Oxford (1985)
Bibby, J., Kent, J., Mardia, K.: Multivariate Analysis. Academic Press, London (1979)
Bjørseth, A.: Handbook of Polycyclic Aromatic Hydrocarbons. Marcel Dekker, New York (1983)
Carpignano, R., Barni, E., Di Modica, G., Grecu, R., Bottaccio, G.: Quantitative relationships between chemical structure and technical properties of 4-aminoazobenzene sulphonic acid dyes. Dyes Pigm. 4(3), 195–211 (1983). https://doi.org/10.1016/0143-7208(83)80017-5
Chen, C.-H., Huang, C.-C.: Hydrogen adsorption in defective carbon nanotubes. Sep. Purif. Technol. 65(3), 305–310 (2009)
Chen, C., Wang, X.: Adsorption of Ni (II) from aqueous solution using oxidized multiwall carbon nanotubes. Ind. Eng. Chem. Res. 45(26), 9144–9149 (2006)
Chen, C., Hu, J., Xu, D., Tan, X., Meng, Y., Wang, X.: Surface complexation modeling of Sr (II) and Eu (III) adsorption onto oxidized multiwall carbon nanotubes. J. Colloid Interface Sci. 323(1), 33–41 (2008)
Chen, C., Wang, X., Nagatsu, M.: Europium adsorption on multiwall carbon nanotube/iron oxide magnetic composite in the presence of polyacrylic acid. Environ. Sci. Technol. 43(7), 2362–2367 (2009)
Davood, A., Reza Nematollahi, A., Iman, M., Shafiee, A.: Synthesis and docking studies of new 1, 4-dihydropyridines containing 4-(5)-chloro-2-ethyl-5-(4)-imidazolyl substituent as novel calcium channel agonist. Arch. Pharm. Res. 32(4), 481–487 (2009)
de Oliveira Galvão, M.F., de Oliveira Alves, N., Ferreira, P.A., Caumo, S., de Castro Vasconcellos, P., Artaxo, P., de Souza Hacon, S., Roubicek, D.A., de Medeiros, S.R.B.: Biomass burning particles in the Brazilian Amazon region: mutagenic effects of nitro and oxy-PAHs and assessment of health risks. Environ. Pollut. 233, 960–970 (2018)
Dumanoglu, Y., Gaga, E.O., Gungormus, E., Sofuoglu, S.C., Odabasi, M.: Spatial and seasonal variations, sources, air-soil exchange, and carcinogenic risk assessment for PAHs and PCBs in air and soil of Kutahya, Turkey, the province of thermal power plants. Sci. Total Environ. 580, 920–935 (2017)
Durrant, J.D., McCammon, J.A.: BINANA: a novel algorithm for ligand-binding characterization. J. Mol. Graph. Model. 29(6), 888–893 (2011)
Fatemi, M.H., Gharaghani, S., Mohammadkhani, S., Rezaie, Z.: Prediction of selectivity coefficients of univalent anions for anion-selective electrode using support vector machine. Electrochim. Acta 53(12), 4276–4282 (2008)
Fatemi, M.H., Heidari, A., Gharaghani, S.: QSAR prediction of HIV-1 protease inhibitory activities using docking derived molecular descriptors. J. Theor. Biol. 369, 13–22 (2015)
Gaur, A., Shim, M.: Substrate-enhanced O2 adsorption and complexity in the Raman G-band spectra of individual metallic carbon nanotubes. Phys. Rev. B 78(12), 125422 (2008)
Goering, J., Kadossov, E., Burghaus, U.: Adsorption kinetics of alcohols on single-wall carbon nanotubes: an ultrahigh vacuum surface chemistry study. J. Phys. Chem. C 112(27), 10114–10124 (2008)
Heidari, A., Fatemi, M.H.: Hybrid docking-nano-QSPR: an alternative approach for prediction of chemicals adsorption on nanoparticles. Nano 11(07), 1650078 (2016)
Herrera-Herrera, A.V., González-Curbelo, M., Hernández-Borges, J., Rodríguez-Delgado, M.: Carbon nanotubes applications in separation science: a review. Anal. Chim. Acta 734, 1–30 (2012). https://doi.org/10.1016/j.aca.2012.04.035
Huey, R., Morris, G.M.: Using AutoDock 4 with AutoDocktools: A Tutorial, pp. 54–56. The Scripps Research Institute, La Jolla (2008)
HyperChem, H.: Release 7 for windows. HyperCube, Ed (2002)
Hyung, H., Kim, J.-H.: Natural organic matter (NOM) adsorption to multi-walled carbon nanotubes: effect of NOM characteristics and water quality parameters. Environ. Sci. Technol. 42(12), 4416–4421 (2008)
Kah, M., Zhang, X., Jonker, M.T., Hofmann, T.: Measuring and modeling adsorption of PAHs to carbon nanotubes over a six order of magnitude wide concentration range. Environ. Sci. Technol 45(14), 6011–6017 (2011)
Katritzky, A., Lobanov, V., Karelson, M.: CODESSA: Reference Manual. University of Florida, Gainesville (1994)
Katritzky, A., Lobanov, V., Karelson, M.: CODESSA: Training Manual. University of Florida, Gainesville (1995)
Katritzky, A.R., Kuanar, M., Slavov, S., Hall, C.D., Karelson, M., Kahn, I., Dobchev, D.A.: Quantitative correlation of physical and chemical properties with chemical structure: utility for prediction. Chem. Rev. 110(10), 5714–5789 (2010)
Kayser, H.: Ueber die verdichtung von gasen an oberflächen in ihrer abhängigkeit von druck und temperatur. Annalen der Physik 250(11), 450–468 (1881)
Khajeh, M., Laurent, S., Dastafkan, K.: Nanoadsorbents: classification, preparation, and applications (with emphasis on aqueous media). Chem. Rev. 113(10), 7728–7768 (2013)
Kirpichenok, M., Zefirov, N.: Electronegativity and geometry of molecules. 1. principles of developed approach and analysis of the effect of nearest electrostatic interactions on the bond length in organic-molecules. Zhurnal Organicheskoi Khimii 23(4), 673–691 (1987)
Li, Y.-H., Wang, S., Wei, J., Zhang, X., Xu, C., Luan, Z., Wu, D., Wei, B.: Lead adsorption on carbon nanotubes. Chem. Phys. Lett. 357(3–4), 263–266 (2002)
Li, Y.-H., Ding, J., Luan, Z., Di, Z., Zhu, Y., Xu, C., Wu, D., Wei, B.: Competitive adsorption of Pb2+, Cu2+ and Cd2+ ions from aqueous solutions by multiwalled carbon nanotubes. Carbon 41(14), 2787–2792 (2003)
Liang, X., Liu, S., Wang, S., Guo, Y., Jiang, S.: Carbon-based sorbents: carbon nanotubes. J. Chromatogr. A 1357, 53–67 (2014)
Liu, Y., Yan, C., Ding, X., Wang, X., Fu, Q., Zhao, Q., Zhang, Y., Duan, Y., Qiu, X., Zheng, M.: Sources and spatial distribution of particulate polycyclic aromatic hydrocarbons in Shanghai, China. Sci. Total Environ. 584, 307–317 (2017)
Marleau, G., Hebert, A., Roy, R.: A user guide for DRAGON. Version DRAGON_000331 release 3.04. Report IGE-174 Rev 5 (2000)
Masenelli-Varlot, K., McRae, E., Dupont-Pavlovsky, N.: Comparative adsorption of simple molecules on carbon nanotubes: dependence of the adsorption properties on the nanotube morphology. Appl. Surf. Sci. 196(1–4), 209–215 (2002)
Morris, G., Goodsell, D., Huey, R., Olson, A.: AutoDock Version 2.4. The Scripps Research Institute, Department of Molecular Biology, La Jolla (1998)
Oyibo, J.N., Wegwu, M.O., Uwakwe, A.A., Osuoha, J.O.: Analysis of total petroleum hydrocarbons, polycyclic aromatic hydrocarbons and risk assessment of heavy metals in some selected finfishes at Focados Terminal Delta State. Environ. Nanotechnol. Monit. Manag. (2017). https://doi.org/10.1016/j.enmm.2017.11.002
Pan, B., Xing, B.: Adsorption mechanisms of organic chemicals on carbon nanotubes. Environ. Sci. Technol. 42(24), 9005–9013 (2008)
Qiao, Y., Wei, Z., Feng, J., Chen, Y., Li, P., Wang, W., Ma, Y., Yuan, Z.: Rapid and efficient screening of adsorbent for oligopeptide using molecular docking and isothermal titration calorimetry. J. Sep. Sci. 32(14), 2462–2468 (2009)
Ren, X., Chen, C., Nagatsu, M., Wang, X.: Carbon nanotubes as adsorbents in environmental pollution management: a review. Chem. Eng. J. 170(2), 395–410 (2011). https://doi.org/10.1016/j.cej.2010.08.045
Stine, R.A.: Graphical interpretation of variance inflation factors. Am. Stat. 49(1), 53–56 (1995)
Todeschini, R., Consonni, V., Mauri, A., Pavan, M.: DRAGON-Software for the calculation of molecular descriptors. Web Version 3 (2003)
Yun, Y., Gao, R., Yue, H., Liu, X., Li, G., Sang, N.: Polycyclic aromatic hydrocarbon (PAH)-containing soils from coal gangue stacking areas contribute to epithelial to mesenchymal transition (EMT) modulation on cancer cell metastasis. Sci. Total Environ. 580, 632–640 (2017)
Zefirov, N., Kirpichenok, M., Ismailov, F., Trofimov, M.: Calculation schemes for atomic electronegativities in molecular graphs within the framework of Sanderson principle. Dokl. Akad. Nauk SSSR 296(4), 883–887 (1987)
Zhang, Y., Wu, B., Xu, H., Liu, H., Wang, M., He, Y., Pan, B.: Nanomaterials-enabled water and wastewater treatment. NanoImpact 3, 22–39 (2016)
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The original version of this article was revised: The errors in the equations have been corrected.
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Pahlavan Yali, Z., Fatemi, M.H. Prediction of the sorption coefficient for the adsorption of PAHs on MWCNT based on hybrid QSPR-molecular docking approach. Adsorption 25, 737–743 (2019). https://doi.org/10.1007/s10450-018-9994-6
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DOI: https://doi.org/10.1007/s10450-018-9994-6