Characterizing bitterness: Identification of key structural features and development of a classification model

Journal of Chemical Information and Modeling

Volumn 46, Issue 2, 2006, Pages 569-576

  Rodgers, Sarah ^a,c   Glen, Robert C ^b   Bender, Andreas ^b,d  

^a UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c AZ R and D Charnwood   (United Kingdom)

^d NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLASSIFICATION (OF INFORMATION); COMPUTER SYSTEMS PROGRAMMING; DATA REDUCTION; DRUG PRODUCTS; MATHEMATICAL MODELS; SCAFFOLDS; SET THEORY; STRUCTURAL DESIGN; SUGAR (SUCROSE);

BITTERNESS; CARBON SCAFFOLDS; MDL DRUG DATA REPOSITORY (MDDR); SUGAR MOIETIES;

MOLECULAR DYNAMICS;

DRUG; PROMETHAZINE; SACCHARIN;

ALGORITHM; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; COMPUTER SIMULATION; DATA BASE; DRUG EFFECT; STIMULATION; STRUCTURE ACTIVITY RELATION; TASTE;

ALGORITHMS; COMPUTER SIMULATION; DATABASES; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PROMETHAZINE; SACCHARIN; STIMULATION, CHEMICAL; STRUCTURE-ACTIVITY RELATIONSHIP; TASTE;

EID: 33646252229     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci0504418     Document Type: Conference Paper

References (35)

1. Glanz, K.; Basil, M.; Maibach, E.; Goldberg, J.; Snyder, D. Why Americans eat what they do: Taste, nutrition, cost, convenience, and weight control concerns as influences on food consumption. J. Am. Diet. Assoc. 1998, 98, 1118-1126.
2. Ninomiya, K. Umami: A Universal Taste. Food Rev. Int. 2002, 18, 23-38.
3. Meyerhof, W. Elucidation of mammalian bitter taste. Rev. Physiol. Bioch. P. 2005, in press. DOI: 10.1007/s10254-005-0041.
4. Heck, G. L.; Mierson, S.; DeSimone, J. A. Salt taste transduction occurs through an amiloride-sensitive sodium transport pathway. Science 1984, 223, 403-405.
5. + channels in taste cells provides the basis for sour taste transduction. P. Natl. Acad. Sci. U.S.A. 1988, 85, 7023-7027.
6. Wong, G. T.; Gannon, K. S.; Margolskee, R. F. Transduction of bitter and sweet taste by gustducin. Nature 1996, 381, 796-800.
7. Chaudhari, N.; Landin, A. M.; Roper, S. D. A metabotropic glutamate receptor variant functions as a taste receptor. Nature Neurosci. 2000, 3, 113-119.
8. Adler, E.; Hoon, M. A.; Mueller, K. L.; Chandrashekar, J.; Ryba, N. J. P.; Zuker, C. S. A novel family of mammalian taste receptors. Cell 2000, 100, 693-702.
9. Chandrashekar, J.; Mueller, K. L.; Hoon, M. A.; Adler, E.; Feng, L.; Guo, W.; Zuker, C. S.; Ryba, J. P. T2Rs function as bitter taste receptors. Cell 2000, 100, 703-711.
10. Bufe, B.; Hofmann, T.; Krautwurst, D.; Raguse, J.-D.; Meyerhof, W. The human TAS2R16 receptor mediates bitter taste in response to β- glucopyranosides. Nat. Genet. 2002, 32, 397-401.
11. Kuhn, C.; Bufe, B.; Winnig, M.; Hofmann, T.; Frank, O.; Behrens, M.; Lewtschenko, T.; Slack. J. P.; Ward, C. D.; Meyerhof, W. Bitter Taste Receptors for Saccharin and Acesulfame K. J. Neurosci. 2004, 24, 10260-10265.
12. Pronin, A. N.; Tang, H.; Connor, J.; Keung, W. Identification of Ligands for Two Human Bitter T2R Receptors. Chem. Senses 2004, 29, 583-593.
13. Behrens, M.; Brockhoff, A.; Kuhn, C.; Bufe, B.; Winnig, M.; Meyerhof, W. The human taste receptor hTAS2R14 responds to a variety of different bitter compounds. Biochem. Bioph. Res. Commun. 2004, 319, 479-485.
14. Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403.
15. Schiffman, S. S.; Zervakis, J.; Heffron, S.; Heald, A. E. Effect of Protease Inhibitors on the Sense of Taste. Nutrition 1999, 15, 767-772.
16. Ney, K. H. Bitterness of Peptides: Amino Acid Composition and Chain Length. ACS Symp. Ser. 1979, 115, 149-173.
17. Spillane, W. J.; Feeney, B. G.; Coyle, C. M. Further studies on the synthesis and tastes of monosubstituted benzenesulfamates. A semi-quantitative structure-taste relationship for the meta-compounds. Food Chem. 2002, 79, 15-22.
18. Carpino, S.; Acree, T. E.; Barbano, D. M.; Licitra, G.; Siebert, K. J. Chemometric Analysis of Ragusano Cheese Flavor. J. Agric. Food Chem. 2002, 50, 1143-1149.
19. FSTA, Food Science and Technology Abstracts, IFIS Publishing: Shinfield, 2003. Database available from Ovid Technologies Inc. at URL http://www.ovid.com/ site/index.jsp.
20. BIOSIS Previews/RN(R), Biological Abstracts Inc.: Philadelphia, PA, 2003. Database is available from STN at URL http:// www.stn-international.de/.
21. WPIDS, Derwent World Patents Index Subscribers file, Thomson Scientific: Philadelphia, 2003. Database is available from STN at URL http://www.stn- international.de/.
22. SciFinder, 2004 edition, software available from the American Chemical Society at URL http://www.cas.org/.
23. DNP, Dictionary of Natural Products, version 8.1, 2004. Database is available from Chapman and Hall/CRC Press at URL http:// www.chemnetbase.com/.
24. WDI, World Drug Index, 2004. Database is available from Derwent Publications Ltd. at URL http://thomsonderwent.com/.
25. ChemDraw, 2001, version 7.0, software is available from Cambridge-Soft at URL http://products.cambridgesoft.com/.
26. Rodgers, S.; Busch, J.; Peters, H.; Christ-Hazelhof, E. Building a Tree of Knowledge: Analysis of Bitter Molecules. Chem. Senses 2005, 30, 547-557.
27. MDL Drug Data Report; MDL ISIS/HOST software, MDL Information Systems, Inc.
28. Bender, A.; Mussa, H. Y.; Glen, R. C. Molecular Similarity Searching Using Atom Environments, Information-Based Feature Selection, and a Naïve Bayesian Classifier. J. Chem. Inf. Comput. Sci. 2004, 44, 170-178.
29. Bender, A.; Glen, R. C. Molecular similarity: a key technique in molecular informatics. Org. Biomol. Chem. 2004, 2, 3204-3218.
30. Bender, A.; Mussa, H. Y.; Glen, R. C. Similarity Searching of Chemical Databases Using Atom Environment Descriptors (MOLPRINT 2D): Evaluation of Performance. J. Chem. Inf. Comput. Sci. 2004, 44, 1708-1718.
31. Hert, J.; Willett, P.; Wilton, D. J.; Acklin, P.; Azzaoui, K.; Jacoby, E.; Schuffenhauer, A. Comparison of Fingerprint-Based Methods for Virtual Screening Using Multiple Bioactive Reference Structures. J. Chem. Inf. Comput. Sci. 2004, 44, 1177-1185.
32. MDL Drug Data Report, MDL ISIS/HOST software, MDL Information Systems, Inc.: San Leandro, CA.
33. Clark, R. D.; Cramer, R. D.; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
34. Klon, A. E.; Click, M.; Davies J. D. Application of Machine Learning To Improve the Results of High-Throughput Docking Against the HIV-1 Protease. J. Chem. Inf. Comput. Sci. 2004, 44, 2216-2224.
35. Bender, A. Studies on Molecular Similarity. Ph.D. Thesis, University of Cambridge, 2005.