Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor

PLoS ONE

Volumn 14, Issue 3, 2019, Pages

  Nakagita, Tomoya ^a,b   Ishida, Akiko ^c   Matsuya, Takumi ^a   Kobayashi, Takuya ^b   Narukawa, Masataka ^a   Hirokawa, Takatsugu ^d,e   Hashimoto, Makoto ^c   Misaka, Takumi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

^d NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^e UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLORPROP; G PROTEIN COUPLED RECEPTOR; LACTISOLE DERIVATIVE; MEMBRANE PROTEIN; METHYL 2 (2,4 DICHLOROPHENOXY)PROPIONIC ACID; METHYL 2 (4 METHOXYPHENOXY)PROPIONIC ACID; PROTEIN INHIBITOR; SWEET PROTEIN; SWEET TASTE RECEPTOR; TRANSMEMBRANE DOMAIN T1R3 SUBUNIT; UNCLASSIFIED DRUG; BENZENE DERIVATIVE; LACTISOLE; TASTE RECEPTORS, TYPE 1;

ARTICLE; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; HUMAN; HUMAN CELL; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; CHEMISTRY; GENETICS; HEK293 CELL LINE; METABOLISM; MUTATION; PROTEIN DOMAIN; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

BENZENE DERIVATIVES; CRYSTALLOGRAPHY, X-RAY; HEK293 CELLS; HUMANS; MOLECULAR DYNAMICS SIMULATION; MUTATION; PROTEIN DOMAINS; RECEPTORS, G-PROTEIN-COUPLED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85063298771     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0213552     Document Type: Article

References (29)

1. Chandrashekar J, Hoon MA, Ryba NJP, Zuker CS. The receptors and cells for mammalian taste. Nature. 2006. pp. 288–294. https://doi.org/10.1038/nature05401 PMID: 17108952
2. Montmayeur J-P, Liberles SD, Matsunami H, Buck LB. A candidate taste receptor gene near a sweet taste locus. Nat Neurosci. 2001; 4: 492–498. https://doi.org/10.1038/87440 PMID: 11319557
3. Hoon MA, Adler E, Lindemeier J, Battey JF, Ryba NJ, Zuker CS. Putative mammalian taste receptors: a class of taste-specific GPCRs with distinct topographic selectivity. Cell. 1999; 96: 541–551. PMID: 10052456
4. Nelson G, Chandrashekar J, Hoon MA, Feng L, Zhao G, Ryba NJP, et al. An amino-acid taste receptor. Nature. 2002; 416: 199–202. https://doi.org/10.1038/nature726 PMID: 11894099
5. Max M, Shanker YG, Huang L, Rong M, Liu Z, Campagne F, et al. Tas1r3, encoding a new candidate taste receptor, is allelic to the sweet responsiveness locus Sac. Nat Genet. 2001; 28: 58–63. https://doi.org/10.1038/88270 PMID: 11326277
6. Kitagawa M, Kusakabe Y, Miura H, Ninomiya Y, Hino A. Molecular genetic identification of a candidate receptor gene for sweet taste. Biochem Biophys Res Commun. 2001; 283: 236–42. https://doi.org/10.1006/bbrc.2001.4760 PMID: 11322794
7. Cui M, Jiang P, Maillet E, Max M, Margolskee RF, Osman R. The heterodimeric sweet taste receptor has multiple potential ligand binding sites. Curr Pharm Des. 2006; 12: 4591–4600. https://doi.org/10.2174/138161206779010350 PMID: 17168764
8. Maillet EL, Cui M, Jiang P, Mezei M, Hecht E, Quijada J, et al. Characterization of the binding site of aspartame in the human sweet taste receptor. Chem Senses. 2015; https://doi.org/10.1093/chemse/ bjv045 PMID: 26377607
9. Masuda K, Koizumi A, Nakajima K ichiro, Tanaka T, Abe K, Misaka T, et al. Characterization of the modes of binding between human sweet taste receptor and low-molecular-weight sweet compounds. PLoS One. 2012; 7: 1–10. https://doi.org/10.1371/journal.pone.0035380 PMID: 22536376
10. Jiang P, Cui M, Zhao B, Snyder LA, Benard LMJ, Osman R, et al. Identification of the cyclamate interaction site within the transmembrane domain of the human sweet taste receptor subunit T1R3. J Biol Chem. 2005; 280: 34296–34305. https://doi.org/10.1074/jbc.M505255200 PMID: 16076846
11. Jiang P, Cui M, Zhao B, Liu Z, Snyder LA, Benard LMJ, et al. Lactisole interacts with the transmembrane domains of human T1R3 to inhibit sweet taste. J Biol Chem. 2005; 280: 15238–15246. https://doi.org/10.1074/jbc.M414287200 PMID: 15668251
12. Winnig M, Bufe B, Kratochwil NA, Slack JP, Meyerhof W. The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor. BMC Struct Biol. 2007; 7: 66. https://doi.org/10.1186/ 1472-6807-7-66 PMID: 17935609
13. Sanematsu K, Kusakabe Y, Shigemura N, Hirokawa T, Nakamura S, Imoto T, et al. Molecular mechanisms for sweet-suppressing effect of gymnemic acids. J Biol Chem. 2014; 289: 25711–25720. https://doi.org/10.1074/jbc.M114.560409 PMID: 25056955
14. Fujiwara S, Imada T, Nakagita T, Okada S, Nammoku T, Abe K, et al. Sweeteners interacting with the transmembrane domain of the human sweet-taste receptor induce sweet-taste synergisms in binary mixtures. Food Chem. Elsevier Ltd; 2012; 130: 561–568. https://doi.org/10.1016/j.foodchem.2011.07. 073
15. Jeffrey Conn P, Lindsley CW, Meiler J, Niswender CM. Opportunities and challenges in the discovery of allosteric modulators of GPCRs for treating CNS disorders. Nat Publ Gr. 2014; 13. https://doi.org/10.1038/nrd4308 PMID: 25176435
16. Servant G, Tachdjian C, Li X, Karanewsky DS. The sweet taste of true synergy: Positive allosteric modulation of the human sweet taste receptor. Trends Pharmacol Sci. Elsevier Ltd; 2011; 32: 631–636. https://doi.org/10.1016/j.tips.2011.06.007 PMID: 21807420
17. Rovira X, Malhaire F, Scholler P, Rodrigo J, Gonzalez-Bulnes P, Llebaria A, et al. Overlapping binding sites drive allosteric agonism and positive cooperativity in type 4 metabotropic glutamate receptors. FASEB J. 2015; 29: 116–130. https://doi.org/10.1096/fj.14-257287 PMID: 25342125
18. O’Brien DE, Conn PJ. Neurobiological insights from mGlu receptor allosteric modulation. Int J Neurop-sychopharmacol. 2016; 19: 1–10. https://doi.org/10.1093/ijnp/pyv133 PMID: 26647381
19. Rathbone EB, Patel GD, Butters RW, Cookson D, Robinson JL. Occurrence of 2-(4-Methoxyphenoxy) propanoic Acid in Roasted Coffee Beans: Analysis by Gas-Liquid Chromatography and by High-Performance Liquid Chromatography. J Agric Food Chem. 1989; 37: 54–58. https://doi.org/10.1021/ jf00085a013
20. Rathbone EB, Butters RW, Cookson D, Robinson JL. Chirality of 2-(4-methoxyphenoxy)propanoic acid in roasted coffee beans: analysis of the methyl esters by chiral high-performance liquid chromatography. J Agric Food Chem. American Chemical Society; 1989; 37: 58–60. https://doi.org/10.1021/ jf00085a014
21. Maillet EL, Margolskee RF, Mosinger B. Phenoxy herbicides and fibrates potently inhibit the human chemosensory receptor subunit T1R3. J Med Chem. 2009; 52: 6931–6935. https://doi.org/10.1021/ jm900823s PMID: 19817384
22. Doré AS, Okrasa K, Patel JC, Serrano-Vega M, Bennett K, Cooke RM, et al. Structure of class C GPCR metabotropic glutamate receptor 5 transmembrane domain. Nature. 2014; 511: 557–562. https://doi.org/10.1038/nature13396 PMID: 25042998
23. Wu H, Wang C, Gregory KJ, Han GW, Cho HP, Xia Y, et al. Structure of a class C GPCR metabotropic glutamate receptor 1 bound to an allosteric modulator. Science (80-). 2014; 344: 58–64. https://doi.org/10.1126/science.1249489 PMID: 24603153
24. Imada T, Misaka T, Fujiwara S, Okada S, Fukuda Y, Abe K. Amiloride reduces the sweet taste intensity by inhibiting the human sweet taste receptor. Biochem Biophys Res Commun. Elsevier Inc.; 2010; 397: 220–225. https://doi.org/10.1016/j.bbrc.2010.05.088 PMID: 20493823
25. Isberg V, De Graaf C, Bortolato A, Cherezov V, Katritch V, Marshall FH, et al. Generic GPCR residue numbers—Aligning topology maps while minding the gaps. Trends in Pharmacological Sciences. 2015. https://doi.org/10.1016/j.tips.2014.11.001
26. Salomon-Ferrer R, Case DA, Walker RC. An overview of the Amber biomolecular simulation package. Wiley Interdiscip Rev Comput Mol Sci. 2013; https://doi.org/10.1002/wcms.1121
27. 5) X-ray Structures. J Med Chem. 2018; https://doi.org/10.1021/acs.jmedchem.7b01722 PMID: 29455526
28. Christopher JA, Aves SJ, Bennett KA, Doré AS, Errey JC, Jazayeri A, et al. Fragment and Structure-Based Drug Discovery for a Class C GPCR: Discovery of the mGlu5 Negative Allosteric Modulator HTL14242 (3-Chloro-5-[6-(5-fluoropyridin-2-yl)pyrimidin-4-yl]benzonitrile). J Med Chem. 2015; 58: 6653–6664. https://doi.org/10.1021/acs.jmedchem.5b00892 PMID: 26225459
29. Chéron JB, Golebiowski J, Antonczak S, Fiorucci S. The anatomy of mammalian sweet taste receptors. Proteins Struct Funct Bioinforma. 2017; https://doi.org/10.1002/prot.25228 PMID: 27936499