Screening of bitterness-suppressing agents for quinine: The use of molecularly imprinted polymers

Journal of Pharmaceutical Sciences

Volumn 94, Issue 2, 2005, Pages 353-362

  Ogawa, Tazuko ^a   Hoshina, Kaori ^a   Haginaka, Jun ^a   Honda, Chie ^a   Tanimoto, Toshiko ^a   Uchida, Takahiro ^a  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

Author keywords

HPLC; Molecular modeling; NMR; Receptor; Structure activity relationship

Indexed keywords

AMINO ACID; ARGININE; CINCHONIDINE; CITRULLINE; LYSINE; METHACRYLIC ACID; MOLECULARLY IMPRINTED POLYMER; ORNITHINE; POLYMER; QUININE; UNCLASSIFIED DRUG;

ARTICLE; BITTER TASTE; COMPLEX FORMATION; DRUG FORMULATION; DRUG SCREENING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY;

EID: 14344256487     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20248     Document Type: Article

References (23)

1. Spielman AI, Nagai H, Sunavala G, Dasso M, Breer H, Boekhoff I, Huque T, Whitney G, Brand JG. 1996. Rapid kinetics of second messenger production in bitter taste. Am J Physiol 270:C926-C931.
2. Ming D, Ruiz-Avila L, Margolskee RF. 1998. Characterization and solubilization of bitter-responsive receptors that couple to gustducin. Proc Natl Acad Sci USA 95:8933-8938.
3. Tsunenari T, Kurahashi T, Kaneko A. 1999. Activation by bitter substances of a cationic channel in membrane patches excised from the bullfrog taste receptor cell. J Physiol 519:397-404.
4. 2+ on the quinine-activated current of bullfrog taste receptor cells. J Physiol 530:235-241.
5. Kober A, Ekman B, Sjöholm I. 1978. Direct and indirect determination of binding constants of drug-protein complexes with microparticles. J Pharm Sci 67:107-109.
6. Noctor TAG, Wainer IW. 1992. Allosteric and competitive displacement of drugs from human serum albumin by octanoic acid, as revealed by high-performance liquid affinity chromatography, on a human serum albumin-based stationary phase. J Chromatogr 577:305-315.
7. Wulff G. 1995. Molecular imprinting in crosslinked materials with the aid of molecular templates. Angew Chem Int Ed Engl 34:1812-1832.
8. Haginaka J, Takehira H, Hosoya K, Tanaka N. 1998. Molecularly imprinted uniform-sized polymer-based stationary phase for naproxen. Comparison of molecular recognition ability of the molecularly imprinted polymers prepared by thermal and redox polymerization techniques. J Chromatogr 816:113-121.
9. Haginaka J, Sanbe H. 2000. Uniform-sized molecularly imprinted polymers for 2-arylpropionic acid derivatives selectively modified with hydrophilic external layer and their applications to direct serum injection analysis. Anal Chem 72:5206-5210.
10. Haginaka J, Kagawa C. 2003. Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases. Anal Sci 19:39-42.
11. Fu Q, Sanbe H, Kagawa C, Kunimoto K, Haginaka J. 2003. Uniformly sized molecularly imprinted polymer for (s)-nilvadipine. Comparison of chiral recognition ability with HPLC chiral stationary phases based on a protein. Anal Chem 75:191-198.
12. Ogawa T, Nakamura T, Tsuji E, Miyanaga Y, Nakagawa H, Hirabayashi H, Uchida T. 2004. The combination effect of L-arginine and NaCl on bitterness suppression of amino acid solutions. Chem Pharm Bull 52:172-177.
13. Takeuchi T, Dobashi A, Kimura K. 2000. Molecular imprinting of biotin derivatives and its application to competitive binding assay using nonisotopic labeled ligands. Anal Chem 72:2418-2422.
14. Katsuragi Y. 1998. Selective inhibitors of bitter taste: Mechanism and application. J Jpn Oil Chem Soc 47:467-474.
15. Caicedo A, Pereira E, Margolskee RF, Rober SD. 2003. Role of the G-protein subunit alpha-gustducin in taste cell responses to bitter stimuli. J Neurosci 23:9947-9952.
16. Ueda T, Ugawa S, Yamamura H, Imaizumi Y, Shimada S. 2003. Functional interaction between T2R taste receptors and G-protein alpha subunits expressed in taste receptor cells. J Neurosci 23: 7376-7380.
17. Chaudhari N, Roper SD. 1998. Molecular and physiological evidence for glutamate (umami) taste transduction via a G protein-coupled receptor. Ann NY Acad Sci 855:398-406.
18. Kalinoski DL, Bryant BP, Shaulsky G, Brand JG, Harpaz S. 1989. Specific L-arginine taste receptor sites in the catfish, Ictalurus punctatus: Biochemical and neurophysiological characterization. Brain Res 488:163-173.
19. Kumazawa T, Brand JG, Teeter JH. 1998. Amino acid-activated channels in the catfish taste system. Biophys J 75:2757-2766.
20. Kirsch GE, Yeh JZ, Parley JM, Narahashi T. 1980. Interaction of n-alkylguanidines with the sodium channels of squid axon membrane. J Gen Physiol 76:315-335.
21. Danko M, Smith-Maxwell C, McKinney L, Begenisich T. 1986. Block of sodium channels by internal mono- and divalent guanidinium analogues. Modulation by sodium ion concentration. Biophys J 49:509-519.
22. Kuhn FJ, Greeff NG. 2003. Gating properties of a sodium channel with three arginines substituted by histidine in the central part of voltage sensor S4D4. J Membr Biol 193:23-34.
23. Nakamura T, Tanigake A, Miyanaga Y, Ogawa T, Akiyoshi T, Matsuyama K, Uchida T. 2002. The effect of various substances on the suppression of the bitterness of quinine: Human gustatory sensation, binding, and taste sensor studies. Chem Pharm Bull 50:1589-1593.