Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Modeling of Log Kow of a Series of PAHs using Computational Chemistry


Affiliations
1 1Department of Material Sciences, Faculty of Science and Technology, Amine Elokkal Elhadj Moussa Eg Akhamouk University – Tamanrasset 11000, Algeria., India
2 Process Engineering Department, Faculty of Technology, Hamma Lakhdar University-El oued 3900, Algeria., India
3 Process Engineering Department, Faculty of Technology, Hamma Lakhdar University-El oued 3900, Algeria ., India
     

   Subscribe/Renew Journal


The importance of Chemometrics Methods in Modeling (in QSAR analysis) of the mathematical model’s study of large datasets of molecules with huge numbers of physicochemical and structural parameters quantitative structure-Toxicity relationship (QSTR) are mainly based on multiple regression analysis in QSAR analysis The study of Least Square in deriving QSTR models for datasets of Quantitative Structure-Toxicity relationship on Log k ow (Octanol-water partition coefficient) for 16 Hydrocarbons compounds has been using the software Hyperchem 6.3 for computing descriptors and MINITAB 16 for data modeling. A three -descriptors model [two electronics molecules’ descriptors (QSER descriptor), HOMO (is Highest occupied molecular orbital) and LUMO (Lowest unoccupied molecular orbital), one QSAR descriptor 𝐸𝐻 (Hydration Energy) by Least Squares with correlation coefficient r=0.868, S=0.635, R 2 = 75.4%, R 2 ajd=73.7% and Durbin-Watson statistic =1.85277 and graphical analysis by diagram of goodness of fit and line plot. The results statistical of new model after removing the aberrant compounds (Toxicity compounds) shows high Coefficient of correlation r=0.9581, S=0.4316, determination coefficient R 2 =91. 8%, ajustemed R 2 ajd = 89.3%, Durbin-Watson statistic D=2.373, Three explanatory Variable model selected is robust and has good fitness. Two influential compounds detected and important the model and absence aberant compounds of the studied sample.

Keywords

Hydrocarbons (PAHs), toxicity 𝐿𝑜𝑔 𝑘𝑜𝑤,HOMO, LUMO,𝐸𝐻,Multiple linearregression, Aberant compounds.
Subscription Login to verify subscription
User
Notifications
Font Size


  • Polynuclear aromatic hydrocarbons (PAH). In: Air quality guidelines for Europe. Copenhagen, World Health Organization Regional Office for Europe, 1987pp. 105–117.

  • Marija Baranac-Stojanović. 2021. Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution. Asian Journal of Research in Chemistry https://doi.org/10.1002/asia.202101261.

  • Agency for toxic substances and disease registry. Toxicological profile for polycyclic aromatic hydrocarbons (PAHs): update. Atlanta, GA, US Department of Health and Human Services, Public Health Services.1994.

  • Kohei Fuchibe.2020. Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes. Asian Journal of Research in Chemistry https://doi.org/10.1002/asia.202000069

  • Masato Honda and Nobuo Suzuki. 2020. Toxicities of Polycyclic Aromatic Hydrocarbons for Aquatic Animals.Int. J. Environ. Res. Public Health,17, 1363; doi:10.3390/ijerph17041363.

  • Hilal Colak.2020. Investigation of Polycyclic Aromatic Hydrocarbons in Foods Asian Journal of Research in Chemistry .22(8):5797-5807.

  • Hylland, K.2006. Polycyclic aromatic hydrocarbon (PAH) ecotoxicology in marine ecosystems. J. Toxicol. Environ., 69, 109–123.

  • Kasama Janvijitsakul*, Vladimir I. Kuprianov 2007. Polycyclic Aromatic Hydrocarbons in Coarse Fly Ash Particles Emitted from Fluidized-bed Combustion of Thai Rice Husk. Asian Journal on Energy and Environment, 08(04), 654-662. ISSN 1513-4121.

  • Collins, J.F.; Brown, J.P.; Alexeeff, G.V.; Salmon, A.G. 1998.Potency equivalency factors for some polycyclic aromatic hydrocarbons and polycyclic aromatic hydrocarbon derivatives. Regul. Toxicol. Pharmacol. 28, 45–54.

  • Monago, C. C., Nwiko, E. B., Chuku, L. C.2010. Assessment of Polycyclic Aromatic Hydrocarbon Levels in Blood of Refinery Workers in Nigeria. Asian Journal of Research in Chemistry Volume - 3(3).

  • Devi, N.L.; Yadav, I.C.; Shihua, Q.; Dan, Y.; Zhang, G.; Raha, P.2016. Environmental carcinogenic polycyclic aromatic hydrocarbons in soil from Himalayas, India: Implications for spatial distribution, sources apportionment and risk assessment.Chemosphere. 144, 493–502

  • Kuo, C.-Y.; Cheng, Y.-W.; Chen, Y.-W.; Lee, H. 1998.Correlation between the amounts of polycyclic aromatic hydrocarbons and mutagenicity of airborne particulate samples from Taichung City, Taiwan. Environ. Res. 78, 43–49.

  • Rengarajan, T.; Rajendran, P.; Nandakumar, N.; Lokeshkumar, B.; Rajendran, P.; Nishigaki, I. 2015.Exposure to polycyclic aromatic hydrocarbons with special focus on cancer. Asian Pac. J. Trop.

  • Biomed.vol 5, 182–189.

  • Bekki, K.; Toriba, A.; Tang, N.; Kameda, T.; Hayakawa, K.2013. Biological effects of polycyclic aromatic hydrocarbon derivatives. J. UOEH, 35, 17–24.

  • Ikenaka, Y.; Oguri, M.; Saengtienchai, A.; Nakayama, S.M.; Ijiri, S.; Ishizuka, M. 2013.Characterization of phase-II conjugation reaction of polycyclic aromatic hydrocarbons in fish species: Unique pyrene metabolism and species specificity observed in fish species. Environ. Toxicol. Pharmacol. 36, 567–578.

  • Jacob, J. 2008.The significance of polycyclic aromatic hydrocarbons as environmental carcinogens. 35 years research on PAH—A retrospective. Polycycl. Aromat. Compd. vol 28, 242– 272.

  • Jørgensen, A.; Giessing, A.M.; Rasmussen, L.J.; Andersen, O.2008. Biotransformation of polycyclic aromatic hydrocarbons in marine polychaetes. Mar. Environ. Res. vol 65, 171–186.

  • Worth, AP, Bassan, A, De, Bruijn, J, Gallegos Saliner, A, Netzeva, T, Patlewicz, G, Tsakovska, L and Eisenreich, S.2007. The role of the European Chemicals Bureau in promoting the regulatory use of QSAR methods, SA Rand QSAR in Environmental Research, Vol 18 Nos 1-2,pp111-125.

  • Hansh, C, Maloney, PP, Fujita, T, and Muir, RM.1962. Correlation of biological activity of phenoxyacetic acids with Hammettsubstituent constants and partition coefficient, Nature Vol 194, pp.80-178.

  • Bordhar, M, Ghasemi, J, Fall, A, Y, and Fazaeli, R.2013.Chemometric modeling to predict aquatic toxicity of benzaene derivatives using stepwise multi linear and partial least square.Assia Journal of Chemistry, Vol 25 No .1,pp.331-342.

  • D. Mackay, W.Y. Shiu, K.C. Ma,.1998. Illustrated Handbook of Physical–Chemical Properties and Environmental Fate for Organic Chemicals, vol. 3, Lewis, London.

  • H.B. Krop, J.M. van Velzen, J.J.R. Parsons, H.A.J. Goves, 1997Chemosphere 34, 107.

  • H. Kubinyi, QSAR: Hansch1993.Analysis and Related Approaches, VCH, Weinheim.

  • S.G. Huling, J.W. Weaver, Dense nonaqueous phase liquids. Ground water issue. EPA/540/4-91-002, US EPA. R.S. Kerr Environmental Research Laboratory, Ada, OK, p. 21.

  • C.J. Newell, S.D. Acree, R.R. Ross, S.G. Huling, Light nonaqueous phase liquids. Ground water issue. EPA/540/S-95/ 500, US EPA. R.S. Kerr Environmental Research Laboratory, Ada, OK, p. 28.

  • Robert A. Yaffee.2002.Robust Regression Analysis:Some Popular Statistical Package Options..ReacGate.https://www.researchgate.net/publication/2664 36942

  • Eriksson, L., Jaworska, J., Worth, A., Cronin, M., Mc Dowell, R.M., Gramatica, P. (2003). Methods for reliability, uncertainty assessment, and applicability evaluations of regression based and classification QSPRs. Environmental Health Perspective Journal, 111(10): 1361-1375. https://doi.org/10.1289/ehp.5758.

  • Tropsha, A., Gramatica, P., Grombar, V.K. (2003). The importance of being Earnest: Validation is the absolute essential for successful application and interpretation of QSPR models. QSAR &Combinatorial Science, 22(1): 69-76. https://doi.org/10.1002/qsar.200390007.

  • Frédéric Jouannin.2004.Etude de la mobilité des hydrocarbures aromatiques polycycliques (HAP) contenus dans un sol industriel pollué. these de doctorat.L’Institut National des Sciences Appliquées de Lyon paris.

  • Draper, N.R., Smith, H. (1998). Applied Regression Analysis. Third Edition. Wiley Series in Probability and Statistics. New York.

  • Ribeiro FAL, Ferreira MMC.2003. QSPR models of boiling point, octanol-water partition coefficient and retention time index of polycyclic aromatic hydrocarbons. Journal of Molecular Structure: THEOCHEM; 663(5): 109-126.

  • FabianaA and Marcia M.2003.QSPR models of boiling point,octanol -water partition coefficient and retention time index of polycyclic aromatic hydrocarbons

  • HyperchemTM Release 6.03 for Windows, Molecular Modelling System, 2000.

  • MINITAB, Release 13.31, Statistical Software, 2000.

  • Ramsay, L.F., Schafer, W.D. (1997). The statistical sleuth, Belmont: Wadsworth Publishing Company.

  • A. Boudehane, S. Atia, L. Kribaa, A. Lounas, C. Balducci, A.Cecinato 2020. Detecting some VOCs (PAH) in hospital and university in Ouargla city Algeria Asian Journal of Research in Chemistry Volume 13(1),. DOI: 10.5958/0974-4150.2020.00004.8

  • Shuchi Gupta, Seema Acharya.2018. Spectrofluorimetric Analysis of Interaction of Benzo (a) Pyrene and Surfactant Micelles. Asian Journal of Research in Chemistry. Volume – 11(3). DOI: 10.5958/0974-4150.2018.00113.X

  • Kadhiravansivasamy, S. Sivajiganesan, T. Periyathambi, V. Nandhakumar, M. Pugazhenthi. 2017.Synthesis and Characterization of Schiff Base CoII, NiII and CuII Complexes derived from 2-Hydroxy-1-naphthaldehyde and Ethylenediamine. Asian Journal of Research in Chemistry Volume– 10(2),.

  • 5958/0974-4150.2017.00016.5.

  • Anthony J. Burke, Carla S. S. Teixeira, Sérgio F. Sousa 2022..Transformation of a Chiral Glycolic Acid to an Isoaurone: Stereochemical Assignment of a Benzilic Acid Rearrangment Product. Asian Journal of Organic Chemistry. DOI: 10.1002/ajoc.202100692.

  • Buralla KK, Parthasarathy V. Central composite design based development and validation of an rp-hplc method for paclitaxel in bulk and pharmaceutical dosage form. Research Journal of Pharmacy and Technology. 2020;13(10):4895-902.

  • Fatmarahmi DC, Susidarti RA, Swasono RT, Rohman A. Identification and quantification of metamizole in traditional herbal medicines using spectroscopy FTIR-ATR combined with chemometrics. Research Journal of Pharmacy and Technology. 2021;14(8):4413-9.

  • Gandhi SV, Sonawane PS. Chemometric–Assisted UV Spectrophotometric Method for Determination of

  • CefiximeTrihydrate and Cloxacillin Sodium in Pharmaceutical Dosage Form. Asian Journal of Research in Chemistry. 2018;11(4):705-9.

  • Jaiswal S, Chavhan SA, Shinde SA, Wawge NK. New Tools for Herbal Drug Standardization. Asian J Res Pharm Sci. 2018;8(3):161-9.

  • Mathew C, Varma S. Green Analytical Methods based on Chemometrics and UV spectroscopy for the simultaneous estimation of Empagliflozin and Linagliptin. Asian Journal of Pharmaceutical Analysis. 2022;12(1).

  • Nangare SA, Rohane SH. Review on Guassion, the General Purpose in Computational Chemistry for Medicinal Chemistry. Asian Journal of Research in Chemistry. 2021;14(1):89-91.

  • Patel K, Shah UA, Joshi HV, Patel JK, Patel CN. QbD Stressed Development and Validation of Stability-Indicating RP-HPLC Method for the Simultaneous Estimation of Linagliptin and Metformin HCl in Pharmaceutical Dosage Form. Research Journal of Pharmacy and Technology. 2022;15(5):1917-23.

  • Rao MVS, Ramam VA, Rao VM, Rao RS. Singular Value Decomposition is used as a Chemo metric Tool for Kinetic Investigations. Research Journal of Science and Technology. 2013;5(4):412-20.

  • Sankar ASK, Vetrichelvan T, Venkappaya D, Nagavalli D, Divya O. Simultaneous Estimation of Ramipril, Aspirin and Atorvastatin Calcium by Classical Least Squares Regression in Capsule Dosage Form. Research Journal of Pharmacy and Technology. 2011;4(3):398-401.

  • Shiyan S, Arifin A, Amriani A, Pratiwi G. Immunostimulatory activity of ethanol extract from Calotropisgigantea L. flower in rats against Salmonella typhimurium infection. Research Journal of Pharmacy and Technology. 2020;13(11):5244-50.


Abstract Views: 281

PDF Views: 0




  • Modeling of Log Kow of a Series of PAHs using Computational Chemistry

Abstract Views: 281  |  PDF Views: 0

Authors

Fatiha Mebarki
1Department of Material Sciences, Faculty of Science and Technology, Amine Elokkal Elhadj Moussa Eg Akhamouk University – Tamanrasset 11000, Algeria., India
Souhaila Meneceur
Process Engineering Department, Faculty of Technology, Hamma Lakhdar University-El oued 3900, Algeria., India
Abderrhmane Bouafia
Process Engineering Department, Faculty of Technology, Hamma Lakhdar University-El oued 3900, Algeria ., India

Abstract


The importance of Chemometrics Methods in Modeling (in QSAR analysis) of the mathematical model’s study of large datasets of molecules with huge numbers of physicochemical and structural parameters quantitative structure-Toxicity relationship (QSTR) are mainly based on multiple regression analysis in QSAR analysis The study of Least Square in deriving QSTR models for datasets of Quantitative Structure-Toxicity relationship on Log k ow (Octanol-water partition coefficient) for 16 Hydrocarbons compounds has been using the software Hyperchem 6.3 for computing descriptors and MINITAB 16 for data modeling. A three -descriptors model [two electronics molecules’ descriptors (QSER descriptor), HOMO (is Highest occupied molecular orbital) and LUMO (Lowest unoccupied molecular orbital), one QSAR descriptor 𝐸𝐻 (Hydration Energy) by Least Squares with correlation coefficient r=0.868, S=0.635, R 2 = 75.4%, R 2 ajd=73.7% and Durbin-Watson statistic =1.85277 and graphical analysis by diagram of goodness of fit and line plot. The results statistical of new model after removing the aberrant compounds (Toxicity compounds) shows high Coefficient of correlation r=0.9581, S=0.4316, determination coefficient R 2 =91. 8%, ajustemed R 2 ajd = 89.3%, Durbin-Watson statistic D=2.373, Three explanatory Variable model selected is robust and has good fitness. Two influential compounds detected and important the model and absence aberant compounds of the studied sample.

Keywords


Hydrocarbons (PAHs), toxicity 𝐿𝑜𝑔 𝑘𝑜𝑤,HOMO, LUMO,𝐸𝐻,Multiple linearregression, Aberant compounds.

References