Application of genetic algorithm-kernel partial least square as a novel non-linear feature selection method: Partitioning of drug molecules

Drug Testing and Analysis

Volumn 5, Issue 2, 2013, Pages 89-95

  Noorizadeh, H ^a   Sobhan Ardakani, S ^b   Ahmadi, T ^a   Mortazavi, S S ^b   Noorizadeh, M ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Drug molecules; Genetic algorithm kernel partial least squares; Immobilized liposome chromatography; QSPR

Indexed keywords

CHROMATOGRAPHY; FEATURE SELECTION; LEAST SQUARES APPROXIMATIONS; MOLECULES;

CROSS VALIDATION; DESCRIPTORS; DRUG COMPOUNDS; DRUG MOLECULES; GENETIC ALGORITHM-KERNEL PARTIAL LEAST SQUARE; IMMOBILIZED LIPOSOME CHROMATOGRAPHIES; KERNEL PLS; LEAST SQUARES TECHNIQUES; PARTIAL LEAST-SQUARES; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS;

GENETIC ALGORITHMS;

ATENOLOL; BUPIVACAINE; CIPROFLOXACIN; ENALAPRILAT; FENBUFEN; FLURBIPROFEN; FUROSEMIDE; GEMFIBROZIL; HYDROCORTISONE; IBUPROFEN; INDOPROFEN; LIDOCAINE; LIPOSOME; METOLAZONE; NAPROXEN; OMEPRAZOLE; PHENAZONE; PIROXICAM; PRILOCAINE; PROCAINE; SALICYLIC ACID; SULINDAC; SULPIRIDE; TERBUTALINE; TETRACAINE; THEOPHYLLINE; TOLMETIN; TRAMADOL; UNINDEXED DRUG; WARFARIN;

ARTICLE; CHROMATOGRAPHY; GENETIC ALGORITHM; KERNEL METHOD; MATHEMATICAL MODEL; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE PROPERTY RELATION; VALIDITY;

EID: 84873745862     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.275     Document Type: Article

References (47)

1. Q. Yang, P. Lundahl, Steric immobilization of liposomes in chromatographic gel beads and incorporation of integral membrane proteins into their lipid bilayers. Anal. Biochem. 1994, 218, 210.
2. Y. Zhang, C.-M. Zeng, Y.-M. Li, S. Hjerten, P. Lundahl, Immobilized liposome chromatography of drugs on capillary continuous beds for model analysis of drug-membrane interactions. J. Chromatogr. A 1996, 749, 13.
3. Q. Yang, X.-Y. Liu, S.-I. Ajiki, M. Hara, P. Lundahl, J. Miyake, Avidin-biotin immobilization of unilamellar liposomes in gel beads for chromatographic analysis of drug-membrane partitioning. J. Chromatogr. B 1998, 707, 131.
4. Q. Yang, X. Y. Liu, M. Yoshimoto, R. Kuboi, J. Miyake, Covalent Immobilization of Unilamellar Liposomes in Gel Beads for Chromatography. Anal. Biochem. 1999, 268, 354.
5. Y. Wang, L. Kong, X. Lei, L. Hu, H. Zou, E. W. beck, S.W. Annie Bligh, Z. Wang, Comprehensive two-dimensional high-performance liquid chromatography system with immobilized liposome chromatography column and reversed-phase column for separation of complex traditional Chinese medicine Longdan Xiegan Decoction. J. Chromatogr. A 2009, 1216, 2185.
6. C. Huang, J. T. Mason, Geometric packing constraints in egg phosphatidylcholine vesicles. P. Natl Acad. Sci. USA. 1978, 75, 308.
7. S. Ong, H. Liu, C. Pidgeon, Immobilized-artificial-membrane chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability. J. Chromatogr. A 1996, 728, 113.
8. P. Lundahl, F. Beigi, Immobilized liposome chromatography of drugs for model analysis of drug-membrane interactions. Adv. Drug Deliv. Rev. 1997, 23, 221.
9. X. Liu, Q. Yang, N. Kamo, J. J. Miyake, Effect of liposome type and membrane fluidity on drug-membrane partitioning analyzed by immobilized liposome chromatography. J. Chromatogr. A 2001, 913, 123.
10. C. Pidgeon, S. Ong, H. Chol, H. Liu, Preparation of Mixed Ligand Immobilized Artificial Membranes for Predicting Drug Binding to Membranes. Anal. Chem. 1994, 66, 2701.
11. C. Pidgeon, S. Ong, Predicting drug-membrane interactions. Chemtech. 1995, 25, 38.
12. S. Ong, H. Liu, X. Qiu, C. Pidgeon, Membrane Partition Coefficients Chromatographically Measured Using Immobilized Artificial Membrane Surfaces. Anal. Chem. 1995, 67, 755.
13. C. Y. Yang, S. J. Cai, H. Liu, C. Pidgeon, Immobilized Artificial Membranes - screens for drug membrane interactions. Adv. Drug Deliv. Rev. 1996, 23, 229.
14. P. Artursson, J. Karlsson, Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880.
15. C. Altomare, R. Tsai, N. E. Tayar, B. Testa, A. Carotti, S. Cellamare, P. G. D. Benedetti, Determination of lipophilicity and hydrogen-bond donor acidity of bioactive sulphonyl-containing compounds by reversedl-phase HPLC and centrifugal partition chromatography and their application to structurel-activity relations. J. Pharm. Pharmacol. 1991, 43, 191.
16. P. Artursson, Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorbtive (Caco-2) cells. J. Pharm. Sci. 1990, 79, 476.
17. F. Beigi, I. Gottschalk, C. Lagerquist Hägglund, L. Haneskog, E. Brekkan, Y. Zhang, T. Österberg, P. Lundahl, Immobilized liposome and biomembrane partitioning chromatography of drugs for prediction of drug transport. J. Pharm. 1998, 164, 129.
18. C. Lagerquist, F. Beigi, A. Karlén, H. Lennernäs, P. Lundahl, Effects of cholesterol and model transmembrane proteins on drug partitioning into lipid bilayers as analysed by immobilized-liposome chromatography. J. Pharm. Pharmacol. 2001, 53, 1477.
19. E. Boija, A. Lundquist, J. J. Martínez Pla, C. Engvall, P. Lundahl, Effects of ions and detergents in drug partition chromatography on liposomes. J. Chromatogr. A 2004, 1030, 273.
20. N. Yoshimoto, M. Yoshimoto, K. Yasuhara, T. Shimanouchi, H. Umakoshi, R. Kuboi, Evaluation of temperature and guanidine hydrochloride-induced protein-liposome interactions by using immobilized liposome chromatography. Biochem. Eng. J. 2006, 29, 174.
21. G. Klopman, H. Zhu, Recent methodologies for the estimation of n-octanol/water partition coefficients and their use in the prediction of membrane transport properties of drugs. Mini Rev. Med. Chem. 2005, 5, 127.
22. G. Schuurmann, R. U. Ebert, R. Kuhne, Prediction of the Sorption of Organic Compounds into Soil Organic Matter from Molecular Structure. Environ. Sci. Technol. 2006, 40, 7005.
23. X. Binbin, M. Weiping, Z. H. Xiaoyun, F. Botaon, Quantitative structure-retention relationships for organic pollutants in biopartitioning micellar chromatography. Anal. Chim. Acta 2007, 598, 12.
24. J. M. Bermudez-Saldana, L. Escuder-Gilabert, M. J. Medina-Hernandez, R. M. Villanueva-Camanas, S. Sagrado, Chromatographic retention-activity relationships for prediction of the toxicity pH-dependence of phenols. Chemosphere 2007, 69, 108.
25. M. Weiping, L. Feng, Z. H. Haixia, Z. H. Xiaoyun, L. Mancang, H. Zhide, F. Botao, Quantitative structure-property relationships for pesticides in biopartitioning micellar chromatography. J. Chromatogr. A 2006, 1113, 140.
26. A. Gajewicz, M. Haranczyk, T. Puzyn, Predicting logarithmic values of the subcooled liquid vapor pressure of halogenated persistent organic pollutants with QSPR: How different are chlorinated and brominated congeners? Atmos. Environ. 2010, 44, 1428.
27. H. Noorizadeh, A. Farmany, QSRR Models to Predict Retention Indices of Cyclic Compounds of Essential Oils. Chromatographia 2010, 72, 563.
28. H. Noorizadeh, A. Farmany, A. Khosravi, Investigation of retention Behaviors of Essential Oils by using QSRR. J. Chin. Chem. Soc. 2010, 57, 1.
29. N. Krämer, A. L. Boulesteix, G. Tutz, Penalized Partial Least Squares with applications to B-spline transformations and functional data. Chemom. Intell. Lab. Syst. 2008, 94, 60.
30. S. Haykin, Neural Networks, Prentice-Hall: New Jersey, 1999.
31. T. Osterberg, M. Svensson, P. Lundahl, Chromatographic retention of drug molecules on immobilised liposomes prepared from egg phospholipids and from chemically pure phospholipids. Eur. J. Pharm. Sci. 2001, 12, 427.
32. R. Todeschini, V. Consonni, A. Mauri, M. Pavan, DRAGON-Software for the Calculation of Molecular Descriptors. Version 3.0 for Windows, 2003.
33. D. E. Goldberg, Genetic algorithms, in Search, Optimization and Machine Learning, Addison-Wesley-Longman: Reading, MA, USA, 2000.
34. S. Riahi, E. Pourbasheer, R. Dinarvand, M. R. Ganjali, P. Norouzi, Exploring QSARs for Antiviral Activity of 4-Alkylamino-6-(2-hydroxyethyl)-2-methylthiopyrimidines by Support Vector Machine. Chem. Biol. Drug Des. 2008, 72, 205.
35. H. Noorizadeh, A. Farmany, J. Chin. Chem. Soc. 2010, 57, 1.
36. U. Depczynski, V. J. Frost, K. Molt, Genetic algorithms applied to the selection of factors in principal component regression. Anal. Chim. Acta 2000, 420, 217.
37. S. Wold, M. Sjostrom, L. Eriksson, PLS-regression: a basic tool of chemometrics. Chemom. Intell. Lab. Syst. 2001, 58, 109.
38. B. M. Nicolaï, K. I. Theron, J. Lammertyn, Kernel PLS regression on wavelet transformed NIR spectra for prediction of sugar content of apple. Chemom. Intell. Lab. Syst. 2007, 85, 243.
39. R. Rosipal, L. J. Trejo, J. Mach. Learn. Res. 2001, 2, 97.
40. K. Kim, J. M. Lee, I. B. Lee, A novel multivariate regression approach based on kernel partial least squares with orthogonal signal correction. Chemom. Intell. Lab. Syst. 2005, 79, 22.
41. J. Acevedo-Martinez, J. C. Escalona-Arranz, A. Villar-Rojas, F. Tellez-Palmero, R. Perez-Roses, L. Gonzalez, R. Carrasco-Velar, Quantitative study of the structure-retention index relationship in the imine family. J. Chromatogr. A 2006, 1102, 238.
42. A. Afantitis, G. Melagraki, H. Sarimveis, P. A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, A novel QSAR model for predicting induction of apoptosis by 4-aryl-4H-chromenes. Bioorg. Med. Chem. 2006, 14, 6686.
43. 2!. J. Mol. Graph. Model. 2002, 20, 269.
44. M. M. Felix, H. Umakoshi, T. Shimanouchi, M. Yoshimoto, R. Kuboi, Evaluation of interaction between liposome membranes induced by stimuli responsive polymer and protein. J. Biosci. Bioeng. 2002, 93, 498.
45. E. Boija, A. Lundquist, J. J. Martínez Pla, C. Engvall, P. Lundahl, Effects of ions and detergents in drug partition chromatography on liposomes. J. Chromatogr. A 2004, 1030, 273.
46. J. V. Turner, B. D. Glass, S. Agatonovic-Kustrin, Prediction of drug bioavailability based on molecular structure. Anal. Chim. Acta 2003, 485, 89.
47. R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH: Weinheim, Germany, 2000.