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Research Papers: Lubricants

Quantitative Structure Tribo-Ability Relationship for Organic Compounds as Lubricant Base Oils Using CoMFA and CoMSIA

[+] Author and Article Information
Xinlei Gao

School of Chemical and Environmental Engineering,
Wuhan Polytechnic University,
Wuhan, Hubei Province 430023, China
e-mail: gaoxl0131@163.com

Denghui Liu, Zhan Wang

School of Chemical and Environmental Engineering,
Wuhan Polytechnic University,
Wuhan, Hubei Province 430023, China

Kang Dai

College of Pharmacy,
South-Central University for Nationalities,
Wuhan, Hubei Province 430074, China
e-mail: kangdai1688@163.com

1Corresponding authors.

Contributed by the Tribology Division of ASME for publication in the JOURNAL OF TRIBOLOGY. Manuscript received April 22, 2015; final manuscript received March 9, 2016; published online May 4, 2016. Assoc. Editor: Mircea Teodorescu.

J. Tribol 138(3), 031802 (May 04, 2016) (7 pages) Paper No: TRIB-15-1132; doi: 10.1115/1.4033191 History: Received April 22, 2015; Revised March 09, 2016

The structures and the wear data of 47 different organic compounds as lubricant base oils were included in a comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA)–quantitative structure tribo-ability relationship (QSTR) model. CoMFA- and CoMSIA-QSTR models illustrate good accuracy, robustness, and predictability, with the latter more accurate than the former. CoMFA-QSTR with both steric and electrostatic fields: R2= 0. 958, R2(LOO) = 0.958, and q2= 0.625; with only a steric field: R2= 0.987, R2(LOO) = 0.987, and q2= 0.692. CoMSIA-QSTR with a steric field: R2= 0.924, R2(LOO) = 0.923, and q2= 0.898, whereas CoMSIA-QSTR with a hydrophobic field gave R2= 0.985, R2(LOO) = 0.985, and q2= 0.899. QSTR with CoMFA and CoMSIA shows a strong correlation to wear scar diameter scales (WDS), and builds statistical and graphical models that relate the wear properties of molecules to their structures.

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References

Hansch, C. , and Steward, A. R. , 1964, “ The Use of Substituent Constants in the Analysis of the Structure–Activity Relationship in Penicillin Derivatives,” J. Med. Chem., 7(6), pp. 691–694. [CrossRef] [PubMed]
Cramer, III, R. D. , Patterson, D. E. , and Bunce, J. D. , 1988, “ Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins,” J. Am. Chem. Soc., 110(18), pp. 5959–5967. [CrossRef] [PubMed]
Dai, K. , and Gao, X. , 2013, “ Estimating Antiwear Properties of Lubricant Additives Using a Quantitative Structure Tribo-Ability Relationship Model With Back Propagation Neural Network,” Wear, 306(1–2), pp. 242–247. [CrossRef]
Gao, X. , Wang, Z. , Zhang, H. , Dai, K. , and Wang, T. , 2015, “ A Quantitative Structure Tribo-ability Relationship Model for Ester Lubricant Base Oils,” ASME J. Tribol., 137(2), p. 021801. [CrossRef]
Gao, X. , Wang, Z. , Zhang, H. , and Dai, K. , 2015, “ A Three Dimensional Quantitative Tribo-Ability Relationship Model,” ASME J. Tribol., 137(2), p. 021802. [CrossRef]
Gao, X. , Wang, R. , Wang, Z. , and Dai, K. , 2016, “ BPNN-QSTR Friction Model for Organic Compounds as Potential Lubricant Base Oils,” ASME J. Tribol. 138(3), p.031801.
Mang, T. , and Dresel, W. , 2001, Lubricants and Lubrication, Wiley, Weinheim, Germany.
Cramer, III, R. D. , Patterson, D. E. , and Bunce, J. D. , 1989, “ Recent Advances in Comparative Molecular Field Analysis (CoMFA),” Prog. Clin. Biol. Res., 291, pp. 161–165. [PubMed]
Kubinyi, H. , Folkers, G. , and Martin, Y. C. , 1998, 3D QSAR in Drug Design, Recent Advances, Springer, The Netherlands.
Bush, B. L. , and Nachbar, R. B. , 1993, “ Sample-Distance Partial Least Squares: PLS Optimized for Many Variables, With Application to CoMFA,” J. Comput.-Aided Mol. Des., 7(5), pp. 587–619. [CrossRef] [PubMed]
Huang, M. , Yang, D. , Shang, Z. , Zou, J. , and Yu, Q. , 2002, “ 3D-QSAR Studies on 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors by Comparative Molecular Field Analysis (CoMFA),” Bioorg. Med. Chem. Lett., 12(17), pp. 2271–2275.
Travis, R. H. , Richard, J. , Sciotti, P. L. , Sandra, D. , Vicky, M. , Avery, O. I. , Matthew, A. , and Timothy, J. H. , 2015, “ The Synthesis, Antimalarial Activity and CoMFA Analysis of Novel Aminoalkylated Quercetin Analogs,” Bioorg. Med. Chem. Lett., 25, pp. 327–332. [CrossRef] [PubMed]
Kubinyi , H., 2003, “ Comparative Molecular Field Analysis (CoMFA),” in Handbook of Chemoinformatics: From Data to Knowledge in 4 Volumes, J. Gasteiger , ed., Wiley-VCH Verlag GmbH, Weinheim, Germany, pp. 1555–1574.
Klebe, G. , Abraham, U. , and Mietzner, T. , 1994, “ Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules Tocorrelate and Predict Their Biological Activity,” J. Med. Chem., 37(24), pp. 4130–4146. [CrossRef] [PubMed]
Klebe, G. , and Abraham, U. , 1999, “ Comparative Molecular Similarity Index Analysis (CoMSIA) to Study Hydrogen-Bonding Properties and to Score Combinatorial Libraries,” J. Comput.-Aided Mol. Des., 13(1), pp. 1–10. [CrossRef] [PubMed]
Hattotuwagama, C. K. , Doytchinova, I . A. , and Flower, D. R. , 2005, “ In Silico Prediction of Peptide Binding Affinity to Class I Mouse Major Histocompatibility Complexes: A Comparative Molecular Similarity Index Analysis (CoMSIA) Study,” J. Chem. Inf. Model., 45(5), pp. 1415–1423. [CrossRef] [PubMed]
Arvind, K. , Solomon, K. A. , and Rajan, S. S. , 2014, “ QSAR Studies on Diclofenac Analogues as Potent Cyclooxygenase Inhibitors Using CoMFA and CoMSIA,” Med. Chem. Res., 23(4), pp. 1789–1796. [CrossRef]
Nilanjan, A. , Amit, K. H. , Chanchal, M. , and Tarun, J. , 2013, “ Exploring Structural Requirements of Aurone Derivatives as Antimalarials by Validated DFT-Based QSAR, HQSAR, and COMFA–COMSIA Approach,” Med. Chem. Res., 22, pp. 6029–6045. [CrossRef]
Bohm, M. , Sturzebecher, J. , and Klebe, G. , 1999, “ Three-Dimensional Quantitative Structure–Activity Relationship Analyses Using Comparative Molecular Field Analysis and Comparative Molecular Similarity Indices Analysis To Elucidate Selectivity Differences of Inhibitors Binding to Trypsin, Thrombin, and Factor Xa,” J. Med. Chem., 42(3), pp. 458–477. [CrossRef] [PubMed]
Bang, S. J. , and Cho, S. J. , 2004, “ Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Index Analysis (CoMSIA) Study of Mutagen X,” Bull. Korean Chem. Soc., 25(10), pp. 1525–1530. [CrossRef]
Clark, M. , and Cramer, III, R. D. , 1993, “ The Probability of Chance Correlation Using Partial Least Squares (PLS),” Quant. Struct.–Act. Relat., 12(2), pp. 137–145. [CrossRef]
Gao, X. , Dai, K. , Wang, Z. , Wang, T. , and He, J. , 2016, “ Establishing Quantitative Structure Tribo-ability Relationship model Using Bayesian Regularization Neural Network,” Friction (accepted).
SYBYL-X 1.1, 2009, Tripos International, St. Louis, MO.

Figures

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Fig. 1

Sketch map of the ball-disk rubbing pair [4,6]

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Fig. 2

Chemical structure of 1-bromotetradecane

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Fig. 3

Database alignment using Tripos SYBYL-X 1.1

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Fig. 4

Total energy versus time for simulation of 1-bromotetradecane using the Tripos force field and constant temperature and pressure (NTP) mode (KE: kinetic energy; PE: potential energy; TIME (fs); PE (Kcals/mol); KE (Kcals/mol))

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Fig. 5

Graph of the observed and predicted values of WDS obtained by CoMFA model (both steric and electrostatic fields) for the test and training sets of compounds (Obs: observed WDS; Pred; predicted WDS)

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Fig. 6

CoMFA contour diagram for wear with embedded 1-bromotetradecane as reference. Green and yellow regions show where steric bulk is favored and disfavored, respectively.

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Fig. 7

CoMFA contour diagram for wear with embedded 2-nitrotoluene as reference. Green and yellow regions show where steric bulk is favored and disfavored, respectively.

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Fig. 8

CoMFA contour diagram for wear with embedded 1-bromotetradecane as reference for both steric and electrostatic fields. Green and yellow regions show where steric bulk is favored and disfavored, respectively. Blue region shows where positive charge is favored while red region shows where negative charge is favored.

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Fig. 9

CoMFA contour diagram for wear with embedded 2-nitrotoluene as reference for both steric and electrostatic fields. Green and yellow regions show where steric bulk is favored and disfavored, respectively. Blue region shows where positive charge is favored while red region shows where negative charge is favored.

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Fig. 10

Graph of observed and predicted values of WDS obtained by CoMSIA model (hydrophobic field) for the test and training sets of molecules (Obs: observed WDS; Pred: predicted WDS)

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Fig. 11

CoMSIA contour diagram for wear with embedded 1-bromotetradecane as reference. Green and yellow regions show where steric bulk is favored and disfavored, respectively.

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Fig. 12

CoMSIA contour diagram for wear with embedded 2-nitrotoluene as reference. Green and yellow regions show where steric bulk is favored and disfavored, respectively.

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Fig. 13

CoMSIA contour diagram for wear with embedded 1-bromotetradecane as reference. Purple and turquoise regions show where hydrophobic substitution is favored and disfavored, respectively.

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Fig. 14

CoMSIA contour diagram for wear with embedded 2-nitrotoluene as reference. Purple and turquoise regions show where hydrophobic substitution is favored and disfavored, respectively.

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