Structure-based screening for discovery of sweet compounds

Food Chemistry

Volumn 315, Issue , 2020, Pages

  Ben Shoshan Galeczki, Yaron ^a   Niv, Masha Y ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Docking; Drug discovery; GPCR; Modeling; Sweet taste receptor; Sweeteners; T1R2; Tas1R2

Indexed keywords

DOCKING; FOOD ADDITIVES; MODELS;

DRUG DISCOVERY; GPCR; SWEET TASTE; SWEETENERS; T1R2; TAS1R2;

MOLECULES;

CHALCONE DERIVATIVE; FLAVONE DERIVATIVE; GALLIC ACID DERIVATIVE; GALLOYL GLUCOSE; HYDROXYBENZOIC ACID DERIVATIVE; INULOBIOSE; MALTOTETRAOSE; MANNAN; MELIBIITOL; MORACHALCONE A; NARIRUTIN; NATURAL PRODUCT; PROANTHOCYANIDIN B2 3,3' DIGALLATE; PROANTHOCYANIDIN DERIVATIVE; PROTOCATECHUIC ACID 4 GLUCOSIDE; SAKEBIOSE; SWEETENING AGENT; TURANOSE; UNCLASSIFIED DRUG; G PROTEIN COUPLED RECEPTOR; GLUCOSE; TASTE RECEPTORS, TYPE 1;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DATA BASE; DRUG DESIGN; DRUG SCREENING; FOOD; HUMAN; MOLECULAR DOCKING; MOLECULE; SCORING SYSTEM; SENSITIVITY AND SPECIFICITY; STRUCTURAL HOMOLOGY; STRUCTURAL MODEL; SWEETNESS; TASTE; VIRTUAL REALITY; BINDING SITE; CHEMISTRY; MOLECULAR MODEL; PROTEIN QUATERNARY STRUCTURE; PROTEIN TERTIARY STRUCTURE;

BINDING SITES; GLUCOSE; HUMANS; MODELS, MOLECULAR; PROTEIN STRUCTURE, QUATERNARY; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, G-PROTEIN-COUPLED;

EID: 85078682689     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2020.126286     Document Type: Article

References (39)

1. Acevedo, W., Ramirez-Sarmiento, C.A., Agosin, E., Identifying the interactions between natural, non-caloric sweeteners and the human sweet receptor by molecular docking. Food Chemistry 264 (2018), 164–171.
2. Baldwin, M.W., Toda, Y., Nakagita, T., O'Connell, M.J., Klasing, K.C., Misaka, T., Liberles, S.D., Sensory biology. Evolution of sweet taste perception in hummingbirds by transformation of the ancestral umami receptor. Science 345:6199 (2014), 929–933.
3. Cheron, J.B., Casciuc, I., Golebiowski, J., Antonczak, S., Fiorucci, S., Sweetness prediction of natural compounds. Food Chemistry 221 (2017), 1421–1425.
4. Cheron, J.B., Golebiowski, J., Antonczak, S., Fiorucci, S., The anatomy of mammalian sweet taste receptors. Proteins 85:2 (2017), 332–341.
5. Damak, S., Rong, M., Yasumatsu, K., Kokrashvili, Z., Varadarajan, V., Zou, S., Margolskee, R.F., Detection of sweet and umami taste in the absence of taste receptor T1r3. Science 301:5634 (2003), 850–853.
6. Di Pizio, A., Ben Shoshan-Galeczki, Y., Hayes, J.E., Niv, M.Y., Bitter and sweet tasting molecules: It's complicated. Neuroscience Letters, 2018.
7. Di Pizio, A., Waterloo, L.A.W., Brox, R., Lober, S., Weikert, D., Behrens, M., Niv, M.Y., Rational design of agonists for bitter taste receptor TAS2R14: From modeling to bench and back. Cellular and Molecular Life Sciences, 2019.
8. DuBois, G.E., Prakash, I., Non-Caloric Sweeteners, Sweetness Modulators, and Sweetener Enhancers. Annual Review of Food Science and Technology 3:3 (2012), 353–380.
9. Fitch, C., Keim, K.S., Position of the Academy of Nutrition and Dietetics: Use of Nutritive and Nonnutritive Sweeteners. Journal of the Academy of Nutrition and Dietetics 112:5 (2012), 739–758.
10. Geng, Y., Mosyak, L., Kurinov, I., Zuo, H., Sturchler, E., Cheng, T.C., Fan, Q.R., Structural mechanism of ligand activation in human calcium-sensing receptor. Elife, 2016, 5.
11. Huang, N., Shoichet, B.K., Irwin, J.J., Benchmarking sets for molecular docking. Journal of Medicinal Chemistry 49:23 (2006), 6789–6801.
12. Irwin, J.J., Shoichet, B.K., Docking screens for novel ligands conferring new biology. Journal of Medicinal Chemistry 59:9 (2016), 4103–4120.
13. Jiang, P.H., Cui, M., Zhao, B.H., Snyder, L.A., Benard, L.M.J., Osman, R., Margolskee, R.F., Identification of the cyclamate interaction site within the transmembrane domain of the human sweet taste receptor subunit T1R3. Journal of Biological Chemistry 280:40 (2005), 34296–34305.
14. Kumari, A., Choudhary, S., Arora, S., Sharma, V., Stability of aspartame and neotame in pasteurized and in-bottle sterilized flavoured milk. Food Chemistry 196 (2016), 533–538.
15. Lim, V.J.Y., Du, W.N., Chen, Y.Z., Fan, H., A benchmarking study on virtual ligand screening against homology models of human GPCRs. Proteins-Structure Function and Bioinformatics 86:9 (2018), 978–989.
16. Loper, H.B., La Sala, M., Dotson, C., Steinle, N., Taste perception, associated hormonal modulation, and nutrient intake. Nutrition Reviews 73:2 (2015), 83–91.
17. Lustig, R.H., Schmidt, L.A., Brindis, C.D., Public health: The toxic truth about sugar. Nature 482:7383 (2012), 27–29.
18. Maillet, E.L., Cui, M., Jiang, P., Mezei, M., Hecht, E., Quijada, J., Max, M., Characterization of the binding site of aspartame in the human sweet taste receptor. Chemical Senses 40:8 (2015), 577–586.
19. Matsunami, H., Montmayeur, J.P., Buck, L.B., A family of candidate taste receptors in human and mouse. Nature 404:6778 (2000), 601–604.
20. Moller, T.C., Moreno-Delgado, D., Pin, J.P., Kniazeff, J., Class C G protein-coupled receptors: Reviving old couples with new partners. Biophysics Reports 3:4 (2017), 57–63.
21. Montmayeur, J.P., Liberles, S.D., Matsunami, H., Buck, L.B., A candidate taste receptor gene near a sweet taste locus. Nature Neuroscience 4:5 (2001), 492–498.
22. Mysinger, M.M., Carchia, M., Irwin, J.J., Shoichet, B.K., Directory of useful decoys, enhanced (DUD-E): Better ligands and decoys for better benchmarking. Journal of Medicinal Chemistry 55:14 (2012), 6582–6594.
23. Nissim, I., Dagan-Wiener, A., Niv, M.Y., The taste of toxicity: A quantitative analysis of bitter and toxic molecules. IUBMB Life 69:12 (2017), 938–946.
24. Nuemket, N., Yasui, N., Kusakabe, Y., Nomura, Y., Atsumi, N., Akiyama, S., Yamashita, A., Structural basis for perception of diverse chemical substances by T1r taste receptors. Nature Ccmmunications, 2017, 8.
25. Pase, M.P., Himali, J.J., Beiser, A.S., Aparicio, H.J., Satizabal, C.L., Vasan, R.S., Jacques, P.F., Sugar- and Artificially Sweetened Beverages and the Risks of Incident Stroke and Dementia A Prospective Cohort Study. Stroke, 48(5), 2017, 1139-+.
26. Ripphausen, P., Nisius, B., Bajorath, J., State-of-the-art in ligand-based virtual screening. Drug Discovery Today 16:9–10 (2011), 372–376.
27. Rojas, C., Todeschini, R., Ballabio, D., Mauri, A., Consonni, V., Tripaldi, P., Grisoni, F., A QSTR-based expert system to predict sweetness of molecules. Frontiers in Chemistry, 5, 2017, 53.
28. Sastry, M., Lowrie, J.F., Dixon, S.L., Sherman, W., Large-scale systematic analysis of 2D fingerprint methods and parameters to improve virtual screening enrichments. Journal of Chemical Information and Modeling 50:5 (2010), 771–784.
29. Spaggiari, G., Di Pizio, A., Cozzini, P., Sweet, umami and bitter taste receptors: State of the art of in silico molecular modeling approaches. Trends in Food Science & Technology 96 (2020), 21–29.
30. Sterling, T., Irwin, J.J., ZINC 15–Ligand Discovery for Everyone. Journal of Chemical Information and Modeling 55:11 (2015), 2324–2337.
31. Suez, J., Korem, T., Zeevi, D., Zilberman-Schapira, G., Thaiss, C.A., Maza, O., Elinav, E., Artificial sweeteners induce glucose intolerance by altering the gut microbiota. Nature 514:7521 (2014), 181–186.
32. Temussi, P.A., Determinants of sweetness in proteins: A topological approach. Journal of Molecular Recognition 24:6 (2011), 1033–1042.
33. Truchon, J.-F., Bayly, C.I., Evaluating virtual screening methods: Good and bad metrics for the “early recognition” problem. Journal of Chemical Information and Modeling 47:2 (2007), 488–508.
34. Winnig, M., Bufe, B., Kratochwil, N.A., Slack, J.P., Meyerhof, W., The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor. Bmc Structural Biology, 2007, 7.
35. Yang, J., Zhang, W., He, B., Walker, S.E., Zhang, H., Govindarajoo, B., Zhang, Y., Template-based protein structure prediction in CASP11 and retrospect of I-TASSER in the last decade. Proteins 84:Suppl 1 (2016), 233–246.
36. Yee, K.K., Sukumaran, S.K., Kotha, R., Gilbertson, T.A., Margolskee, R.F., Glucose transporters and ATP-gated K+ (KATP) metabolic sensors are present in type 1 taste receptor 3 (T1r3)-expressing taste cells. Proceedings of the National Academy of Sciences of the United States of America 108:13 (2011), 5431–5436.
37. Zhang, F., Klebansky, B., Fine, R.M., Liu, H., Xu, H., Servant, G., Li, X., Molecular mechanism of the sweet taste enhancers. Proceedings of the National Academy of Sciences of the United States of America 107:10 (2010), 4752–4757.
38. Zhao, G.Q., Zhang, Y., Hoon, M.A., Chandrashekar, J., Erlenbach, I., Ryba, N.J., Zuker, C.S., The receptors for mammalian sweet and umami taste. Cell 115:3 (2003), 255–266.
39. Zheng, S.Q., Chang, W.P., Xu, W.X., Xu, Y., Lin, F., e-Sweet: A machine-learning based platform for the prediction of sweetener and its relative sweetness. Frontiers Chemistry, 2019, 7.