Two- and three-dimensional QSAR of carrier-mediated transport of β-lactam antibiotics in Caco-2 cells

Journal of Pharmaceutical Sciences

Volumn 93, Issue 12, 2004, Pages 3057-3065

  Wanchana, Suchada ^a   Yamashita, Fumiyoshi ^a   Hara, Hideto ^a   Fujiwara, Shin Ichi ^a   Akamatsu, Miki ^a   Hashida, Mitsuru ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Caco 2 cells; Computational ADME; Membrane transport transporters; Partial least squares; QSAR; Structure transport relationship

Indexed keywords

AMPICILLIN; BETA LACTAM ANTIBIOTIC; CARRIER PROTEIN; CEFACLOR; CEFADROXIL; CEFALEXIN; CEFALORIDINE; CEFALOTIN; CEFAMANDOLE; CEFAPIRIN; CEFIXIME; CEFMETAZOLE; CEFODIZIME; CEFOTAXIME; CEFPIROME; CEFRADINE; CEFSULODIN; CEFTAZIDIME; CEFTIBUTEN; CEFTRIAXONE; CEFUROXIME; CYCLACILLIN; DRUG CARRIER; PENICILLIN DERIVATIVE; PEPTIDE;

ARTICLE; AUTOMATION; CELL STRAIN CACO 2; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG STRUCTURE; DRUG TRANSPORT; DRUG UPTAKE; HUMAN; HUMAN CELL; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

EID: 10644256566     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20220     Document Type: Article

References (35)

1. Tsuji A, Tamai I. 1996. Carrier-mediated intestinal transport of drugs. Pharm Res 13(7):963-977.
2. Lee VH, Chu C, Mahlin ED, Basu SK, Ann DK, Bolger MB, Haworth IS, Yeung AK, Wu SK, Hamm-Alvarez S, Okamoto CT. 1999. Biopharmaceutics of transmucosal peptide and protein drug administration: Role of transport mechanisms with a focus on the involvement of PepT1. J Controlled Release 62(1-2):129-140.
3. Zhang EY, Phelps MA, Cheng C, Ekins S, Swaan PW. 2002. Modeling of active transport systems. Adv Drug Delivery Rev 54(3):329-354.
4. Allen FH, Davies JE, Galloy JJ, Johnson O, Kennard O, Macrae CF, Mitchell EM, Mitchell GF, Smith JM, Watson DG. 1991. The development of versions 3 and 4 of the Cambridge Structural Database System. J Chem Inf Comput Sci 31(2):187-204.
5. Simon Z, Badilescu I, Racovitan T. 1977. Mapping of dihydrofolate- reductase receptor site by correlation with minimal topological (steric) differences. J Theor Biol 66(3):485-495.
6. Rhyu KB, Patel HC, Hopfinger AJ. 1995. A 3D-QSAR study of anticoccidial triazines using molecular shape analysis. J Chem Inf Comput Sci 35(4):771-778.
7. Cramer RD III, Patterson DE, Bunce JD. 1988. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110(18):5959-5967.
8. Swaan PW, Szoka FC Jr, Oie S. 1997. Molecular modeling of the intestinal bile acid carrier: A comparative molecular field analysis study. J Comput Aided Mol Des 11(6):581-588.
9. Li J, Hidalgo IJ. 1996. Molecular modeling study of structural requirements for the oligopeptide transporter. J Drug Target 4(1):9-17.
10. Swaan PW, Koops BC, Moret EE, Tukker JJ. 1998. Mapping the binding site of the small intestinal peptide carrier (PepT1) using comparative molecular field analysis. Receptors Channels 6(3):189-200.
11. Pilger C, Bartolucci C, Lamba D, Tropsha A, Fels G. 2001. Accurate prediction of the bound conformation of galanthamine in the active site of Torpedo californica acetylcholinesterase using molecular docking. J Mol Graph Model 19(3-4):288-296, 374-378.
12. Cho SJ, Garsia ML, Bier J, Tropsha A. 1996. Structure-based alignment and comparative molecular field analysis of acetylcholinesterase inhibitors. J Med Chem 39(26):5064-5071.
13. Kier LB, Hall LH. 1986. Topological information. In: Kier LB, Hall LH, editors. Molecular connectivity in structure-activity analysis. Hertfordshire: Research Studies, pp 43-68.
14. Katritzky AR, Gordeeva EV. 1993. Traditional topological indices vs electronic, geometrical, and combined molecular descriptors in QSAR/QSPR research. J Chem Inf Comput Sci 33(6):835-857.
15. Huuskonen JJ, Villa AE, Tetko IV. 1999. Prediction of partition coefficient based on atom-type electrotopological state indices. J Pharm Sci 88(2):229-233.
16. Sutter JM, Jurs PC. 1996. Prediction of aqueous solubility for a diverse set of heteroatom-containing organic compounds using a quantitative structure-property relationship. J Chem Inf Comput Sci 36(1):100-107.
17. Huuskonen J, Salo M, Taskinen J. 1998. Aqueous solubility prediction of drugs based on molecular topology and neural network modeling. J Chem Inf Comput Sci 38(3):450-456.
18. Wanchana S, Yamashita F, Hashida M. 2002. Quantitative structure/property relationship analysis on aqueous solubility using genetic algorithm-combined partial least squares method. Pharmazie 57(2):127-129.
19. Norinder U, Osterberg T. 2001. Theoretical calculation and prediction of drug transport processes using simple parameters and partial least squares projections to latent structures (PLS) statistics. The use of electrotopological state indices. J Pharm Sci 90(8):1076-1085.
20. Yamashita F, Wanchana S, Hashida M. 2002. Quantitative structure/property relationship analysis of Caco-2 permeability using a genetic algorithm-based partial least squares method. J Pharm Sci 91(10):2230-2239.
21. Wanchana S, Yamashita F, Hashida M. 2003. QSAR analysis of the inhibition of recombinant CYP3A4 activity by structurally diverse compounds using a genetic algorithm-combined partial least squares method. Pharm Res 20(9):1401-1408.
22. Cabrera Perez MA, Garcia AR, Teruel CF, Alvarez IG, Sanz MB. 2003. A topological-substructural molecular design (TOPS-MODE) approach to determining pharmacokinetics and pharmacological properties of 6-fluoroquinolone derivatives. Eur J Pharm Biopharm 56(2):197-206.
23. +/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res 16(1):55-61.
24. Kier LB, Hall LH. 2000. Intermolecular accessibility: The meaning of molecular connectivity. J Chem Inf Comput Sci 40(3):792-795.
25. Hall LH, Kier LB. 2000. The E-state as the basis for molecular structure space definition and structure similarity. J Chem Inf Comput Sci 40(3):784-791.
26. Horwitz JP, Massova I, Wiese TE, Besler BH, Corbett TH. 1994. Comparative molecular field analysis of the antitumor activity of 9H-thioxanthen-9-one derivatives against pancreatic ductal carcinoma 03. J Med Chem 37(6):781-786.
27. Kroemer RT, Koutsilieri E, Hecht P, Liedl KR, Riederer P, Kornhuber J. 1998. Quantitative analysis of the structural requirements for blockade of the N-methyl-D-aspartate receptor at the phencyclidine binding site. J Med Chem 41(3):393-400.
28. Debnath AK. 1998. Comparative molecular field analysis (CoMFA) of a series of symmetrical bis-benzamide cyclic urea derivatives as HIV-1 protease inhibitors. J Chem Inf Comput Sci 38(4):761-767.
29. Miyashita M, Akamatsu M, Hayashi Y, Ueno T. 2000. Three-dimensional quantitative structure-activity relationship analyses of RGD mimetics as fibrinogen receptor antagonists. Bioorg Med Chem Lett 10(9):859-863.
30. Okazawa A, Akamatsu M, Ohoka A, Nishiwaki H, Cho W, Nakagawa Y, Nishimaru K, Ueno T. 1998. Prediction of the binding mode of imidacloprid and related compounds to house-fly head acetylcholine receptors using three-dimensional QSAR analysis. Pestic Sci 54:134-144.
31. Geladi P, Kowalski BR. 1986. Partial least-squares regression: A tutorial. Anal Chim Acta 185:1-17.
32. Swaan PW, Tukker JJ. 1997. Molecular determinants of recognition for the intestinal peptide carrier. J Pharm Sci 86(5):596-602.
33. Bailey PD, Boyd CA, Bronk JR, Collier ID, Meredith D, Morgan KM, Temple CS. 2000. How to make drugs orally active: A substrate template for peptide transporter PepT1. Angew Chem Int Ed Engl 39(3):505-508.
34. Van Drie JH, Weininger D, Martin YC. 1989. ALADDIN: An integrated tool for computer-assisted molecular design and pharmacophore recognition from geometric, steric, and substructure searching of three-dimensional molecular structures. J Comput Aided Mol Des 3(3):225-251.
35. Goldberg DE. 1989. Genetic algorithms in search, optimization, and machine learning. New York: Addison-Wesley.