2D binary QSAR modeling of LPA3 receptor antagonism

Journal of Molecular Graphics and Modelling

Volumn 28, Issue 8, 2010, Pages 828-833

  Fells, James I ^a   Tsukahara, Ryoko ^b   Liu, Jianxiong ^b   Tigyi, Gabor ^b   Parrill, Abby L ^a  

^a University of Memphis   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

Binary QSAR; Lysophosphatidic acid receptor; Similarity searching

Indexed keywords

COMPOUND SELECTION; DATA SETS; INACTIVE COMPOUNDS; LYSOPHOSPHATIDIC ACID; QSAR MODEL; QSAR MODELING; SIMILARITY SEARCHING; TEST SETS; TRAINING SETS;

ACIDS; PHOSPHOLIPIDS;

MOLECULAR GRAPHICS;

LYSOPHOSPHATIDIC ACID RECEPTOR BLOCKING AGENT; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; DRUG DESIGN; DRUG DETERMINATION; DRUG STRUCTURE; PREDICTION; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY;

ALGORITHMS; DATABASES, FACTUAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, LYSOPHOSPHATIDIC ACID; REPRODUCIBILITY OF RESULTS;

EID: 77951974258     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2010.03.002     Document Type: Article

References (29)

1. Rivera R., and Chun J. Biological effects of lysophospholipids. Rev. Physiol. Biochem. Pharmacol. 160 (2008) 25-46
2. Parrill A.L., and Baker D.L. Autotaxin inhibition: challenges and progress toward novel anti-cancer agents. Anticancer Agents Med. Chem. 8 (2008) 917-923
3. Pasternack S.M., von Kügelgen I., Aboud K.A., Lee Y.A., Rüschendorf F., Voss K., Hillmer A.M., Molderings G.J., Franz T., Ramirez A., Nürnberg P., Nöthen M.M., and Betz R.C. G protein-coupled receptor P2Y5 and its ligand LPA are involved in maintenance of human hair growth. Nat. Genet. 40 (2008) 329-334
4. Murakami M., Shiraishi A., Tabata K., and Fujita N. Identification of the orphan GPCR, P2Y(10) receptor as the sphingosine-1-phosphate and lysophosphatidic acid receptor. Biochem. Biophys. Res. Commun. 371 (2008) 707-712
5. Kotarsky K., Boketoft A., Bristulf J., Nilsson N., Norberg A., Hansson S., Sillard R., Owman C., Leeb-Lundberg F., and Olde B. Lysophosphatidic acids binds to and activates GPR92. A G protein-coupled receptor highly expressed in gastro-intestinal lymphocytes. J. Pharmacol. Exp. Ther. (2006) 619-628
6. Choi J.W., Lee C.W., and Chun J. Biological roles of lysophospholipid receptors revealed by genetic null mice: an update. Biochim. Biophys. Acta 1781 (2008) 531-539
7. Murph M.M., Nguyen G.H., Radhakrishna H., and Mills G.B. Sharpening the edges of understanding the structure/function of the LPA1 receptor: expression in cancer and mechanisms of regulation. Biochim. Biophys. Acta 1781 (2008) 547-557
8. Fells J.I., Tsukahara R., Fujiwara Y., Liu J., Perygin D.H., Osborne D.A., Tigyi G., and Parrill A.L. Identification of non-lipid LPA3 antagonists by virtual screening. Bioorg. Med. Chem. 16 (2008) 6207-6217
9. Ljjaali I., Petitet F., Dubus E., Barberan O., and Michel A. Assessing potency of c-Jun N-terminal kinase 3 (JNK3) inhibitors using 2D molecular descriptors and binary QSAR methodology. Bioorg. Med. Chem. 15 (2007) 4256-4264
10. Thai K.-M., and Ecker G.F. A binary QSAR model for classification of hERG potassium channel blockers. Bioorg. Med. Chem. 16 (2008) 4107-4119
11. Parrill A.L., Echols U., Nguyen T., Pham T.-C.T., Hoeglund A., and Baker D.L. Virtual screening approaches for the identification of non-lipid autotaxin inhibitors. Bioorg. Med. Chem. 16 (2008) 1784-1795
12. Durgam G.G., Tsukahara R., Makarova N., Walker M.D., Fujiwara Y., Pigg K.R., Baker D.L., Sardar V.M., Parrill A.L., Tigyi G., and Miller D.D. Synthesis and pharmacological evaluation of second-generation phosphatidic acid derivatives as lysophosphatidic acid receptor ligands. Bioorg. Med. Chem. Lett. 16 (2006) 633-640
13. Durgam G.G., Virag T., Walker M.D., Tsukahara R., Yasuda S., Liliom K., van Meeteren L.A., Moolenaar W.H., Wilke N., Siess W., Tigyi G., and Miller D.D. Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARgamma, and inhibitors of autotaxin. J. Med. Chem. 48 (2005) 4919-4930
14. Fischer D.J., Nusser N., Virag T., Yokoyama K., Wang D., Baker D.L., Bautista D., Parrill A.L., and Tigyi G. Short-chain phosphatidates are subtype-selective antagonists of lysophosphatidic acid receptors. Mol. Pharmacol. 60 (2001) 776-784
15. Heasley B.H., Jarosz R., Carter K.M., Van S.J., Lynch K.R., and Macdonald T.L. A novel series of 2-pyridyl-containing compounds as lysophosphatidic acid receptor antagonists: development of a nonhydrolyzable LPA3 receptor-selective antagonist. Bioorg. Med. Chem. Lett. 14 (2004) 4069-4074
16. Heasley B.H., Jarosz R., Lynch K.R., and Macdonald T.L. Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist. Bioorg. Med. Chem. Lett. 14 (2004) 2735-2740
17. Lynch K.R., and Macdonald T.L. Structure-activity relationships of lysophosphatidic acid analogs. Biochim. Biophys. Acta 1582 (2002) 289-294
18. Ohta H., Sato K., Murata N., Damirin A., Malchinkhuu E., Kon J., Kimura T., Tobo M., Yamazaki Y., Watanabe T., Yagi M., Sato M., Suzuki R., Murooka H., Sakai T., Nishitoba T., Im D.S., Nochi H., Tamoto K., Tomura H., and Okajima F. Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors. Mol. Pharmacol. 64 (2003) 994-1005
19. Virag T., Elrod D.B., Liliom K., Sardar V.M., Parrill A.L., Yokoyama K., Durgam G., Deng W., Miller D.D., and Tigyi G. Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors. Mol. Pharmacol. 63 (2003) 1032-1042
20. MOE. MOE, version 2008.10. Chemical Computing Group Inc.: Montreal, 2008.
21. Fells J.I., Tsukahara R., Liu J., Tigyi G., and Parrill A.L. Structure-based drug design identifies novel LPA3 antagonists. Bioorg. Med. Chem. 17 (2009) 7457-7464
22. Parrill A.L. Lysophospholipid interactions with protein targets. Biochim. Biophys. Acta 1781 (2008) 540-546
23. Kano K., Arima N., Ohgami M., and Aoki J. LPA and its analogs-attractive tools for elucidation of LPA biology and drug development. Curr. Med. Chem. 15 (2008) 2122-2131
24. Heise C.E., Santos W.L., Schreihofer A.M., Heasley B.H., Mukhin Y.V., Macdonald T.L., and Lynch K.R. Activity of 2-substituted lysophosphatidic acid (LPA) analogs at LPA receptors: discovery of a LPA1/LPA3 receptor antagonist. Mol. Pharmacol. 60 (2001) 1173-1180
25. Tropsha A., and Golbraikh A. Predictive QSAR modeling workflow, model applicability domains, and virtual screening. Curr. Pharm. Des. 13 (2007) 3494-3504
26. Golbraikh A., and Tropsha A. Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection. Mol. Divers. 5 (2002) 231-243
27. Hawkins D.M. The problem of overfitting. J. Chem. Inf. Comput. Sci. 44 (2004) 1-12
28. Sprous D.G. Fingerprint-based clustering applied to define a QSAR model use radius. J. Mol. Graph. Modell. 27 (2008) 225-232
29. Zhang H., Xu X., Gajewiak J., Tsukahara R., Fujiwara Y., Liu J., Fells J.I., Perygin D., Parrill A.L., Tigyi G., and Prestwich G.D. Dual activity lysophosphatidic acid receptor pan-antagonist/autotaxin inhibitor reduces breast cancer cell migration in vitro and causes tumor regression in vivo. Cancer Res. 69 (2009) 5441-5449